Isolation and x-ray structural determination of both folded and twisted conformers of bis{4H,8H-4-(dicyanomethylene)-benzo[1,2-c:4,5-c′]bis[1,2,5]thiadiazol-8- ylidene}, an overcrowded ethylene with high electron affinity

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 22, 1997, Pages 2495-2497

  Suzuki, Takanori ^a   Fukushima, Takanori ^a,b   Miyashi, Tsutomu ^b   Tsuji, Takashi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

Isomerizations; Molecular devices; Radical ions; Redox chemistry; Thermochromism

Indexed keywords

EID: 0031468304     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199724951     Document Type: Article

References (23)

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13. D. H. Evans, N. Xie, J. Am. Chem. Soc. 1983, 105, 315; D. H. Evans, R. W. Busch, ibid. 1982, 104, 5057; P. Neta, D. H. Evans, ibid. 1981, 103, 7041; B. A. Olsen, D. H. Evans, ibid. 1981, 103, 839.
14. D. H. Evans, N. Xie, J. Am. Chem. Soc. 1983, 105, 315; D. H. Evans, R. W. Busch, ibid. 1982, 104, 5057; P. Neta, D. H. Evans, ibid. 1981, 103, 7041; B. A. Olsen, D. H. Evans, ibid. 1981, 103, 839.
15. The folded isomer of bis[1,3-bis(dicyanomethylene)indan-2-ylidene] undergoes one-way isomerization to the severely twisted conformer, and X-ray analyses on both forms were successfully carried out: A. Beck, R. Gompper, K. Polborn, H.-U. Wagner, Angew. Chem. 1993, 105, 1424; Angew. Chem. Int. Ed. Engl. 1993, 32, 1352. Of the three structures of 2-(thio.xanthen-9-ylidene)-indane-1,3-dione, the folded and folded-twisted conformers were determined by X-ray but the twisted one is missing: J. J. Stezowski, P. U. Biedermann, T. Hildenbrand, J. A. Dorsch, C. J. Eckhardt, I. Agranat, J. Chem. Soc. Chem. Commun. 1993, 213.
16. The folded isomer of bis[1,3-bis(dicyanomethylene)indan-2-ylidene] undergoes one-way isomerization to the severely twisted conformer, and X-ray analyses on both forms were successfully carried out: A. Beck, R. Gompper, K. Polborn, H.-U. Wagner, Angew. Chem. 1993, 105, 1424; Angew. Chem. Int. Ed. Engl. 1993, 32, 1352. Of the three structures of 2-(thio.xanthen-9-ylidene)-indane-1,3-dione, the folded and folded-twisted conformers were determined by X-ray but the twisted one is missing: J. J. Stezowski, P. U. Biedermann, T. Hildenbrand, J. A. Dorsch, C. J. Eckhardt, I. Agranat, J. Chem. Soc. Chem. Commun. 1993, 213.
17. The folded isomer of bis[1,3-bis(dicyanomethylene)indan-2-ylidene] undergoes one-way isomerization to the severely twisted conformer, and X-ray analyses on both forms were successfully carried out: A. Beck, R. Gompper, K. Polborn, H.-U. Wagner, Angew. Chem. 1993, 105, 1424; Angew. Chem. Int. Ed. Engl. 1993, 32, 1352. Of the three structures of 2-(thio.xanthen-9-ylidene)-indane-1,3-dione, the folded and folded-twisted conformers were determined by X-ray but the twisted one is missing: J. J. Stezowski, P. U. Biedermann, T. Hildenbrand, J. A. Dorsch, C. J. Eckhardt, I. Agranat, J. Chem. Soc. Chem. Commun. 1993, 213.
18. T. Suzuki, H. Fujii, Y. Yamashita, C. Kabuto, S. Tanaka, M. Harasawa, T. Mukai, T. Miyashi, J. Am. Chem. Soc. 1992, 114, 3034.
19. 4): C 38.20, H 0.34, N 28.13; found: C 38.80, H 0.66, N 28.26.
20. -1, R = 0.061. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100324. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: int. code + (1223)336-033; e-mail: deposit@chemerys.cam.ac.uk).
21. -1, respectively. The estimated atomic charges on heterocycles in 2B (+ 0.61 on S; -0.29 on N) are marginally larger than those in 2A (+ 0.58 on S; -0.26 on N), which might be related to the preference of 2B in solution caused by effective solvation.
22. S. Yamaguchi, T. Hanafusa, T. Tanaka, M. Sawada, K. Kondo, M. Irie, H. Tatemitsu, Y. Sakata, S. Misumi, Tetrahedron Lett. 1986, 27, 2411.
23. -1, respectively.