Synthesis, structure and mechanofluorochromic properties of phenothiazine-S-oxide and phenothiazine-S,S-dioxide derivatives.

Spectrochim Acta A Mol Biomol Spectrosc

Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, PR China. Electronic address:

Published: May 2023


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Article Abstract

In this work, two novel luminescent molecules containing distorted phenothiazine-S-oxide and phenothiazine-S,S dioxide skeletons were synthesized by oxidation reactions using different oxidants (m-chloroperoxybenzoic acid, acetic acid /hydrogen peroxide). The target compounds were all confirmed by H NMR, C NMR and EI-MS. Combined with the results of UV-vis absorption spectra and fluorescence emission spectra, we found that the different oxidation states of S-atom, from sulfide (+2) to sulfoxide (+4) and sulfone (+6), led to the blue, yellow-green and yellowish fluorescence of these compounds in the solid states. Subsequent studies showed that the molecule containing the phenothiazine-S-oxide skeleton exhibited obvious solvatochromism, and the increase of solvent polarity induced a red-shift in the emission wavelength. Moreover, this molecule also exhibited a rare self-recovery mechanochromatic behavior. In addition, these properties were further confirmed by theoretical calculations and X-ray single-crystal diffraction analysis.

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http://dx.doi.org/10.1016/j.saa.2023.122427DOI Listing

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