We thank Mr. M. Morimoto and K. Yamakawa of Perkin Elmer Japan Co., Ltd. Osaka Branch Office for the use of Perkin Elmer Spectrum Spotlight 300. This work was supported by Sumitomo Foundation, and a Grant-in-Aid for Scientific Research (C) No. 12640567 from the Ministry of Education, Science, Sports, and Culture.
Synthesis of Novel Photochromic Films by Oxidation Polymerization of Diarylethenes Containing Phenol Groups†
Article first published online: 7 OCT 2003
Copyright © 2003 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Advanced Functional Materials
Volume 13, Issue 10, pages 755–762, October, 2003
How to Cite
Uchida, K., Takata, A., Saito, M., Murakami, A., Nakamura, S. and Irie, M. (2003), Synthesis of Novel Photochromic Films by Oxidation Polymerization of Diarylethenes Containing Phenol Groups. Adv. Funct. Mater., 13: 755–762. doi: 10.1002/adfm.200304369
- Issue published online: 7 OCT 2003
- Article first published online: 7 OCT 2003
- Manuscript Accepted: 13 MAY 2003
- Manuscript Received: 7 MAR 2003
- Non-destructive readout;
- Photochromic materials
We report the synthesis of some diarylethene derivatives attached to phenol moieties, which show remarkable photochromic reactions. A dithienylethene group attached to the o-phenol moiety (1,2-bis[2,4-dimethyl-5-(o-hydroxyphenyl)-3-thienyl]hexafluorocyclopentene) was polymerized according to Hay's method; the resulting film was insoluble to any solvents, and showed no absorption band attributable OH group in its IR spectrum. Isomeric dithienylethenes attached to m- and p-phenol moieties did not form films under the same oxidation conditions, but instead formed films by copolymerization with 4,4′-dihydroxyphenyl ether. Although the homopolymer film and copolymer films showed reversible photochromic reactions by alternate irradiation with UV and visible light, the coloration was not remarkable. Polymerization of closed-ring isomers of the dithienylethenes did not give pre-polymers and instead decomposed, while the closed-ring isomer of a bisbenzothienylethene derivative attached to the o-phenol moiety (1,2-bis[2-methyl-6-(o-hydroxyphenyl)-1-benzothiophen-3-yl]hexafluorocyclopentene) formed a polymer film by the same procedure. This polymer film showed a remarkable photochromic reaction, indicating the photo-reactive conformation was fixed in polymer matrix, and X-ray diffraction measurements show that the film is in the amorphous phase. The photochromic reaction can also be monitored by IR spectroscopy, making it applicable for non-destructive read-out recording films.