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A cholesterol-based organogelator bearing an anthraquinone imide(AQI) group was synthesized and characterized.It self-assembled into chiral gels in acetonitrile at low concentrations,which displayed a combination of electrochromic and chiroptical properties.Upon electrochemical reduction at -700 mV,the gel exhibited new absorption bands at around 820 nm corresponding toπ~*-π~*(SOMO→LUMO) transitions of the radical anion of AQI and strong negative Cotton effects in the same spectral region.With further reduction at -1000 mV,a new CD band with a negative Cotton effect in the range from 500 nm to 800 nm appeared concomitant with the variation of absorption spectrum.Thus, with the use of electrochromic AQI chromophore as a switch-responsive unit and the stable gel of compound N-[3β-cholest-5 -en-3-yl N-(2-aminoethyl) carbamate]anthraquinone-2,3-dicarboxylic imide as a chiral scaffold,a redox-triggered chiroptical switch operating in visible and near-infrared region was realized.
A cholesterol-based organogelator bearing an anthraquinone imide (AQI) group was synthesized and characterized. It self-assembled into chiral gels in acetonitrile at low concentrations, which showed a combination of electrochromic and chiroptical properties. Indeed electrochemical reduction at -700 mV, the the new absorption bands at around 820 nm correspond to π ~ * -π ~ * (SOMO → LUMO) transitions of the radical anion of AQI and strong negative Cotton effects in the same spectral region. Further reduction at -1000 mV, a new CD band with a negative Cotton effect in the range from 500 nm to 800 nm concomitant with the variation of absorption spectrum. Thus, with the use of electrochromic AQI chromophore as a switch-responsive unit and the stable gel of compound N- [3β -cholest-5 -en-3-yl N- (2-aminoethyl) carbamate] anthraquinone-2,3-dicarboxylic imide as a chiral scaffold, a redox-triggered chiroptical switch operating in visible and near-infrared region was realized.