A concise synthesis and electrochemical behavior of functionalized poly(thieno[3,4-b]thiophenes): New conjugated polymers with low bandgap

European Polymer Journal

Volumn 46, Issue 8, 2010, Pages 1790-1795

  Park, Jin Hong ^a   Seo, Young Gin ^a   Yoon, Dae Hyun ^a   Lee, Youn Sik ^a   Lee, Soo Hyoung ^a   Pyo, Myoungho ^b   Zong, Kyukwan ^a  

^a Chonbuk National University   (South Korea)

^b Sunchon National University   (South Korea)

Author keywords

Conjugated polymer; Low bandgap polymer; n Doping; Thienothiophene

Indexed keywords

AROMATIC RESONANCES; BAND GAPS; BAND-GAP POLYMERS; CONCISE SYNTHESIS; ELECTROCHEMICAL BEHAVIORS; ELECTROCHEMICAL STUDIES; ELECTRON WITHDRAWING GROUP; FUNCTIONALIZED; LOW BANDGAP; N-DOPING; SYNTHETIC ROUTES; THIENOTHIOPHENE; THIENOTHIOPHENES; THIOPHENE DERIVATIVES;

AROMATIC POLYMERS; CONJUGATED POLYMERS; ENERGY GAP; FUNCTIONAL POLYMERS; THIOPHENE;

ORGANIC POLYMERS;

EID: 77955470612     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2010.04.019     Document Type: Article

References (24)

1. G. Yu, J. Gao, J.C. Hummelen, F. Wudl, and A.J. Heeger Polymer photovoltaic cells: enhanced efficiencies via a network of internal donor-acceptor heterojunctions Science 270 1995 1789 1791
2. J. Brabec, N.S. Sariciftci, and J.C. Hummelen Plastic solar cells Adv Funct Mater 11 2001 15 26
3. K.M. Coakley, and M.D. McGehee Conjugated polymer photovoltaic cells Chem Mater 16 2004 4533 4542
4. J. Hou, H.Y. Chen, S. 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 J Am Chem Soc 130 2008 16144 16145
5. J.Y. Kim, K. Lee, N.E. Coates, D. Moses, T.Q. Nguyen, and M. Dante Efficient tandem polymer solar cells fabricated by all-solution processing Science 317 2007 222 225 (Pubitemid 47076192)
6. F. Zhang, E. Perzon, X. Wang, W. Mammo, M.R. Andersson, and O. Inganäs Polymer solar cells based on a low-bandgap fluorene copolymer and a fullerene derivative with photocurrent extended to 850 nm Adv Funct Mater 15 2005 745 750
7. Y. Yang, R.T. Farley, T.T. Steckler, S.H. Eom, J.R. Reynolds, and K.S. Schanze Near infrared organic light-emitting devices based on donor-acceptor-donor oligomers Appl Phys Lett 93 2008 1633051 1633053
8. T.T. Steckler, X. Zhang, J. Hwang, R. Honeyager, S. Ohira, and X.H. Zhang A spray-processable, low bandgap, and ambipolar donor-acceptor conjugated polymer J Am Chem Soc 131 2009 2824 2826
9. J. Hou, H.Y. Chen, S. Zhang, R.I. Chen, Y. Yang, and Y. Wu Synthesis of a low band gap polymer and its application in highly efficient polymer solar cells J Am Chem Soc 131 2009 15586 15587
10. Y. Liang, Y. Wu, D. Feng, S.T. Tsai, H.J. Son, and G. Li Development of new semiconducting polymers for high performance solar cells J Am Chem Soc 131 2009 56 57
11. Y. Liang, D. Feng, Y. Wu, S.T. Tsai, G. Li, and C. Ray Highly efficient solar cell polymers developed via fine-tuning of structural and electronic properties J Am Chem Soc 131 2009 7792 7799
12. H. Wynberg, and D.J. Zwanenburg Thieno[3,4-b]thiophene: the third thiophthene Tetrahedron Lett 8 1967 761 764
13. L. Brandsma, and H.D. Verkruijsse An alternative synthesis of thieno[3,4-b]thiophene Synth Commun 20 1990 2275 2277
14. M. Pomerantz, X. Gu, and S.X. Zhang Poly(2-decylthieno[3,4-b]thiophene): a new soluble low band-gap conducting polymer Synth Met 84 1997 243 244
15. M. Pomerantz, X. Gu, and S.X. Zhang Poly(2-decylthieno[3,4-b]thiophene-4, 6-diyl): a new low band gap conducting polymer Macromolecules 34 2001 1817 1822
16. C.J. Neef, I.D. Brotherston, and J.P. Ferraris Synthesis and electronic properties of poly(2-phenylthieno[3,4-b]thiophene): a new low band gap polymer Chem Mater 11 1999 1957 1958
17. K. Lee, and G.A. Sotzing Poly(thieno[3,4-b]thiophene): a new stable low band gap conducting polymer Macromolecules 34 2001 5746 5747
18. G.A. Sotzing, and K. Lee Poly(thieno[3,4-b]thiophene): a p- and n-dopable polythiophene exhibiting high optical transparency in the semiconducting state Macromolecules 35 2002 7281 7286
19. B. Lee, V. Seshadri, H. Palko, and G.A. Sotzing Ring-sulfonated poly(thienothiophene) Adv Mater 17 2005 1792 1795
20. D.W. Hawkins, B. Iddon, D.S. Longthorne, and P.J. Rosyk Synthesis of thieno-[2,3-b]-, -[3,2-b]- and -[3,4-b]-thiophenes and thieno-[3′, 2′:4,5]-, -[2′,3′:4,5]- and -[3′,4′:4,5]-thieno[3, 2-d]pyrimidin-7(6H)-ones starting from thiophene J Chem Soc Perkin Trans 1 1994 2735 2743
21. S. Jammi, S. Sakthivel, L. Rout, T. Mukherjee, S. Mandal, and R. Mitra CuO nanoparticles catalyzed CN, CO, and CS cross-coupling reactions: scope and mechanism J Org Chem 74 2009 1971 1976
22. G. Zotti, G. Schiavon, and S. Zecchin Irreversible processes in the electrochemical reduction of polythiophenes: chemical modifications of the polymer and charge-trapping phenomena Synth Met 72 1995 275 281
23. G. Sonmez, H. Meng, and F. Wudl Very stable low band gap polymer for charge storage purposes and near-infrared applications Chem Mater 15 2003 4923 4929
24. J. Roncali Synthetic principles for bandgap control in linear π-conjugated systems Chem Rev 97 1997 173 205