Electrochiroptical Response of 2,2‘-(2,2-Diarylethenyl)binaphthyl-Type Electron Donors That Undergo Reversible C−C Bond Formation/Breaking upon Two-Electron Transfer
Authors:
- 22 July 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (17) , 6605-6610
Abstract
2,2‘-[2,2-Bis(4-dimethylaminophenyl)ethenyl]biphenyl (1) is a strong electron donor that undergoes oxidative C−C bond formation to give a stable dication rac-22+, the 9,10-dihydrophenanthrene derivative substituted with two bis(4-dimethylaminophenyl)methylium chromophores. This dication salt regenerates the starting diolefin 1 by reductive C−C bond breaking, thus realizing a new electrochromic system with high electrochemical bistability and a vivid change in color from yellow to deep blue. Similarly, the binaphthylic diolefin rac-3 and the helicene-type dication rac-42+ are interconvertible upon two-electron transfer. Both the UV−vis and CD spectra changed drastically upon electrochemical transformation between optically pure 3 and 42+, which represents a new electrochiroptical system.Keywords
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