Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 10, Issue 8, Pages 1698-1702Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201500499
Keywords
dyes; pigments; luminescence; maleimides; mechanochromism; X-ray diffraction
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A mechanochromic luminescent dye based on a simple aminomaleimide skeleton was readily synthesized in a one-pot process. It exhibited an on/off mechanochromic luminescent switching property dependent on external stimuli, unlike a traditional mechanochromic color change. The green emission was turned on by grinding in a mortar and turned off by heating or treatment with dichloromethane. In the crystalline state, two molecules were stacked by cofacial - interactions, which caused concentration self-quenching. The crystalline-to-amorphous transition induced by grinding removed cofacial - stacking, which led to intensive emission. Crystallizing processes recovered the cofacial - stacking, resulting in elimination of the emission. Theoretical calculations and X-ray diffraction analyses revealed that the dye molecule was distorted in the crystalline state; thus even a mechanical stimulus caused the crystalline-to-amorphous transition.
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