Photocontrolled chiroptical switch based on the self-assembly of azobenzene-bridged bis-tryptophan enantiomers

Shuo Guo; Lin-Yi Hu; Qing-Yu Meng; Yu-Ying Zhang; Cai-Cai Zhang; Li-Juan Xing; Haitao Yu; He-Lue Sun

doi:10.1016/j.jcis.2023.12.052

Photocontrolled chiroptical switch based on the self-assembly of azobenzene-bridged bis-tryptophan enantiomers

J Colloid Interface Sci. 2024 Mar:657:913-920. doi: 10.1016/j.jcis.2023.12.052. Epub 2023 Dec 10.

Authors

Shuo Guo¹, Lin-Yi Hu¹, Qing-Yu Meng¹, Yu-Ying Zhang¹, Cai-Cai Zhang¹, Li-Juan Xing², Haitao Yu³, He-Lue Sun⁴

Affiliations

¹ College of Chemistry and Materials Science, Hebei Key Laboratory of Organic Functional Molecules, Hebei Normal University, Shijiazhuang 050024, PR China.
² College of Chemistry and Materials Science, Hebei Key Laboratory of Organic Functional Molecules, Hebei Normal University, Shijiazhuang 050024, PR China. Electronic address: xinglijuan@hebtu.edu.cn.
³ College of Chemistry and Materials Science, Hebei Key Laboratory of Organic Functional Molecules, Hebei Normal University, Shijiazhuang 050024, PR China. Electronic address: haitaoyu@hebtu.edu.cn.
⁴ College of Chemistry and Materials Science, Hebei Key Laboratory of Organic Functional Molecules, Hebei Normal University, Shijiazhuang 050024, PR China. Electronic address: heluesun@hebtu.edu.cn.

PMID: 38091914
DOI: 10.1016/j.jcis.2023.12.052

Abstract

Chirality dynamic tuning plays fundamental roles in chemistry, material science and biological system. Herein, a pair of azobenzene-bridged bis-tryptophan enantiomers (Azo-di-d/l-Trp) were designed and synthesized via simple reactions. With the fuel of glucono-δ-lactone (GdL), releasing protons during its hydrolysis, the alkaline solution of Azo-di-d/l-Trp gradually self-assembled into contrast chiral helical structures and displayed magnitude and mirror image of circular dichroism (CD) signals. While the chiral helices converted to CD silent nanoparticles when the azobenzene moiety isomerized from trans- to cis-form under UV irradiation. More importantly, this chiroptical switch, displaying reversible interconversion between chiral amplification and silent, can be smartly controlled via photoirradiation at various wavelengths.

Keywords: Chiroptical switch; Photo-responsive; Self-assembly; Soft matter; Supramolecular chemistry.