Issue 1, 2021, Issue in Progress

A novel donor–π–acceptor halochromic 2,6-distyrylnaphthalene chromophore: synthesis, photophysical properties and DFT studies

Abstract

In this study a new 2,6-distyryl naphthalene [2-((4-((E)-2-(6-((E)-2,4-bis(methylsulfonyl)styryl)naphthalen-2-yl)vinyl)phenyl)(ethyl)amino)ethan-1-ol; ASDSN] was synthesized successfully using Heck chemistry as the main reaction. The ASDSN compound is a donor–pi–acceptor (D–π–A) conjugated system with amino as electron donating and sulfonyl as electron withdrawing groups. The UV-vis absorption of ASDSN was observed in the range of 403–417 nm with high molar extinction coefficients (ε = 15 300–56 200 M−1 cm−1) in some different solvents. This new fluorescent 2,6-distyryl naphthalene compound emits in the yellow region of the visible spectrum (557 nm) with Stokes shifts of 5930 cm−1. ASDSN is a pH-responsive fluorescence compound that shows yellow fluorescence in neutral form and blue fluorescence in the protonated form. A white light emission (WLE) for the chromophore was observed at pH = 3.0. The ASDSN chromophore presented a satisfactory white light quantum yield (Φ) of 13% which was desirable for producing white light emitting devices. Density functional theory (DFT) and time-dependent (TD)-DFT were applied to study structural and electronic properties of the chromophore.

Graphical abstract: A novel donor–π–acceptor halochromic 2,6-distyrylnaphthalene chromophore: synthesis, photophysical properties and DFT studies

Supplementary files

Article information

Article type
Paper
Submitted
06 Oct 2020
Accepted
09 Dec 2020
First published
22 Dec 2020
This article is Open Access
Creative Commons BY license

RSC Adv., 2021,11, 168-176

A novel donor–π–acceptor halochromic 2,6-distyrylnaphthalene chromophore: synthesis, photophysical properties and DFT studies

F. Panahi, A. Mahmoodi, S. Ghodrati and F. Eshghi, RSC Adv., 2021, 11, 168 DOI: 10.1039/D0RA08508A

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