Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 26, Pages 5047-5053Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201100676
Keywords
Photochromism; Hydrogen bonds; Cyclization; Conformation analysis; Quantum yield
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Funding
- Ministry of Education, Culture, Sports, Science and Technology (MEXT) of Japan [22350062, 21021017]
- Grants-in-Aid for Scientific Research [21021017, 22350062] Funding Source: KAKEN
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A triangular dithiazolyl-azaindole derivative has been synthesized as a highly sensitive photochromic molecule. 2,4-Dimethyl-5-phenylthiazol derivative la, and a reference compound, 5-methyl-2-phenylthiophene derivative 2a, both showed photochromism with quantum yields of 90 and 45 %, respectively, in hexane, and 90 and 35%, respectively, in methanol. In the single-crystal state, la revealed photochromic coloration. Its conformation was assigned to a photoreactive state with C-2-symmetry around the hexatriene reaction center. Temperature-dependent NMR studies and quantum chemical calculations indicated the contribution of intramolecular hydrogen-bonding between the central azaindole unit and the side thiazole units, which stabilizes the photoreactive C-2-symmetric conformation and elevates the photoreactivity in both non-polar and polar solvents.
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