Organic Letters
Organic Letters
5 years ago

Triplet Energy and π-Conjugation Effects on Photoisomerization of Chiral N,C-Chelate Organoborons with PAH Substituents

Triplet Energy and π-Conjugation Effects on Photoisomerization of Chiral N,C-Chelate Organoborons with PAH Substituents
Andreas Lorbach, Lisa Häfele, Soren K. Mellerup, Xiang Wang, Suning Wang
Chiral, PAH substituted N,C-chelate boron compounds are systematically investigated to establish the effect of triplet energy and substitution position on their photoreactivity. They all undergo regioselective photoisomerization, forming new dark isomers with quantum efficiencies reflecting these various factors. New PAH fused 4bH-azaborepins are obtained via thermal isomerization of the dark isomers. These results further implicate a photoactive triplet state in the photoisomerization process and its utility in achieving rare PAH-fused azaborepin-like heterocycles.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01724

DOI: 10.1021/acs.orglett.7b01724

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