Intense Chiroptical Switching in a Dicationic Helicene-Like Derivative: Exploration of a Viologen-Type Redox Manifold of a Non-Racemic Helquat
Journal of the American Chemical Society2014Vol. 136(31), pp. 10826–10829
Citations Over TimeTop 10% of 2014 papers
Lubomı́r Pospı́šil, Lucie Bednářová, Petr Štěpánek, Petr Slavı́ček, Jan Vávra, Magdaléna Hromadová, Helena Dlouhá, Ján Tarábek, Filip Teplý
Abstract
Two-step redox switching in enantiopure helquat system [P-1](2+) ⇌ [P-1](•+) ⇌ [P-1](0) is demonstrated. The viologen-type electroactive unit embedded directly in the helical scaffold of 1 is responsible for the prominent chiroptical switching at 264 nm. This process is associated with a marked sign-reversal of Cotton effect ramping between Δε = +35 M(-1) cm(-1) for [P-1](2+) and Δε = -100 M(-1) cm(-1) for [P-1](0). This helically chiral system features the most intense chiroptical switch response documented in the field of helicenoids.
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