DNA‐induced circularly polarized luminescence of helicene racemates

Author:

Gan Fuwei1,Yang Peng1,Liang Juncong1,Shen Chengshuo1ORCID,Crassous Jeanne2ORCID,Qiu Huibin1ORCID

Affiliation:

1. School of Chemistry and Chemical Engineering, Zhangjiang Institute for Advanced Study, Frontiers Science Center for Transformative Molecules, State Key Laboratory of Metal Matrix Composites Shanghai Jiao Tong University Shanghai People's Republic of China

2. Institut des Sciences Chimiques de Rennes, UMR 6226, Campus de Beaulieu, CNRS‐Université de Rennes 1 Rennes Cedex France

Abstract

AbstractEnantiopure helicenes have been extensively investigated due to their outstanding chiroptical properties, while helicene racemates are considered as chiroptically silent. Here, we describe a facile method to produce circularly polarized luminescence (CPL) from helicene racemates via supramolecular association with DNA in aqueous solution. Racemic cationic helicene derivatives are immobilized in the grooves of commercially available double‐stranded right‐handed DNA, and the discrimination of left‐ and right‐handed helicenes by chiral DNA is monitored by single molecule force spectroscopy. This subsequently leads to the generation of prominent CPL with dissymmetric factor |glum| of close to 0.01, which is approximate to enantiopure helicenes. The strategy developed in this work avoids the tedious and expensive chiral resolution process and provides a distinctive insight into the fabrication of CPL‐emitting systems.

Funder

National Key Research and Development Program of China

National Natural Science Foundation of China

Science and Technology Commission of Shanghai Municipality

Publisher

Wiley

Subject

Organic Chemistry,Spectroscopy,Drug Discovery,Pharmacology,Catalysis,Analytical Chemistry

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