The Ring-Opening Reaction of 7,7’-Dimethyl-2, 5-bis(trimethylsilyl)-dithieno[2,3-b:3’,2’-d]silole in the Presence of NXS (X = Cl, Br, I)
Caiyun Zhao, Li Xu, Jianwu Shi, Chunli Li, Zhihua Wang, Hua Wang
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DOI: 10.4236/ijoc.2011.14024   PDF   HTML     4,326 Downloads   7,903 Views   Citations

Abstract

In this paper, the synthetic method for making 7,7’-dimethyl-2,5-bis(trimethylsilyl)-dithieno[2,3-b:3’,2’-d] silole (1) was developed by using 2,2’-dibromo-5,5’-bis-trimethyl-silanyl[3,3’]bithiophenyl as starting material in one pot reaction. In the presence of NXS (X = Cl, Br, I), a novel ring-opening reation was occurred on the silole ring of 1 in DMF or THF. By using such kind of reaction, two types of ring opened products, (2’-halo-5,5’-bis(trimethylsilanyl)[3,3’]bithiophenyl-2-yl)-dimethylsilanols and 2,2’-dihalo-5,5’-bis(trimethylsi- lanyl)[3,3’]bithiophenyls were obtained efficiently.

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C. Zhao, L. Xu, J. Shi, C. Li, Z. Wang and H. Wang, "The Ring-Opening Reaction of 7,7’-Dimethyl-2, 5-bis(trimethylsilyl)-dithieno[2,3-b:3’,2’-d]silole in the Presence of NXS (X = Cl, Br, I)," International Journal of Organic Chemistry, Vol. 1 No. 4, 2011, pp. 162-166. doi: 10.4236/ijoc.2011.14024.

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1] A. P. Sadimenko, “Organometallic Compounds of Pyrrole, Indole, Carbazole, Phospholes, Siloles, and Boroles,” Advances in Heterocyclic Chemistry, Vol. 79, 2001, pp. 115-197. doi:10.1016/S0065-2725(01)79023-X
[2] B.-H. Kim and H.-G. Woo, “Dehydrocoupling of 1,1-Di- hydrotetraphenylsilole to an Electroluminescent Polysilole,” Organometallics, Vol. 21, No. 13, 2002, pp. 2796- 2798. doi:10.1021/om0200151
[3] P. M. Beaujuge, W. Pisula, H. N. Tsao, S. Ellinger, K. Müllen and J. R. Reynolds, “Tailoring Structure-Property Relationships in Dithienosilole-Benzothiadiazole Donor- Acceptor Copolymers,” Journal of the American Chemical Society, Vol. 131, No. 22, 2009, pp. 7514-7515.
[4] M. S. Liu, J. D. Luo and A. K.-Y. Jen, “Efficient Green- Light-Emitting Diodes from Silole-Containing Copolymers,” Chemistry of Materials, Vol. 15, No.18, 2003, pp. 3496-3450. doi:10.1021/cm030063r
[5] J. Ohshita, T. Sumida and A. Kunai, “Synthesis of Polymers Composed of Alternating Diphenylenedithienosilole and Diethynylenesilylene Units and Their Applications to Hole Transport in Double-Layer EL Devices,” Macromolecules, Vol. 33, No.23, 2000, pp. 8890-8893. doi:10.1021/ma0005062
[6] K.-H. Lee, J. Ohshita, K. Kimura, Y. Kunugi and A. Kunai, “Synthesis of Oligomers Having a Pendant Dithienosilole Unit and Their Applications to EL Device Materials,” Journal of Organometallic Chemistry, Vol. 690, No. 2, 2005, pp. 333-337. doi:10.1016/j.jorganchem.2004.09.039
[7] J. Ohshita, K. Kimura, K.-H. Lee, A. Kunai, Y.-H. Kwak, E.-C. Son and Y. Kunugi, “Synthesis of Silicon-Bridged Polythiophene Derivatives and Their Applications to EL Device Materials,” Journal of Polymer Science Part A: Polymer Chemistry, Vol. 45, No. 20, 2007, pp. 4588- 4596. doi:10.1002/pola.22196
[8] L. J. Huo, H.-Y. Chen, J. H. Hou, T. L. Chen and Y. Yang, “Low Band Gap Dithieno[3,2-b:2’,3’-d]silole-Con- taining Polymers, Synthesis, Characterization and Photovoltaic Application,” Chemical Communications, No. 37, 2009, pp. 5570-5572. doi:10.1039/b910443g
[9] J. H. Hou, H.-Y. Chen, S. Q. Zhang, G. Li and Y. Yang, “Synthesis, Characterization, and Photovoltaic Properties of a Low Band Gap Polymer Based on Silole-Containing Polythiophenes and 2,1,3-Benzothiadiazole,” Journal of the American Chemical Society, Vol. 130, No. 48, 2008, pp. 16144-16145. doi:10.1021/ja806687u
[10] S. Ko, H. Choi, M.-S. Kang, H. Hwang, H. Ji, J. Kim, J. Ko and Y. Kang, “Silole-Spaced Triarylamine Derivatives as Highly Efficient Organic Sensitizers in Dye- Sensitized Solar Cells (DSSCs),” Journal of Material Chemistry, Vol. 20, No. 12, 2010, pp. 2391-2399. doi:10.1039/b926163j
[11] W. D. Zeng, Y. M. Cao, Y. Bai, Y. H. Wang, Y. S. Shi, M. Zhang, F. F. Wang, C. Y. Pan and P. Wang, “Efficient Dye-Senstized Solar Cells with an Organic Photosensitizer Featuring Orderly Conjugated Ethylenedioxythiophene and Dithienosilole Blocks,” Chemistry of Materials, Vol. 22, No. 5, 2010, pp. 1915-1925. doi:10.1021/cm9036988
[12] H. Usta, G. Lu, A. Facchetti and T. J. Marks, “Dithienosilole- and Dibenzosilole-Thiophene Copolymers as Semiconductors for Organic Thin-Film Transistors,” Jour- nal of the American Chemical Society, Vol. 128, No. 28, 2006, pp. 9034-9035. doi:10.1021/ja062908g
[13] J. Ohshita, “Conjugated Oligomers and Polymers Containing Dithienosilole Units,” Macromolecular Chemistry and Physics, Vol. 210, No. 17, 2009, pp. 1360-1370. doi:10.1002/macp.200900180
[14] J. W. Chen and Y. Cao, “Silole-Containing Polymers: Chemistry and Optoelectronic Properties,” Macromolecular Rapid Communications, Vol. 28, No. 17, 2007, pp. 1714-1742. doi:10.1002/marc.200700326
[15] H. Jung, H. Hwang and K.-M. Park, “Palladium-Cata- lyzed Cross-Coupling Reactions of Dithienosilole with Indium Reagents: Synthesis and Characterization of Dithienosilole Derivatives and Their Application to Organic Light-Emitting Diodes,” Organometallics, Vol. 29, No. 12, 2010, pp. 2715-2723. doi:10.1021/om100222b
[16] J. Ohshita, M. Nodono and T. Watanabe, “Synthesis and Properties of Dithienosiloles,” Journal of Organometallic Chemistry, Vol. 553, No. 1-2, 1998, pp. 487-491. doi:10.1016/S0022-328X(97)00643-8
[17] K.-H. Lee, J. Ohshita and A. Kunai, “Synthesis and Properties of Bis(methylthio)dithieno-silole and Its Oxides,” Organometallics, Vol. 23, No. 23, 2004, pp. 5481-5487. doi:10.1021/om049642b
[18] M. Iyoda, M. Miura, S. Sasaki, S. M. H. Kabir, Y. Kuwatani and M. Yoshida, “Synthesis of Dithieno- thiophenes, Cyclophentadithiophene and Silacyclopenta- dithiophenes Using Palladium-Catalyzed Cyclization,” Tetrahedron Letters, Vol. 38, No. 26, 1997, pp. 4581- 4582. doi:10.1016/S0040-4039(97)00979-9
[19] G. Lu, H. Usta, C. Risko, L. Wang, A. Facchetti, M. A. Ratner and T. J. Marks, “Synthesis, Characterization, and Transistor Response of Semiconducting Silole Polymers with Substantial Hole Mobility and Air Stability. Expe- riment and Theory,” Journal of the American Chemical Society, Vol. 130, No. 24, 2008, pp. 7670-7685. doi:10.1021/ja800424m
[20] L. Liao, L. Dai, A. Smith, M. Durstock, J. Lu, J. Ding and Y. Tao, “Photovoltaic-Active Dithienosilole-Containing Polymers,” Macromolecules, Vol. 40, No. 26, 2007, pp. 9406-9412. doi:10.1021/ma071825x
[21] Y. He, G. Zhao, M. Zhang, J. Min and Y. F. Li, “Sy- nthesis and Characterization of Low Bandgap Poly (Dithienosilole Vinylene) Derivatives,” Synthetic Metals, Vol. 160, No. 9-10 , 2010, pp. 1045-1049. doi:10.1016/j.synthmet.2010.02.024
[22] J. Braddock-Wilking, Y. Zhang, J. Y. Corey and N. P. Rath, “Preparation of 1,1-Disubstituted Silacyclopentadienes,” Journal of Organometallic Chemistry, Vol. 693, No. 7, 2008, pp. 1233-1242. doi:10.1016/j.jorganchem.2008.01.017
[23] Q. Luo, C. Wang, Y. X. Li, K. B Ouyang, L. Gu, M. Uchiyama and Z. F. Xi, “Opening the Silole Ring: Eff- icient and Specific Cleavage of the endo-C(sp2)-Si Bond with AcOH/ROH System,” Chemical Science, Vol. 2, No. 11, 2011, pp. 2271-2274. doi:10.1039/c1sc00356a
[24] Y. G. Wang, Z. H. Wang, D. F. Zhao, Z. Wang, Y. X. Cheng and H. Wang, “Efficient Synthesis of Trimethy- lsilyl-Substituted Dithieno[2,3-b:3’,2’-d]-thiophene, Te- tra-[2,3-thienylene] and Hexa[2,3- thienylene] from Sub- stituted [3,3’]Bithiophenyl,” Synlett, Vol. 15, 2007, pp. 2390-2394.

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