The title heterocyclic donors undergo reversible C-C bond formation/cleavage upon electron transfer (dynamic redox behavior). The helical sense in both neutral and cationic states is interconvertible by facile ring flipping. The pi-type asymmetric center on the azepine nitrogen atom induces a significant degree of diasteromeric preference, thus endowing strong CD activity based on exciton coupling. Chiroptical properties could be modified not only by redox reactions but also by heat and protonation. The present redox pairs can serve as unprecedented three-way-input (e, H+, delta) and two-way-output (UV/Vis, CD) response systems.
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Suzuki et al. (2006) studied this question.
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