Fluorene-based organic dyes containing acetylene linkage for dye-sensitized solar cells

Dyes and Pigments

Volumn 95, Issue 3, 2012, Pages 523-533

  Singh, Prachi ^a   Baheti, Abhishek ^a   Thomas, K R Justin ^a   Lee, Chuan Pei ^b   Ho, Kuo Chuan ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY ROORKEE   (India)

^b NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

Acetylene; Dye sensitized solar cells; Fluorene; Optical spectra; Organic dyes; TDDFT calculations

Indexed keywords

CHARGE GENERATION; DIPHENYLAMINOFLUORENE; DYE-SENSITIZED SOLAR CELL; ETHYNYLBENZENE; FILL FACTOR; FLUORENES; FLUORESCENCE EMISSION; NON-POLAR SOLVENTS; OPTICAL SPECTRA; ORGANIC DYE; PHENYLACETYLENES; SOLVATOCHROMIC BEHAVIOR; SOLVATOCHROMISMS; STRUCTURAL REORGANIZATION;

ACETYLENE; BENZENE; LIGHTING; OPEN CIRCUIT VOLTAGE; OPTICAL PROPERTIES; PHOTOELECTROCHEMICAL CELLS; THIOPHENE;

SOLAR CELLS;

EID: 84864040406     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2012.06.004     Document Type: Article

References (63)

1. A. Hagfeldt, G. Boschloo, L. Sun, L. Kloo, and H. Pettersson Dye-sensitized solar cells Chem Rev 110 2010 6595 6663
2. A. Mishra, and P. Bäuerle Small molecule organic semiconductors on the move: promises for future solar energy technology Angew Chem Int Ed 51 2012 2020 2067
3. B. Walker, C. Kim, and T.Q. Nguyen Small molecule solution-processed bulk heterojunction solar cells Chem Mater 23 2011 470 482
4. 2 films Nature 253 1991 737 740
5. M. Grätzel Recent advances in sensitized mesoscopic solar cells Acc Chem Res 42 2009 1788 1798
6. Z. Ning, and H. Tian Triarylamine: a promising core unit for efficient photovoltaic materials Chem Commun 2009 5483 5495
7. H. Han, M. Liang, K. Tang, X. Cheng, X. Zong, and Z. Sun Molecular design of triarylamine dyes incorporating phenylene spacer and the influence of alkoxy substituent on the performance of dye-sensitized solar cells J Photochem Photobiol A-Chem 225 2011 8 16
8. M.D. Zhang, H. Pan, X.H. Ju, Y.J. Ji, L. Qin, and H.G. Zheng Improvement of dye-sensitized solar cells' performance through introducing suitable heterocyclic groups to triarylamine dyes Phys Chem Chem Phys 14 2012 2809 2815
9. Z. Ning, Q. Zhang, W. Wu, H. Pei, B. Liu, and H. Tian Starburst triarylamine based dyes for efficient dye sensitized solar cells J Org Chem 73 2008 3791 3797
10. W. Lee, N. Cho, J. Kwon, J. Ko, and J.I. Hong New organic dye based on a 3,6-disubstituted carbazole donor for efficient dye-sensitized solar cells Chem Asian J 7 2012 343 350
11. J. Tang, J. Hua, W. Wu, J. Li, Z. Jin, and Y. Long New starburst sensitizer with carbazole antennas for efficient and stable dye-sensitized solar cells Energy Environ Sci 3 2010 1736 1745
12. N. Koumura, Z.S. Wang, M. Miyashita, Y. Uemura, H. Sekiguchi, and Y. Cui Substituted carbazole dyes for efficient molecular photovoltaics: long electron lifetime and high open circuit voltage performance J Mater Chem 12 2009 4829 4836
13. M. Marszalek, S. Nagane, A. Ichake, R. Humphry-Baker, V. Paul, and S.M. Zakeeruddin Tuning spectral properties of phenothiazine based donor-π-acceptor dyes forefficient dye-sensitized solar cells J Mater Chem 22 2012 889 894
14. D. Cao, J. Peng, Y. Hong, X. Fang, L. Wang, and H. Meier Enhanced performance of the dye-sensitized solar cells with phenothiazine-based dyes containing double D-A branches Org Lett 13 2011 1610 1613
15. Z.S. Wang, Y. Cui, Y. Dan-Oh, C. Kasada, A. Shinpo, and K. Hara Molecular design of coumarin dyes for stable and efficient organic dye-sensitized solar cells J Phys Chem C 112 2008 17011 17017
16. K. Hara, T. Sato, R. Katoh, A. Furube, Y. Ohga, and A. Shinpo Molecular design of coumarin dyes for efficient dye-sensitized solar cells J Phys Chem B 107 2003 597 606
17. S. Ito, H. Miura, S. Uchida, M. Takata, K. Sumioka, and P. Liska High-conversion-efficiency organic dye-sensitized solar cells with a novel indoline dye Chem Commun 2008 5194 5196
18. S. Higashijima, Y. Inoue, H. Miura, Y. Kubota, K. Funabiki, and T. Yoshida Organic dyes containing fluorene-substituted indoline core for zinc oxide dye-sensitized solar cell RSC Adv 2 2012 2721 2724
19. K.R.J. Thomas, Y.C. Hsu, J.T. Lin, K.M. Lee, K.C. Ho, and C.H. Lai 2,3-Disubstituted thiophene-based organic dyes for solar cells Chem Mater 20 2008 1830 1840
20. X.H. Zhang, Z.S. Wang, Y. Cui, N. Koumura, A. Furube, and K. Hara Organic sensitizers based on hexylthiophene-functionalized indolo[3,2-b]carbazole for efficient dye-sensitized solar cells J Phys Chem C 113 2009 13409 13415
21. Z.S. Wang, N. Koumura, Y. Cui, M. Takahashi, H. Sekiguchi, and A. Mori Hexylthiophene-functionalized carbazole dyes for efficient molecular photovoltaics: tuning of solar-cell performance by structural modification Chem Mater 20 2008 3993 4003
22. A. Baheti, C.P. Lee, K.R.J. Thomas, and K.C. Ho Pyrene-based organic dyes with thiophene containing π-linkers for dye-sensitized solar cells: optical, electrochemical and theoretical investigations Phys Chem Chem Phys 13 2011 17210 17221
23. X.H. Zhang, Y. Cui, R. Katoh, N. Koumura, and K. Hara Organic dyes containing thieno[3,2-b]indole donor for efficient dye-sensitized solar cells J Phys Chem C 114 2010 18283 18290
24. M. Mao, J.B. Wang, Z.F. Xiao, S.Y. Dai, and Q.H. Song New 2,6-modified BODIPY sensitizers for dye-sensitized solar cells Dyes Pigm 94 2012 224 232
25. S. Erten, E. Eren, and S. Icli Dye sensitized solar cell based on 1,8-naphthalene benzimidazole comprising carboxyl group Eur Phys J App Phys 38 2007 227 230
26. D. Kumar, K.R.J. Thomas, C.P. Lee, and K.C. Ho Novel pyrenoimidazole- based organic dyes for dye-sensitized solar cells Org Lett 13 2011 2622 2625
27. Y.Z. Wu, X. Zhnag, W.Q. Li, Z.S. Wang, H. Tian, and W.H. Zhu Hexylthiophene-featured D-A-π-A structural indoline chromophores for coadsorbent-free and panchromatic dye-sensitized solar cells Adv Energy Mater 2 2012 149 156
28. J.J. Kim, H. Choi, J.W. Lee, M.S. Kang, K. Song, and S.O. Kang A polymer gel electrolyte to achieve ≥6% power conversion efficiency with a novel organic dye incorporating a low-band-gap chromophore J Mater Chem 18 2008 5223 5229
29. H. Lai, J. Hong, P. Liu, C. Yuan, Y. Li, and Q. Fang Multi-carbazole derivatives: new dyes for highly efficient dye-sensitized solar cells RSC Adv 2 2012 2427 2432
30. Y. Ooyama, S. Inoue, T. Nagano, K. Kushimoto, J. Ohshita, and I. Imae Dye-sensitized solar cells based on donor-acceptor π-conjugated fluorescent dyes with a pyridine ring as an electron-withdrawing anchoring group Angew Chem Int Ed 50 2011 7429 7433
31. K. Panthi, R.M. Adhikari, and T.H. Kinstle Carbazole donor-carbazole linker-based compounds: preparation, photophysical properties, and formation of fluorescent nanoparticles J Phys Chem A 114 2010 4550 4557
32. W. Li, Y. Wu, X. Li, Y. Xie, and W. Zhu Absorption and photovoltaic properties of organic solar cell sensitizers containing fluorene unit as conjunction bridge Energy Environ Sci 4 2011 1830 1837
33. K.R.J. Thomas, J.T. Lin, Y.C. Hsu, and K.C. Ho Organic dyes containing thienylfluorene conjugation for solar cells Chem Commun 2005 4098 4100
34. H. Zhou, P. Xue, Y. Zhang, X. Zhao, J. Jia, and X. Zhang Fluorenylvinylenes bridged triphenylamine-based dyes with enhanced performance in dye-sensitized solar cells Tetrahedron 67 2011 8477 8483
35. P. Shen, Y. Tang, S. Jiang, H. Chen, X. Zheng, and X. Wang Efficient triphenylamine-based dyes featuring dual-role carbazole, fluorene and spirobifluorene moieties Org Electronics 12 2011 125 135
36. Y. Bai, J. Zhang, D. Zhou, Y. Wang, M. Zhang, and P. Wang Engineering organic sensitizers for iodine-free dye-sensitized solar cells: red-shifted current response concomitant with attenuated charge recombination J Am Chem Soc 133 2011 11442 11445
37. L. Schmidt-Mende, U. Bach, R. Humphry-Baker, T. Horiuchi, H. Miura, and S. Ito Organic dye for highly efficient solid-state dye-sensitized solar cells Adv Mater 17 2005 813 815
38. H. Tian, I. Bora, X. Jiang, E. Gabrielsson, K.M. Karlsson, and A. Hagfeldt Modifying organic phenoxazine dyes for efficient dye-sensitized solar cells J Mater Chem 21 2011 12462 12472
39. A. Mishra, M.K.R. Fischer, and P. Bäuerle Metal-free organic dyes for dye-sensitized solar cells: from structure: property relationships to design rules Angew Chem Int Ed 48 2009 2474 2499
40. J. Liu, R. Li, X. Si, D. Zhou, Y. Shi, and Y. Wang Oligothiophene dye-sensitized solar cells Energy Environ Sci 3 2010 1924 1928
41. T.H. Kwon, V. Armel, A. Nattestad, D.R. MacFarlane, U. Bach, and S.J. Lind Dithienothiophene (DTT)-based dyes for dye-sensitized solar cells: synthesis of 2,6-dibromo-DTT J Org Chem 76 2011 4088 4093
42. S. Paek, H. Choi, H. Choi, C.W. Lee, M.S. Kang, and K. Song Molecular engineering of efficient organic sensitizers incorporating a binary π-conjugated linker unit for dye-sensitized solar cells J Phys Chem C 114 2010 14646 14653
43. Y.C. Chen, H.H. Chou, M.C. Tsai, S.Y. Chen, J.T. Lin, and C.F. Yao Thieno[3,4-b]thiophene-based organic dyes for dye-sensitized solar cells Chem Eur J 18 2012 5430 5437
44. J. Song, F. Zhang, C. Li, W. Liu, B. Li, and Y. Huang Phenylethyne-bridged dyes for dye-sensitized solar cells J Phys Chem C 113 2009 13391 13397
45. C. Teng, X.C. Yang, C. Yang, S.F. Li, M. Cheng, and A. Hagfeldt Molecular design of anthracene-bridged metal-free organic dyes for efficient dye-sensitized solar cells J Phys Chem C 114 2010 9101 9110
46. S. Kim, J.K. Lee, S.O. Kang, J. Ko, J.H. Yum, and S. Fantacci Molecular engineering of organic sensitizers for solar cell applications J Am Chem Soc 128 2008 16701 16707
47. H. Choi, C. Baik, S.O. Kang, J. Ko, M.S. Kang, and M.K. Nazeeruddin Highly efficient and thermally stable organic sensitizers for solvent-free dye-sensitized solar cells Angew Chem Int Ed 47 2008 327 330
48. A. Baheti, P. Tyagi, K.R.J. Thomas, Y.C. Hsu, and J.T. Lin Simple triarylamine-based dyes containing fluorene and biphenyl linkers for efficient dye-sensitized solar cells J Phys Chem C 113 2009 8541 8547
49. A. Baheti, P. Singh, C.P. Lee, K.R.J. Thomas, and K.C. Ho 2,7-Diaminofluorene-based organic dyes for dye-sensitized solar cells: effect of auxiliary donor on optical and electrochemical properties J Org Chem 76 2011 4910 4920
50. K.R.J. Thomas, N. Kapoor, C.P. Lee, and K.C. Ho Organic dyes containing pyrenylamine-based cascade donor system with different aromatic π-linkers for dye-sensitized solar cells: optical, electrochemical and device characteristics Chem Asian J 7 2012 738 750
51. C.D. Andrade, C.O. Yanez, L. Rodriguez, and K.D. Belfield A series of fluorene-based two-photon absorbing molecules: synthesis, linear and nonlinear characterization, and bioimaging J Org Chem 75 2010 3975 3982
52. A.D. Becke A new mixing of Hartree-Fock and local density-functional theories J Chem Phys 98 1993 1372 1377
53. T. Yanai, D.P. Tew, and N.C. Handy A new hybrid exchange-correlation functional using the Coulomb-attenuating method (CAM-B3LYP) Chem Phys Lett 393 2004 51 57
54. K. Sonogashira, Y. Tohda, and N. Hagihara A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines Tetrahedron Lett 16 1975 4467 4470
55. E. Knoevenagel Chem Ber 29 1896 172
56. A. Baheti, P. Singh, and K.R.J. Thomas The synthesis and spectral characterization of red dyes containing biphenyl or fluorene conjugation and dicyanovinyl acceptors Dyes Pigm 88 2011 195 203
57. C.H. Chen, Y.C. Hsu, H.H. Chou, K.R.J. Thomas, J.T. Lin, and C.P. Hsu Dipolar compounds containing fluorene and a heteroaromatic ring as the conjugating bridge for high-performance dye-sensitized solar cells Chem Eur J 16 2010 3184 3193
58. C. Reichardt Solvatochromic dyes as solvent polarity indicator Chem Rev 94 1994 2319 2358
59. H.M. Ko, H. Choi, S. Paek, K. Kim, K. Song, and J.K. Lee Molecular engineering of push-pull chromophore for efficient bulkheterojunction morphology in solution processed small molecule organic photovoltaics J Mater Chem 21 2011 7248 7253
60. C.M. Cardona, W. Li, A.E. Kaifer, D. Stockdale, and G.C. Bazan Electrochemical considerations for determining absolute frontier orbital energy levels of conjugated polymers for solar cell applications Adv Mater 23 2011 2367 2371
61. P. Wang, S.M. Zakeeruddin, J.E. Moser, and M. Grätzel A new ionic liquid electrolyte enhances the conversion efficiency of dye-sensitized solar cells J Phys Chem B 107 2003 13280 13285
62. M. Grätzel Photoelectrochemical cells Nature 414 2001 338 344
63. 2 solar cells:a study by electrical impedance and optical modulation techniques J Phys Chem B 104 2000 2044 2052