Photochromic properties of tetrakis(2-methylthien-3-yl)ethene and its tetrakis(methylthio) derivative

Tetrahedron Letters

Volumn 49, Issue 33, 2008, Pages 4972-4976

  Ikeda, Hiroshi ^a   Sakai, Azusa ^a   Kawabe, Akinori ^a   Namai, Hayato ^b   Mizuno, Kazuhiko ^a  

^a Osaka Prefecture University   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

Electrochromism; Photochromism; Reaction mechanism; Tetrathienylethene

Indexed keywords

ETHYLENE DERIVATIVE; METHYL GROUP; TETRAKIS(2 METHYLTHIEN 3 YL)ETHENE; TETRAKIS(METHYLTHIO) DERIVATIVE; TIENILIC ACID;

ARTICLE; CHEMICAL ANALYSIS; ELECTRON TRANSPORT; EXCITATION; ISOMER; PHOTOCHEMISTRY; PHOTOREACTIVITY; REACTION ANALYSIS; STRUCTURE ANALYSIS; ULTRAVIOLET IRRADIATION;

EID: 46049098326     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.05.080     Document Type: Article

References (28)

1. Ikeda H., Sakai A., Namai H., Kawabe A., and Mizuno K. Tetrahedron Lett. 48 (2007) 8338-8342
2. Matsuda K., and Irie M. J. Photochem. Photobiol., C 5 (2004) 169-182
3. Matsuda K., and Irie M. Chem. Lett. 35 (2006) 1204-1209
4. Irie M. Chem. Rev. 100 (2000) 1685-1716
5. Recently, Maurel and Belen'kii reported the synthesis and photochromic properties of tri- and tetrathienylethenes. See Ref. 4.
6. Bougdid, L.; Perrier, A.; Heynderickx, A.; Maurel, F.; Shilova, E.A.; Muostrou, C. 'Synthesis and Photochromic Properties of Tri-thienyl Substituted Ethylene: Combined Experimental and Theoretical Study'; International Symposium on Photochromism 2007, 2007, Vancouver: British Columbia, Canada.
7. Belen'kii L.I., Gromova G.P., Kolotaev A.V., Nabatov B.V., and Krayushkin M.M. Russ. Chem. Bull. Int. Ed. 54 (2005) 1208-1213
8. Gorodetsky B., and Branda N.R. Adv. Funct. Mater. 17 (2007) 786-796
9. Matsuda K., Yokojima S., Moriyama Y., Nakamura S., and Irie M. Chem. Lett. 35 (2006) 900-901
10. Moriyama Y., Matsuda K., Tanifuji N., Irie S., and Irie M. Org. Lett. 7 (2005) 3315-3318
11. Gorodetsky B., Samachetty H.D., Donkers R.L., Workentin M.S., and Branda N.R. Angew. Chem., Int. Ed. 43 (2004) 2812-2815
12. Peters A., and Branda N.R. J. Am. Chem. Soc. 125 (2003) 3404-3405
13. Peters A., and Branda N.R. Chem. Commun. (2003) 954-955
14. Suzuki T., Ohta E., Kawai H., Fujiwara K., and Fukushima T. Synlett (2007) 851-869
15. Suzuki T., Shiohara H., Monobe M., Sakimura T., Tanaka S., Yamashita Y., and Miyashi T. Angew. Chem., Int. Ed. Engl. 31 (1992) 455-458
16. -5 M) was irradiated with a 150 W Xe lamp [λ = 350 nm for UV, 450 or 490 nm for vis, band pass 20 nm] through a spectrometer equipped to a JASCO FP-6300 spectrofluorometer.
17. The relative stereochemistry of the methyl groups in 2 that would arise from the conrotately cyclization of the metastable antiparallel conformers of 1 is trans. This result is strongly suggested by PM3 calculations. Alternatively, the cis conformer 2′ is suggested to have high internal energy (ca. 40 kcal/mol) as compared with 2, which is unlikely from the point of view of the conservation of orbital symmetry theory (Woodward-Hoffmann rules){A figure is presented}.
18. It may be assumed that one of the possible photoproducts of 2a is 3a. However, this is not likely because Figures 1b and 2b demonstrate different behavior of 2a and 2b on vis irradiation.
19. 2) 289, 320, 493 nm.
20. 3 at -35 °C. For the detail, see the Supplementary data.
21. - (0.1 M) as a supporting electrolyte.
22. 1H NMR bands were reported by Uchida and Irie for a diarylethene derivative with the steric hindrance. See:. Uchida K., Nakayama Y., and Irie M. Bull. Chem. Soc. Jpn. 63 (1990) 1311-1315
23. a observed at 1.95-2.16 ppm at -35 °C are due to a pair of 2 equiv Me protons of 3b (two singlet peaks of parallel-A and -B at 1.95 and 2.00 ppm), and two nonequivalent Me protons of 3b (two singlet peaks of antiparallel, 2.15 and 2.16 ppm).
24. 17
25. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. gaussian 98, Revision A.11.4; Gaussian: Pittsburgh PA, 1998.
26. Winmopac 3.9, Fujitsu Ltd, Tokyo, Japan, 2004.
27. Irie M., Lifka T., Uchida K., Kobatake S., and Shindo Y. Chem. Commun. (1999) 747-750
28. Higashiguchi K., Matsuda K., Kobatake S., Yamada T., Kawai T., and Irie M. Bull. Chem. Soc. Jpn. 73 (2000) 2389-2394