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Recipients are HONORED for contributions of major significance to chemistry THIS IS THE FINAL set of vignettes of
recipients of awards administered by the American Chemical Society for 2011. A profile of Ahmed H. Zewail, the 2011 Priestley Medalist, is scheduled to appear in the March 28 issue of C&EN along with his award address. Nicholas J. Turro, winner of the Arthur C. Cope Award, and most other national award winners will be honored at an awards ceremony that will be held on Tuesday, March 29, in conjunction with the 241st ACS national meeting in Anaheim, Calif. The 2011 Arthur C. Cope Scholar awardees will be honored at the 242nd ACS national meeting in Denver on Aug. 28–Sept. 1. The Arthur C. Cope Award recognizes and encourages excellence in organic chemistry; it consists of a medal, a cash prize of $25,000, and an unrestricted research grant of $150,000 to be assigned by the recipient to any university or research institution. Each Cope Scholar Award consists of $5,000, a certificate, and an unrestricted research grant of $40,000. Arthur C. Cope and Arthur C. Cope Scholar Awards are sponsored by the Arthur C. Cope Fund.
ARTHUR C. COPE AWARD NICHOLAS J. TURRO, the William P.
Schweitzer Professor of Chemistry at Columbia University, is receiving this year’s Arthur C. Cope Award “for laying the foundations for modern organic photochemistry, supramolecular photochemistry, and spin chemistry through his imaginative and pioneering research.” Turro, 72, says he probably first became interested in chemistry as many other children do, “with explosions and fireworks and that type of thing.” But he really became captivated by his first high school physics course. “We began talking about the ideas and concepts of molecules and how they’re organized in various ways,” Turro recalls. “It was an exciting and stun-
ning way to think about the world around us in universal terms.” Turro then majored in chemistry at Wesleyan University, receiving a B.A. in 1960. He went on to graduate school at California Institute of Technology, where he worked in George S. Hammond’s lab. Turro earned a Ph.D. in organic chemistry in 1963. After a postdoctoral year with Paul D. Bartlett at Harvard University, Turro joined the faculty at Columbia, where he has stayed ever since. Turro initially didn’t plan to work in photochemistry, he says, because he thought it would be too similar to Hammond’s research. Instead, he focused on synthesizing high-energy materials, in particular cyclopropanone. “At the time, many people didn’t think you could make it,” Turro says. “It’s basically carbon monoxide and ethylene,” and, before the advent of the Woodward-Hoffmann rules, “there was no reason at the time that people could imagine it would be stable to collisions,” Turro says. But he and graduate student Willis B. Hammond (no relation to George) managed to synthesize the molecule and studied its reactions with other organic compounds. Photochemistry still intrigued Turro, however, and when George Hammond Turro moved on to assume administrative and industrial positions, Turro stepped back into the field, pioneering time-resolved spectroscopic techniques to study photochemical reaction pathways. In the late 1970s, Turro experimented with the photolysis of ketones in micelles, discovering large magnetic isotope effects. He went on to design synthetic systems that could produce dramatically different products “by the application of magnetic fields whose strength is on the order of magnetic stirrer bars,” says Miguel A. WWW.CEN-ONLINE.ORG
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COURTESY OF NICHOLAS TURRO
2011 ACS NATIONAL AWARD WINNERS
Garcia-Garibay, a chemistry professor at the University of California, Los Angeles. “This research exemplified Turro’s ability to pull together ideas from interdisciplinary fields, such as colloidal and supramolecular chemistry, the theory of magnetic resonance, and the chemistry of radical pairs and photochemistry to synthesize a new framework for physical organic investigations,” Garcia-Garibay adds. Turro continued to explore the structurereactivity relations of guest-host supramolecular systems, investigating photochemical reactions of organic molecules adsorbed on the surfaces of micelles, zeolites, dendrimers, DNA, and other materials and documenting how those environmental interactions affect the resulting chemistry. Turro’s “groundbreaking experiments on the steady-state and time-resolved photoreactions of molecules adsorbed on porous silica and zeolites revealed a rich array of novel supramolecular effects and demonstrated the dominating influence of size, shape, and site of the host geometry and chemical structure on the reaction channels and dynamics of reactive intermediates generated in porous solids,” Garcia-Garibay says. Vaidhyanathan Ramamurthy, a chemistry professor at the University of Miami, highlights Turro’s work with radical pairs in supramolecular systems as particularly noteworthy. Turro demonstrated in zeolites the ability to double the enantioselectivity of the recombination of a radical pair containing 13C compared with 12C. He also showed how to use supramolecular steric effects to stabilize radical pairs in preference to their combination products. “At a time when weak interactions and supramolecular chemistry were being recognized and systematically studied for groundstate processes by many in our community, Turro was already using them as tools to control and uncover the subtle interplay between restricted environments, chemical dynamics, and spin effects,” says Kendall N. Houk, who holds the Winstein Chair in Organic Chemistry at UCLA and received the Arthur C. Cope Award in 2010. In addition to his research to advance the field of photochemistry, Turro wrote
KEMSLEY
ARTHUR C. COPE SCHOLAR AWARDS As a child, ZHENAN BAO remembers spending hours in her mother’s chemistry lab at China’s Nanjing University. “I played, in a safe manner, with squeeze bottles, distilled water, and pH paper,” she recalls. Today, Bao still tinkers with chemistry, but, as one of the world’s foremost experts in organic semiconductors and electronics, she now has considerably more sophisticated toys. “Her accomplishments span an extraordinary range,” Stanford University chemistry professor Robert M. Waymouth notes, “from illuminating fundamental structure-property relationships in new families of electroactive acenes to the engineering, design, and optimization of sophisticated electronic devices based on semiconducting organic materials.” Bao, an associate professor of chemical engineering at Stanford, might not seem like a typical recipiBao ent of an Arthur C. Cope Scholar Award, which recognizes excellence in organic chemistry. But Bao points out that her work is rooted in organic chemistry. “I apply the fundamentals of organic chemistry to make semiconducting materials,” she explains. After emigrating from China to the U.S., Bao earned her doctoral degree from the University of Chicago. She then spent eight years working at Lucent Technologies’ Bell Labs, in Murray Hill, N.J., before joining the faculty at Stanford in 2004. Bao’s myriad accomplishments include discovering the high charge-transport property of regioregular polythiophene. Working with her Bell Labs colleagues, she used the material to demonstrate the first all-printed plastic circuit. She also came up with design rules for organic semiconductors, notably n-type semiconductors. Bao’s work with dielectric materials is particularly noteworthy—one such material enabled the first demonstration of flexible electronic paper. Another dielectric led to transistors and sensors that work underwater to detect chemicals at partsper-billion concentrations. Her group recently developed a pressure-sensitive elastic dielectric polymer that could one
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day lead to medical gloves for doctors that can distinguish healthy cells from cancerous ones. “Her research evidences great chemical and physical insight, highly creative synthetic and materials processing approaches, incisive implementation of an awesome array of physical techniques, and the highest scientific standards of meticulous execution,” remarks Tobin J. Marks, a chemistry professor at Northwestern University and another 2011 Cope Scholar. “What is remarkable about her work is the level of innovation and deep scholarship she brings to the challenge of constructing functional organic semiconducting devices, which require knowledge and mastery of the materials chemistry, the processing challenges, and the fabrication of functioning devices,” Waymouth adds. To other organic chemists who may be looking to enter the materials arena, Bao offers this advice: “In any interdisciplinary work, one needs to learn the language of another discipline, and it may be difficult at the beginning. But if one is persistent and makes the effort, the reward is tremendous. People are, in general, always happy to share their knowledge and take the time to explain things to someone who is willing to learn.” Bao attributes her success to the many mentors and collaborators she’s had over the years. “I thank them for their support and friendship,” she says, “and I want to do the same for my students and other young scientists.”—BETHANY HALFORD JE FF SHAW
the seminal textbook on photochemistry, which was first published in 1964. Back then, Turro put together a set of notecards with every published photochemical reaction to use as a resource for writing the text, he says. Finding the time to boil down the subject matter for the most recent iteration, published last year, was a much more difficult endeavor. Turro has been recognized with a number of ACS awards, including the ACS Award in Pure Chemistry, an Arthur C. Cope Scholar Award, the James Flack Norris Award in Physical Organic Chemistry, and the ACS Award in Colloid & Surface Chemistry. Turro also received the Ernest Orlando Lawrence Award for chemistry and metallurgy from the Department of Energy. Turro received the National Science Foundation Director’s Award for Distinguished Teaching Scholars in 2002 and ACS’s George C. Pimentel Award in Chemical Education in 2004. Both awards recognized his efforts to bring information technology tools—including a software program for teaching or self-learning infrared spectroscopy—to chemistry classrooms. “I’m very proud of that,” Turro says. He is now embarking on a similar effort to promote the use of online tools to enhance research, teaching, and learning, including the use of freely available software to provide easy personal access to resources. For example, his group regularly “meets” for seminars with far-flung collaborators by using the Internet video phone service Skype. Taking advantage of such tools is a critical part of research scholarship, Turro says, to promote discussion and ensure experiments are done thoughtfully and efficiently. In the lab, Turro continues to apply the chemical principles he has developed to an ever wider array of problems, including the development of fluorescent molecular beacons to track RNA in living cells and novel methods for the construction of polymer networks. He has also been working on the spin chemistry of small molecules such as H2 and H2O that have been inserted into fullerenes. In particular, he has found a way to polarize the spins of H2@C60 to enhance the nuclear magnetic resonance signal for medical applications. This effort again brings together the fields of supramolecular chemistry, spin chemistry, and photochemistry, but in a new way. “The combination provides a delightful platform for future research,” Turro says.—JYLLIAN
Research on molecular prosthetics—the use of small molecules that carry out proteinlike functions to cure human diseases—and groundbreaking advances in the field of organic synthesis have earned assistant professor MARTIN D. BURKE of the University of Illinois, Urbana-Champaign, a 2011 Arthur C. Cope Scholar Award. Burke’s “pioneering vision for molecular prosthetics has the potential to be revolutionary,” chemistry professor Stuart L. Schreiber of Harvard University notes. And his “nascent research program is already having a major impact on the field of organic synthesis, a trend that promises to continue far into the future,” he adds. Burke’s concept for molecular prosthet-
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DAVID CRICH’s contributions to organic
chemistry have been so rich and varied that his nominators for the Arthur C. Cope Scholar Award found it impossible to limit their recognition of his work to just one area. Ultimately, they split the award citation, honoring Crich, 51, “for his contributions to methodology development and mechanistic investigation in the fields of synthetic carbohydrate and freeradical chemistry.” Todd L. Lowary, a chemistry professor at the University of Alberta, in Edmonton, calls Crich “an undisputed international leader in the field of synthetic carbohydrate chemistry,” adding that “his work has changed the way the scientists in the area think about their discipline.” David J. Hart, a chemistry professor at Ohio State University, describes Crich’s contribuCrich tions to free-radical chemistry as “an elegant ballet where synthetic and physical organic chemistry play the major roles.” As an undergraduate at the University of Surrey, in England, Crich studied both chemistry and French, the latter proving especially useful when he spent a year of his undergraduate studies in France work-
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ing with Sir Derek Barton at the Institut de Chimie des Substances Naturelles (ICSN), part of the Centre National de la Recherche Scientifique, in Paris. This experience prompted Crich to pursue his Ph.D. and postdoctoral studies with Barton. Since establishing his own research effort, Crich has held faculty positions at England’s University College London; the University of Illinois, Chicago; and Wayne State University, where he was the first Schaap Professor of Organic Chemistry. Two years ago, he was lured back to France to become the director of ICSN. His numerous accomplishments in carbohydrate chemistry include an important direct stereocontrolled synthesis of β-mannopyranosides. His synthesis remains the only general and direct method for the construction of these molecules and has since been applied to carbohydrates with similar structures. Furthermore, his efforts to elucidate the mechanism of this transformation revealed that the high level of stereocontrol is due to the in situ generation of a glycosyl triflate intermediate that reacts stereoselectively with the acceptor alcohol. “Crich’s work is organic chemistry at its best,” says Peter H. Seeberger, director of the biomolecular systems department at the Max Planck Institute of Colloids & Interfaces, in Germany. “He develops novel methods that he uses to construct biologically important molecules. In contrast to so many of the practitioners in the field, he has a very strong interest in the area of physical organic chemistry and has spent much effort to elucidate reaction mechanisms and determine the exact course of the reactions he uses.” “I’m very proud of the fact that I’m an organic chemist, and I’m very proud of the many contributions that organic chemistry has made to society and to the innumerable improvements to our health and lifestyle over the past century or more,” Crich says. “I’m absolutely confident that chemistry conducted in a proper responsible manner still has many, many contributions to make to society, and I still think it’s a great field for young people to go into. It’s very exciting. It’s very challenging. And it has many things to give.”—BETHANY HALFORD ZONGMIN DAI
Burke’s group is currently working to build a machine, similar to a peptide synthesizer, that would construct complex molecules via iterative coupling of MIDA boronates. “Achieving this goal would have substantial and broad impact, perhaps even extending the power of organic synthesis to the nonchemist,” Schreiber comments. The machine, he notes, is an “ambitious but now likely attainable goal.” Burke, 34, earned a bachelor’s degree in chemistry at Johns Hopkins University in 1998, a Ph.D. in chemistry from Harvard in 2003, and an M.D. at Harvard Medical School and Massachusetts Institute of Technology in 2005. He was named a Howard Hughes Medical Institute Early Career Scientist in 2009.—STU BORMAN LEAH DELCAMP
ics involves the replacement of functionally deficient proteins with small-molecule surrogates. A prototype for the development of such agents is the small-molecule natural product amphotericin B, which self-assembles into transmembrane ion-conducting aggregates. A mechanism explaining how amphotericin B undergoes remodeling into an ion channel had been proposed, but in 2007 Burke and coworkers demonstrated that that model was itself in need of remodeling. By deleting key amphotericin B functional groups, they Burke showed that a carboxylate that had been proposed to play a critical role in the mechanism was in fact not needed for channel self-assembly and ion transport. The researchers are currently trying to develop a highly efficient and flexible total synthesis of amphotericin B to provide access to derivatives for systematic structure-function studies. Directly stimulated by the goal of achieving that total synthesis, Burke and coworkers recently devised a new synthetic strategy called iterative cross-coupling in which relatively simple molecular building blocks are combined into complex molecules with a single reaction type. The idea is to use bifunctional haloboronic acids like Lego pieces that combine by SuzukiMiyaura reactions to assemble complex architectures. In 2007, Burke and coworkers discovered that an inexpensive and environmentally benign ligand, methyliminodiacetic acid (MIDA), can control the reactivity of haloboronic acids and thus prevent them from combining in random ways. They used MIDA boronates to achieve the first total synthesis of the natural product ratanhine and to make challenging polyenes such as retinal, parinaric acid, and peridinin, in each case employing only a single reaction type to assemble the parts. They also used MIDA boronates to couple notoriously challenging substrates such as 2-pyridyl boronic acids. Bristol-Myers Squibb and other pharmaceutical companies in the U.S. and Europe are using Burke’s boronates in drug discovery programs, and Sigma-Aldrich offers more than 70 MIDA boronates commercially.
Colleagues call CRAIG J. HAWKER “one of the world’s most outstanding leaders in the design and synthesis of functionalized macromolecules,” “simply a chemistry superstar,” and “absolutely the most distinguished organic/polymer/materials chemist of his generation.” But Hawker, 47, remains humble, generous, and supportive of others. From his school days in Australia to his current polymer research, Hawker, a professor of materials, chemistry, and biochemistry and director of the Materials Research Laboratory at the University of California, Santa Barbara, says, “I just went down what was the most fun path for me.” As an undergraduate at the University of Queensland, he enjoyed organic chemistry, so he continued with graduate work at the University of Hawker
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Cambridge. In postdoctoral work with Jean Fréchet, then at Cornell University, Hawker began to make waves by developing the first convergent synthesis of dendritic macromolecules. His synthetic procedures allowed such precise control over structure, composition, and properties, a colleague says, that they “changed the direction of polymer science.” Timothy M. Swager, a professor of chemistry at Massachusetts Institute of Technology, adds that the work is among the most-cited synthetic polymer papers ever published. After a few years at the University of Queensland as a Queen Elizabeth II Fellow, Hawker accepted a research position at IBM’s Almaden Research Center in 1993. Again, he looked for scientific simplicity with real-world applications: He wanted to make porous dielectric materials with starting materials that didn’t require the rigorous conditions necessary for anionic polymerization. “That was when we started our work in living free-radical polymerization, a much easier way to make these welldefined materials,” he says. “That satisfied an IBM demand and also really caught the imagination of the external community.” The work, which involved the reversible capping of radical chain ends with nitroxyl radicals, was “pioneering,” according to a colleague. The colleague adds that it enabled the synthesis of novel polymers for a wide array of applications, including block copolymer lithography. Hawker continued his quest for “very simple but very powerful chemistry” when he moved to UC Santa Barbara in 2005. He wanted to extend to polymer synthesis the concept of click chemistry, a method of joining together “spring-loaded” small molecules in a modular fashion. He recognized that he could, in benign solvents, use click chemistry to selectively control multiple functional groups on a polymer. In one dramatic demonstration, he ran a reaction in tequila. “If I could get 100% yield in José Cuervo,” he says, “it gets the message across that even within cheap alcohol containing impurities, additives, and who knows what, you can do the chemistry with the same efficiency.” Hawker’s contributions have been recognized by many other awards, inMATTH EW KADE
the importance of hockey, snow, and Tim Hortons,” a chain of coffee shops. At Toronto, Dong has developed creative methods for making heterocycles of interest to medicinal chemistry, including indoles, benzofurans, lactones, and lactams. Robert H. Morris, a colleague there, admires the productivity and originality Dong has shown in the few years she has been at the university. “Professor Vy Dong is an exceptional young organic chemist who has already demonstrated outstanding imagination and leadership in her independent academic career,” he says. Dong’s catalytic approach for making lactones from simple ketoaldehydes has received significant recognition. Using a rhodium catalyst, she can prepare small and medium-sized lactones—including ones found in nature—with complete regio- and enantioselectivity and without generating any waste products. Bergman calls the work “groundbreaking.” And although she may have broken glassware as a student, Bergman says Dong’s independent career has gotten off to a “meteoric start.”—LILA GUTERMAN P HI DO N G
Inspired by her first semester of sophomore organic chemistry with Larry E. Overman at the University of California, Irvine, VY M. DONG switched her major from ecology to chemistry. “I was amazed that relatively simple but powerful concepts in chemistry could be used to make molecules that had function in biology,” she recalls. As an undergraduate, she explored that ability by doing research in Overman’s laboratory. “It was an eye-opening experience that made me realize how little I knew about organic synthesis,” recalls Dong, now an associate professor at the University of Toronto. “I spent most of my time trying not to break the glassware.” Determined to learn more, Dong began graduate studies with David W. C. Dong MacMillan at UC Berkeley. Two years later, she helped MacMillan move his laboratory to California Institute of Technology, where Dong completed her doctoral studies on developing tandem reactions for streamlining the synthesis of macrolide antibiotics. To extend her training to organometallic and supramolecular chemistry, Dong returned to UC Berkeley for postdoctoral work with Robert G. Bergman and Kenneth N. Raymond. In a collaborative project, she investigated the formation and stabilization of iminium ions within a chiral nanovessel. In the summer of 2006, she moved north to set up her own research laboratory at the University of Toronto, where she focuses on inventing new catalytic transformations. Dong has made progress in challenging areas of catalysis, including the functionalization of C–H bonds, activation of carbon dioxide, and vicinal oxidation of simple olefins. She aims to invent organometallic pathways that facilitate the synthesis of biologically interesting molecules. Dong, 34, says, “There is still a need for developing transformations that are closer to meeting the high standards defined by green chemistry.” Dong also finds motivation in mentoring students. “It’s great to work with talented students who are working hard to turn rough ideas into useful synthetic methods,” she says. Dong, a Texas native, adds, “Besides chemistry, I’m learning about Canadian culture from my students, including
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vancement of Science, the Optical Society of America, SPIE, and the American Physics Society, Marder notes, “The physicists and engineers may not be intrinsically interested in physical organic chemistry, but they do like working with better materials.”—ROBIN GIROUX What do the areas of organic electronic materials, organometallic bonding energetics, metallocene-mediated olefin polymerization, and metal-organic catalysis have in common? They have all been significantly advanced by TOBIN J. MARKS. In recognition of his body of pioneering work in these areas, Marks, the Vladimir N. Ipatieff Professor of Catalytic Chemistry and a professor of materials science and engineering at Northwestern University, is being honored with an Arthur C. Cope Scholar Award. “Tobin’s pioneering achievements in an impressive number of scientific areas, ranging from olefin polymerization and organic electronic materials to metal-organic catalysis and metal-ligand bond energy systemization, have dramatically influenced the science our community does,” says M. Frederick Hawthorne, a professor of chemistry and radiology at the University of Missouri. “He is able to target important problems and to couple elegant synthetic strategies with incisive mechanistic studies and the application of diverse physicochemical techniques.” Likewise, Robert H. Grubbs, a professor of chemistry at California Institute of Technology, says, “Tobin chooses important problems and finds solutions through deep mechanistic understanding and the application of an array of physical techniques.” For his part, Marks says he is “delighted” to receive this honor. “It is a wonderful recognition of the research my students and I have carried out in several areas of organic chemistry.” The Marks lab has four project themes. The first is organometallics, which includes the development of f-element catalysts for hydrosilation, hydroalkoxylation, hydroamination, and hydrothiolation. Another research focus is the development of novel active-layer materials to incorporate into organic COURTESY OF TOBI N MARKS
A material is said to exhibit nonlinear optical effects if exposure to intense low- or high-frequency electric fields changes its properties such that the transmission, frequency, or phase of light passing through it is altered. In 1985, as SETH R. MARDER was beginning a postdoc at Oxford University, nonlinear optics was in the realm of physics. But Marder, an organometallic chemist, was intrigued: What is the underlying physical chemistry? How do the chemical structures of molecules relate to their electronic and optical properties? His curiosity is 25 years strong, and he’s still being surprised by where it leads him. Marder is best known for Marder his fundamental contributions to the understanding of the relationships between the chemical structure of organic molecules and their optical properties, says Charles P. Casey, Marder’s Ph.D. adviser at the University of Wisconsin, Madison. “His work on the nonlinear polarizabilities and nonlinear absorptive properties of organic materials profoundly changed how the chemistry, materials, and physics communities think about the molecular basis for nonlinear optical applications and how materials chemists design optimized structures for nonlinear optical applications.” Through a combination of synthesis, theory, and characterization, Marder and his collaborators developed a model to understand how to tailor molecules for second- and third-order nonlinear applications in photonics. Their work in the area of optimizing two-photon absorption in organic materials has implications for
materials processing, biological imaging, medicine, and information storage. “Marder was able to essentially translate the field of organic nonlinear optics into the language of chemists,” says Larry R. Dalton, a chemistry professor at the University of Washington, Seattle. Now 49, Marder was barely a teenager when he was first attracted to chemistry when his older brother, Todd, a chemistry major at Massachusetts Institute of Technology, brought home nuclear magnetic resonance spectra. “I fell in love with NMR spectra,” Marder said. “It amazed me that you can look at a spectrum and find out so much about a molecule.” He followed his brother to MIT, graduating with a bachelor’s degree in 1981. He then went to Wisconsin, where in 1985 he earned a Ph.D. in organic chemistry. After his postdoctoral fellowship at Oxford, he did another at the Jet Propulsion Laboratory at California Institute of Technology. He worked in various positions at Caltech through 1998 before moving to the University of Arizona with his longtime collaborator Joe Perry, a characterization phenom. There, they were joined by Jean-Luc Brédas, who contributes the theoretical piece of the nonlinear optics puzzle. The trio moved in 2003 to Georgia Institute of Technology, where Marder was appointed the founding director of the Center for Organic Photonics & Electronics. “Being part of a team that can achieve more than any one member individually is a gratifying experience,” Marder says. Working as part of an interdisciplinary team also gives him the ability to teach students from “a wonderfully rich platform, one that makes it impossible for students to get stuck in any one niche,” he says. Marder has authored more than 300 peer-reviewed articles—including one in Science and another in Nature that have each been cited more than 1,000 times—and holds 19 patents. A fellow of the American Marks Association for the AdCOURTESY OF SETH MARDER
cluding election as a Fellow of the Royal Society, the International Union of Pure & Applied Chemistry’s DSM International Performance Materials Award, and the ACS Award in Applied Polymer Science. His 300 or so publications have been cited over 25,000 times, and a colleague notes that Hawker is among the 100 most-cited living chemists—particularly impressive given his youth. “Professor Hawker is unrivaled,” his colleague says, “in terms of the number of novel and important new concepts that he discovered and new fields that he helped launch.”—LILA GUTERMAN
SUSAN MORRISSEY
Contributions made during a 30-year-long academic career by KEIJI MARUOKA, a professor of chemistry at Japan’s Kyoto University, rank him among the most creative and productive synthetic chemists in the world, according to his colleagues. His major achievements encompass a wide variety of new synthetic methodologies, including the creation of new reagents and catalysts. These contributions have been chronicled in more than 300 scientific publications and three dozen patents. In particular, his work in asymmetric organocatalysis has advanced the field into
new areas. His novel approaches have led to the design of chiral phase-transfer catalysts for artificial amino acid synthesis, chiral bifunctional organocatalysts, and chiral organodiacid catalysts for asymmetric transformations. In 1999, for example, Maruoka designed and synthesized nonnatural, C2 symmetric, chiral phasetransfer catalysts, now known collectively as the Maruoka Maruoka Catalyst, derived from optically pure binaphthol. Using these catalysts, he developed a practical approach for the asymmetric synthesis of natural and nonnatural amino acid derivatives. Refining his results, Maruoka took the important step of rationally redesigning these catalysts. The resulting structurally simplified version, known as the Simplified Maruoka Catalyst, still possesses extremely high catalytic performance and virtually complete enantioselectivity. Available from chemical suppliers and made on the kilogram scale, these catalysts are used in the large-scale production of nonnatural α-alkyl and α,α-dialkyl-α-amino acids from glycine derivatives. “In an age when chiral phase-transfer catalysts were all derived from Cinchona alkaloids, he introduced a design not reliant on [a chiral starting material], which has proven to be more malleable and, more importantly, far more effective,” Colorado State University chemistry professor Tomislav Rovis says. “Given that about 20% of the top 500, best-selling medicines utilize α-amino acids as starting materials and pharmaceutical intermediates, his technology is of great significance and will likely prove to be more and more important in pharmaceutical areas in the near future,” Rovis adds. Maruoka’s ongoing research interests are in the areas of bidentate Lewis acids in organic synthesis, molecular recognition with bowl-shaped molecules, and practical asymmetric synthesis with chiral organocatalysts. Recently, he received a five-year, $5 million Japan Society for the Promotion of Science grant. He used the funding to establish the Organocatalytic Chemistry Special Laboratory, which is devoted to designing high-performance organocatalysts for application in fine chemicals synthesis.
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Maruoka, 57, received a B.S. in chemistry from Kyoto University and then completed his graduate work at the University of Hawaii. He began his academic career at Nagoya University in 1980, then moved to Hokkaido University in 1995, and returned to Kyoto as a professor of chemistry in 2000. There, he served as department chair in 2004. In addition to an extensive number of published scientific papers and patents, he has presented more than 160 lectures about organocatalysis since 2000. His work has been recognized with several honors, including the Inoue and Ichimura Prizes, the Nagoya Silver Medal, the Synthetic Organic Chemistry Award of Japan, the Green & Sustainable Chemistry Award, and the Chemical Society of Japan Award.—ANN THAYER COU RT ESY O F K EIJI M ARUO K A
photovoltaic cells, thereby improving the cells’ efficiency. The study of transparent oxides, including the application of thin films with higher conductivity to electronic devices, is a third area of work in the Marks lab. The fourth area of focus is molecular electronics, or the search for new organic or inorganic semiconductors and dielectric materials. Marks, 66, has mentored more than 100 Ph.D. students throughout his career. These students have helped Marks generate a body of work that has led to nearly 1,000 publications and more than 190 patents. When asked what his most significant research accomplishment is, Marks tells C&EN that “a major one would be using organic chemical concepts to create and understand interesting and useful new materials, produced either stoichiometrically or catalytically.” Marks earned a B.S. in chemistry from the University of Maryland in 1966 and a Ph.D. in chemistry from Massachusetts Institute of Technology in 1971. He joined the faculty of Northwestern that same year and rose through the professorial ranks to his current position. Among his numerous honors are the 2003 Karl Ziegler Prize of the German Chemical Society, the 2005 U.S. National Medal of Science, the Spanish 2008 Principe de Asturias Prize for Technical & Scientific Research, the 2009 Materials Research Society von Hippel Medal, the 2008 ACS Award for Distinguished Service in the Advancement of Inorganic Chemistry, the 2010 William H. Nichols Medal of the ACS New York Section, and the 2011 Carol & Harry Mosher Award of the ACS Santa Clara Section. He has served on many editorial and advisory boards and is currently an associate editor for Organometallics.—
Try as he might, ANDREW J. PHILLIPS couldn’t run from a life as a chemist. Growing up in New Zealand with a chemistry teacher for a father, Phillips initially did what many children do—steer clear of anything remotely resembling their parents’ interests. “I spent quite a bit of time racing road bikes,” he says. But like a chemistry version of the prodigal son, he eventually returned, with a little encouragement and inspiration from John Blunt, Murray Munro, and Jonathan Morris, chemists at New Zealand’s University of Canterbury, where Phillips attended college and graduate school, the latter under the guidance of Andrew Abell. Today a professor of chemistry at Yale University, Phillips, 40, has won an Arthur C. Cope Scholar Award for his outstanding accomplishments in natural product total synthesis and synthetic methodology. “I am absolutely blown away by how much Andy has accomplished,” says William R. Roush, a professor of chemistry at Scripps Florida. The Phillips team is known for using tandem ring-opening–ring-closing–crossmetathesis reactions for building complex ring systems, such as the one found in the natural product norhalichondrin B. The team also uses titanium(II) to stitch molecules together in innovative ways. “Importantly, Phillips is not just cranking out
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“Fearless.” This is how more than one colleague describes SUZANNE WALKER and her work in natural product antibiotics. Walker is receiving the Arthur C. Cope Scholar Award for her chemoenzymatic characterization of glycosyl transfer steps in
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on the assembly of the bacterial cell wall layers, the mechanism of antibiotics, and the reprogramming of biosynthetic pathways to make optimized therapeutic agents.” “Professor Walker is remarkable in her ability to move into new fields with conviction and fearlessness,” says Laura L. Kiessling, Hilldale Professor of Chemistry & Biochemistry at the University of Wisconsin, Madison. “It is not only her ability to acquire and apply methods and ideas from diverse fields that distinguishes her but also that she identifies key problems and offers new solutions.” But Walker attributes her lab’s success to the students and postdocs who carried out the studies. “They are the ones who make things happen,” she says, “so my accomplishments are really theirs.” After Walker received a B.A. in English literature from the University of Chicago in 1983, she followed “a meandering and bumpy road” to a chemistry Ph.D. from Princeton University in 1992. She is an active member of the ACS Division of Biological Chemistry. She received an Alfred P. Sloan Research Fellowship in 2002, a Camille Dreyfus Teacher-Scholar Award in 2003, and the Protein Society’s Emil Thomas Kaiser Award in 2010.—RACHEL M IK E QU IN N
bacterial cell wall biosynthesis as targets for antibiotics. Walker, a microbiology and molecular genetics professor at Harvard Medical School, is honored to receive the award. “It is amazing to find myself in the company of scientists whose work has been highly influential,” she says. In fact, the first person she told of her achievement was Christopher T. Walsh, Hamilton Kuhn Professor of Biological Chemistry & Walker Molecular Pharmacology at Harvard Medical School and a previous Cope Scholar Award recipient. “I admire him as a scientist and a person. I knew he would be pleased for me,” Walker explains. “The second person I told was my husband, who wanted to know why he wasn’t the first person I told.” Walker’s interest in bacterial cell wall biosynthesis was prompted by concern about antibiotic resistance. When she began to read about the pathway required to build cell walls, she was surprised to learn that some of the steps hadn’t been studied, let alone well characterized. “It seemed to me that the major impediment to studying the pathway steps was that suitable substrates were not available,” she says. In order to solve that problem, Walker turned her attention to developing synthetic substrates to stand in for natural cell wall precursors. Her lab completed the first syntheses of lipid-linked substrates to study key steps in the peptidoglycan biosynthetic pathway. “Access to substrates has allowed us to do all kinds of mechanistic studies on peptidoglycan biosynthetic enzymes and the antibiotics that target them,” Walker says. She adds that her group has “established a tremendously successful collaboration” in this area with Daniel Kahne’s lab at Harvard Medical School. “And we have used a similar approach to enable the study of other important bacterial cell surface polymers,” she says. Walsh says that Walker “embodies the best of modern chemical biology focused COU RT ESY O F AN DREW P HI LL IPS
syntheses but rather striving to develop lasting solutions” to challenges in his field, says Paul A. Wender, Bergstrom Professor of Chemistry at Stanford University. Phillips “is one of the few young chemists in the field taking total synthesis to the next level of efficiency and practicality,” adds Phil S. Baran, a professor of chemistry at Scripps Research Institute. “I’m very motivated to think of complex natural product synthesis with brevity as an overarching concern,” Phillips explains. That philosophy of efficiency crystallized during his postdoctoral stint with Peter Wipf at the University of Pittsburgh, an experience Phillips calls “the most special time of my scientific career.” Phillips says he came to Wipf ’s lab in the U.S. for two reasons: to work on the kind of complex molecule synthesis work that isn’t easily done in New Zealand, and to follow a fellow chemistry graduate student at Canterbury who became his wife. “It worked out okay in both dimensions,” he quips. In 2001, after his time in the Wipf group, Phillips began his independent career at the University of Colorado, Boulder. In the spring of 2009, he was a visiting associate professor at the department of chemistry and chemical biology at Harvard University and the Broad Institute, an experience he calls “transformative—it is having profound effects on my scientific thinking.” He Phillips joined Yale’s faculty in 2010. Among other honors, Phillips has won an Eli Lilly Grantee Award, a National Science Foundation Career Award, and an Alfred P. Sloan Research Fellowship, all in 2006. Phillips says he’s thankful for the talented coworkers he’s had over the years. “I’m always in awe of their efforts,” he says. He still rides his bike on occasion but prefers spending time with his wife, who conducts research at a biotechnology company, and their two children.—CAR-
PEPLING
HACKERMAN AWARD TO JASON HAFNER Jason H. Hafner, an associate professor
of physics and chemistry at Rice University, received the Welch Foundation’s Hackerman Award in Chemical Research at a ceremony on Jan. 27. The $100,000 award, named in honor of academic scientist Norman Hackerman, is presented annually to recognize a young scientist conducting basic chemistry research in Texas. Hafner’s interests lie in applying nanomaterials and nanoscale tools to study biological systems. Using an atomic force
microscope, he has developed ways of detecting the electrical fields inside a cell’s lipid membrane. By mapping these fields, he hopes to understand how they affect the interactions of small biomolecules with the membrane. In other work, Hafner and coworkers have modified the surface chemistry of newly discovered metal nanoparticles and studied how they grow and interact with living cells. For example, gold nanostars, with elongated points that absorb and scatter light at varying wavelengths, may be useful for imaging and sensing in cellular systems. When interacting with laser light, these nanostars also create nanobubbles, which can pinpoint and kill cancer cells and thus may have therapeutic applications. The Texas native grew up near Dallas and attended Trinity University, in San Antonio. He obtained a Ph.D. at Rice, working as a graduate student with the late Nobel Laureate Richard E. Smalley. After completing postdoctoral work at Harvard University, he returned to Rice as a faculty member in 2001. He is an associate editor of the journal ACS Nano.—AMT
VICTOR MCCRARY NAMED SCIENTIST OF THE YEAR Victor McCrary, president of the National
Organization for the Professional Advancement of Black Chemists & Chemical Engineers and the business executive for science and technology at Johns Hopkins University’s Applied Physics Laboratory (APL), is the recipient of the 2011 Scientist of the Year Award from the Black Engineer of the Year Awards (BEYA) conference. At APL, McCrary supports research projects in sensor networks, autonomous systems, cognitive engineering, advanced materials and nanostructures, and concepts for natural systems exploitation. Prior to joining APL, McCrary was chief of the Convergent Information Systems Division at the National Institute of Standards & Technology. He also worked at AT&T Bell Laboratories, in Murray Hill, N.J., where he conducted research in crystal growth for semiconductor lasers. The BEYA conference helps corporate America identify, nurture, and promote
the careers of its black achievers. McCrary received the award during the 2011 BEYA STEM Global Competitiveness Conference, held on Feb. 17–19 in Washington, D.C.
HURVITZ AND WILCHEK WIN ISRAEL CHEMICAL SOCIETY MEDAL The Israel Chemical Society awarded its most prestigious honor, the Israel Chemical Society Medal, to scientists Eli Hurvitz and Meir Wilchek during a ceremony before the Knesset, the Israeli legislative branch, on Jan. 4. Hurvitz, former chief executive officer of Teva Pharmaceutical Industries, led the company for 35 years, transforming it from a small, unknown pharmaceutical business into a world leader in generic pharmaceuticals. Today, Teva is Israel’s largest company, employing roughly 40,000 people around the world. Wilchek, Marc R. Gutwirth Chair of Molecular Biology at the Weizmann Institute of Science, is credited with the development of affinity chromatography, which is used to separate and purify proteins.
BILL DELLINGER RECEIVES TECHNICIAN AWARD Bill Z. Dellinger, a senior technologist at
Dow Chemical, is the 2011 winner of the National Chemical Technician Award, sponsored by ACS’s former Division of Chemical Technicians. The award recognizes technical and communication skills, safety, reliability, leadership, teamwork, publications, and presentations. Dellinger’s contributions include epoxy synthesis and formulation, product testing, performance evaluations, scaleup, and analytical testing. He has trained others on titrations, gel permeation chromatography, high-performance liquid chromatography, rheology measurements, mechanical testing, and other analytical methods. He has contributed to several global projects in China and Europe. Dellinger will receive $1,000 and a plaque during the spring ACS national meeting in Anaheim. WWW.CEN-ONLINE.ORG
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RADDING AWARD SEEKS NOMINATIONS The ACS Santa Clara Valley Section seeks nominations for the 2011 Shirley B. Radding Award, which honors leadership, service, and significant contributions to industrial, applied, or academic chemistry and to ACS through elected or appointed positions at local, district, and national levels. Nominees must have been an ACS member for at least 20 years. The award consists of an honorarium of $1,000 and an inscribed memento. Nominations must include at least one letter of nomination stating how the nominee’s work relates to the award criteria. Seconding letters are also strongly encouraged. Nominations are due on May 1 and should be sent electronically to
[email protected] or mailed to Radding Award Committee, Santa Clara Valley Section ACS, P.O. Box 395, Palo Alto, CA 94302. For more information, visit the local section’s website at scvacs.org.
ACS BUILDING GARNERS GREEN AWARD The Donald F. & Mildred Topp Othmer building at ACS headquarters in Washington, D.C., has achieved Platinum Certification in the Leadership in Energy & Environmental Design, Existing Building: Operations & Maintenance Version 2009 program, sponsored by the U.S. Green Building Council, the nation’s leading nonprofit authority for green buildings. LEED is the nationally accepted benchmark for the design, construction, and operation of high-performance green buildings. The building is the second in Washington, D.C., and one of only nine in the entire country, to achieve this certification. This achievement “supports the sustainability goal set forth by the ACS Board of Directors,” ACS Executive Director and Chief Executive Officer Madeleine Jacobs says. In 2010, ACS was among the winners of the 2010 D.C. Mayor’s Environmental Excellence Awards for its achievements in environmental stewardship, innovative best practices, pollution prevention, and resource conservation. LINDA WANG compiles this section.
Announcements of awards may be sent to
[email protected].
