Issue 6, 2017

Benzothiazoles-substituted tetraphenylethylenes: synthesis, structure, aggregation-induced emission and biological studies

Abstract

New tetraphenylethylene (TPE) bearing benzothiazoles at the ortho-position to OH and OCH3 groups, 1a and 1b, respectively, were prepared. Benzothiazole tetraphenylethylenes 1a/1b were synthesized by the acid-catalysed condensation reaction of an appropriate di-aldehyde, such as 5,5′-(2,2-diphenylethylene-1,1-diyl)bis(2-hydroxybenzaldehyde) 2a or 5,5′-(2,2-diphenylethylene-1,1-diyl)bis(2-methoxybenzaldehyde) 2b, with 2-aminothiophenol. Compound 1a exhibited an excited state intramolecular proton transfer (ESIPT) phenomenon. The photophysical properties of compounds 1a/1b in solution and aggregated form, along with their structure–property relationships, were comparatively investigated. The study showed that the substituent groups on TPE at the ortho position to benzothiazole have a great influence on the electronic structure, molecular packing, and aggregation-induced emission properties. Moreover, the cell viability studies by MTT assay and fluorescence cell imaging experiments proved the low-toxicity of 1a and that it can be used as a potential contrasting agent in cell imaging studies.

Graphical abstract: Benzothiazoles-substituted tetraphenylethylenes: synthesis, structure, aggregation-induced emission and biological studies

Supplementary files

Article information

Article type
Research Article
Submitted
22 Dec 2016
Accepted
17 Jan 2017
First published
18 Jan 2017

Mater. Chem. Front., 2017,1, 1207-1216

Benzothiazoles-substituted tetraphenylethylenes: synthesis, structure, aggregation-induced emission and biological studies

K. Keshav, M. K. Kumawat, R. Srivastava and M. Ravikanth, Mater. Chem. Front., 2017, 1, 1207 DOI: 10.1039/C6QM00374E

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