Arene-perfluoroarene interaction induced chiroptical inversion and precise ee% detection of chiral acids in a benzimidazole-involved ternary coassembly
Flexible regulation of chirality and handedness of chiral functional materials and quantitative sensing of natural chiral compounds remains a considerable challenge. Herein, an achiral fluorescent 1-pyrenecarboxylic acid-benzimidazole derivative ( PBI ) was synthesized and its chiroptical properties...
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Published in | Nanoscale Vol. 14; no. 5; pp. 1779 - 1786 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
England
Royal Society of Chemistry
03.02.2022
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Subjects | |
Online Access | Get full text |
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Summary: | Flexible regulation of chirality and handedness of chiral functional materials and quantitative sensing of natural chiral compounds remains a considerable challenge. Herein, an achiral fluorescent 1-pyrenecarboxylic acid-benzimidazole derivative (
PBI
) was synthesized and its chiroptical properties upon coassembly with chiral acids (
TA
and
MA
) and octafluoronaphthalene (
OFN
) through hydrogen bonds between benzimidazole and chiral acids as well as an arene-perfluoroarene (AP) interaction between a pyrene moiety and
OFN
were systemically studied. The binary assemblies of
PBI/TA
and
PBI/MA
displayed opposite chiroptical properties including circular dichroism (CD) and circularly polarized luminescence (CPL) signals. Interestingly, the handedness of CPL was further inverted in ternary assemblies due to the synergistic effect of the AP interaction and hydrogen bonds. Besides, the highly accurate chiral sensing of chiral acids
via
binary assemblies was successfully achieved with a high correlation coefficient. This work provides a simple method for regulating the handedness of chiroptical active materials and quantitative sensing of chiral acids through orthogonal multiple component coassemblies.
A simple method was developed for regulating the handedness of chiroptical active materials and quantitative sensing of chiral acids through orthogonal multiple component coassemblies. |
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Bibliography: | 10.1039/d1nr06254a Electronic supplementary information (ESI) available. See DOI ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 2040-3364 2040-3372 |
DOI: | 10.1039/d1nr06254a |