Journal
TETRAHEDRON LETTERS
Volume 54, Issue 39, Pages 5307-5310Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.07.094
Keywords
Photochromism; Diarylethene; Naphthalene moiety; Heteroaryl effect; Optical property
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Funding
- National Natural Science Foundation of China [21162011, 21262015]
- Project of Jiangxi Advantage Sci-Tech Innovative Team [20113BCB24023]
- Project of Jiangxi Natural Science Foundation [20114BAB203007, 20132BAB203005]
- Project of the Science Funds of Jiangxi Education Office [KJLD12035, GJJ11026, GJJ12587]
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Three new asymmetrical naphthalene-containing diarylethenes with different heteroaryl groups have been synthesized to investigate the heteroaryl effects on their properties. The three diarylethenes exhibited distinctive photochromism with good thermal stability, which may be attributed to the different heteroaryl effects. Their cycloreversion quantum yields increased in the order of 2-methylbenzofuran < 2-methylbenzothiophene < 1,2-dimethylindole, while the cyclization quantum yields exhibited a reverse trend. Compared to indole and benzothiophene, the benzofuran moiety could effectively shift the absorption maximum to a shorter wavelength and notably enhance the cyclization quantum yield and fluorescence quantum yield of the diarylethene. The results indicated that the category of heteroaryl groups played a vital role during the process of photoisomerization of naphthalene-containing diarylethene derivatives. (C) 2013 Elsevier Ltd. All rights reserved.
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