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2015 ACS NATIONAL AWARD WINNERS Recipients are HONORED FOR CONTRIBUTIONS of major significance to chemistry EDITED BY SOPHIE L. ROVNER
GEORGE A. OLAH AWARD IN HYDROCARBON OR PETROLEUM CHEMISTRY Sponsored by the George A. Olah Award Endowment For the past 30 years, Jingguang G. Chen, the Thayer Lindsley Professor of Chemical Engineering at Columbia University, has worked to uncover hidden details at the core of catalytic surface chemistry. The breadth of his contributions leads catalysis experts in academia and industry alike to categorize Chen as a world leader in experimental and theoretical studies of carbide and bimetallic catalysts. Through a series of investigations, Chen’s group demonstrated that low-cost transition-metal carbides Chen can function as active catalysts that selectively transform hydrocarbons and oxygen-containing organic molecules. These studies, which the group extended to electrocatalysis, grabbed the
attention of the catalysis community because such transformations are typically mediated by platinum and other preciousmetal catalysts. In one study in this area, Chen’s group showed that tungsten carbide capped with a minuscule quantity of platinum catalyzes evolution of hydrogen from water nearly as effectively as pure platinum does. The work suggested cost-saving strategies for producing and using hydrogen in environmentally benign ways. Subsequently, the group identified methods for using carbide catalysts to react CO2 with hydrogen to produce valuable products. In related work, Chen and coworkers applied theoretical and experimental methods to reveal hidden connections between electronic and catalytic properties of bimetallic (alloy) catalysts. The team then used those correlations to design thin-film alloy catalysts and showed that they outperform thick catalysts composed of either metal alone. In one study of this type, the group demonstrated the enhanced selectivity in hydrocarbon reactions afforded by platinum coated with just a single atomic layer of nickel. Alloy catalysts had been studied for years prior to this work. But such catalysts typically were prepared on a trialand-error basis. As an undergraduate student at Nanjing University, in China, Chen, now 53, majored in chemistry. Upon graduating in 1982, he went to the University of Pittsburgh, where he earned a Ph.D. degree in 1988 working with noted surface chemist John T. Yates Jr. He then served as an Alexander von Humboldt Postdoctoral Fellow at the Jülich Research Center, in Germany, before accepting a position as a staff scientist at Exxon’s corporate COURTESY OF JINGGUANG G. CHEN
The following vignettes highlight some of the recipients of national awards administered by the American Chemical Society for 2015. C&EN will publish the remaining sets of vignettes over the next several weeks. A profile of Jacqueline K. Barton, the 2015 Priestley Medalist, will appear in the March 23 issue of C&EN along with her award address. Most of the award recipients will be honored at an awards ceremony that will be held on March 24 in conjunction with the spring ACS national meeting in Denver. However, the Arthur C. Cope Scholar awardees will be honored at the fall ACS national meeting in Boston, Aug. 16–20.
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research laboratory, in Annandale, N.J. After nine years of industry research, Chen began an academic career in 1998 at the University of Delaware, where he served in several capacities including professor of chemical engineering, materials science and engineering, and chemistry, and director of Delaware’s Center for Catalytic Science & Technology. Since 2012, Chen has served as a professor of chemical engineering at Columbia University and as a staff scientist at Brookhaven National Laboratory. Chen is editor of Applied Surface Science and has served on the editorial boards of several scholarly journals including Surface Science, Langmuir, and Surface Science Reports. He is the recipient of several awards and accolades. For example, he is a fellow of the American Chemical Society and of the American Vacuum Society, and he was honored with the Herman Pines Award in Catalysis by the Chicago Catalysis Club and the Excellence in Catalysis Award by the New York Catalysis Society. Chen has published some 300 scientific articles and holds 20 U.S. patents. Chen will present his award address before the Division of Catalysis Science & Technology.—MITCH JACOBY
ACS AWARD IN INDUSTRIAL CHEMISTRY Sponsored by the ACS Division of Business Development & Management and the ACS Division of Industrial & Engineering Chemistry The head of research and development in the area of homogeneous catalysis at Johnson Matthey, Thomas J. Colacot has been a leading contributor to the development of numerous homogeneous catalysts that are widely used both in academia and in a range of industries that implement chemical processes. Over the years, Colacot has developed numerous catalysts for key transformations that enabled these technologies to be used on a commercial scale. He has also conducted fundamental research on the understanding of structure-activity relationships, which has led to new ligands and catalysts for fine-tuning reactivity patterns on palladium. An effective communicator, he has delivered about 400 scientific presentations at universities, industrial R&D labs, and technical conferences over the past 10 years.
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NATIONAL FRESENIUS AWARD Sponsored by Phi Lambda Upsilon, the National Chemistry Honor Society As a high school student, Abigail Doyle enjoyed all of her subjects—economics, literature, languages, and science. She was a serious musician and considered becoming a professional oboist. Luckily for chemistry, it was science that Doyle loved. Still, she can’t quite identify what inspired her to choose chemistry as her university major—before she even took her first college class. Doyle, 34, entered Harvard University in 1998 and took organic chemistry in the spring. “Organic chemistry combines what I love about music and art and what I love about science, and it definitely resonated Doyle with me,” Doyle remembers. But it was getting into the lab that cemented a passion for chemical research. She interned at Bristol-Myers Squibb and pursued undergraduate research as a junior at Harvard. The internship jump-started Doyle’s interest in medicinal and synthetic chemistry. Then, her undergraduate research CEN.ACS.ORG
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drew her to transition-metal catalysis. Doyle graduated in 2002 with bachelor’s and master’s degrees in chemistry. She then went on to Stanford University to do a predoctoral fellowship in which she researched the hydration of unactivated alkenes catalyzed by gold complexes. In 2003, Doyle returned to Harvard for Ph.D. work under adviser Eric N. Jacobsen. Her thesis focused on using alkyl halides and oxocarbenium ions in asymmetric catalysis. While at Harvard, she coauthored an article in Chemical Reviews on hydrogenbond donor catalysis that has received more than 1,000 citations (2007, DOI: 10.1021/cr068373r). From Harvard, Doyle was hired as an assistant professor of chemistry at Princeton University. In 2013, she became an associate professor and has continued her indepth studies of transition-metal catalysis. One area of research that has been particularly fruitful has been fluorination chemistry. Doyle learned from friends in the pharmaceutical industry that introducing fluorine into molecules was very difficult but also very important. What they needed were mild and selective catalytic methods, they told her. Doyle and her research team set to work. “It is remarkable to consider that only a few catalytic methods exist for the asymmetric installation of fluoride onto carbogenic frameworks,” says David W. C. MacMillan, a professor of chemistry at Princeton. “The work that is coming out of Abby’s lab is a direct solution to this problem.” A second area of research at Doyle’s lab is the use of iminium and oxonium substrates in enantioselective coupling reactions. “Abby’s transformation is now being used extensively” by several pharmaceutical companies, MacMillan says, even as additional papers are in press from the group. Doyle says the reason for her success is that she had several encouraging mentors early on, including M. Christina White, who was a postdoctoral researcher at Harvard and is now a professor of chemistry at the University of Illinois, Urbana-Champaign. “Every place I’ve been I’ve had a great group of people supporting me,” Doyle says. DENISE APPLEWHITE
research work at Johnson Matthey.” Catalysis, he believes, is one of the most critical areas of chemistry. “Catalysis is the future of chemical technology because reduction of waste, sustainability, and greener processes are the way forward.” ACS is hosting a symposium in Colacot’s honor on “New Trends in CrossCoupling Catalysis for Industry & Academia.” It will feature 13 international speakers including 2010 Chemistry Nobel Laureate Ei-ichi Negishi. Colacot will present his award address before the Division of Business Development & Management and the Division of Industrial & Engineering Chemistry.—JEAN-FRANÇOIS TREMBLAY COURTESY OF THOMAS J. COLACOT
“He is an academician in industrial clothing,” says Bruce H. Lipshutz, a professor of chemistry at the University of California, Santa Barbara. Catalysts developed by Colacot allowed Lipshutz’s group to develop several crosscoupling reactions in water, including unexpected Negishi type couplings using water-sensitive organozinc reagents, generated in situ. They are now implemented in the discovery programs of major drug companies. Lipshutz credits Colacot’s seminal contributions and assistance for enabling him and his group to win a Presi- Colacot dential Green Chemistry Challenge Award in 2011. Colacot’s status as a world-renowned scientist is evidenced by his coauthorship of an acclaimed review published recently in Angewandte Chemie International Edition that traced the history of the three 2010 Nobel Prize winners who had discovered cross-coupling chemistry, Lipshutz notes. In addition, he recently edited a Royal Society of Chemistry (RSC) book entitled “New Trends in Cross-Coupling: Theory and Applications.” Colacot joined Johnson Matthey as a development associate in 1995 and advanced until he became global homogeneous catalysis R&D head in 2006. A native of India, Colacot earned his Ph.D. in chemistry at the Indian Institute of Technology Madras in 1989. He holds an M.B.A. from Pennsylvania State University and is a recipient of the 2012 RSC Applied Catalysis Award. He is also an RSC Fellow. Many academic researchers are wary of industrial careers, but Colacot finds his work at Johnson Matthey highly stimulating. “I was always interested in carrying out research geared toward the advancement of society,” he says. And it was his employer that got him started with catalysts. “I began to explore this area of catalysis accidently when I was hired at Johnson Matthey to do process chemistry,” he recalls. “I combined the phosphine and arsine synthesis experiences that I gained from my research at the Indian Institute of Technology and the University of Alabama, Birmingham, and my exposure to catalysis while I was a researcher at SMU/AMOCO-ATP, to start the catalysis
Sponsored by the Ronald Breslow Award Endowment For the past two decades, Eric T. Kool has designed novel analogs of DNA bases. When he started, biochemistry textbooks explained that DNA’s key feature was the hydrogen bonding between its bases. This so-called Watson-Crick base pairing, the conventional wisdom said, helped stabilize DNA helices and allowed enzymes to accurately replicate and repair a cell’s genome. But it turns out there’s more to the story. Over the past two decades, Kool’s group has synthesized and Kool tested myriad functional DNA bases of varying shapes, sizes, and properties. This work has shown that DNA helices and cellular enzymes can tolerate significant deviations from the norm, even the removal of those signature hydrogen bonds. “Kool’s discovery that DNA helix formation and replication can function without canonical Watson-Crick base pairing has transformed our thinking about DNA structure and function,” says biochemist Paul A. Wender of Stanford University. Kool, who is also at Stanford, first developed noncanonical DNA bases that were nonpolar versions of the natural ones, maintaining the sizes and shapes but removing hydrogen-bond accepting and donating groups. For example, he took the pyrimidine base thymine and replaced its two carbonyl bonds with C–F bonds and its N–H bond with a C–H. In 1997, Kool reported that DNA polymerases readily incorporated the resulting analog, difluorotoluene,
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Hilda M. Daubert Professor of Chemistry. Kool will present his award address before the Division of Organic Chemistry.— MICHAEL TORRICE
JOEL HENRY HILDEBRAND AWARD IN THE THEORETICAL & EXPERIMENTAL CHEMISTRY OF LIQUIDS Sponsored by ExxonMobil Research & Engineering Mark Maroncelli was first inspired to study solvation dynamics by a maverick professor with whom he took a tutorial on elementary statistical mechanics while an undergraduate student at Williams College. During this tutorial, “I learned that there was a lot of activity directed at understanding the fundamentals of liquids,” Maroncelli says. “And for some reason, I got jazzed on the topic.” Maroncelli lost track of this professor. On the other hand, he remained enthusiastic about the study of the chemistry of liquids, making a uniquely long-term commitment to the field. Maroncelli received his Ph.D. in chemistry from the University of California, Berkeley, in 1983. But his focus on the chemistry of liquids began when he was a postdoctoral student at the University of Chicago, where he worked for Graham Fleming, a pioneer in the field and previous Hildebrand Award recipient. He began his academic career as a chemistry professor at Pennsylvania State University in 1987. Maroncelli’s laboratory at Penn State has made pioneering contributions to the understanding of solvation, especially in the area of solvation dynamics or the mechanisms by which the nonequilibrium configuration of solvent molecules around excited-state reactants and newly formed products relaxes to lower energy states. Maroncelli’s research has also achieved key insights into electron- and proton-transfer reactions. Among his 113 peerreviewed papers is a landmark study titled “Subpicosecond Measurements of Polar Solvation Dynamics: DEPARTMENT OF CHEMISTRY/PENN STATE
RONALD BRESLOW AWARD FOR ACHIEVEMENT IN BIOMIMETIC CHEMISTRY
selectively pairing it with thymine’s natural partner even though it couldn’t form the proper hydrogen bonds. The interesting properties of these nonpolar analogs fueled Kool’s group to see how far they could push DNA base pairing. “Once the genie was out of the bottle, we started to make bigger and bigger modifications to DNA bases,” Kool says. To date, his group has synthesized and characterized several dozen novel bases. In 2003, Kool’s group reported xDNA, or expanded DNA. These stretched bases retain the natural hydrogen-bond accepting and donating groups but have an extra benzene ring. Each xDNA pairs with the complementary natural DNA base, forming helices with structural properties similar to natural DNA, albeit one benzene ring wider. Polymerases in bacteria can recognize and copy xDNA sequences. Studying these DNA base analogs has led Kool’s group to a better understanding of how cellular enzymes determine the proper base at each position in a helix. They found that when DNA replicating enzymes pair up bases, the proteins care more about shape than about hydrogen bonding. Also, repair enzymes seem to detect DNA lesions by looking for specific shapes of DNA bases that have been chemically altered. Because of the biochemical insights obtained with these molecules, Wender calls Kool’s unnatural bases, in particular the nonpolar analogs, some of the most important biomimetic molecules ever made. Kool, 54, earned a bachelor’s degree in chemistry from Miami University in 1982, followed by a doctorate in organic chemistry from Columbia University in 1988. From 1988 to 1990, he was a postdoctoral fellow at California Institute of Technology. He then joined the chemistry department at the University of Rochester, where he became a full professor in 1997. Two years later, Kool moved to Stanford, where he now serves as the George A. & Maroncelli HOLLIS KOOL
Now she has turned her attention to mentoring chemists in her own lab. Her research group includes 13 graduate students and three postdoctoral fellows, as well as undergraduate researchers. Doyle will present her award address before the Division of Organic Chemistry.—MELODY BOMGARDNER
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is really fantastic at what he does because he gets a terrier-like grip on the details and does not let them go.” “What I think I am best at is hitting something until I think I understand it,” Maroncelli says. “I’m not good at innovating or doing something totally novel, but when I get into a problem, I like to do as much as I can do to understand it as deeply as I can. If I have made any mark, that is the reason.” Maroncelli, who is 57, will present his award address before the Division of Physical Chemistry.—RICK MULLIN
E. V. MURPHREE AWARD IN INDUSTRIAL & ENGINEERING CHEMISTRY Sponsored by ExxonMobil Research & Engineering Eastman Chemical wouldn’t be as successful as it is without its research fellow Joseph R. Zoeller, and particularly his work beginning in the 1980s investigating, developing, and improving methyl acetate carbonylation chemistry. That’s according to Shawn M. Dougherty, Eastman’s chemistry research lab group leader; Gregory W. Nelson, retired Eastman chief technology officer; and Kevin J. Edgar, professor of biomaterials and bioprocessing for Virginia Tech. Zoeller, 61, was a key member of a team that developed a methyl acetate carbonylation process for making industrial quantities of acetic anhydride using rhodium chloride in the presence of lithium iodide as the catalyst. “It is difficult to appreciate now what a daring innovation the Eastman acetic anhydride process was,” Edgar states. Zoeller’s deep Zoeller mechanistic work enabled greatly improved catalyst recovery and process efficiency and reduced downtime in methyl acetate carbonylation, Edgar adds. Acetic anhydride is a reagent with a broad range of applications from coatings to wood preservation, bakery additives, starch modifiers, and even sweeteners. Zoeller attributes part of his success to his ability to consider an industrial plant as a whole system, a skill he learned CEN.ACS.ORG
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when studying total synthesis as an organic chemist. Another important part of Zoeller’s approach is his first-rate mechanistic work for enhancing the understanding of the most important catalytic processes and then applying that understanding, Edgar says. Zoeller’s impact at Eastman is as long as it is distinguished: He has been donning Eastman lab goggles in Kingsport, Tenn., ever since he finished his Ph.D. in organic chemistry at Virginia Tech in 1981. During his more than 30 years at Eastman, Zoeller has contributed to the development of a broad range of chemical products and polymer intermediates. He has been granted 62 U.S. patents with a further nine patents pending and has published 22 scientific papers in journals or serial publications. Among other fields of chemistry, he is keen to investigate what happens in the first few layers of molecules of dissimilar surfaces. “I am fascinated by what we are going to learn to do with surface and interfacial chemistry,” he says. Zoeller knew he was going to be a scientist even before he received his first microscope at the age of seven and a Gilbert chemistry set when he was eight. But until he was 15, he was convinced he would be a biologist. Then, at Farmingdale Senior High School in New York state, he encountered chemistry teacher Lousetta Turner. Rather than answer Zoeller’s questions, Turner encouraged him to discover the answers himself by opening up the lab for him every day after school hours. “Unencumbered, hands-on access to a chemistry lab was an addictive experience and sealed my future,” he says. Zoeller’s importance to Eastman doesn’t end with chemistry. He also mentors and teaches incoming Eastman staffers. “Joe’s boundless energy and dedication to the field of chemistry serves as a great example,” Dougherty states. Edgar, Nelson, and Dougherty also consider that there is far more to Zoeller than excellence in chemistry. As Edgar states, “Zoeller is a brilliant, hardworking scientist, but his character is even more stellar.” Zoeller will present his award address before the Division of Industrial & Engineering Chemistry.—ALEX SCOTT EASTMAN CHEMICAL
Coumarin 153 Revisited” (J. Phys. Chem. 1995, DOI: 10.1021/j100048a004). “That paper has been cited well over 1,000 times now,” says Edward Castner Jr., professor of chemistry and chemical biology at Rutgers University, who met and worked with Maroncelli when Castner was a grad student at the University of Chicago. “But he didn’t just let that one ride.” Castner points to a new study published this past year by Maroncelli and Nikolaus P. Ernsting, chemistry professor at Humboldt University of Berlin, that investigates ionic liquid solvents. The paper, “Solvation Dynamics in a Prototypical Ionic Liquid and Dipolar Aprotic Liquid Mixture” (J. Phys. Chem. B 2014, DOI: 10.1021/jp412086t), is a second touchstone in the field, according to Castner. Castner notes that experimentation in solvation dynamics is under way in many laboratories, including his own. “But Mark has been key in doing not only the seminal experiments, but also the theoretical and computational chemistry work to go along with it,” says Castner, who characterizes Maroncelli as a traditional scholar. “Mark
