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Synfacts 2009(7): 0739-0739  
DOI: 10.1055/s-0029-1217217
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

2 + 2 = Super-Acceptors

Contributor(s): Timothy M. Swager
M. Kivala, C. Boudon, J.-P. Gisselbrecht, B. Enko, P. Seiler, I. B. Müller, N. Langer, P. D. Jarowski, G. Gescheidt, F. Diederich*
ETH Zürich, Switzerland
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Publikationsdatum:
22. Juni 2009 (online)

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Significance

This contribution expands on previous studies by the same group for the utilization of [2+2] cycloaddition ring-opening sequences to produce high nitrile content molecules. The small steric demands and strong electron-withdrawing character (both σ and π) make nitrile groups the most important electronic withdrawing for the design of electron acceptors for nonlinear optical materials. These materials have the unusual attributes of having strong charge transfer optical transitions resulting from the donor (aromatic amine) to the cyanoalkenes.