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Special Issue in Honor of David C. Sherrington’s 60th Birthday Dave Sherrington was born in the city of Liverpool (U.K.) in 1945. He went to school there and then went on to read Chemistry at Liverpool University. In the late 1940s and early 1950s, it was generally considered self-evident that polymer science, including polymer chemistry, would play a major role in the future development of chemistry, materials, and industry. This prompted several U.K. universities to strengthen and develop their polymer activity. Liverpool University especially strengthened their polymer chemistry, first by the appointment of Cecil Bawn in the late 1940s and then later by the appointment of Clement Bamford, Harry Block, Geoff Eastmond, Tony Ledwith, Don Margerison, and Alistair North. The teaching and research in polymer chemistry had a strong industrial flavor, indeed: Bamford, Block, and Eastmond all joined directly from the Courtaulds Research Laboratory in Maidenhead.
Dave Sherrington is very much a product of the strong Liverpool polymer school. He was awarded a First Class Honors B.Sc. Degree in Chemistry in 1966 and completed his Ph.D. in 1969 on “The Reactivity of Free Ions in Vinyl Polymerization”, under the guidance of Tony Ledwith. After 2 more years as a Research Assistant, he joined the Chemistry Department at Strathclyde University, located in “downtown” Glasgow, as a Lecturer. His early interest in cationic polymerization continued, and over the next few years, about 20 papers were published on this topic. Meanwhile, he was searching for a new area to explore. In the mid-1970s, there was a small but rapidly growing interest in the application of reactive polymers in organic chemistry. Dave began to devote his skills and efforts to this area and published his first paper on this topic in 1976.1 Many more were to follow! Initially, his interests in reactive polymers were concerned mainly with polymer-supported (PS) phase-
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transfer catalysts. How did the choice of polymer affect performance? What were the best polymer supports for such catalysts? What was the appropriate hydrophiliclipophilic balance of the support? How did the catalytic activity compare with low-molecular-weight systems? In a series of more than 15 papers, Dave largely answered these questions. Over the course of such studies, he developed a deep interest in suspension polymerization and the synthesis of cross-linked polymers. This continues today. By the late 1970s, the field of PS organic reactions had developed appreciably. It was, and still is, very much an interdisciplinary field, with major contributions from both polymer science and organic chemistry, which are areas of chemistry that, at least in the U.K., do not have a long history of collaboration. At the time, notable researchers included Jean Fre´chet, Warren Ford, Georges Gelbard, Pierre Le Perchec, and Charles Pittman. Dave is easy to get along with, and he and I got together at a Moretonhampstead Meeting and decided to edit a book with the aim of pulling together, for the first time, virtually all that was known or relevant to PS organic reactions. It was published in 1980;2 however, by a few months, it was not quite the first book on the subject! Even so, for many years, it was regularly referenced in publications on PS reactions. Russian and Chinese translations soon followed. About this same time (1982), Georges Gelbard, in Lyon (France), organized the first international conference that was devoted to this topic. This was so successful, Dave and I volunteered to organize a second conference in Lancaster in 1984. Bruce Merrifield accepted an invitation to lecture and, luckily for us, between accepting our invitation and attending the conference, Merrifield was awarded the Nobel Prize. There was much excitement and celebration at the conference. This series of biannual international conferences continues today, thanks in no small part to the efforts of Spiro Alexandratos, Romuald Bogoczek, Warren Ford, Karel Jerabek, Takeo Shimidzu, the late Abraham Warshawsky, and Zhengpu Zhang, among others. The next conference will be held in 2006 in Okazaki, Japan, and is being organized by Shinichi Itsuno. Throughout, Dave has played a key role in their success, both by serving on the Advisory Panels and by lecturing. Following in the footsteps of the initial book, a second book on the preparation and application of PS species was published in 1988.3 During the later 1980s, interest in the field of PS organic reactions waned; however, since about 1990, with the advent of combinatorial chemistry, the major organic chemists and the pharmaceutical industry have also taken a keen interest in PS organic reactions and the field is once again one of great research activity and promise. Dave’s interest in suspension polymerization has led him to develop techniques for the preparation of a very wide range of functionalized beads and polymeric materials. These include beads based on styrene-divinylbenzene, methacrylate-ethylene glycol bismethacrylate, and, most noteworthy, polybenzimidazole.4 PolyHIPE monoliths were also championed and a derived composite used for “solid phase” peptide synthesis.5 He has been keen to understand, in detail, the internal structure of supports and the role this plays in their performance. To this end, he has applied a very wide variety of characterization techniques to the problem, often in cross-disciplinary collaborations.6-8 More than
a dozen papers have been published on the characterization alone of cross-linked beads or other supports. The end result has been that, for many years, Dave has been a well-recognized world expert in this area. An invited review was published in 1998.9 During the lull in interest in PS organic chemistry in the late 1980s, Dave’s interest in PS species continued, with the preparation and application of PS metalcontaining species, especially complexes of molybdenum, platinum, titanium, and palladium, as catalysts for reactions of olefins, especially epoxidation reactions. The main focus here was the support. He has published more than 40 papers on this subject. Especially noteworthy are his papers on epoxidations using: PS Mo[VI] complexes;10,11 highly efficient PS Sharpless-type oxidation catalysts;12 PS Jacobsen-type epoxidation catalysts;13,14 PS Wacker-type oxidation catalysts;15 and PS hydrosilylation catalysts.16 Another major theme involving metals has been the use of ligand-containing resins for metal-ion extraction and recovery. Resins have been described, for example, that efficiently extract copper salts17-19 Work on these and other ion-exchange resins20 brought Dave into frequent contact with Fred Helfferich and probably led to him becoming the Editor of Reactive and Functional Polymers for several years. Dave has always had a major interest in industry and industrial processes, and, from 1984 to 1987, he was seconded from Strathclyde to Unilever Research, in Port Sunlight, finishing there as the Polymer Science Area Head. Just about this time, he made novel contributions to the chemistry of surfactants.21,22 A current and growing area of interest is the synthesis of branched polymers using vinyl polymerization. Dave’s novel approach promises to make such polymers readily available on a large scale.23,24 Dave was promoted to Professor of Polymer Chemistry at Strathclyde in 1987. His enthusiasm for research and a keen interest in his students has resulted in several of them now being lecturers or professors in the U.K., France, and Egypt. Dave’s research has been supported by a large number of industrial companies, the U.K. Research Councils, and the European Union schemes. His work has been recognized by his election to the Royal Society of Edinburgh in 1990, the award of a D.Sc. degree by Liverpool University in 1992, the award of the Royal Society of Chemistry Beilby Medal and Lectureship in 1993, and the award of the Royal Society of Chemistry/ Society of Chemical Industry Macro Group Silver Medal and Lectureship in 2000. He has given innumerable plenary or other invited lectures at international conferences and industrial research laboratories. To date, he has more than 300 publications, including numerous authoritative reviews and 17 patents. Dave has supported the scientific community in many other ways. For example, he has served on various Science and Engineering Research Council (the major U.K. government granting agency) committees, as well as the “High Polymer Research Group” Committee (which organizes the well-known Moretonhampstead/ Shrigley Hall conferences in the U.K.), and, in collaboration with David Bergbreiter, he recently chaired a Gordon Conference on “Facilitated Chemical Synthesis”. Throughout his career, he has been enthusiastically supported by his wife Valerie, who is also from Liver-
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pool. They married in 1972. His hobbies include salmon fishing, mainly from Scottish lochs, but also from rivers and lakes abroad. If you have time, he will tell you in detail about some of the huge salmon he (and Val) have caught in Alaska. As big as a human being I believe! This issue is to commemorate Dave’s 60th birthday: he, of course, has not retired! In the U.K. system, this means he has at least another five years to entertain us with his excellent lectures and publications. I am sure we all look forward to hearing and/or reading these and that we all wish him and Val all the best for the future. Literature Cited (1) Sherrington, D. C.; Craig, D. J.; Dalgleish, J.; Domin, G.; Taylor, J. Highly Cross-linked Polymeric Reagents. Polymersupported Phosphines and their use in the Conversion of Alcohols to Chloroalkanes. Eur. Polym. J. 1976, 13, 73. (2) Hodge, P., Sherrington, D. C., Eds. Polymer-Supported Reactions in Organic Synthesis; Wiley: Chichester, U.K., 1980. (3) Sherrington, D. C., Hodge, P., Eds. Syntheses and Separations Using Functional Polymers; Wiley: Chichester, U.K., 1988. (4) Brock, T.; Sherrington, D. C. Preparation of Spherical Polybenzimidazole Particulates Using a Nonaqueous Suspension Methodology. Polymer 1992, 33, 1773. (5) Sherrington, D. C.; Small, P. W. Design and Application of a New Rigid Support for High Efficiency Continuous-Flow Peptide Synthesis. J. Chem. Soc., Chem. Commun. 1989, 21, 1589. (6) See, for example: Hainey, P.; Huxham, I. M.; Rowatt, B.; Sherrington, D. C.; Tetley, L. Synthesis and Ultrastructural Studies of Styrene-Divinylbenzene PolyHIPE. Macromolecules 1991, 24, 117. (7) See, for example: Huxham, I. M.; Rowatt, B.; Sherrington, D. C.; Tetley, L. Molecular Architectural Changes in Hydrated Macroporous Styrene-Divinylbenzene Resin Sorbents Revealed by Transmission Electron Microscopy Using Image Analysis. Polymer 1992, 33, 2768. (8) See, for example: Law, R. V.; Sherrington, D. C.; Snape, C. E.; Ando, I.; Korosu, H. Solid State 13C MAS NMR Studies of Hypercross-linked Polystyrene Resins. Macromolecules 1996, 29, 6284. (9) Sherrington, D. C. Preparation, Structure and Morphology of Polymer Supports. J. Chem. Soc., Chem. Commun. 1998, 2275. (10) Miller, M. M.; Sherrington, D. C. Alkene Epoxidations Catalysed by Mo[VI] Supported on Imidazole-Containing Polymers. III. Epoxidation of Oct-1-ene and Propene. J. Chem. Soc., Perkin Trans. 2 1994, 2091. (11) Leinonen, S.; Sherrington, D. C.; Sneddon, A.; McLouglin, D.; Corker, J.; Canevali, C.; Morazzoni, F.; van Albada, G.; Reedijk, J.; Spratt, S. B. D. Molecular Structural and Morphological Characterisation of Polymer-supported Mo[VI] Alkene Epoxidation Catalysts. J. Catal. 1999, 183, 251.
(12) Kaarjalainen, J. K.; Hormi, C. E. O.; Sherrington, D. C. Highly Efficient Heterogeneous Sharpless Alkene Epoxidation Catalysts. Tetrahedron Asymm. 1998, 9, 1563. (13) Canali, L.; Cowan, E.; Deleuze, H.; Gibson C. L.; Sherrington, D. C. Remarkable Matrix Effect in Polymer-Supported Jacobsen’s Alkene Epoxidation Catalyst. J. Chem. Soc., Chem. Commun. 1998, 2561. (14) Canali, L.; Cowan, E.; Deleuze, H.; Gibson, C. L.; Sherrington, D. C. Polystyrene and Polymethacrylate - resin. Supported Jacobsen’s Alkene Epoxidation Catalyst. J. Chem. Soc., Perkin Trans. 1 2000, 2055. (15) Tang, H. G.; Sherrington, D. C. Polymer-supported Pd(II) Wacker-type Catalysts. II. Application in the Oxidation of Dec-1ene. J. Catal. 1993, 142, 540. (16) Drake, R.; Sherrington, D. C.; Thomson, S. J. High Surface Area Polystyrene Resin Supported Pt Catalysts in Room Temperature, Solventless, Octene Hydrosilylation Using Methyldichlorosilane. J. Chem. Soc., Perkin Trans. 1 2002, 1523. (17) Lindsay, D.; Sherrington, D. C.; Greig, J. A.; Hancock, R. Novel Chelating Resins with Remarkably High Selectivity for Cu(II) Over Zn(II) Ions. J. Chem. Soc., Chem. Commun. 1987, 1270. (18) Lindsay, D.; Sherrington, D. C.; Greig, J. A.; Hancock, R. Copper-Selective Chelating Resins. II. Column Extractions. React. Polym. 1990, 12, 75. (19) Verweij, P. D.; Driessen, W. L.; J. Reedijk, J.; Rowatt, B.; Sherrington, D. C. Selective and Rapid Up-take of Cu(II) by a Novel Chelating Resin Containing Imidazole Groups. React. Polym. 1990, 13, 83. (20) Ottens, M.; Leene, G.; Beenackers, A. A. C. M.; Cameron, N. R.; Sherrington, D. C. PolyHIPE: A New Polymeric Support for Heterogeneous Catalytic Reactions. Kinetics of Hydration of Cyclohexene in a 2 and 3 Phase System over a Strongly Acidic Sulfonated PolyHIPE. Ind. Eng. Chem. Res. 2000, 39, 259. (21) Hamid, S. M.; Sherrington, D. C. Polymerised Micelless Fact or Fancy? J. Chem. Soc., Chem. Commun. 1986, 936. (22) Dunkin, I. R.; Gittinger, A.; Sherrington, D. C.; Whittaker, P. Synthesis, Characterisation and Application of Azo-containing Photodestructible Surfactants. J. Chem. Soc., Perkin Trans. 2 1996, 1837. (23) Isaure, F.; Cormack, P. A. G.; Sherrington, D. C. Synthesis of Branched Poly (methyl methacrylate)s: Effect of the Branching Comonomer Structure. Macromolecules 2004, 37, 2096. (24) Isaure, F.; Cormack, P. A. G.; Graham, S.; Sherrington, D. C.; Armes, S. P.; Bu¨tu¨n, V. Synthesis of Branched Poly(methyl methacrylate)s via Controlled/Living Polymerisations Exploiting EGDMA as Branching Agent. Chem. Commun. 2004, 1138.
Philip Hodge Department of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, United Kingdom IE058067O
