Synthesis, ionisation potentials and electron affinities of hexaazatrinaphthylene derivatives

Chemistry - A European Journal

Volumn 13, Issue 12, 2007, Pages 3537-3547

  Barlow, Stephen ^a,b   Zhang, Qing ^a   Kaafarani, Bilal R ^a,b,c   Risko, Chad ^a   Amy, Fabrice ^d   Chan, Calvin K ^d   Domercq, Benoit ^e   Starikova, Zoya A ^f   Antipin, M Yu ^f,g   Timofeeva, Tatiana V ^g   Kippelen, Bernard ^e   Brédas, Jean Luc ^a   Kahn, Antoine ^d   Marder, Seth R ^a,b  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

^b University of Arizona   (United States)

^c AMERICAN UNIVERSITY OF BEIRUT   (Lebanon)

^d Princeton University   (United States)

^e GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

^f A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^g NEW MEXICO HIGHLANDS UNIVERSITY   (United States)

Author keywords

Electron affinities; Electron transport; Heterocycles; Ionization potentials; Pi stacking

Indexed keywords

DENSITY FUNCTIONAL THEORY; DERIVATIVES; ELECTRON AFFINITY; IONIZATION POTENTIAL; REACTION KINETICS; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION;

EXOTHERMIC ELECTRON AFFINITIES; HETEROCYCLES; PI STACKING;

AROMATIC COMPOUNDS;

EID: 34250374923     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601298     Document Type: Article

References (60)

1. H. Bock, A. Babeau, I. Seguy, P. Jolinat, P. Destruel, Chem PhysChem 2002, 3, 532.
2. B. R. Kaafarani, T. Kondo, J. Yu, Q. Zhang, D. Dattilo, C. Risko, S. C. Jones, S. Barlow, B. Domercq, F. Amy, A. Khan, J. L. Brédas, B. Kippelen, S. R. Marder. J. Am. Chem. Soc. 2005, 727, 16358.
3. G. Kestemont, V. de Halleux, M. Lehmann, D. A. Ivanov, M. Watson. Y. H. Geerts, Chem. Commun. 2001, 2074.
4. V. Lemaur, D. A. de Silva Filho, V. Coropceanu, M. Lehmann, Y. Geerts. J. Piris, M. G. Debije, A. M. van de Craats, K. Senthilkumar, L. D. Siebbeles, J. M. Warman, J. L. Brédas, J. Cornil, J. Am. Chem. Soc. 2004, 126, 3271.
5. X. Crispin, J. Cornil, R. Friedlein, K. K. Okudaira, V. Lemaur, A. Crispin, G. Kestemont, M. Lehmann, M. Fahlman, R. Lazzaroni, Y. Geerts, G. Wendin, N. Ueno, J. L. Brédas, W. R. Salaneck, J. Am. Chem. Soc. 2004, 126, 11889.
6. M. Lehmann, G. Kestemont, R. G. Aspe, C. Buess-Herman, M. H. J. Koch, M. G. Debije, J. Piris, M. P. de Haas, J. M. Warman, M. D. Watson, V. Lemaur, J. Cornil, Y. H. Geerts, R. Gearba, D. A. Ivanov, Chem. Eur. J. 2005, 11, 3349.
7. C. W. Ong, S.-C. Liao, T. H. Chang, H.-F. Hsu, Tetrahedron Lett. 2003, 44, 1477.
8. C. W. Ong, S.-C. Liao, T. H. Chang, H.-F. Hsu, J. Org. Chem. 2004, 69, 3181.
9. T. Ishi-i, K. Yaguma, R. Kuwahara, Y. Taguri, S. Mataka, Org. Lett. 2006, 8, 585.
10. C. K. Chan, F. Amy, O. Zhang, S. Barlow, S. R. Marder, A. Kahn, Chem. Phys. Lett. 2006, 431, 67.
11. S. Skujins, G. A. Webb, Tetrahedron 1969, 25, 3935.
12. M. Du, X.-H. Bu, K. Biradha, Acta Crystallogr. Sect. C 2001, 57, 199.
13. S. K. Kotovskaya, N. M. Perova, Z. M. Baskakova, S. A. Romanova, V. N. Charushin, O. N. Chupakhin, Zh. Org. Khim. 2001, 37, 598.
14. R. B. Baudy, L. P. Greenblatt, I. L. Jirkovsky, M. Conklin, R. J. Russo, D. R. Bramlett, T. A. Emrey, J. T. Simmonds, D. M. Kowal, R. P. Stein, R. P. Tasses, J. Med. Chem. 1993, 36, 331.
15. A. Heaton, M. Hill, F. Drakesmith, J. Fluorine Chem. 1997, 81, 133.
16. J. F. W. Keana, S. M. Kher, S. X. Cai, C. M. Dinsmore, A. G. Glenn, J. Guastella, J. Huang, V. Ilyin, Y. Lu, P. L. Mouser, R. M. Wood-ward, E. Weber, J. Med. Chem. 1995, 38, 4367.
17. We were unable to obtain 8 analytically pure and so did not obtain PES and IPES spectra.
18. M. Alfonso, H. Stoeckli-Evans, Acta Crystallogr. Sect. E 2001, 57, 0242.
19. 32.25MeCN (X.-H. Bu, K. Biradha, T. Yamaguchi, M. Nishimura, T. Ito, K. Tanaka, M. Shionoya, Chem. Commun. 2000, 1953) are not included, since these were rather imprecisely determined.
20. The structures of the radical ions of 6, in which there are a large number of degrees of freedom, could not be successfully minimised. Accordingly, we were also unable to calculate reorganisation energies and adiabatic values of IP and EA for this compound.
21. R. A. Marcus, J. Chem. Phys. 1956, 24, 966.
22. For example, see: R. D. Hreha, C. P. George, A. Haldi, B. Domercq, M. Malagoli, S. Barlow, J.-L. Brédas, B. Kippelen, S. R. Marder, Adv. Funct. Mater. 2003, 13, 967. While the barrier is strictly ΔH†. ΔS† can be neglected due to similar vibrational degrees of freedom associated with the two adiabatic surfaces, meaning λ/4 is also a good estimate of the free-energy barrier, ΔG†.
23. The reorganisation energy can also be obtained from a full vibrational analysis through summation of the contributions of the vibrational modes involved (R. A. Marcus, N. Sutin, Biochim. Biophys. Acta 1985, 811, 265).
24. M. Malagoli, J.-L. Brédas, Chem. Phys. Lett. 2000, 327, 13.
25. B. C. Lin. C. P. Cheng. Z.-Q. You, C.-P. Hsu, J. Am. Chem. Soc. 2005, 127, 66.
26. X. Zhan, C. Risko, F. Amy, C. Chan, W. Zhao, S. Barlow, A. Kahn, J.-L. Brédas, S. R. Marder, J. Am. Chem. Soc. 2005, 727, 9021.
27. F. Gamier, G. Horowitz, D. Fichou, A. Yassar, Synth. Met. 1996, 81, 163.
28. H. E. Katz, Z. Bao, J. Phys. Chem. B 2000, 104, 671.
29. R. C. Haddon, X. Chi, M. E. Itkis, J. E. Anthony, D. L. Eaton, T. Siegrist, C. C. Mattheus. T. T. M. Palstra, J. Phys. Chem. B 2002, 106, 8288.
30. Y. Olivier, V. Lemaur, J. L. Brédas. J. Cornil, J. Phys. Chem. A 2006, 110, 6356.
31. A.M. van de Craats, N. Stutzmann, O. Bunk, M. M. Nielsen, M. Watson. K. Müllen, H. D. Chanzy, H. Sirringhaus, R. H. Friend, Adv. Mater. 2003, 15, 495.
32. Z. An, J. Yu, S. C. Jones, S. Barlow, S. Yoo, B. Domercq, P. Prins, L. D. A. Siebbeles, B. Kippelen, S. R. Marder, Adv. Mater. 2005, 17, 2580.
33. K. O. Sylvester-Hvid, J. Phys. Chem. B 2006, 110, 2618.
34. A. R. Murphy, J. S. Liu, C. Luscombe, D. Kavulak, J. M. J. Fréchet, R. J. Kline, M. D. McGehee, Chem. Mater. 2005, 17, 4892.
35. H. Xu, Y. Wang. G. Yu, W. Xu, Y. B. Song, D. Q. Zhang, Y. Q. Liu, D. B. Zhu, Chem. Phys. Lett. 2005, 414, 369.
36. J. E. Anthony, J. S. Brooks, D. L. Eaton, S. R. Parkin, J. Am. Chem. Soc. 2001, 123, 9482.
37. X.-C. Li, H. Sirringhaus, F. Garnier, A. B. Holmes, S. C. Moratti, N. Feeder, W. Clegg, S. J. Teat, R. H. Friend, J. Am. Chem. Soc. 1998, 120, 2206.
38. J. E. Anthony, D. L. Eaton, S. R. Parkin, Org. Lett. 2002, 4, 15.
39. K. Kobayashi, R. Shimaoka, M. Kawahata, M. Yamanaka, K. Yamaguchi, Org. Lett. 2006, 8, 2385.
40. A. M. van de Craats, J. M. Warman, H. Hasebe, R. Naito, K. Ohta, J. Phys. Chem. B 1997, 101, 9224.
41. S. Kumar, D. S. S. Rao, S. K. Prasad, J. Mater. Chem. 1999, 9, 2751.
42. R. I. Gearba, M. Lehmann, J. Levin, D. A. Ivanov, M. H. J. Koch, J. Barbera, M. G. Debije, J. Piris, Y. H. Geerts, Adv. Mater. 2003, 15, 1614.
43. +/TPD potential and the IP of TPD gave EAs almost 1 eV more exothermic than the values obtained by direct measurement. See reference [26].
44. L. Segev, A. Salomon, A. Natan, D. Cahen, L. Kronik, F. Amy, C. K. Chan, A. Kahn, Phys. Rev. B 2006, 74, 165323/1.
45. F. Amy, C. K. Chan, W. Zhao, J. Hyung, A. Kahn, M. Ono, N. Ueno, D. Cahen, L. Kronik, G. Nesher, A. Salomon, L. Segev, O. Seitz, H. Shpaisman, A. Scholl. E. Umbach, 7. Phys. Chem. B 2006, 110, 21826.
46. N. Sato, H. Inokuchi, E. A. Silinish, Chem. Phys. 1987, 115, 269.
47. J. D. Anderson, E. M. McDonald, P. A. Lee, M. L. Anderson, E. L. Ritchie, H. K. Hall, T. Hopkins, E. A. Nash, J. Wang, A. Padias, S. Thayumanavan, S. Barlow, S. R. Marder, G. Jabbour, S. Shaheen, B. Kippelen. N. Peyghambarian, R. M. Wightman, N. R. Armstrong, 7. Am. Chem. Soc. 1998, 720, 9646.
48. W. Y. Gao, A. Kahn, J. Appl. Phys. 2003, 94, 359.
49. A. Kahn, N. Koch, W. Gao, J. Polym, Sci. Part B 2003, 41, 2529-2548.
50. D. Cahen, A. Kahn, Adv. Mater. 2003, 15, 271.
51. These values are taken from J. E. Huheey, E. A. Keiter, R. L. Keiter, Inorganic Chemistry: Principles of Structure and Reactivity, 4th ed., Harper Collins, New York, 1993, p. 187. in which values according to a variety of other scales are also given.
52. R. Dudde, B. Reihl, A. Olio, J. Chem. Phys. 1990, 92, 3930.
53. The compeling inductive and resonance effects of F and Cl can of course be gauged by Hammett coefficients. See for example J. March, Advanced Organic Chemistry, 3rd ed.. Wiley, New York, 1985.
54. D. D. Kenning, K. A. Mitchell, T. R. Calhoun, M. R. Funfar, D. J. Sattler, S. C. Rasmussen, J. Org. Chem. 2002, 67, 9073.
55. R. G. Kultyshev, G. K. S. Prakash, G. A. Olah, J. W. Faller, J. Parr. Organometallics 2004, 23, 3184.
56. A. D. Becke, Phys. Rev. A 1988, 38, 3098.
57. A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
58. C. T. Lee, W. T. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
59. Gaussian 98 (Revision A.11), M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, 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, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, 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, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 1998.
60. Gaussian 03, Revision B.05, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, O.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Wallingford CT, 2004.