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Coumarin–tetraphenylethylene regioisomers: synthesis, photophysical and aggregation-induced emission properties

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Abstract

Coumarin–tetraphenylethylene (CTPE) regioisomers with different linkage types (single-bond, vinyl, and acetylene) and substitution positions (coumarin C5, C6, C7) were synthesized and characterized using 1H NMR, 13C NMR, and high-resolution mass spectroscopy. The effects of substitution position and conjugation in CTPEs 1–9 on absorption, fluorescence, and aggregation-induced emission enhancement were explored. Electronic absorption and emission spectra indicate that CTPEs with C7 substitution are red-shifted compared to those substituted at C5 or C6. CTPEs 1–9 form aggregates in tetrahydrofuran/water (1 : 99, v/v) and exhibit aggregation-induced emission. Nanoaggregates were characterized using scanning electron microscopy and dynamic light scattering. The structure of CTPE 1 was confirmed by single crystal X-ray diffraction analysis.

Graphical abstract: Coumarin–tetraphenylethylene regioisomers: synthesis, photophysical and aggregation-induced emission properties

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Article information


Submitted
03 Jan 2020
Accepted
08 Feb 2020
First published
10 Feb 2020

New J. Chem., 2020, Advance Article
Article type
Paper

Coumarin–tetraphenylethylene regioisomers: synthesis, photophysical and aggregation-induced emission properties

T. S. Reddy, H. Moon and M. Choi, New J. Chem., 2020, Advance Article , DOI: 10.1039/D0NJ00037J

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