James Flack Norris Award in Physical Organic Chemistry

Sponsored by the Northeastern Section of ACS

Ben L. Feringa, Distinguished Jacobus H. van't Hoff Professor in Molecular Sciences at the University of Groningen, the Netherlands, is honored for his outstanding work in stereochemistry, in particular for the design and synthesis of molecular motors and other nanodevices.

"Feringa is, in my view, the Netherlands' most distinguished chemical scientist and ranks among the two or three most outstanding physical organic chemists in Europe," comments Ernest L. Eliel, W. R. Kenan Jr. Professor, emeritus, at the University of North Carolina, Chapel Hill. "In the area of stereochemistry, he is arguably the foremost, and he has applied his deep knowledge of and insight into this field in a number of outstanding investigations."

Feringa pursued his undergraduate and graduate studies in chemistry at the University of Groningen, where he received his Ph.D. in 1978 for his research on asymmetric oxidations of phenols under the supervision of professor of organic chemistry Hans Wynberg. He then took up an appointment as a research chemist at the Shell Laboratories in Amsterdam. In 1984, he left Shell to become a lecturer in organic chemistry at the University of Groningen. Four years later, he succeeded Wynberg as chair of organic chemistry at Groningen. He was appointed distinguished professor at the university in 2003.

One of Feringa's most spectacular and widely cited achievements is his design and synthesis of nanomolecular machines. His group has prepared optical molecular switches in which chirality is controlled by light. The group has used the switches for optical data storage at the molecular level and to control organization in supramolecular materials. In other work, Feringa and coworkers showed that liquid-crystal films can be switched photochemically. They also prepared the first light-driven unidirectional rotary molecular motor.

Feringa's wide-ranging interests include biochemical systems. He has, for example, created a nanovalve by attaching a photochemically switchable organic compound to a channel protein such that the channel can be opened by irradiation with ultraviolet light and closed by visible light. This type of nanovalve could be used to release naturally occurring or synthetic drugs. In related work, Feringa teamed up with other researchers in Groningen to develop a low-molecular-weight hydrogel-drug system that relies on the consecutive action of two trigger mechanisms to release a drug. The gel compounds are covalently linked to the drug to form, in water, a dense network that holds the drug tightly. Lowering the pH or raising the temperature breaks the network and releases the gelator-drug complex into solution, where it is further cleaved by an enzyme to produce the drug.

Feringa has also employed the mechanistic principles of physical organic chemistry to develop new catalytic methods for synthetic organic chemistry. One of his major breakthroughs in asymmetric catalysis is his preparation of a series of novel monodentate chiral phosphoramidite ligands, which he used for the first enantioselective catalytic 1,4-addition of organometallic reagents to enones with absolute stereocontrol. He has also used the ligands for tandem conjugate addition, ring annulations, kinetic resolutions, epoxide ring openings, and cross-coupling reactions. In other work, Feringa's group has attached DNA molecules to catalytically active metal complexes and used them to catalyze enantioselective reactions.

An author of over 400 publications and 16 patents and a contributor to several books, Feringa has received many awards and honors, including the 1997 Pino gold medal of the Italian Chemical Society; the Novartis Chemistry Lectureship Award 2000-01 in recognition of outstanding contributions to natural products synthesis and the development of new synthetic methodology; the Guthikonda Award, Columbia University, 2003; the Spinoza Award (the highest Netherlands scientific award, sometimes called the "Dutch Nobel Prize"); and the Prelog gold medal for stereochemistry from the Swiss Federal Institute of Technology, Zurich, in 2005.

The award address will be presented before the Division of Organic Chemistry.—Michael Freemantle