Synthesis and organic photovoltaic (OPV) properties of triphenylamine derivatives based on a hexafluorocyclopentene "core"

Solar Energy Materials and Solar Cells

Volumn 95, Issue 3, 2011, Pages 992-1000

  Fan, Congbin ^a,e   Yang, Ping ^a   Wang, Xiaomei ^a,b   Liu, Gang ^a,e   Jiang, Xiaoxia ^d   Chen, Hongzheng ^d   Tao, Xutang ^c   Wang, Mang ^d   Jiang, Minghua ^c  

^a SOOCHOW UNIVERSITY   (China)

^b SUZHOU UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^c SHANDONG UNIVERSITY   (China)

^d ZHEJIANG UNIVERSITY   (China)

^e JIANGXI SCIENCE AND TECHNOLOGY NORMAL UNIVERSITY   (China)

Author keywords

Hexafluorocyclopentene thiophene; N type semiconductor organic photovoltaic; Triphenylamine

Indexed keywords

ABSORPTION BAND; BENZENE RING; CLOSED-RING ISOMERS; ELECTRON DELOCALIZATION; ELECTRON-DONATING GROUP; FLUORINE SUBSTITUTION; HEXAFLUOROCYCLOPENTENE THIOPHENE; HOLE TRANSPORTS; MOLECULAR CENTERS; N-TYPE SEMICONDUCTORS; OPEN-RING ISOMERS; ORGANIC PHOTOVOLTAICS; P-TYPE; POTENTIAL APPLICATIONS; POWER CONVERSION EFFICIENCIES; SEMICONDUCTOR PROPERTIES; TRIPHENYL AMINES; TRIPHENYLAMINE DERIVATIVES; TRIPHENYLAMINE GROUPS; TRIPHENYLAMINE MOIETY;

BENZENE; CONVERSION EFFICIENCY; FLUORINE; HETEROJUNCTIONS; ISOMERS; OPEN CIRCUIT VOLTAGE; ORGANIC POLYMERS; PHOTOVOLTAIC EFFECTS; QUANTUM YIELD; SEMICONDUCTOR DEVICES; SWITCHING CIRCUITS; THIOPHENE;

CHROMOPHORES;

EID: 78751643988     PISSN: 09270248     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.solmat.2010.12.010     Document Type: Article

References (39)

1. T.D. Nielsen, C. Cruickshank, S. Foged, J. Thorsen, and F.C. Krebs Business market and intellectual property analysis of polymer solar cells Sol. Energy Mater. Sol. Cells 94 2010 1553 1571
2. F.C. Krebs, and K. Norrman Using light-induced thermocleavage in a roll-to-roll process for polymer solar cells ACS Appl. Mater. Interfaces 2 2010 877 887
3. L.M. Chen, Z.R. Hong, G. Li, and Y. Yang Recent progress in polymer solar cells: manipulation of polymer: fullerene morphology and the formation of efficient inverted polymer solar cells Adv. Mater. 21 2009 1434 1449
4. F.C. Krebs, T. Tromholt, and M. Jørgensen Upscaling of polymer solar cell fabrication using full roll-to-roll processing Nanoscale 2 2010 873 886
5. E. Bundgaard, O. Hagemann, M. Manceau, M. Jørgensen, and F.C. Krebs Low band gap polymers for roll-to-roll coated polymer solar cells Macromolecules 43 2010 8115 8120
6. F.C. Krebs, J. Fyenbo, and M. Jørgensen Product integration of compact roll-to-roll processed polymer solar cell, modules: methods and manufacture using exographic printing, slot-die coating and rotary screen printing J. Mater. Chem. 20 2010 8994 9001
7. F.C. Krebs, S.A. Gevorgyan, and J. Alstrup A roll-to-roll process to exible polymer solar cells: model studies, manufacture and operational stability studies J. Mater. Chem. 19 2009 5442 5451
8. B. Kippelen, and BredasJ.-L. Brdas Organic photovoltaics Energy Environ. Sci. 2 2009 251 261
9. F.C. Krebs, T.D. Nielsen, J. Fyenbo, M. Wadstrøm, and M.S. Pedersen Manufacture, integration and demonstration of polymer solar cells in a lamp for the "Lighting Africa" initiative Energy Environ. Sci. 3 2010 512 525
10. X.X. Jiang, H. Xu, L.G. Yang, M.M. Shi, M. Wang, and H.Z. Chen Effect of CsF interlayer on the performance of polymer bulk heterojunction solar cell Sol. Energy Mater. Sol. Cells 93 2009 650 653
11. N.S. Sariciftci, L. Smilowitz, A.J. Heeger, and F. Wudl Photoinduced electron transfer from a conducting polymer to buckminsterfullerene Science 258 1992 1474 1476
12. M. Helgesen, R. Søndergaard, and F.C. Krebs Advanced materials and processes for polymer solar cell devices J. Mater. Chem. 20 2010 36 60
13. M. Campoy-Quiles, T. Ferenczi, T. Agostinelli, P.G. Etchegoin, Y. Kim, T.D. Anthopoulos, P.N. Stavrinou, D.D.C. Bradley, and J. Nelson Morphology evolution via self-organization and lateral and vertical diffusion in polymer:fullerene solar cell blends Nat. Mater. 7 2008 158 164
14. G. Li, Y. Yao, H. Yang, V. Shrotriya, G. Yang, and Y. Yang "Solvent annealing" effect in polymer solar cells based on poly(3-hexylthiophene) and methanofullerenes Adv. Funct. Mater. 17 2007 1636 1644
15. G. Li, V. Shrotriya, J. Huang, Y. Yao, T. Moriarty, K. Emery, and Y. Yang High-efficiency solution processable polymer photovaoltaic cells by self-organization of polymer blends Nat. Mater. 4 2005 864 868
16. W. Ma, C. Yang, X. Gong, K. Lee, and A.J. Heeger Thermally stable, efficient polymer solar cells with nanoscale control of the interpenetrating network morphology Adv. Funct. Mater. 15 2005 1617 1622
17. C.H. Woo, B.C. Thompson, B.J. Kim, M.F. Toney, and J.M.J. Frechet The influence of poly(3-hexylthiophene) regioregularity on fullerene-composite solar cell performance J. Am. Chem. Soc. 130 2008 16324 16329
18. M. Sommer, S.M. Lindner, and M. Thelakkat Microphase-separated donoracceptor diblock copolymers: influence of HOMO energy levels and morphology on polymer solar cells Adv. Funct. Mater. 17 2007 1493 1500
19. M. Lenes, G.-J.A.H. Wetzelaer, F.B. Kooistra, S.C. Veenstra, J.C. Hummelen, and P.W.M. Blom Fullerene bisadducts for enhanced open-circuit voltages and efficiencies in polymer solar cells Adv. Mater. 20 2008 2116 2119
20. W.W. Li, C. Du, F.H. Li, Y. Zhou, M. Fahlman, Z.S. Bo, and F.L. Zhang Benzothiadiazole-based linear and star molecules: design, synthesis, and their application in bulk heterojunction organic solar cells Chem. Mater. 21 2009 5327 5334
21. Pinzon J.R. Pinzn, D.C. Gasca, S.G. Sankaranarayanan, G. Bottari, T. Torres, D.M. Guldi, and L. Echegoyen Photoinduced charge transfer and electrochemical properties of triphenylamine Ih-Sc3N@C80 donor-acceptor conjugates J. Am. Chem. Soc. 131 2009 7727 7734
22. C. He, Q. He, X.D. Yang, G.L. Wu, C.H. Yang, F.L. Bai, Z.G. Shuai, L.X. Wang, and Y.F. Li Synthesis and photovoltaic properties of a solution-processable organic molecule containing triphenylamine and DCM moieties J. Phys. Chem. C 111 2007 8661 8666
23. H.Z. Wei, W.L. Li, W.M. Su, M.T. Li, Z.R. Hong, and B. Li New organic electroluminescence and photovoltaic device J. Optoelectron. Laser 15 2004 750 752
24. C.B. Fan, S.Z. Pu, G. Liu, and T.S. Yang Substituent position effect on the properties of new unsymmetrical isomeric diarylethenes having a chlorine atom J. Photochem. Photobiol. A 197 2008 415 425
25. H. Tian, and S.J. Yang Recent progresses on diarylethene based photochromic switches Chem. Soc. Rev. 33 2004 85 97
26. S.Z. Pu, C.B. Fan, W.J. Miao, and G. Liu The effect of substituent position upon unsymmetrical isomeric diarylethenes bearing a methoxy group Dyes Pigments 84 2010 25 35
27. S.Z. Pu, T.S. Yang, J.K. Xu, L. Shen, G.Z. Li, Q. Xiao, and B. Chen Syntheses and optoelectronic properties of four photochromic dithienylethenes Tetrahedron 61 2005 6623 6629 (Pubitemid 40812965)
28. A. Osuka, D. Fujikane, H. Shinmori, S. Kobatake, and M. Irie Synthesis and photoisomerization of dithienylethene-bridged diporphyrins J. Org. Chem. 66 2001 3913 3923
29. 2, a photochromic diarylethene Z. Kristallogr. 217 2002 415 416
30. Z.Z. Huang, X.M. Wang, B. Li, C.G. Lv, J. Xu, W.L. Jiang, X.T. Tao, S.X. Qian, Y.P. Chui, and P. Yang Two-photon absorption of new multibranched chromophores based on bis(diphenylamino)stilbene Opt. Mater. 29 2007 1084 1090
31. T.S. Yang, S.Z. Pu, B. Chen, and J.K. Xu Electron-donating methoxy group position effect on properties of diarylethene derivatives having a pyrazole unit Can. J. Chem. 85 2007 12 20
32. S.Z. Pu, G. Liu, G.Z. Li, R.J. Wang, and T.S. Yang Synthesis, crystal structure and its optical and electrochemical properties of a new unsymmetrical diarylethene J. Mol. Struct. 833 2007 23 29
33. S. Yamamoto, K. Matsuda, and M. Irie Characterisation of an optical sensor membrane based on the metal ion indicator Pyrocatechol Violet Chem. Eur. J. 9 2003 4878 4886
34. G.H. Liu, P. Yang, W.L. Jiang, X.Z. Guo, G.B. Xu, X.Z. Jiang, L. Shen, and X.M. Wang Synthesis and strong two-photo absorption of carbazole derivatives: NT-G1 and NO-G1 J. Funct. Mater. 36 2005 600 603
35. P. Qin, X.C. Yang, R.K. Chen, and L.C. Sun Influence of π-conjugation units in organic dyes for dye-sensitized solar cells J. Phys. Chem. C 111 2007 1853 1860
36. K. Kasatani, S. Kambe, and M. Irie Photochromic reaction and fluorescence of dithienylethenes in the solid state J. Photochem. Photobiol. A 122 1999 11 15
37. Y. Shirota, and H. Kageyama Charge carrier transporting molecular materials and their applications in devices Chem. Rev. 107 2007 953 1010
38. Y. Shirota Photo- and electroactive amorphous molecular materialsmolecular design, syntheses, reactions, properties, and applications J. Mater. Chem. 15 2005 75 93
39. T. Tsujioka, and M. Irie Electrical functions of photochromic molecules J. Photochem. Photobiol. C 11 2010 1 14