Intense Redox-Driven Chiroptical Switching with a 580 mV Hysteresis Actuated Through Reversible Dimerization of an Azoniahelicene

Jochen R. Brandt, Lubomír Pospíšil, Lucie Bednárová, Rosenildo Da Costa, Andrew J. P. White, Tadashi Mori, Filip Teplý, Matthew J. Fuchter

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Abstract

Molecular switches are of interest for the construction of molecular-scale memory devices. Switches based on redox-triggered helicenes can achieve intense chiroptical read-out values but most systems only display a small potential difference between the “ON” and the “OFF” switch states (redox hysteresis). Although a larger hysteresis could be achieved by coupling the electron transfer to a fast follow-on reaction, this approach has been limited to the intramolecular ring-opening of helicene-like systems to axially chiral biaryls. Here, we present the first intermolecular follow-on reaction: an azoniahelicene system that dimerises upon reduction, leading to intense, reversible chiroptical switching with a >500 mV hysteresis and a >300 mV “read-only” potential range. The reported helicene dimerization is supported by detailed electrochemical investigations and the comparison of experimental and calculated electronic circular dichroism (ECD) spectra.
Original languageEnglish
Article numberc7cc04903j
Pages (from-to)9059-9062
Number of pages4
JournalChemical Communications
Volume53
Issue number65
DOIs
Publication statusPublished - 17 Jul 2017

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