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Visible and near-infrared chiroptical gels containing electrochromic anthraquinone imide groups

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Abstract

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 to π*-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.

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Authors and Affiliations

  1. Beijing National Laboratory for Molecular Sciences, Key Laboratory of Polymer Chemistry and Physics of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871, China

    Jia Zheng, Yi-jun Zheng & Xin-hua Wan  (宛新华)

  2. State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, China

    Zhi Yuan Wang

Authors
  1. Jia Zheng
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  2. Yi-jun Zheng
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  3. Xin-hua Wan  (宛新华)
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  4. Zhi Yuan Wang
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Corresponding author

Correspondence to Xin-hua Wan  (宛新华).

Additional information

This work was financially supported by the National Natural Science Foundation of China (Nos. 20674001, 20325415, 20834001) and the Research Fund for Doctoral Program of Higher Education of MOE of China (No. 20060001029).

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Zheng, J., Zheng, Yj., Wan, Xh. et al. Visible and near-infrared chiroptical gels containing electrochromic anthraquinone imide groups. Chin J Polym Sci 30, 328–336 (2012). https://doi.org/10.1007/s10118-012-1128-0

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  • DOI: https://doi.org/10.1007/s10118-012-1128-0

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