Structural tuning enables piezochromic and photochemical properties in N -aryl-β-enaminones

An efficient synthesis of -aryl-β-enaminones Et N-mediated, one-pot three-component reaction of 4-hydroxycoumarin/dimedone, β-nitrostyrene/2-(2-nitrovinyl)thiophene, and arylamine in toluene under refluxed conditions is herein presented. Some prepared compounds were found to exhibit piezochromic pro...

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Published inRSC advances Vol. 9; no. 58; pp. 34088 - 34094
Main Authors Hsieh, Wan-Chi, Manjappa, Kiran B, Yang, Ding-Yah
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 23.10.2019
The Royal Society of Chemistry
Subjects
Aromatic compounds
Chemistry
Crystallography
Morphology
Photochemical reactions
Toluene
Ultraviolet radiation
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Summary:An efficient synthesis of -aryl-β-enaminones Et N-mediated, one-pot three-component reaction of 4-hydroxycoumarin/dimedone, β-nitrostyrene/2-(2-nitrovinyl)thiophene, and arylamine in toluene under refluxed conditions is herein presented. Some prepared compounds were found to exhibit piezochromic properties. The XRD and SEM measurements of the piezochromic compound showed substantial crystal packing and morphology changes before and after grinding. Further, one prepared compound was found to be light-sensitive and can be converted to a furo[3,2- ]pyridin-2(4 )-one derivative upon UV irradiation. A plausible mechanism for this photochemical reaction was proposed.
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ISSN:2046-2069
2046-2069
DOI:10.1039/c9ra07598d