The molecular structures and electrochemical response of "twisted" tetra(aryl)benzidenes

Journal of Materials Chemistry

Volumn 14, Issue 16, 2004, Pages 2516-2523

  Low, Paul J ^a   Paterson, Michael A J ^a   Goeta, Andrés E ^a   Yufit, Dmitry S ^a   Howard, Judith A K ^a   Cherryman, Julian C ^b   Tackley, Daniel R ^b   Brown, Bev ^b  

^a DURHAM UNIVERSITY   (United Kingdom)

^b Avecia Biologics Limited   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROCHEMISTRY; MOLECULAR STRUCTURE; OLIGOMERS; OXIDATION; THERMODYNAMIC STABILITY; ULTRAVIOLET SPECTROSCOPY;

ELECTRON OXIDATIONS; ELECTRONIC SPECTROSCOPY; SPECTROELECTROCHEMISTRY;

AROMATIC COMPOUNDS;

AROMATIC AMINE; BENZIDINE DERIVATIVE; BIPHENYL DERIVATIVE; CATION; DIAMINE DERIVATIVE; METHYL GROUP; N,N,N',N' TETRAKIS(4 METHYLPHENYL)(1,1' BIPHENYL) 4,4' DIAMINE; N,N,N',N' TETRAKIS(4 METHYLPHENYL)(2,2' DIMETHYL)(1,1' BIPHENYL) 4,4' DIAMINE; N,N,N',N' TETRAKIS(4 METHYLPHENYL)(2,2',6,6' TETRAMETHYL)(1,1' BIPHENYL) 4,4' DIAMINE; N,N,N',N' TETRAPHENYL (2,2' DIMETHYL)(1,1' BIPHENYL) 4,4' DIAMINE; N,N,N',N' TETRAPHENYL (2,2',6,6' TETRAMETHYL)(1,1' BIPHENYL) 4,4' DIAMINE; PHENYL GROUP; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; ELECTROCHEMISTRY; ELECTRON; MOLECULAR STABILITY; OLIGOMERIZATION; OXIDATION; OXIDATION REDUCTION POTENTIAL; POLYMERIZATION; STRUCTURE ANALYSIS; TECHNIQUE; THERMODYNAMICS; ULTRAVIOLET SPECTROSCOPY;

EID: 4744375979     PISSN: 09599428     EISSN: None     Source Type: Journal    
DOI: 10.1039/b404731a     Document Type: Article

References (41)

1. (a) U. Mitschke and P. Bäuerle, J. Mater. Chem., 2000, 10, 1471;
2. (b) P. M. Borsenberger and D. S. Weiss, Organic Photoreceptors for Xerography, Marcel Dekker, New York, 1998;
3. (c) D. M. Pai and B. E. Springett, Rev. Mod. Phys., 1993, 65, 163;
4. (d) M. Strukelj, J. Am. Chem. Soc., 1996, 118, 1213;
5. (e) J. Kalinaswki, Appl. Phys. Lett., 1996, 118, 2317.
6. J. Cornil, D. Beljonne, J. P. Calbert and J. L. Bredas, Adv. Mater., 2001, 13, 1053.
7. See, for example: (a) T. D. Selby, K.-Y. Kim and S. C. Blackstock, Chem. Mater., 2002, 14, 1685;
8. (b) J. Pang, Y. Tao, S. Freiberg, X.-P. Yang, M. D'Iorio and S. Wang, J. Mater. Chem., 2002, 12, 206;
9. (c) H. B. Goodbrand and N.-X. Nu, J. Org. Chem., 1999, 64, 670;
10. (d) C. G. Frost and P. Mendonça, J. Chem. Soc., Perkin Trans. 1, 1998, 2615;
11. (e) H. Tanaka, S. Tokito, Y. Taga and A. Okada, Chem. Commun., 1996, 2175;
12. (f) M. Thelakkat, R. Fink, F. Haubner and H.-W. Scmidt, Macromol. Symp., 1997, 125, 157;
13. (g) P. Strohriegl, G. Jesberger, J. Heinze and T. Moll, Makromol. Chem., 1992, 193, 909;
14. (h) H. Weingarten, J. Org. Chem., 1964, 29, 3624; H. Weingarten, J. Org. Chem., 1964, 29, 977;
15. (h) H. Weingarten, J. Org. Chem., 1964, 29, 3624; H. Weingarten, J. Org. Chem., 1964, 29, 977;
16. (i) J. Lindley, Tetrahedron, 1984, 40, 1433.
17. (a) S. Tanaka, T. Iso and Y. Doke, Chem. Commun., 1997, 2063;
18. (b) M. Ishikawa, M. Kawai and Y. Ohsawa, Synth. Met., 1991, 40, 231.
19. E. T. Seo, R. F. Nelson, J. M. Fritsch, L. S. Marcoux, D. W. Leedy and R. N. Adams, J. Am. Chem. Soc., 1966, 88, 3498.
20. A. Petr, C. Kvarnström, L. Dunsch and A. Ivaska, Synth. Met., 2000, 108, 245.
21. H. Sato, A. Kanegae, R. Yamaguchi, K. Ogino and J. Kurjata, Chem. Lett., 1999, 79.
22. C. Lambert and G. Nöll, 2003, personal communication.
23. M. Leung, M.-Y. Chou, Y. O. Su, C. L. Chiang, H.-L. Chen, C. F. Yang, C.-C. Yang, C.-C. Lin and H.-T. Chen, Org. Lett., 2003, 5, 839.
24. A. D. Becke, Phys. Rev. A, 1988, 38, 3098.
25. J. P. Perdew, K. Burke and Y. Wang, Phys. Rev. B, 1996, 54, 16533; Erratum: Phys. Rev. B, 1998, 57, 14999.
26. J. P. Perdew, K. Burke and Y. Wang, Phys. Rev. B, 1996, 54, 16533; Erratum: Phys. Rev. B, 1998, 57, 14999.
27. (a) R. Ditchfield, W. J. Hehre and J. A. Pople, J. Chem. Phys., 1971, 54, 724;
28. (b) W. J. Hehre, R. Ditchfield and J. A. Pople, J. Chem. Phys., 1972, 56, 2257;
29. (c) P. C. Hariharan and J. A. Pople, Mol. Phys., 1974, 27, 209;
30. (d) M. S. Gordon, Chem. Phys. Lett., 1980, 76, 163;
31. (e) P. C. Hariharan and J. A. Pople, Theor. Chim. Acta., 1973, 28, 213.
32. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, P. Salvador, J. J. Dannenberg, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle and J. A. Pople, GAUSSIAN 98 (Revision A.11), Gaussian, Inc., Pittsburgh, PA, 2001.
33. S. Portmann and H. P. Lüthi, Chimia, 2000, 54, 766.
34. V. Coropceanu, M. Malagoli, J. M. André and J. L. Brédas, J. Am. Chem. Soc., 2002, 124, 10519.
35. P. J. Low, M. A. J. Paterson, H. Puschmann, A. E. Goeta, J. A. K. Howard, C. Lambert, J. C. Cherryman, D. R. Tackley, S. Leeming and B. Brown, Chem. Eur. J., 2004, 10, 83.
36. A. R. Kennedy, W. E. Smith, D. R. Tackley, W. I. F. David, K. Shankland, B. Brown and S. J. Teat, J. Mater. Chem., 2002, 12, 168.
37. C. Lambert and G. Nöll, J. Am. Chem. Soc., 1999, 121, 8434.
38. S. F. Nelsen, R. F. Ismagilov, K. E. Gentile and D. R. Powell, J. Am. Chem. Soc., 1999, 121, 7108.
39. A. Helms, D. Heiler and G. McLendon, J. Am. Chem. Soc., 1992, 114, 6227.
40. R. B. Carlin, J. Am. Chem. Soc., 1945, 67, 928.
41. C. M. Duff and G. A. Heath, Inorg. Chem., 1991, 30, 2528.