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Updated: Jul 13, 2026

Time-resolved Photophysical Characterization of Triplet-harvesting Organic Compounds at an Oxygen-free Environment Using an iCCD Camera
Published on: December 27, 2018
Experimental probe for hyperconjugative resonance contribution in stabilizing the singlet state of
Manabu Abe1, Masanori Hattori, Akinobu Takegami
1Department of Applied Chemistry, Graduate School of Engineering, Osaka University (HANDAI), Suita 565-0871, Osaka, Japan. abe@chem.eng.osaka-u.ac.jp
Abstract:
A detailed study of the regioselectivity of 1,2-oxygen migration was conducted using the unsymmetrically substituted singlet 2,2-dialkoxy-1,3-diarylcyclopentane-1,3-diyls 5. The alkoxy group selectively migrates to the electron-donating p-methoxyphenyl-substituted carbon. The regioselective migration of oxygen clearly indicates a hyperconjugative resonance structure, that is, zwitterionic characteristics, in singlet 2,2-dialkoxy-1,3-diyls. This represents the first attempt to experimentally probe the contribution of hyperconjugation to stabilizing the singlet state.
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