It takes more than an imine: The role of the central atom on the electron-accepting ability of benzotriazole and benzothiadiazole oligomers

Journal of the American Chemical Society

Volumn 134, Issue 5, 2012, Pages 2599-2612

  Patel, Dinesh G ^a   Feng, Fude ^a   Ohnishi, Yu Ya ^a,b   Abboud, Khalil A ^a   Hirata, So ^a,b   Schanze, Kirk S ^a   Reynolds, John R ^a,c  

^a University of Florida   (United States)

^b UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^c GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 ,1 ,3-BENZOTHIADIAZOLE; ACCEPTOR MOIETIES; BENZOTHIADIAZOLES; BENZOTRIAZOLES; CENTRAL ATOM; ELECTRON ACCEPTOR; ELECTRON-ACCEPTING; ELECTRON-DEFICIENT; ELECTRON-DONATING; ELECTRON-DONATING ABILITY; HETEROCYCLIC RINGS; INTERSYSTEM CROSSING; PHOTOPHYSICAL; PHOTOPHYSICAL PROPERTIES; SINGLET OXYGEN; THIADIAZOLES; TRANSIENT ABSORPTION SPECTRA; TRIAZOLE RING; TRIPLET STATE; X RAY CRYSTAL STRUCTURES;

ELECTRONS; NITROGEN COMPOUNDS; ORGANIC COMPOUNDS; SULFUR;

OLIGOMERS;

BENZOTRIAZOLE DERIVATIVE; IMINE; OLIGOMER; THIADIAZOLE DERIVATIVE;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; ELECTROCHEMICAL ANALYSIS; ELECTRON TRANSPORT; MICHAEL ADDITION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION; X RAY CRYSTALLOGRAPHY;

ELECTRONS; IMINES; MOLECULAR STRUCTURE; QUANTUM THEORY; STEREOISOMERISM; THIADIAZOLES; TRIAZOLES;

EID: 84856759258     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja207978v     Document Type: Article

References (65)

1. Nazeeruddin, M. K.; Kay, A.; Rodicio, I.; Humphry-Baker, R.; Müller, E.; Liska, P.; Vlachopoulos, N.; Grätzel, M. J. Am. Chem. Soc. 1993, 115, 6382-6390.
2. Nazeeruddin, M. K.; Klein, C.; Liska, P.; Grätzel, M. Coord. Chem. Rev. 2005, 249, 1460-1467.
3. Nazeeruddin, M. K.; Péchy, P.; Renouard, T.; Zyss, J.; Humphry-Baker, R.; Comte, P.; Liska, P.; Cevey, L.; Costa, E.; Shklover, V.; Spicca, L.; Deacon, G. B.; Bignozzi, C. A.; Grätzel, M. J. Am. Chem. Soc. 2001, 123, 1613-1624.
4. Amb, C. M.; Chen, S.; Graham, K. R.; Subbiah, J.; Small, C. E.; So, F.; Reynolds, J. R. J. Am. Chem. Soc. 2011, 133, 10062-10065.
5. Chen, H. Y.; Hou, J. H.; Zhang, S. Q.; Liang, Y. Y.; Yang, G. W.; Yang, Y.; Yu, L. P.; Wu, Y.; Li, G. Nat. Photonics 2009, 3, 649-653.
6. Wang, E.; Ma, Z.; Zhang, Z.; Vandewal, K.; Henriksson, P.; Inganäs, O.; Zhang, F.; Andersson, M. R. J. Am. Chem. Soc. 2011, 133, 14244-14247.
7. Havinga, E. E.; Tenhoeve, W.; Wynberg, H. Synth. Met. 1993, 55, 299-306.
8. Roncali, J. Macromol. Rapid Commun. 2007, 28, 1761-1775.
9. Mishra, A.; Fischer, M. K. R.; Bauerle, P. Angew. Chem., Int. Ed. 2009, 48, 2474-2499.
10. Patel, D. G.; Bastianon, N. M.; Tongwa, P.; Leger, J. M.; Timofeeva, T. V.; Bartholomew, G. P. J. Mater. Chem. 2011, 21, 4242-4250.
11. Kira, A.; Matsubara, Y.; Iijima, H.; Umeyama, T.; Matano, Y.; Ito, S.; Niemi, M.; Tkachenko, N.; Lemmetyinen, H.; Imahori, H. J. Phys. Chem. C 2010, 114, 11293-11304.
12. Velusamy, M.; Thomas, K. R. J.; Lin, J. T.; Hsu, Y.-C.; Ho, K.-C. Org. Lett. 2005, 7, 1899-1902.
13. Balan, A.; Baran, D.; Gunbas, G.; Durmus, A.; Ozyurt, F.; Toppare, L. Chem. Commun. 2009, 44, 6768-6770.
14. Balan, A.; Gunbas, G.; Durmus, A.; Toppare, L. Chem. Mater. 2008, 20, 7510-7513.
15. Baran, D.; Balan, A.; Celebi, S.; Esteban, B. M.; Neugebauer, H.; Sariciftci, N. S.; Toppare, L. Chem. Mater. 2010, 22, 2978-2987.
16. Fang, Q.; Tanimoto, A.; Yamamoto, T. Synth. Met. 2005, 150, 73-78.
17. Peng, B.; Najari, A.; Liu, B.; Berrouard, P.; Gendron, D.; He, Y.; Zhou, K.; Leclerc, M.; Zou, Y. Macromol. Chem. Phys. 2010, 211, 2026-2033.
18. Tanimoto, A.; Yamamoto, T. Adv. Synth. Catal. 2004, 346, 1818-1823.
19. Tanimoto, A.; Yamamoto, T. Macromolecules 2006, 39, 3546-3552.
20. Tam, T. L.; Li, H.; Lam, Y. M.; Mhaisalkar, S. G.; Grimsdale, A. C. Org. Lett. 2011, 13, 4612-4615.
21. Cozzolino, A. F.; Gruhn, N. E.; Lichtenberger, D. L.; Vargas-Baca, I. Inorg. Chem. 2008, 47, 6220-6226.
22. Akbasoglu, N.; Balan, A.; Baran, D.; Cirpan, A.; Toppare, L. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 5603-5610.
23. Liu, L.; Hong, D.-J.; Lee, M. Langmuir 2009, 25, 5061-5067.
24. Liu, B. K.; Wu, Q.; Qian, X. Q.; Lv, D. S.; Lin, X. F. Synthesis 2007, 17, 2653-2659.
25. Katritzky, A. R.; Pastor, A.; Voronkov, M.; Tymoshenko, D. J. Comb. Chem. 2001, 3, 167-170.
26. Seitz, D. E.; Lee, S. H.; Hanson, R. N.; Bottaro, J. C. Synth. Commun. 1983, 13, 121-128.
27. Karikomi, M.; Kitamura, C.; Tanaka, S.; Yamashita, Y. J. Am. Chem. Soc. 1995, 117, 6791-6792.
28. Steckler, T. T.; Abboud, K. A.; Craps, M.; Rinzler, A. G.; Reynolds, J. R. Chem. Commun. 2007, 46, 4904-4906.
29. Wang, E. R.; Hou, L. T.; Wang, Z. Q.; Hellstrom, S.; Mammo, W.; Zhang, F. L.; Inganas, O.; Andersson, M. R. Org. Lett. 2010, 12, 4470-4473.
30. Perzon, E.; Zhang, F. L.; Andersson, M.; Mammo, W.; Inganas, O.; Andersson, M. R. Adv. Mater. 2007, 19, 3308-3311.
31. Salhi, F.; Lee, B.; Metz, C.; Bottomley, L. A.; Collard, D. M. Org. Lett. 2002, 4, 3195-3198.
32. Cramer, C. J. Essentials of Computational Chemistry: Theories and Models, 2nd ed.; Wiley: Chichester, West Sussex, England; Hoboken, NJ, 2004.
33. Audebert, P.; Sadki, S.; Miomandre, F.; Clavier, G.; Vernieres, M. C.; Saoud, M.; Hapiot, P. New J. Chem. 2004, 28, 387-392.
34. Zhang, G.; Musgrave, C. B. J. Phys. Chem. A 2007, 111, 1554-1561.
35. Price, S. C.; Stuart, A. C.; Yang, L.; Zhou, H.; You, W. J. Am. Chem. Soc. 2011, 133, 8057-8057.
36. Fraind, A. M.; Tovar, J. D. J. Phys. Chem. B 2010, 114, 3104-3116.
37. Pham, C. V.; Burkhardt, A.; Shabana, R.; Cunningham, D. D.; Mark, H. B.; Zimmer, H. Phosphorus, Sulfur Silicon Relat. Elem. 1989, 46, 153-168.
38. Rurack, K.; Spieles, M. Anal. Chem. 2011, 83, 1232-1242.
39. Guldi, D. M.; Luo, C. P.; Prato, M.; Dietel, E.; Hirsch, A. Chem. Commun. 2000, 5, 373-374.
40. Jayakannan, M.; Van Hal, P. A.; Janssen, R. A. J. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 251-261.
41. Kono, T.; Kumaki, D.; Nishida, J.; Tokito, S.; Yamashita, Y. Chem. Commun. 2010, 46, 3265-3267.
42. Bard, A. J.; Faulkner, L. R. Electrochemical Methods: Fundamentals and Applications, 2nd ed.; Wiley: New York, 2001; p xxi, 833 p.
43. Cardona, C. M.; Li, W.; Kaifer, A. E.; Stockdale, D.; Bazan, G. C. Adv. Mater. 2011, 23, 2367-2371.
44. Thompson, B. Variable Band Gap Poly(3,4-alkylenedioxythiophene)-Based Polymers for Photovoltaic and Electrochromic Applications. Ph.D. Dissertation, University of Florida, Gainesvlle, FL, 2005.
45. Casado, J.; Zgierski, M. Z.; Ewbank, P. C.; Burand, M. W.; Janzen, D. E.; Mann, K. R.; Pappenfus, T. M.; Berlin, A.; Perez-Inestrosa, E.; Ortiz, R. P.; Navarrete, J. T. L. J. Am. Chem. Soc. 2006, 128, 10134-10144.
46. Peart, P. A.; Tovar, J. D. Org. Lett. 2007, 9, 3041-3044.
47. Kitamura, C.; Tanaka, S.; Yamashita, Y. Chem. Mater. 1996, 8, 570-578.
48. Akhtaruzzaman, M.; Kamata, N.; Nishida, J.; Ando, S.; Tada, H.; Tomura, M.; Yamashita, Y. Chem. Commun. 2005, 25, 3183-3185.
49. Akhtaruzzaman, M.; Tomura, M.; Nishida, J.; Yamashita, Y. J. Org. Chem. 2004, 69, 2953-2958.
50. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, S1-S19.
51. Ono, K.; Tanaka, S.; Yamashita, Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 1977-1979.
52. Wang, M. F.; Sun, Y. M.; Tong, M. H.; Chesnut, E. S.; Seo, J. H.; Kumar, R.; Wudl, F. J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 441-451.
53. Wang, M. F.; Wudl, F. J. Mater. Chem. 2010, 20, 5659-5663.
54. Salzner, U.; Karalti, O.; Durdagi, S. J. Mol. Model. 2006, 12, 687-701.
55. Leusser, D.; Henn, J.; Kocher, N.; Engels, B.; Stalke, D. J. Am. Chem. Soc. 2004, 126, 1781-1793.
56. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899-926.
57. Walters, K. A.; Ley, K. D.; Cavalaheiro, C. S. P.; Miller, S. E.; Gosztola, D.; Wasielewski, M. R.; Bussandri, A. P.; van Willigen, H.; Schanze, K. S. J. Am. Chem. Soc. 2001, 123, 8329-8342.
58. Caspar, J. V.; Meyer, T. J. J. Phys. Chem. 1983, 87, 952-957.
59. Henry, B. R.; Siebrand, W. In Organic Molecular Photophysics; Birks, J. B., Ed.; J. Wiley: New York, 1973.
60. de Melo, J. S.; Silva, L. M.; Arnaut, L. G.; Becker, R. S. J. Chem. Phys. 1999, 111, 5427-5433.
61. Zhou, Z.; Corbitt, T. S.; Parthasarathy, A.; Tang, Y.; Ista, L. F.; Schanze, K. S.; Whitten, D. G. J. Phys. Chem. Lett. 2010, 1, 3207-3212.
62. Karsten, B. P.; Bijleveld, J. C.; Viani, L.; Cornil, J.; Gierschner, J.; Janssen, R. A. J. J. Mater. Chem. 2009, 19, 5343-5350.
63. Dempster, D. N.; Thompson, G. F.; Morrow, T.; Rankin, R. J. Chem. Soc., Faraday Trans. 1972, 68, 1479-1496.
64. Wilkinson, F.; Helman, W. P.; Ross, A. B. J. Phys. Chem. Ref. Data 1993, 22, 113-262.
65. Burrows, H. D.; de Melo, J. S.; Serpa, C.; Arnaut, L. G.; Monkman, A. P.; Hamblett, I.; Navaratnam, S. J. Chem. Phys. 2001, 115, 9601-9606.