Abstract
Recently, the organic synthesis and electronic device applications of π-conjugated polymer-based materials with low energy band gap (below 2 eV) and high values of incident photon to current efficiency have been presented. In the present study, the physical properties of polythiophene (PTH) and its derivative systems (PTs) were investigated as π-conjugated low energy band gap polymers. Density functional theory with periodic boundary condition (PBC), the B3LYP functional, and the 6-31G(d) basis set was applied to determine their geometric and electronic structures and corresponding energies (E HOMO, E LUMO, and E g = E LUMO − E HOMO) from the monomer of thiophene and its derivatives for one-dimensional (1D) extension to polymer. The effects of 3-substitution in PTs including electron-donating (CH3–, C6H13–, OH–, Cl–, OCH3–, and CHO–) and electron-withdrawing groups (Cl–, CHO–, CN–, NO2–, CF3–, and COOH–) compared with PTH were investigated. According to the calculation results, PTs with electron-donating and electron-withdrawing substituents should exhibit red- and blue-shifts, respectively, compared with PTH. These calculation results show good agreement with experimental data and provide further information for molecular design considerations.
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E. Zhou, K. Hashimoto, K. Tajima, Polymer 54, 6501–6509 (2013)
M.Y. Jo, J.H. Bae, G.E. Lim, Y.E. Ha, H.E. Katz, J.H. Kim, Synth. Met. 176, 41–46 (2013)
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, W.R. Salaneck, Nature 397, 121 (1999)
S. Berson, S. Cecioni, M. Billon, Y. Kervella, R. de Bettignies, S. Bailly, S. Guillerez, Sol. Energy Mater. Sol. Cells 94, 699–708 (2010)
H.J. Wang, Y.P. Chen, Y.C. Chen, C.P. Chen, R.H. Lee, L.H. Chan, R.J. Jeng, Polymer 53, 4091–4103 (2012)
I. Riedel, J. Parisi, V. Dyakonov, P. Schilinsky, C. Waldauf, C. Brabec, Proc. SPIE 82, 5520 (2004)
E. Bundgaard, F.C. Krebs, Macromolecules 39, 2823 (2006)
J. Hou, C. Yang, J. Qiao, Y. Li, Synth. Met. 150, 297 (2005)
H.J. Wang, L.H. Chan, C.P. Chen, S.L. Lin, R.H. Lee, R.J. Jeng, Polymer 52, 326–338 (2011)
C. Climent, D. Casanova, Chem. Phys. 423, 157–166 (2013)
H.G. Flesch, R. Resel, C.R. McNeill, Org. Electron. 10, 1549–1555 (2009)
J. Pei, W.L. Yu, W. Huang, A.J. Heeger, Macromolecules 33, 2462–2471 (2000)
H. Saadeh, T. Goodson, L. Yu, Macromolecules 30, 4608–4612 (1997)
M.E. Rincón, R.A. Guirado-López, J.G. Rodríguez-Zavala, M.C. Arenas-Arrocena, Sol. Energy Mater. Sol. Cells 87, 33–47 (2005)
E. Armelin, O. Bertran, F. Estrany, R. Salvatella, C. Alemán, Eur. Polym. J. 45, 2211–2221 (2009)
P. Otto, J. Ladik, Synth. Met. 36, 327–335 (1990)
J.-W. van der Horst, P.A. Bobbert, M.A.J. Michels, G. Brocks, P.J. Kelly, Synth. Met. 101, 333–334 (1999)
J.J. Tindale, H. Holm, M.S. Workentin, O.A. Semenikhin, J. Electroanal. Chem. 612, 219–230 (2008)
H.W. Wang, B.C. Wang, W.H. Chen, M. Hayashi, J. Phys. Chem. A 112, 1783 (2008)
Y.M. Chou, W.H. Chen, C.C. Liang, J. Mol. Struct. (Theochem) 894, 117–120 (2009)
A.D. Becke, J. Chem. Phys. 98, 5648–5652 (1993)
B. Miehlich, A. Savin, H. Stoll, H. Preuss, Chem. Phys. Lett. 157, 200–206 (1989)
C. Lee, W. Yang, R.G. Parr, Phys. Rev. B 37, 785–789 (1988)
H. Cao, J. Ma, G. Zhang, Y. Jiang, Macromolecules 38, 1123 (2005)
K.N. Kudin, G.E. Scuseria, Phys. Rev. B 61, 16440 (2000)
C. Pisani (ed.), Lecture Notes in Chemistry, Vol. 67 (Springer, Heidelberg, 1996)
P.J. Feibelman, Phys. Rev. B 35, 2626 (1987)
J.E. Jaffe, A.C. Hess, J. Chem. Phys. 105, 10983 (1996)
S. Hirata, S. Iwata, J. Chem. Phys. 107, 10075 (1997)
J.Q. Sun, R.J. Bartlett, J. Chem. Phys. 109, 4249 (1998)
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 C.02 (Gaussian, Wallingford, 2004)
J. Ma, S. Li, Y. Liang, Macromolecules 38, 1123–1130 (2005)
S. Hotta, S.D.D.V. Rughooputh, A.J. Heeger, F. Wudi, Macromolecules 20, 212–215 (1987)
Y. Li, G. Vamvounis, S. Holdcroft, Macromolecules 35, 6900–6906 (2002)
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We thank the National Science Council of Taiwan for financially supporting this research.
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Tai, CK., Yeh, PL., Chang, CC. et al. A theoretical investigation of low energy band gap polymers: polythiophene systems. Res Chem Intermed 40, 2355–2362 (2014). https://doi.org/10.1007/s11164-014-1612-y
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DOI: https://doi.org/10.1007/s11164-014-1612-y