Adaptive chirality of achiral tetraphenylethene-based tetracationic cyclophanes with dual responses of fluorescence and circular dichroism in water

Two tetraphenylethene-based tetracationic cyclophanes 1 and 2 were synthesized via a one-step S N 2 reaction without using any template. Based on the fluorescence and rotational conformation of the tetraphenylethene units, these water-soluble cyclophanes exhibited adaptive chirality with dual respon...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2021-03, Vol.57 (25), p.3135-3138
Main Authors: Zhang, Haiyang, Cheng, Lin, Nian, Hao, Du, Jiang, Chen, Tao, Cao, Liping
Format: Article
Language:English
Subjects:
Chirality
Crystallography
Dichroism
Fluorescence
Format
NMR
Nuclear magnetic resonance
Nucleotides
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Summary:Two tetraphenylethene-based tetracationic cyclophanes 1 and 2 were synthesized via a one-step S N 2 reaction without using any template. Based on the fluorescence and rotational conformation of the tetraphenylethene units, these water-soluble cyclophanes exhibited adaptive chirality with dual responses of turn-on fluorescence and induced circular dichroism when combined with nucleotides and DNA in water. Tetraphenylethene-based tetracationic cyclophanes exhibited adaptive chirality with fluorescence enhancement or/and induced CD when combined with ATP and DNA via hydrophobic effects and electrostatic interactions in water.
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc00303h