A New Class of Chiroptical Molecular Switches Based on the Redox-Induced Conformational Changes

Abstract

A series of optically active bis(catecholketal)s 1-3 were prepared, and their chiroptical properties were investigated experimentally and theoretically, demonstrating that they undergo conformational changes upon 1-e(-) oxidation and can be used as redox-responsive chiroptical molecular switches.

Intense redox-driven chiroptical switching with a 580 mV hysteresis actuated through reversible dimerization of an azoniahelicene

“…1B). [29][30][31][32][33][34] Here, we report a new approach based on the intermolecular dimerization 35 of a pyridinium helicene that achieves strong, reversible chiroptical redox switching with a prominent 4500 mV hysteresis (see Fig. 1C and 2).…”

Chiroptical inversion of a planar chiral redox-switchable rotaxane

“…Nevertheless, no TTF derivative is reported that shows a sign reversal in the maximum of an ECD spectrum without a shi in the wavelength. Apart from TTF derivatives, chiroptical switching via a redox process can be achieved with catechol, 65 viologen, 66 and tetraarylethylene 67 building blocks. Intense switching with a sign reversal was also observed for a viologentype dicationic helquat.…”

Redox-Dependent Conformational Switching of Diphenylacetylenes

“…The most well known of these involve the use of redox active catenanes, [5][6][7][8] metal coordination compounds, [9][10][11][12][13][14][15] rotaxanes, [11,12,14,[16][17][18][19][20][21][22] π-systems, [23][24][25][26][27][28] and crowded alkenes [29]. These systems are finding increasing application in solid-state electronic devices.…”