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Synthesis and photochromic properties of 4,5-bisaryl-3(2H)-pyridazinones

Paper ID Volume ID Publish Year Pages File Format Full-Text
26377 43949 2016 7 PDF Available
Title
Synthesis and photochromic properties of 4,5-bisaryl-3(2H)-pyridazinones
Abstract

•Six novel photochromic and fluorescent bisarylpyridazinones were synthesized.•Their closed forms showed slight negative solvatochromism.•Their open forms are fluorescent while the closed forms are not.•N-methyl-(5-phenylthiazolyl)pyridazinone showed 94% conversion to the closed form.

Six novel photochromic bisarylpyridazinones containing 2,5-dimethylthiophene or 5-methyl-2-phenylthiazole unit were synthesized, and their photochromic and fluorescence properties were investigated. The bisarylpyridazinones underwent reversible color change upon irradiation with UV or visible light. The effect of solvents on the absorption spectra of the bisarylpyridazinones was investigated. The closed-ring forms of bisarylpyridazinones displayed negative solvatochromism which was attributed to the high dipolar characters of the molecule. The open-ring forms of bisarylpyridazinones showed fluorescence at 400–480 nm upon excitation at 302 nm, and the intensities of emission bands gradually decreased during the ring-closing photoreactions. Among the synthesized bisarylpyridazinones, 4,5-bis(5-methyl-2-phenylthiazol-4-yl)-2-methyl(or 2-phenyl) pyridazin-3(2H)-ones (5O and 6O) displayed rather large absorption and emission spectral change, higher quantum efficiency during the photoreaction compared to others. A high conversion ratio (94%) to the closed form was observed for 5O.

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Keywords
Photochromism; Diarylethene; Pyridazinone; Bisarylpyridazinone; Solvent effect; Fluorescence switch
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Synthesis and photochromic properties of 4,5-bisaryl-3(2H)-pyridazinones
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 314, 1 January 2016, Pages 164–170
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us