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Issue 21, 2017
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Polymorphism and mechanochromism of N-alkylated 1,4-dihydropyridine derivatives containing different electron-withdrawing end groups

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Abstract

Organic compounds exhibiting polymorphic and/or mechanochromic (MC) properties are promising for applications in multiple areas. However, the design strategy for such compounds is not very clear. Herein, several series of N-alkylated 1,4-dihydropyridine (DHP) derivatives incorporating different electron-withdrawing end groups were synthesized and compared. The electron-withdrawing groups were responsible for their polymorphic and MC properties. Additionally, a number of polymorphs of these DHP derivatives showed a decreasing trend as length of the alkyl chain increased, indicating that a longer alkyl chain was not conducive to formation of the polymorphs. Although differences in emissions of the polymorphs were mainly attributed to their different intermolecular interactions and molecular packing patterns, a subtle difference in the distances of their intermolecular interactions could also be a key factor in the formation of specific polymorphs. Different polymorphs of DHP derivatives could be interconverted by a simple recrystallization process with a specific solvent or through the application of pressure and vapor stimuli. Additionally, the MC properties of these DHP derivatives were ascribed to a phase transition between different crystalline states, instead of the more common transformation between crystalline and amorphous states.

Graphical abstract: Polymorphism and mechanochromism of N-alkylated 1,4-dihydropyridine derivatives containing different electron-withdrawing end groups

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Publication details

The article was received on 21 Jan 2017, accepted on 08 May 2017 and first published on 09 May 2017


Article type: Paper
DOI: 10.1039/C7TC00362E
Citation: J. Mater. Chem. C, 2017,5, 5183-5192
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    Polymorphism and mechanochromism of N-alkylated 1,4-dihydropyridine derivatives containing different electron-withdrawing end groups

    Y. Lei, Y. Zhou, L. Qian, Y. Wang, M. Liu, X. Huang, G. Wu, H. Wu, J. Ding and Y. Cheng, J. Mater. Chem. C, 2017, 5, 5183
    DOI: 10.1039/C7TC00362E

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