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5-(2,6-Bis((E)-4-(dimethylamino)styryl)-1-ethylpyridin-4(1H)-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione: aggregation-induced emission, polymorphism, mechanochromism, and thermochromism

Abstract

A new 1,4-dihydropyridine derivative containing 2,2-dimethyl-1,3-dioxane-4,6-dione and N,N-dimethylaniline was synthesized. This compound was found to exhibit aggregation-induced emission property due to highly twisted conformation and have three crystalline polymorphs, whose exhibited yellow (DHPM-y), orange (DHPM-o), and red (DHPM-r) fluorescence, respectively. The different emissions of the polymorphs were found to be mainly depended on their molecular conformations due to the weak intermolecular interactions, as revealed by the single crystal structural analysis. More importantly, these three crystalline polymorphs showed different mechanochromic phenomena under different pressure. The fluorescent color changes of DHPM-o and DHPM-r upon gentle grinding were attributed to a crystal-to-crystal transformation by altering the molecular conformations, whereas, those of DHPM-y and DHPM-o upon strong grinding were ascribed to the transformation from a crystalline state to an amorphous state. Additionally, DHPM-y and DHPM-o also displayed thermochromic properties. These results will provide useful information for obtaining intriguing multifunctional fluorescent materials by rational modification of classical luminogens.

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Publication details

The article was received on 20 Jun 2017, accepted on 04 Aug 2017 and first published on 07 Aug 2017


Article type: Paper
DOI: 10.1039/C7TC02746J
Citation: J. Mater. Chem. C, 2017, Accepted Manuscript
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    5-(2,6-Bis((E)-4-(dimethylamino)styryl)-1-ethylpyridin-4(1H)-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione: aggregation-induced emission, polymorphism, mechanochromism, and thermochromism

    Y. Zhou, L. Qian, M. Liu, X. Huang, Y. Wang, G. Wu, Y. Cheng, W. Gao and H. Wu, J. Mater. Chem. C, 2017, Accepted Manuscript , DOI: 10.1039/C7TC02746J

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