Synthesis, crystal structure and electrochemical property of 3a,4,5,8,9,9a,10,11-Octahydro-2H,3H-1,6,7,12-tetrathiaperylene (H10TTPR)
Xiang-Feng Shao
Laboratory of Organic Solids, Center for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China
Graduate School, Chinese Academy of Sciences, Beijing 100080, China
Search for more papers by this authorChuan-Lang Zhan
Colloid and Interface Science Laboratory, Center for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China
Search for more papers by this authorCheng Wang
Laboratory of Organic Solids, Center for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China
Graduate School, Chinese Academy of Sciences, Beijing 100080, China
Search for more papers by this authorDe-Qing Zhang
Laboratory of Organic Solids, Center for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China
Search for more papers by this authorWei Xu
Laboratory of Organic Solids, Center for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China
Search for more papers by this authorCai-Ming Liu
Laboratory of Organic Solids, Center for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China
Search for more papers by this authorDao-Ben Zhu
Laboratory of Organic Solids, Center for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China
Search for more papers by this authorXiang-Feng Shao
Laboratory of Organic Solids, Center for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China
Graduate School, Chinese Academy of Sciences, Beijing 100080, China
Search for more papers by this authorChuan-Lang Zhan
Colloid and Interface Science Laboratory, Center for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China
Search for more papers by this authorCheng Wang
Laboratory of Organic Solids, Center for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China
Graduate School, Chinese Academy of Sciences, Beijing 100080, China
Search for more papers by this authorDe-Qing Zhang
Laboratory of Organic Solids, Center for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China
Search for more papers by this authorWei Xu
Laboratory of Organic Solids, Center for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China
Search for more papers by this authorCai-Ming Liu
Laboratory of Organic Solids, Center for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China
Search for more papers by this authorDao-Ben Zhu
Laboratory of Organic Solids, Center for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, China
Search for more papers by this authorAbstract
H10TTPR was prepared starting from terephthalaldehyde and characterized. Crystal structure of H10TTPR and an intermediate compound 11 were determined by X-ray diffraction analysis. A quasi-reversible redox wave at 1.15 V (vs. SCE) was observed for H10TTPR, indicating that it is a weak electron donor.
References
- 1(a) Perlstein, J. H. Angew. Chem, Int. Ed Engl. 1977, 16, 519. (b) Torrance, J. B. Acc. Chem Res. 1979, 12, 79. (c) Wudl, F. Acc. Chem Res. 1984, 17, 227.
- 2 Cowan, D. O.; Kini, A.; Chiang, L.-Y.; Lertstrup, K.; Talham, D. R. Mol. Cryst. Liq. Cryst. 1982, 86, 1.
- 3 Wudl, F.; Huddon, R. C.; Zellers, E. T.; Bramwell, F. B. J. Org. Chem. 1979, 44, 2491.
- 4(a) Akamatsu, H.; Inokuchi, H.; Matsunaga, Y. Nature 1954, 173, 168. (b) Ayllh, J. A.; Santos, I. C.; Henriques, R. T.; Almeida, M.; Lopes, E. B.; Morgado, J.; Alcácer, L.; Luis F. Veiros, L. F.; Duarte, M. T. J. Chem Soc, Dalton Trans. 1995. 3543. (c) Kao, H-C. I.; Jones, M.; Labes, M. M. J. Chem. Soc., Chem. Commun. 1979, 329.
- 5(a) Lapouyade, R.; Morand, J. P. J. Chem. Soc., Chem Commun. 1987, 223. (b) Heywang, G.; Roth, S. Angew. Chem., Int. Ed. Engl. 1991, 30, 176. (c) Tani, H.; Nii, K.; Masumoto, K.; Azuma, N.; Ono, N. Chem Lett. 1993, 1055.
- 6(a) Wudl, F.; Schafer, D. E.; Müller, B. J. Am. Chem. Soc 1976, 98, 252. (b) Otsubo, T.; Sukenobe, N.; Aso, Y.; Ogura, F. Synth. Met. 1988, 27, B509. (c) Takimiya, K.; Shibata, Y.; Ohnishi, A.; Aso, Y.; Ohtsubo, T.; Ogura, F. J. Matel. Chem 1995, 5, 1539.
- 7(a) Nakasuji, K.; Kubota, H.; Kotani, T.; Murata, I.; Saito, G.; Enoki, T.; Imaeda, K.; Inokuchi, H.; Honda, M.; Katayama, C.; Tanaka, J. J. Am Chem Soc 1986, 108, 3460. (b) Nakasuji, K.; Oda, A.; Murata, I.; Imaeda, K.; Inokuchi, H. J. Chem Soc, Chem Commun. 1989, 1553 (c) Nakasuji, K.; Oda, A.; Toyoda, J.; Murata, I. J. Chem. Soc, Chem Commun 1990, 366. (d) Kono, Y.; Miyamoto, H.; Aso, Y.; Otubo, T.; Ogura, F.; Tanaka, T.; Sawada, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1222.
- 8 Verheijen, J. H.; Kloosterzeil, H. Synthesis 1975, 451.
- 9 Scholz, O. Liebigs. Ann. Chem. 1984, 259.
- 10 Schiemenz, G. P.; Engelhard, H. Chem. Ber 1962, 195.
- 11 Newkome, G. R.; Arai, S.; Fronczek, F. R.; Moorefield, C. N.; Xin, X. F.; Weis, C. D. J. Org. Chem 1993, 58, 898.
- 12 Sheldrick, G. M. SHELXL97, Program for the Refinement of Crystal Structure, University of Gottingen, Germany, 1997.