Abstract
In this work, we investigate oligopyrroles and derivatives, which serve as models for corresponding polymers. In order to discuss these materials, we carried out DFT calculations and used DFT methods to calculate ground state electronic structures. We are particularly interested in exploring the potential of several substituent groups as electron donors with numerous ties to electronic materials by exploring and comparing the energies of HOMO, LUMO, Gap energies, and structural properties. Results are discussed in comparison with the properties of the doped oligomers. The theoretical ground-state geometry and electronic structure of the studied molecules were obtained by the DFT method at B3LYP level with 6-31G(d) basis set. The opto-electronic properties of these materials were determined by ZINDO/s and TD//B3LYP/6-31G(d) calculations performed on the B3LYP/6-31(d) optimized geometries. The results of this study demonstrate how electronic properties can be tuned by the backbone ring or side group and suggest these compounds as good candidates for opto-electronic applications.
Similar content being viewed by others
References
G. Horowitz, M.E. Hajlaoui, Adv. Mater. 12, 1046 (2000)
H. Meng, J. Zheng, A.J. Lovinger, B.C. Wang, P.G. Van Patten, Z. Bao, Chem. Mater. 15, 1778 (2003)
M. Mushrush, A. Facchetti, M. Lefenfeld, H.E. Katz, T.J. Marks, J. Am. Chem. Soc. 125, 9414 (2003)
M. Pasini, S. Destri, W. Porzio, C. Botta, U. Giovanella, J. Mater. Chem. 13, 807 (2003)
M. Suzuki, M. Fukuyama, Y. Hori, S. Hotta, J. Appl. Phys. 91, 5706 (2002)
I.F. Perepichka, D.F. Perepichka, H. Meng, F. Wudl, Adv. Mater. 17, 2281 (2005)
Q.B. Pei, Y. Yang, J. Am. Chem. Soc. 118, 7416 (1996)
A. Xia, Z. Yuan, S.T. Tan, Y.P. Zou, Z.A. Tan, Y. Yang, Y.F. Li, Eur. Polym. J. 43, 1394 (2007)
D. Pisignano, M. Anni, G. Gigli, R. Cingolani, M. Zavelani-Rossi, G. Lanzani, G. Barbarella, L. Favaretto, Appl. Phys. Lett. 81, 3534 (2002)
L. Torsi, A.J. Lovinger, B. Crone, T. Someya, A. Dodabalapur, H.E. Katz, A. Gelperin, J. Phys. Chem. B 106, 12563 (2002)
J. Roncali, J. Mater. Chem. 9, 1875 (1999)
X.H. Zhou, J.C. Yan, J. Pei, Macromolecules 37, 7078 (2004)
T. Yasuda, I. Yamaguchi, T. Yamamoto, Adv. Mater. 15, 293 (2003)
N. Noma, T. Tsuzuki, Y. Shirota, Adv. Mater. 7, 647 (1995)
C. Videlot, A. El Kassmi, D. Fichou, Sol. Energy Mater. Sol. Cells 63, 69 (2000)
K. Hara, M. Kurashige, Y. Dan-Oh, C. Kasada, A. Shinpo, S. Suga, K. Sayama, H. Arakawa, New J. Chem. 27, 783 (2003)
J. Ackermann, C. Videlot, A. El Kassmi, R. Guglielmetti, F. Fages, Adv. Mater. 16, 1709 (2004)
J.H. Hou, Z.A. Tan, Y. Yan, Y.J. He, C.H. Yang, Y.F. Li, J. Am. Chem. Soc. 128, 4911 (2006)
S.L. Lu, M.J. Yang, J. Luo, Y. Cao, F.L. Bai, Macromol. Chem. Phys. 206, 664 (2005)
K.L. Sang, S.C. Nam, H.K. Joong, S.L. Koeng, K.S. Hong, D.H. Hwang, J.B. Christoph, Thin Solid Films 158, 511 (2006)
X.Y. Deng, L.P. Zheng, C.H. Yang, Y.F. Li, G. Yu, Y. Cao, J. Phys. Chem. B 108, 3451 (2004)
S.S. Sun, C. Zhang, A. Ledbetter, S. Choi, K. Seo, C.E. Bonner, J.M. Drees, N.S. Sariciftci, Appl. Phys. Lett. 90, 43117 (2007)
A.F. Diaz, K.K. Kanazawa, G.P. Gardini, J. Chem. Soc. Chem. Commun. 183 (1988)
K.K. Kanazawa, A.F. Diaz, W.D. Gill, P.H. Grant, G.B. Street, G.P. Gardini, J.F. Kwak, Synth. Met. 1, 329 (1980)
L.P. Prezyna, Y.J. Qiu, J.R. Reynolds, G.E. Wnek, Macromolecules 24, 5283 (1991)
S.K. Ghoshal, Chem. Phys. Lett. 158, 65 (1989)
B.Z. Lubentsov, G.I. Zvereva, Ya.H. Samovarov, S.M. Bystriak, O.N. Timofeeva, M.L. Khidekel, Synth. Met. 41, 1143 (1991)
T.C. Pearce, J.W. Gardner, S. Friel, P.N. Bartlett, N. Blair, Analyst 118, 371 (1993)
P. Evans, N.M. Ratcliffe, J.R. Smith, S.A. Compbll, J. Mater. Chem. 6, 295 (1996)
P.R. Teasdale, G.G. Vallace, Analyst 118, 329 (1993)
E.V. Thillo, G. Defieuw, W. de Winter, Bull. Soc. Chim. Belg. 99, 981 (1990)
C.J. Gow, C.F. Zukoski, J. Colloid Interface Sci. 136, 175 (1990)
T. Sata, T. Yamaguchi, K. Matsusaki, J. Phys. Chem. 100, 16633 (1996)
G.C. Teare, N.M. Ractcliffe, J. Mater. Chem. 6, 301 (1996)
J.R. Ghimaraes, J.G. Amazonas, C.A.B. Silva Junior, C.P. Melo, J.D. Nero, Mater. Sci. Eng. 28, 1076 (2008)
P. Bäurele, K. Müllen, G. Wegner (eds.), Electronic Materials: The Oligomer Approach (Wiley, Weinheim, 1998)
J. Ma, S. Li, Y. Jiang, Macromolecules 35, 1109 (2002)
S.M. Bouzzine, M. Hamidi, M. Bouachrine, Orbital 2, 203 (2009)
H. Zgou, S.M. Bouzzine, S. Bouzakraoui, M. Hamidi, M. Bouachrine, Chin. Chem. Lett. 19, 123 (2008)
A. Cravino, N.S. Sariciftci, J. Mater. Chem. 12, 1931 (2002)
R. Ditchfield, W.J. Hehre, J.A. Pople, J. Chem. Phys. 54, 76 (1971)
A.D. Becke, J. Chem. Phys. 98, 5648 (1993)
W.J. Hehre, R. Ditchfiesld, J.A. Pople, J. Chem. Phys. 56, 643 (1972)
P.C. Hariharan, J.A. Pople, Mol. Phys. 27, 209 (1974)
M.S. Gordon, Chem. Phys. Lett. 76, 33 (1980)
Gaussian 03 Revision D.O.I, 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, G.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 03, Revision B. 04 (Gaussian, Pittsburgh, 2003)
M.C. Zener, in Reviews in Computational Chemistry, vol. 2, ed. by K.B. Lipkowitz, D.B. Boyd (VCH, New York, 1991), p. 313
M.A. Thompson, M.C.J. Zener, Am. Chem. Soc. 113, 8210 (1991)
L. Bartolloti, J. Phys. Rev. 26, 2243 (1982)
E. Runge, E.K.U. Gross, Phys. Rev. Lett. 52, 997 (1984)
M.E. Casida, in Recent Advances in Density Functional Methods, vol. 1, ed. by D.P. Chang (Word Scientific Singapore, 1995)
H. Zgou, M. Hamidi, M. Bouachrine, Phys. Chem. News 32, 81 (2006)
L. Yang, J. Feng, A. Ren, Polymer 46, 10970 (2005)
J.L. Bredas, R. Silbey, D.S. Boudreaux, R.R. Chance, J. Chem. Soc. 105, 6555 (1983)
D. Fichou, G. Horowitz, F. Garnier, Synth. Met. 39, 125 (1990)
D. Fichou, G. Horowitz, Y. Nishikitani, F. Garnier, Synth. Met. 28, 66 (1989)
M. Nisoli, V. Pruneri, S. De Silvestri, V. Magni, A.M. Gallazzi, C. Romanoni, G. Zerbi, G. Zotti, Chem. Phys. Lett. 220, 64 (1994)
U. Salzner, J.B. Lagowski, P.G. Pickup, R.A. Poirier, Synth. Met. 96, 17 (1998)
H. Li, C. Lambert, R. Stahl, Macromolecules 39, 2049 (2006)
J. Casado, V. Hernàndez, F.J. Ramirez, J.T. López Navarrete, J. Mol. Struct. THEOCHEM 463(1–2), 211 (1999)
V. Hernandez, D. Grebner, M. Helbig, S. Rentsh, Chem. Phys. 201, 309 (1995)
F.C. Grozema, L.P. Candeias, M. Swart, P. Van Duijnen, J. Wildemen, G.J. Hadziioanou, Chem. Phys. 117(24), 11366 (2002)
C. Alemán, E. Armelin, J.I. Iribarren, F. Liesa, Synth. Met. 149, 151 (2005)
S.M. Bouzzine, S. Bouzakraoui, M. Bouachrine, M. Hamidi, J. Mol. Struct. THEOCHEM 726(1–3), 271 (2005)
S. Bouzakraoui, S.M. Bouzzine, M. Bouachrine, M. Hamidi, J. Mol. Struct. THEOCHEM 851(1–3), 254 (2005)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Toufik, H., Bouzzine, S.M., Ninis, O. et al. Opto-electronic properties and molecular design of new materials based on pyrrole studied by DFT. Res Chem Intermed 38, 1375–1388 (2012). https://doi.org/10.1007/s11164-011-0469-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-011-0469-6