Efficient synthesis of substituted dithieno[2,3-b:3',2'-D]siloles and A 10- Membered silicon-bridged thiophene-based cyclophane

Letters in Organic Chemistry

Volumn 8, Issue 10, 2011, Pages 728-731

  Zhao, Caiyun ^a   Shi, Jianwu ^a   Li, Chunli ^a   Wang, Hua ^a  

^a HENAN UNIVERSITY   (China)

Author keywords

Cross coupling; Dithieno 2,3 b:3',2' d silole; Heterocycles; Silicon bridged thiophene based cyclophane

Indexed keywords

EID: 84858962380     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017811799304179     Document Type: Article

References (20)

1. Jung H.; Hwang H.; Park K.-M.; Kim J.; Kim D.-H.; Kang Y. Palladium-catalyzed cross-coupling reactions of dithienosilole with indium reagents: synthesis and characterization of dithienosilole derivatives and their application to organic light-emitting diodes. Organometallics 2010, 29, 2715-2723.
2. (b). Zhan X.; Haldi A.; Yu J.; Kondo T.; Domercq B.; Cho J.-Y.; Barlow S.; Kippelen B.; Marder S.R. Synthesis, electron mobility, and electroluminescence of a polynorbornene-supported silole. Polymer 2009, 50, 397-403.
3. (c). Ohshita, J. Conjugated oligomers and polymers containing dithienosilole units. Macromol. Chem. Phys. 2009, 210, 1360-1370.
4. Beaujuge P.M.; Pisula W.; Tsao H.N.; Ellinger S.; Müllen K.; Reynolds J.R. Tailoring structure-property relationships in dithienosilole- benzothiadiazole donor-acceptor copolymers. J. Am. Chem. Soc. 2009, 131, 7514-7515.
5. Lu G.; Usta H.; Risko C.; Wang L.; Facchetti A.; Ratner M.A.; Marks T.J. Synthesis, characterization, and transistor response of semiconducting silole polymers with substantial hole mobility and air stability. experiment and theory. J. Am. Chem. Soc., 2008, 130, 7670-7685. (Pubitemid 351842132)
6. Usta H.; Lu G.; Facchetti A.; Marks T.J. Dithienosilole-and dibenzosilole-thiophene copolymers as semiconductors for organic thin-film transistors. J. Am. Chem. Soc. 2006, 128, 9034-9035. (Pubitemid 44078977)
7. Lee S.K.; Lee J.; Lee H.Y.; Yoon S.C.; Kim J.R.; Kim K.N.; Kim H.J.; Shin W.S.; Moon S.-J. Synthesis and characterization of new dithienosilole-based copolymers for polymer solar cells. J. Nanosci. Nanotechnol. 2011, 11, 4279-4284.
8. Caputo B.J.A.; Welch G.C.; Kamkar D.A.; Henson Z.B.; Nguyen T.-Q.; Bazan G.C. A dithienosilole-benzooxadiazole donor-acceptor copolymer for utility in organic solar cells. Small 2011, 7, 1422-1426.
9. Huo L.; Chen H.Y.; Hou J.; Chen T.L.; Yang Y. Low band gap dithieno[3,2-b:2,3+-d]silole-containing polymers, synthesis, characterization and photovoltaic application. Chem. Commun. 2009, 5570-5572.
10. Hou J.; Chen H.-Y.; Zhang S.; Li G.; Yang Y. Synthesis, characterization, and photovoltaic properties of a low band gap polymer based on silole-containing polythiophenes and 2,1,3-benzothiadiazole. J. Am. Chem. Soc. 2008, 130, 16144-16145.
11. Ko S.; Choi H.; Kang M.-S.; Hwang H.; Ji H.; Kim J.; Ko J.; Kang Y. Silole-spaced triarylamine derivatives as highly efficient organic sensitizers in dye-sensitized solar cell (DSSCs). J. Mater. Chem., 2010, 20, 2391-2399.
12. Lin L.; Tsai C.; Wong K.; Huang T.; Hsieh L.; Liu S.; Lin H.; Wu C.; Chou S.; Chen S.; Tsai A. Organic dyes containing coplanar diphenyl-substituted dithienosilole core for efficient dye-sensitized solar cells. J. Org. Chem., 2010, 75, 4778-4785.
13. Zeng W.D.; Cao Y.M.; Bai Y.; Wang Y.H.; Shi Y.S.; Zhang M.; Wang F.F.; Pan C.Y.; Wang P. Efficient dye-sensitized solar cells with an organic photosensitizer featuring orderly conjugated ethylenedioxythiophene and dithienosilole blocks. Chem. Mater., 2010, 22, 1915-1925.
14. Iyoda M.; Miura M.; Sasaki S.; Kabir S.M.H.; Kuwatani Y.; Yoshida M. Synthesis of dithienothiophenes, cyclopentadithiophene and silacyclopentadithiophenes using palladium-catalyzed cyclization. Tetrahedron Lett., 1997, 38, 4581-4582. (Pubitemid 27263306)
15. Kabir S. M. H.; Miura M.; Sasaki S.; Harada G.; Kuwatani Y.; Yoshida M.; Iyoda M. New synthesis of tricyclic thiophenes and cyclic tetrathiophenes using transition-metalcatalyzed cyclization. Heterocycles, 2000, 52, 761-774.
16. Zhao C.; Xu L.; Shi J.; Li C.; Wang Z.; Wang H. 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). Int. J. Org. Chem., accepted.
17. Wang Y.; Wang Z.; Zhao D.; Wang Z.; Cheng Y.; Wang H. Efficient synthesis of trimethylsilyl-substituted sithieno[2,3-b:3',2'-d]thiophene, tetra[2,3-thienylene] and hexa[2,3-thienylene] from substituted [3,3']bithiophenyl. Synlett. 2007, 15, 2390-2394. (Pubitemid 47522002)
18. Marsella M.J.; Yoon K.; Tham F.S. Synthesis and crystal structure of a tubular sexithiophene. Org. Lett. 2001, 3, 2129-2131. (Pubitemid 33631731)
19. Miyake Y., Wu M.; Rahman M.J.; Iyoda M. Novel electrontransfer oxidation of Lipshutz cuprates with 1,4-benzoquinones: an efficient homo-coupling reaction of aryl halides and its application to the construction of macrocyclic systems. Chem. Commun., 2005, 411-413. (Pubitemid 40187652)
20. Miyake Y.; Wu M.; Rahman M. J.; Kuwatani Y.; Iyoda M. Efficient construction of biaryls and macrocyclic cyclophanes via electron-transfer oxidation of Lipshutz cuprates. J. Org. Chem., 2006, 71, 6110-6117. (Pubitemid 44200279)