Organic dyes containing indolo[2,3-b]quinoxaline as a donor: Synthesis, optical and photovoltaic properties

Tetrahedron

Volumn 70, Issue 36, 2014, Pages 6318-6327

  Venkateswararao, A ^a   Tyagi, Payal ^a   Justin Thomas, K R ^a   Chen, Ping Wei ^b   Ho, Kuo Chuan ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY ROORKEE   (India)

^b NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

Dye sensitized solar cells; Indolo 2,3 b quinoxaline; Optical properties; Organic semiconductors; TDDFT computations

Indexed keywords

ACETONITRILE; CYANOACRYLATE; DICHLOROMETHANE; DIMETHYL SULFOXIDE; DYE; ELECTROLYTE; INDOLO[2,3 B]QUINOXALINE; ORGANIC DYE; QUINOXALINE DERIVATIVE; TERT BUTYL ALCOHOL; THIOPHENE; TITANIUM DIOXIDE; UNCLASSIFIED DRUG;

ABSORPTION; AQUEOUS SOLUTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONJUGATION; DYE SENSITIZED SOLAR CELL; ELECTRIC POTENTIAL; ELECTROCHEMICAL ANALYSIS; ELECTRON; OPTICS; PHASE TRANSITION; PHOTOCHEMISTRY; PHOTOVOLTAIC PROPERTY; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; REGENERATIVE ABILITY; SENSITIZATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 84925875870     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.04.009     Document Type: Article

References (84)

1. B. O'Regan, and M. Grätzel Nature 353 1991 737
2. M. Grätzel Acc. Chem. Res. 42 2009 1788
3. A. Hagfeldt, G. Boschloo, L. Sun, L. Kloo, and H. Pettersson Chem. Rev. 110 2010 6595
4. M.K. Nazeeruddin, A. Kay, I. Rodicio, R. Humphry-Baker, E. Müller, P. Liska, N. Vlachopoulos, and M. Grätzel J. Am. Chem. Soc. 115 1993 6382
5. A. Mishra, M.K.R. Fischer, and P. Bäuerle Angew. Chem., Int. Ed. 48 2009 2474
6. W. Zeng, Y. Cao, Y. Bai, Y. Wang, Y. Shi, M. Zhang, F. Wang, C. Pan, and P. Wang Chem. Mater. 22 2010 1915
7. F. Labat, T.L. Bahers, I. Ciofini, and C. Adamo Acc. Chem. Res. 45 2012 1268
8. M. Liang, and J. Chen Chem. Soc. Rev. 42 2013 3453
9. Y. Ooyama, and Y. Harima ChemPhysChem 13 2012 4032
10. Z. Ning, and H. Tian Chem. Commun. 2009 5483
11. T. Horiuchi, H. Miura, K. Sumioka, and S. Uchida Chem. Commun. 2003 3036
12. T. Horiuchi, H. Miura, K. Sumioka, and S. Uchida J. Am. Chem. Soc. 126 2004 12218
13. B. Liu, Q. Liu, D. You, X. Li, Y. Naruta, and W. Zhu J. Mater. Chem. 22 2012 13348
14. Y. Wu, M. Marszalek, S.M. Zakeeruddin, Q. Zhang, H. Tian, M. Grätzel, and W. Zhu Energy Environ. Sci. 5 2012 8261
15. T. Khanasa, N. Jantasing, S. Morada, N. Leesakul, R. Tarsang, S. Namuangruk, T. Kaewin, S. Jungsuttiwong, T. Sudyoadsuk, and V. Promarak Eur. J. Org. Chem. 2013 2608
16. Y. Ooyama, N. Yamaguchi, I. Imae, K. Komaguchi, J. Ohshita, and Y. Harima Chem. Commun. 2013 2548
17. A. Venkateswararao, K.R.J. Thomas, C.-P. Lee, and K.-C. Ho Tetrahedron Lett. 54 2013 3985
18. Y. Ooyama, S. Inoue, T. Nagano, K. Kushimoto, J. Ohshita, I. Imae, K. Komaguchi, and Y. Harima Angew. Chem., Int. Ed. 50 2011 7429
19. A. Venkateswararao, K.R.J. Thomas, C.-P. Lee, C.-T. Li, and K.-C. Ho ACS Appl. Mater. Interfaces 6 2014 2528
20. A. Venkateswararao, and K.R.J. Thomas A. Tiwari, R. Boukherroub, M. Sharon, Solar Cell Nanotechnology 2014 Scrivener Publishing LLC Massachusetts, USA 41 96 Chapter 2
21. S. Cai, G. Tian, X. Li, J. Su, and H. Tian J. Mater. Chem. A 1 2014 11295
22. X. Chen, C. Jia, Z. Wan, and X. Yao Dyes Pigm. 104 2014 48
23. L. Zhou, C. Jia, Z. Wan, X. Chen, and X. Yao Org. Electron. 14 2013 1755
24. M. Velusamy, Y.-C. Hsu, J.T. Lin, C.-W. Chang, and C.-P. Hsu Chem. - Asian J. 5 2010 87
25. D. Kumar, K.R.J. Thomas, C.P. Lee, and K.C. Ho Org. Lett. 13 2011 2622
26. M. Velusamy, K.R.J. Thomas, J.T. Lin, Y.-C. Hsu, and K.-C. Ho Org. Lett. 7 2005 1899
27. H. Zhu, W. Li, Y. Wu, B. Liu, S. Zhu, X. Li, H. Ågren, and W. Zhu ACS Sustainable Chem. Eng. 2 2014 1026
28. W. Li, C. Du, F. Li, Y. Zhou, M. Fahlman, Z. Bo, and F. Zhang Chem. Mater. 21 2009 5327
29. X. Chen, G.L. Schulz, X. Han, Z. Zhou, and S. Holdcroft J. Phys. Chem. C 113 2009 8505
30. B.P. Karsten, J.C. Bijleveld, L. Viani, J. Cornil, J. Gierschner, and R.A.J. Janssen J. Mater. Chem. 19 2009 5343
31. S. Steinberger, A. Mishra, E. Reinold, E. Mena-Osteritz, H. Müller, C. Uhrich, M. Pfeiffer, and P. Bäuerle J. Mater. Chem. 22 2012 2701
32. Y.-J. Hwang, F.S. Kim, H. Xin, and S.A. Jenekhe Macromolecules 45 2012 3732
33. G.C. Welch, and G.C. Bazan J. Am. Chem. Soc. 133 2011 4632
34. M.E. Köse J. Phys. Chem. A 116 2012 12503
35. N. Blouin, A. Michaud, D. Gendron, S. Wakim, E. Blair, R. Neagu-Plesu, M. Belletête, G. Durocher, Y. Tao, and M. Leclerc J. Am. Chem. Soc. 130 2008 732
36. X. Liu, Y. Sun, L.A. Perez, W. Wen, M.F. Toney, A.J. Heeger, and G.C. Bazan J. Am. Chem. Soc. 134 2012 20609
37. S.Y. Qu, W.J. Wu, J.L. Hua, C. Kong, Y.T. Long, and H. Tian J. Phys. Chem. C 114 2010 1343
38. S.Y. Qu, B. Wang, F.L. Guo, J. Li, W.J. Wu, C. Kong, Y.T. Long, and J.L. Hua Dyes Pigm. 92 2012 1384
39. S.Y. Qu, C.J. Qin, A. Islam, Y.Z. Wu, W.H. Zhu, J.L. Hua, H. Tian, and L.Y. Han Chem. Commun. 2012 6972
40. H. Tan, X. Deng, J. Yu, B. Zhao, Y. Wang, Y. Liu, W. Zhu, H. Wu, and Y. Cao Macromolecules 46 2013 113
41. S. Loser, C.J. Bruns, H. Miyauchi, R.P. Ortiz, A. Facchetti, S.I. Stupp, and T.J. Marks J. Am. Chem. Soc. 133 2011 8142
42. D.W. Chang, H.J. Lee, J.H. Kim, S.Y. Park, S.-M. Park, L. Dai, and J.-B. Baek Org. Lett. 13 2011 3880
43. T. Kono, T.N. Murakami, J. Nishida, Y. Yoshida, K. Hara, and Y. Yamashita Org. Electron. 13 2012 3097
44. K. Pei, Y. Wu, A. Islam, Q. Zhang, L. Han, H. Tian, and W. Zhu ACS Appl. Mater. Interfaces 5 2013 4986
45. X. Lu, Q. Feng, T. Lan, G. Zhou, and Z.-S. Wang Chem. Mater. 24 2012 317
46. S.-R. Li, C.-P. Lee, H.-T. Kuo, K.-C. Ho, and S.-S. Sun Chem. - Eur. J. 18 2012 12085
47. J. Shi, Z. Chai, J. Su, J. Chen, R. Tang, K. Fan, L. Zhang, H. Han, J. Qin, T. Peng, Q. Li, and Z. Li Dyes Pigm. 98 2013 405
48. J. Shi, J. Chen, Z. Chai, H. Wang, R. Tang, K. Fan, M. Wu, H. Han, J. Qin, T. Peng, Q. Li, and Z. Li J. Mater. Chem. 22 2012 18830
49. K. Pei, Y. Wu, A. Islam, S. Zhu, L. Han, Z. Geng, and W. Zhu J. Phys. Chem. C 2014 10.1021/jp412259t
50. X. Lu, X. Jia, Z.-S. Wang, and G. Zhou J. Mater. Chem. A 1 2013 9697
51. W. Ying, J. Yang, M. Wielopolski, T. Moehl, J.-E. Moser, P. Comte, J. Hua, S.M. Zakeeruddin, H. Tian, and M. Grätzel Chem. Sci. 5 2014 206
52. K.R.J. Thomas, J.T. Lin, Y.-T. Tao, and C.-H. Chuen Chem. Mater. 14 2002 2796
53. K.R.J. Thomas, M. Velusamy, J.T. Lin, C.-H. Chuen, and Y.-T. Tao Chem. Mater. 17 2005 1860
54. J.F. Wang, Y. Kawabe, S.E. Shaheen, M.M. Morrell, G.E. Jabbour, P.A. Lee, J. Anderson, N.R. Armstrong, B. Kippelen, E.A. Mash, and N. Peyghambarian Adv. Mater. 10 1998 230
55. D. O'Brien, M.S. Weaver, D.G. Lidzey, and D.D.C. Bradley Appl. Phys. Lett. 69 1996 881
56. T. Yamamoto, K. Sugiyama, T. Kushida, T. Inoue, and T. Kanbara J. Am. Chem. Soc. 118 1996 3930
57. C. Schmitz, P. Pösch, M. Thelakkat, H.-W. Schmidt, A. Montali, K. Feldman, P. Smith, and C. Weder Adv. Funct. Mater. 11 2001 41
58. S. Eu, S. Hayashi, T. Umeyama, Y. Matano, Y. Araki, and H. Imahori J. Phys. Chem. C 112 2008 4396
59. M.-S. Tsai, Y.-C. Hsu, J.T. Lin, H.-C. Chen, and C.-P. Hsu J. Phys. Chem. C 111 2007 18785
60. K.R.J. Thomas, and P. Tyagi J. Org. Chem. 75 2010 8100
61. P. Tyagi, A. Venkateswararao, and K.R.J. Thomas J. Org. Chem. 76 2011 4571
62. J.K. Stille Angew. Chem., Int. Ed. Engl. 25 1986 508
63. R. Chinchilla, and C. Nájera Chem. Rev. 107 2007 874
64. K. Sonogashira, Y. Tohda, and N. Hagihara Tetrahedron Lett. 16 1975 4467
65. E. Knoevenagel Chem. Ber. 29 1896 172
66. O. van den Berg, W.F. Jager, and S.J. Picken J. Org. Chem. 71 2006 2666
67. A. Granzhan, H. Ihmels, and G. Viola J. Am. Chem. Soc. 129 2007 1254
68. K.R.J. Thomas, Y.-C. Hsu, J.T. Lin, K.-M. Lee, K.-C. Ho, C.-H. Lai, Y.-M. Cheng, and P.-T. Chou Chem. Mater. 20 2008 1830
69. A. Baheti, P. Tyagi, K.R.J. Thomas, Y.-C. Hsu, and J.T. Lin J. Phys. Chem. C 113 2009 8541
70. M.K. Nazeeruddin, P. Péchy, T. Renouard, S.M. Zakeeruddin, R. Humphry-Baker, P. Comte, P. Liska, L. Cevey, E. Costa, V. Shklover, L. Spiccia, G.B. Deacon, C.A. Bignozzi, and M. Grätzel J. Am. Chem. Soc. 123 2001 1613
71. M.K. Nazeeruddin, S.M. Zakeeruddin, R. Humphry-Baker, M. Jirousek, P. Liska, N. Vlachopoulos, V. Shklover, C.H. Fisher, and M. Grätzel Inorg. Chem. 38 1999 6298
72. K. Sayama, S. Tsukagoshi, K. Hara, Y. Ohga, A. Shinpou, Y. Abe, S. Suga, and H. Arakawa J. Phys. Chem. B 106 2002 1363
73. C. Teng, X. Yang, C. Yang, H. Tian, S. Li, X. Wang, A. Hagfeldt, and L. Sun J. Phys. Chem. C 114 2010 11305
74. Y.-D. Lin, C.-T. Chien, S.-Y. Lin, H.-H. Chang, C.-Y. Liu, and T.J. Chow J. Photochem. Photobiol., A 222 2011 192
75. P. Singh, A. Baheti, K.R.J. Thomas, C.-P. Lee, and K.-C. Ho Dyes Pigm. 95 2012 523
76. M. Grätzel Nature 414 2001 338
77. A. Hagfeldt, and M. Grätzel Chem. Rev. 95 1995 49
78. R.G. Parr, and W. Yang Annu. Rev. Phys. Chem. 46 1995 701
79. B.J. Lynch, P.L. Fast, M. Harris, and D.G. Truhlar J. Phys. Chem. A 104 2000 4811
80. H. Tian, X. Yang, R. Chen, R. Zhang, A. Hagfeldt, and L. Sun J. Phys. Chem. C 112 2008 11023
81. E. Palomares, L. Otero, D. Kuang, S.M. Zakeeruddin, and M. Grätzel J. Phys. Chem. C 111 2007 6550
82. J.A. Anta, F. Casanueva, and G. Oskam J. Phys. Chem. B 110 2006 5372
83. I. Mora-Seró, S. Giménez, F. Fabregat-Santiago, R. Gòmez, Q. Shen, T. Toyoda, and J. Bisquert Acc. Chem. Res. 41 2009 1848
84. J. van de Lagemaat, N.-G. Park, and A.J. Frank J. Phys. Chem. B 104 2000 2044