Synthesis, spectral and electrochemical properties of pyrimidine-containing dyes as photosensitizers for dye-sensitized solar cells

Dyes and Pigments

Volumn 100, Issue 1, 2014, Pages 201-214

  Verbitskiy, Egor V ^a   Cheprakova, Ekaterina M ^a   Subbotina, Julia O ^a,b   Schepochkin, Aleksandr V ^a   Slepukhin, Pavel A ^a   Rusinov, Gennady L ^a,b   Charushin, Valery N ^a,b   Chupakhin, Oleg N ^a,b   Makarova, Nadezhda I ^c   Metelitsa, Anatoly V ^c   Minkin, Vladimir I ^c,d  

^a INSTITUTE OF ORGANIC SYNTHESIS   (Russian Federation)

^b URAL FEDERAL UNIVERSITY   (Russian Federation)

^c SOUTHERN FEDERAL UNIVERSITY   (Russian Federation)

^d SOUTHERN SCIENTIFIC CENTER   (Russian Federation)

Author keywords

Carbazole; Dye sensitized solar cells; Nucleophilic aromatic substitution of hydrogen; Pyrimidine; Solvatochromism; Triphenylamine

Indexed keywords

CARBAZOLE; DYE-SENSITIZED SOLAR CELL; NUCLEOPHILIC AROMATIC SUBSTITUTION; PYRIMIDINE; SOLVATOCHROMISMS; TRIPHENYL AMINES;

AROMATIC COMPOUNDS; ELECTROCHEMICAL PROPERTIES; HYDROGEN; PHOTOELECTROCHEMICAL CELLS; PHOTOSENSITIZERS; TITANIUM DIOXIDE;

SOLAR CELLS;

EID: 84884760530     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2013.09.006     Document Type: Article

References (66)

1. M. Thelakkat, C. Schmitz, C. Hohle, P. Strohriegl, H.-W. Schmidt, and U. Hofmann Novel functional materials based on triarylamines - synthesis and application in electroluminescent devices and photorefractive systems Phys Chem Chem Phys 1 1999 1693 1698
2. S.-L. Lin, L.-H. Chan, R.-H. Lee, M.-Y. Yen, W.-J. Kuo, and C.-T. Chen Highly efficient carbazole-π-dimesitylborane bipolar fluorophores for nondoped blue organic light-emitting diodes Adv Mater 20 2008 3947 3952
3. P. Jiang, D.-D. Zhao, X.-L. Yang, X.-L. Zhu, J. Chang, and H.-J. Zhu Blue-light-emitting multifunctional triphenylamine-centred starburst quinolines: synthesis, electrochemical and photophysical properties Org Biomol Chem 10 2012 4704 4711
4. J. Kwak, Y.-Y. Lyu, H. Lee, B. Choi, K. Char, and C. Lee New carbazole-based host martial for low-voltage and highly efficient red phosphorescent organic light-emitting diodes J Mater Chem 22 2012 6351 6355
5. R.J. Mortimer Electrochromic materials Chem Soc Rev 26 1997 147 156 (Pubitemid 127097197)
6. A. Hagfelft, G. Boschloo, L. Kloo, and H. Pettersson Dye-sensitized solar cells Chem Rev 110 2010 6595 6663
7. J. Baldenebro-López, J. Castorena-González, N. Flores-Holguín, J. Almaral-Sánchez, and D. Glossman-Mitnik Density functional theory (DFT) study of triphenylamine-based dyes for their use as sensitizers in molecular photovoltaics Int J Mol Sci 13 2012 4418 4432
8. C. Sakong, H.J. Kim, S.H. Kim, J.W. Namgoong, J.H. Park, and J.-H. Ryu Synthesis and application of new triphenylamine dyes with donor-donor-(bridge)- acceptor structure for organic dye-sensitized solar cells New J Chem 36 2012 2025 2032
9. Y. Lin, Y. Li, and X. Zhan Small molecule semiconductors for high-efficiency organic photovoltaics Chem Soc Rev 41 2012 4245 4272
10. A. Mishra, and P. Bäuerle Small organic molecule semiconductors on the move: promises for future solar energy technology Angew Chem Int Ed 51 2012 2020 2067
11. R.K. Kanaparthi, J. Kandhdi, and L. Giribabu Metal-free organic dyes for dye-sensitized solar cells: recent advances Tetrahedron 68 2012 8383 8393
12. N. Koumura, and K. Hara Development of carbazole dyes for efficient molecular photovoltaics Heterocycles 87 2013 275 301
13. M.-D. Zhang, H.-X. Xie, X.-H. Ju, Qin, Q.-X. Yang, and H.-G. Zheng D-D-π-A organic dyes containing 4,4′-di(2-thyenyl)-triphenylamine moiety for efficient dye-sensitized solar cells Phys Chem Chem Phys 15 2013 634 641
14. M. Liangw, and J. Chen Arylamine organic dyes for dye-sensitized solar cells Chem Soc Rev 42 2013 3453 3488
15. Y. Song, C. Di, W. Xu, Y. Liu, D. Zhang, and D. Zhu New semiconductors based on triphenylamine with macrocyclic architecture: synthesis, properties and applications in OFETs J Mater Chem 17 2007 4483 4491 (Pubitemid 47628746)
16. S. Allard, M. Forster, B. Souharce, H. Thiem, and U. Scherf Organic semiconductors for solution-processable field-effect transistors (OFETs) Angew Chem Int Ed 47 2008 4070 4098
17. C. Wang, H. Dong, W. Hu, Y. Liu, and D. Zhu Semiconducting π-conjugated systems in field-effect transistors: a material odyssey of organic electronics Chem Rev 112 2012 2208 2267
18. R.R. King, D.C. Law, K.M. Edmondson, C.M. Fetzer, G.S. Kinsey, and H. Yoon Advances in high-efficiency III-V multijunction solar cells Adv Optoelectron 2007 Article ID 29523
19. C.R. Zhang, Z.J. Liu, Y.H. Chen, H.S. Chen, Y.Z. Wu, and L.H. Yuan DFT and TDDFT study on organic dye sensitizers D5, DST and DSS for solar cells J Mol Struct THEOCHEM 899 2009 86 93
20. H.W. Ham, and Y.S. Kim Theoretical study of indoline dyes for dye-sensitized solar cells Thin Solid Films 518 2010 6558 6563
21. C.-R. Zhang, Z.-J. Liu, Y.-H. Chen, H.-S. Chen, Y.-Z. Wu, and W. Feng DFT and TD-DFT study on structure and properties of organic dye sensitizer TA-St-CA Curr Appl Phys 10 2010 77 83
22. W.-L. Ding, D.-M. Wang, Z.-Y. Geng, X.-L. Zhao, and W.-B. Xu Density functional theory characterization and verification of high-performance indoline dyes with D-A-π-A architecture for dye-sensitized solar cells Dyes Pigm 98 2013 125 135
23. W. Sang-aroon, S. Saekow, and V. Amornkitbamrung Density functional theory study on the electronic structure of Monascus dyes as photosensitizer for dye-sensitized solar cells J Photochem Photobiol A: Chem 236 2012 35 40
24. S. Cai, X. Hu, J. Han, Z. Zhang, X. Li, and C. Wang Efficient organic dyes containing dibenzo heterocycles as conjugated linker part for dye-sensitized solar cells Tetrahedron 69 2013 1970 1977
25. Z. Ci, X. Yu, M. Bao, C. Wang, and T. Ma Influence of the benzo[d]thiazole-derived π-bridges on the optical and photovoltaic performance of D-π-A dyes Dyes Pigm 96 2013 619 625
26. Y.J. Chang, and T.J. Chow Dye-sensitized solar cell utilizing organic dyads containing triarylene conjugates Tetrahedron 65 2009 4726 4734
27. T. Khanasa, N. Jantasing, S. Morada, N. Leesakul, R. Tarsang, and S. Namuangruk Synthesis and characterization of 2D-D-π-A-type organic dyes bearing bis(3,6-di-tert-butylcarbazol-9-ylphenyl)aniline as donor moiety for dye-sensitized solar cells Eur J Org Chem 2013 2608 2620
28. S. Tamba, R. Fujii, A. Mori, K. Hara, and N. Koumura Synthesis and properties of seleno-analog MK-organic dye for photovoltaic cells prepared by CH functionalization reactions of selenophene derivatives Chem Lett 40 2011 922 924
29. Y. Ooyama, T. Nagano, S. Inoue, I. Imae, K. Komaguchi, and J. Ohshita Dye-sensitized solar cells based on donor-π-acceptor fluorescent dyes with a pyridine ring as an electron-withdrawing-injecting anchoring group Chem Eur J 17 2011 14837 14843
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. Y. Ooyama, and Y. Harima Photophysical and electrochemical properties, and molecular structures of organic dyes for dye-sensitized solar cells Chem Phys Chem 13 2012 4032 4080
32. Y. Ooyama, N. Yamaguchi, I. Imae, K. Komaguchi, J. Ohshita, and Y. Harima Dye-sensitized solar cells based on D-π-A fluorescent dyes with two pyridyl groups as an electronwithdrawing-injecting anchoring group Chem Commun 49 2013 2548 2550
33. 2 surface for adsorption of organic dye having pyridyl group as anchoring unit J Phys Chem C 117 2013 16364 16370
34. J. Lu, X. Xu, Z. Li, K. Cao, J. Cui, and Y. Zhang Zinc porphyrins with a pyridine-ring-anchoring group for dye-sensitized solar cells Chem Asian J 8 2013 956 962
35. Y. Ooyama, Y. Hagiwara, T. Mizumo, Y. Harima, and J. Ohshita Photovoltaic performance of dye-sensitized solar cells based on D-π-A type BODIPY dye with two pyridyl groups New J Chem 37 2013 2479 2485
36. R. Gompper, H.-J. Mair, and K. Polborn Synthesis of oligo(diazaphenyls). Tailor-made fluorescent heteroaromatics and pathways to nanostructures Synthesis 1997 696 708
37. T. Kanbara, T. Kushida, N. Saito, I. Kuwajima, K. Kubota, and T. Yamamoto Preparation and properties of highly electron-accepting poly(pyrimidine2,5- diyl) Chem Lett 1992 583 586
38. K.-T. Wong, T.-S. Hung, Y. Lin, C.-C. Wu, G.-H. Lee, and S.-M. Peng Suzuki coupling approach for the synthesis of phenylene-pyrimidine alternating oligomers for blue light-emitting material Org Lett 4 2002 513 516
39. S. Achelle, Y. Ramodenc, F. Marsais, and N. Ple Star- and banana-shaped oligomers with a pyrimidine core: synthesis and light-emitting properties Eur J Org Chem 2008 3129 3140
40. R.P. Ortiz, J. Casado, V. Hernández, J.T. López Navarrete, J.A. Letizia, and M.A. Ratner Thiophene-diazine molecular semiconductors: synthesis, structural, electrochemical, optical, and electronic structural properties; implementation in organic field-effect transistors Chem Eur J 15 2009 5023 5039
41. T. Kojima, J. Nishida, S. Tokito, and Y. Yamashita New n-type field-effect transistors based on pyrimidine-containing compounds with (trifluoromethyl)phenyl groups Chem Lett 38 2009 428 429
42. Ling Q, Huang W, Mei Q, Weng J. Preparation of 4-(hetero)-arylpyrimidins compounds as luminescent materials. Patent CN102206207; 2011.
43. 2+ based on 4-pyren-1-yl-pyrimidine Tetrahedron 68 2012 3129 3134
44. O.N. Chupakhin, V.N. Charushin, and H.C. van der Plas Nucleophilic aromatic substitution of hydrogen 1994 Academic Press San Diego, New York
45. H methodology anew approach to condensed hetrocyclic systems Pure Appl Chem 76 2004 1621 1631
46. V.N. Charushin, and O.N. Chupakhin Nucleophilic aromatic substitution of hydrogen and related reactions Mendeleev Commun 17 2007 249 254
47. M. Makosza, and K. Wojciechowski Nucleophilic substitution of hydrogen in heterocyclic chemistry Chem Rev 104 2004 2631 2666
48. M. Makosza Nucleophilic substitution of hydrogen in electron-deficient arenes, a general process of great practical value Chem Soc Rev 39 2010 2855 2868
49. G.M. Sheldrick SHELXTL, Version 5.1 1998 Bruker Analytical X-ray Instruments Inc. Madison, WI
50. G.M. Sheldrick SHELXL-97, PC Version 1997 University of Gottingen Gottingen, Germany
51. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, and J.R. Cheeseman The molecular orbital calculation was carried out using the Gaussian 09, Revision C.01 2009 Fox DJ. Gaussian Wallingford CT
52. D. Jacquemin, E. Brémond, A. Planchat, I. Ciofini, and C. Adamo TD-DFT vibronic couplings in anthraquinones: from basis set and functional benchmarks to applications for industrial dyes J Chem Theory Comput 7 2011 1882 1892
53. A. Charaf-Eddin, A. Planchat, B. Mennucci, C. Adamo, and D. Jacquemin Choosing a functional for computing absorption and fluorescence band shapes with TD-DFT J Chem Theory Comput 9 2013 2749 2760
54. A.D. Laurent, and D. Jacquemin TD-DFT benchmarks: a review Int J Quantum Chem 113 2013 2019 2039
55. D. Jacquemin, E.A. Perpète, G.E. Scuseria, I. Ciofini, and C. Adamo TD-DFT performance for the visible absorption spectra of organic dyes: conventional versus long-range hybrids J Chem Theory Comput 4 2008 123 135
56. H) reactions as a versatile route to pyrimidines bearing thiophene fragments Tetrahedron 68 2012 5445 5452
57. D.P. Hagberg, T. Marinado, K.M. Karlsson, K. Nonomura, P. Qin, and G. Boschloo Tuninig the HOMO and LUMO energy levels of organic chromophores for dye sensitized solar cells J Org Chem 72 2007 9550 9556 (Pubitemid 350231800)
58. C.-K. Tai, Y.-J. Chen, H.-W. Chang, P.-L. Yeh, and B.-C. Wang DFT and TD - DFT investigation of metal free dye sensitizers for solar cells: effects of electron donors and π-conjugated linker Comput Theor Chem 971 2011 42 50
59. H and Suzuki-Miyaura cross-coupling reactions - an efficient synthetic strategy to pyrimidines bearing pyrroles and indole fragments Eur J Org Chem 2012 6612 6621
60. H) in 5-bromopyrimidine by action of bithiophene and its analogues Tetrahedron 69 2013 5164 5172
61. Y. Ooyama, Y. Oda, T. Mizumo, and J. Ohshita Specific solvatochromism of D-π-A type pyridinium dyes bearing various counter anions in halogenated solvents Tetrahedron 69 2013 1755 1760
62. J.A. Barltrop, and J.D. Coyle Excited states in organic chemistry 1975 Wiley London, New York 376
63. 13C NMR and quantum chemical NMR shift calculations J Phys Chem A 105 2001 6780 6784 (Pubitemid 35378060)
64. N.J. Turro Modern molecular photochemistry 1991 University Science Books Sausalito, CA 628
65. J. Michl, and V. Bonacic-Koutecký Electronic aspects of organic photochemistry 1991 Wiley-Interscience New York 475
66. 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.