Journal
TETRAHEDRON
Volume 66, Issue 36, Pages 7268-7271Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.07.018
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Funding
- Ministry of Education, Science, Sports and Culture of Japan [19350094]
- Japan Science and Technology Agency (JST)
- Japan Securities Scholarship Foundation
- Grants-in-Aid for Scientific Research [19350094] Funding Source: KAKEN
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This paper reports that mechanofluorochromism is found for a series of benzofuro[2,3-c]oxazolo[4,5-a] carbazole-type fluorophores (1a-5a) with different p-substituted phenyl groups as acceptor and dibutylamino groups as donor. Grinding of as-recrystallized dyes 1a-3a with strong electron-accepting group induces a fluorescent color change with an enhanced quantum yield and the fluorescent color is recovered by heating or exposure to solvent vapor. On the basis of experimental results and semi-empirical molecular orbital calculations (AM1 and INDO/S), we clarified that the mechanofluorochromism is attributed to a reversible switching between crystalline and amorphous states with changes of dipole-dipole interaction and intermolecular pi-pi interaction by changes of the densities of the solids before and after grinding. (C) 2010 Elsevier Ltd. All rights reserved.
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