[en] We report on a detailed quantum-chemical comparison of the electronic structures, vertical electron affinities, and intramolecular reorganization energies for bis-aryl substituted dioxaborine, oxadiazole, and silole derivatives. The results indicate that the HOMO and LUMO energies of the substituted compounds can be tuned on the order of 2-3 eV via minor changes in the substitution patterns, with the HOMO and LUMO levels for the dioxaborine derivatives consistently the most energy stabilized. Additionally, large vertical electron affinities and comparable intramolecular reorganization energies confirm that dioxaborine systems are interesting candidates for electron transport materials.
Brédas, Jean-Luc ; Université de Mons > Faculté des Sciences > Chimie des matériaux nouveaux
Language :
English
Title :
Bis-aryl Substituted Dioxaborines as Electron-Transport Materials: A Comparative Density Functional Theory Investigation with Oxadiazoles and Siloles
Publication date :
27 June 2005
Journal title :
Chemical Physics
ISSN :
0301-0104
Publisher :
Elsevier, Netherlands
Volume :
313
Issue :
1-3
Pages :
151-157
Peer reviewed :
Peer Reviewed verified by ORBi
Research unit :
S817 - Chimie des matériaux nouveaux
Research institute :
R400 - Institut de Recherche en Science et Ingénierie des Matériaux
Commentary :
Lecture en ligne: http://www.sciencedirect.com/science?_ob=MImg&_imagekey=B6TFM-4FBM1T4-1-1&_cdi=5230&_user=532054&_pii=S0301010404007372&_orig=search&_coverDate=06%2F27%2F2005&_sk=996869998&view=c&wchp=dGLzVzb-zSkzV&md5=6a356b5fff5f2beb8b69bd9fcad76393&i
Publié en ligne le 26 janvier 2005
R.H. Friend, R.W. Gymer, A.B. Holmes, J.H. Burroughes, R.N. Marks, C. Taliani, D.D.C. Bradley, D.A. Dos Santos, J.L. Bredas, M. Logdlund, and W.R. Salaneck Nature 397 1999 121
C. Dimitrakopoulos, and P. Malenfant Adv. Mater. 14 2002 99
F. Würthner Angew. Chem., Int. Ed. 40 2001 1037
K. Sakanoue, M. Motoda, M. Sugimoto, and S. Sakaki J. Phys. Chem. A 103 1999 5551
H. Tokuhisa, M. Era, T. Tsutsui, and S. Saito Appl. Phys. Lett. 66 1995 3433
Y.D. Zhang, K.G. Jespersen, M. Kempe, J.A. Kornfield, S. Barlow, B. Kippelen, and S.R. Marder Langmuir 19 2003 6534
H. Tokuhisa, M. Era, and T. Tsutsui Adv. Mater. 10 1998 404
D.M. de Leeuw, M.M.J. Simenon, A.R. Brown, and R.E.F. Einerhand Synth. Met. 87 1997 53
H. Murata, G.G. Malliaras, M. Uchida, Y. Shen, and Z.H. Kafafi Chem. Phys. Lett. 339 2001 161
C. Adachi, T. Tsutsui, and S. Saito Appl. Phys. Lett. 55 1989 1489
G. Brocks, and A. Tol J. Chem. Phys. 106 1997 6418
J. Bettenhausen, M. Greczmiel, M. Jandke, and P. Strohriegl Synth. Met. 91 1997 223
H. Murata, Z.H. Kafafi, and M. Uchida Appl. Phys. Lett. 80 2002 189
Y.L. Chow, S.S. Wang, C.I. Johansson, and Z.L. Liu J. Am. Chem. Soc. 118 1996 11725
Y.L. Chow, Z.L. Liu, C.I. Johansson, and J. Ishiyama Chem. Eur. J. 6 2000 2942
M. Halik, W. Wenseleers, C. Grasso, F. Stellacci, E. Zojer, S. Barlow, J.L. Brédas, J.W. Perry, and S.R. Marder Chem. Commun. 2003 1490
B. Domercq, C. Grasso, J.L. Maldonado, M. Halik, S. Barlow, S.R. Marder, and B. Kippelen J. Phys. Chem. B 108 2004 8647
J. Fabian, and H. Hartmann J. Phys. Org. Chem. 17 2004 359
J.C. Rienstra-Kiracofe, G.S. Tschumper, H.F. Schaefer, S. Nandi, and G.B. Ellison Chem. Rev. 102 2002 231
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., J.A.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. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, and J.A. Pople Gaussian 98, Rev. A.11 1998
J.L. Brédas, D. Beljonne, V. Coropceanu, and J. Cornil Chem. Rev. 104 2004 4971
J. Cornil, D.A. dos Santos, D. Beljonne, and J.L. Brédas J. Phys. Chem. 99 1995 5604
T. Koopmans Physica 1 1933 104
S.W. Staley, and J.T. Strnad J. Phys. Chem. 98 1994 116