Issue 64, 2017

Chiral and non-conjugated fluorescent salen ligands: AIE, anion probes, chiral recognition of unprotected amino acids, and cell imaging applications

Abstract

Natural products are usually non-conjugated and chiral, but organic luminescent materials are commonly polycyclic aromatic molecules with extended π-conjugation. In the present work, we combine with the advantages of non-conjugation and chirality to prepare a series of novel and simple salen ligands (41 samples), which have a non-conjugated and chiral (S,S) and (R,R) cyclohexane or 1,2-diphenylethane bridge but display strong blue, green, and red aggregation-induced emission (AIE) with large Stokes shifts (up to 186 nm) and high fluorescence quantum yields (up to 0.35). Through hydrogen and halogen bonds, these flexible salen ligands can be used as universal anion probes and chiral receptors of unprotected amino acids (enantiomeric selectivity up to 0.11) with fluorescence quantum yields up to 0.29 and 0.27, respectively. Moreover, the effects of different chiral bridges on the molecule arrangement, AIE, and anion and chiral recognition properties are also explored, which provide unequivocal insights for the design of non-conjugated chiral and soft fluorescent materials.

Graphical abstract: Chiral and non-conjugated fluorescent salen ligands: AIE, anion probes, chiral recognition of unprotected amino acids, and cell imaging applications

Supplementary files

Article information

Article type
Paper
Submitted
27 júl. 2017
Accepted
12 ágú. 2017
First published
21 ágú. 2017
This article is Open Access
Creative Commons BY license

RSC Adv., 2017,7, 40640-40649

Chiral and non-conjugated fluorescent salen ligands: AIE, anion probes, chiral recognition of unprotected amino acids, and cell imaging applications

G. Shen, F. Gou, J. Cheng, X. Zhang, X. Zhou and H. Xiang, RSC Adv., 2017, 7, 40640 DOI: 10.1039/C7RA08267C

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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