Swiss Federal Institute of Technology
The [2+2] cycloaddition-retro-electrocyclization (CA–RE) click reaction between donor-activated alkynes, such as anilino-substituted acetylenes, and electron-accepting olefins, such as tetracyanoethene (TCNE) and 7,7,8,8-tetracyano-p-quinodimethane (TCNQ), has enormously widened the chemical structural space for molecular and polymeric push-pull chromophores. This high-yielding, atom-economic, thermodynamically driven transformation affords soluble, stable non-planar donor-acceptor chromophores with large third-order nonlinear optics properties that have successfully been applied to the formation of silicon-organic-hybrid waveguide devices for all-optical processing. Some of the new chromophores, which also include a diversity of 6,6-dicyanopentafulvene derivatives, are "super acceptors", with the first reduction occurring at positive potentials (against ferrocene, in CH2Cl2), and form intermolecular charge-transfer complexes with metallocene donors. The broad scope of the CA–RE reaction in molecular transformations is further demonstrated in dendrimer chemistry, the formation of Aviram-Ratner-type molecular rectifyers, and in the generation of chiral, optically stable buta-1,3-dienes. It has also been successfully applied in polymer chemistry, both for side-chain postfunctionalization of polymers and formation of polymer main chains, yielding chromophoric materials for optoelectronic device applications.
Professor Diederich (b. 1952) received his diploma in 1977 and his doctoral degree (Dr. rer. nat.) in 1979 from the University of Heidelberg. Following postdoctoral studies at the University of California at Los Angeles (UCLA) from 1979 to 1981, he was a research associate at the Max-Planck-Institute for medical research in Heidelberg. After his habilitation in 1985, he joined the faculty of the Department of Chemistry and Biochemistry at UCLA as an associate professor (1985-1989) and as a full professor (1989-1992). Since April 1992, he is a professor of organic chemistry at ETH Zürich. He received the Otto Hahn Medal of the Max-Planck-Society (1979), the Dreyfus Teacher-Scholar Award (1987), the ACS Arthur C. Cope Scholar Award (1992), the Otto-Bayer-Preis für Chemie (1993), the Janssen Prize for Creativity in Organic Synthesis (2000) and the Havinga Medal (2000), the Humboldt Research Prize (2005), the Burkhard-Helferich Prize (2005), the August-Wilhelm-von-Hofmann-Denkmünze (GDCh, 2006), the ACS Ronald Breslow Award for Achievements in Biomimetic Chemistry (2007), and the Adolf-von-Baeyer-Denkmünze (GDCh, 2011), the Ernst Hellmut Vits-Preis (2014), the Prix Paul Metz (2014), and the EFMC Nauta Award for Pharmacochemistry (2016). He is a member of the Deutsche Akademie der Naturforscher Leopoldina and of the Berlin-Brandenburgische Akademie der Wissenschaften (BBAW), and the European Academy of Sciences and Arts, a foreign honorary member of the American Academy of the Arts and Sciences and of the Real Academia Española de Ciencias, and a foreign associate of the US National Academy of Sciences. Since 2012, he holds an honorary doctoral degree from the Technion (Haifa). Work in the Diederich group has been documented in more than 750 original publications.