Volume 8, Issue 1, June 2020, Page: 1-10
Acceptor/Donor End Capped Phenylene-Thiophene Co-oligomers Toward Efficiencies Organic Electronic Devices
Abdelkader Hlel, Department of Physics, Preparatory Institute for Engineering Studies, University of Monastir, Monastir, Tunisia
Saber Ghomrasni, Department of Physics, Faculty of Sciences, University of Monastir, Monastir, Tunisia
Walid Taouali, Department of Physics, Faculty of Sciences, University of Monastir, Monastir, Tunisia
Kamel Alimi, Department of Physics, Faculty of Sciences, University of Monastir, Monastir, Tunisia
Received: Nov. 11, 2019;       Accepted: Dec. 3, 2019;       Published: Jan. 4, 2020
DOI: 10.11648/j.ijctc.20200801.11      View  239      Downloads  48
Abstract
In this paper, geometrical (in ground and excited states), electronic, optical and charge transfer properties, (ionization potentials (IP), electron affinities (EA) and HOMO-LUMO gaps (ΔEH-L), as well as the lowest excitation energies (Eex) and reorganization energies) of the phenylene-tiophene oligomers are studied by the density functional theory (DFT) and Time-dependent DFT approaches. Based on the density functional theory (DFT/B3LYP and CAM –B3LYP functional with 6-31G (d,p) basis set), we will highlight the effect of terminal acceptor/donor (CN, NO2, and CF3) /OCH3, N(CH3)2 substituents on thiophene-phenylene derivatives. The excited state indicates more planar structures of the co-oligomers, which leads to a decrease in the (HOMO-LUMO) gap compared with the ground state, especially when the acceptor character increases. Furthermore, the vinyl spacer and cyanide ((–CN) functional group (Compound C8) stabilize the LUMO levels of energy and improve the transport properties of the thiophene-phenylene derivatives. Comparing with the donor groups, the results show that the electron withdrawing substituents are remarkable on the energy levels of the frontier molecular orbitals, and on the transport charge proprieties in these co-oligomers. Thus, the LUMO energy levels become more stabilized for co-oligomers having more acceptor moieties and the HOMO–LUMO energy gap is reduced, therefore, the improvement of the conduction properties of these species is, then, observed. Moreover, the absorption spectra, computed in the presence or not of solvent at PCM model in chloroform, shows that the increase of acceptor character induces a red shift and important absorption intensity. The decrease injection barrier and smaller reorganization energies are revealing that our designed co-oligomers would be an efficient hole as well as electron transfer materials. The predicted values have shown that the designed derivatives would be efficient for the organic field effect transistors, photovoltaics and light emitters.
Keywords
Thiophene-phenylene, DFT, CAM–B3LYP, B3LYP, Optical Absorption, Reorganization Energies
To cite this article
Abdelkader Hlel, Saber Ghomrasni, Walid Taouali, Kamel Alimi, Acceptor/Donor End Capped Phenylene-Thiophene Co-oligomers Toward Efficiencies Organic Electronic Devices, International Journal of Computational and Theoretical Chemistry. Vol. 8, No. 1, 2020, pp. 1-10. doi: 10.11648/j.ijctc.20200801.11
Copyright
Copyright © 2020 Authors retain the copyright of this article.
This article is an open access article distributed under the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Reference
[1]
T. Hiramatsu, T. Shimada, S. Hotta, H. Yanagi (2008). Photoluminescence dynamics of thiophene/phenylene co-oligomer thin films based on Förster energy transfer, Thin Solid Films 516, 2700-2703.
[2]
T. Yamao, K. Juri, A. Kamoi, S. Hotta (2009). Field-effect transistors based on organic single crystals grown by an improved vapor phase method, Organic Electronics 10, 1241-1247.
[3]
S. Ae Lee, S. Hotta, F. Nakanishi (2000), Spectroscopic Characteristics and Intermolecular Interactions of Thiophene/Phenylene Co-Oligomers in Solutions, J. Phys. Chem. A, 104, 1827-1833.
[4]
Q. Lia, Y. Duana, H. Z. Gaob, Z. М. Sua, Y. Genga (2015) Theoretical investigations into the electronic structures and electron transport properties of fluorine and carbonyl end-functionalized quarter thiophenes, J. Mol. Graphics and Modell. 59, 50-58.
[5]
A. Hlel, A. Mabrouk, M. Chemek, I. Ben Khalifa, K. Alimi (2015). A DFT study of charge-transfer and opto-electronic properties of some new materials involving carbazole units. Computational Condensed Matter 3, 30-40.
[6]
S. Hotta, T. Yamao (2011). The thiophene/phenylene co-oligomers: exotic molecular semiconductors integrating high-performance electronic and optical functionalities, J. Mater. Chem. 21, 1295-1304.
[7]
S. Kanazawa, A. Uchida, M. Ichikawa, T. Koyama, Y. Taniguchi (2008). Photoluminescence and Optical Gain Properties of a Crystalline Thiophene/Phenylene Co-oligomer, Jpn. J. Appl. Phys. 47, 8961-8964.
[8]
P. Lère-Porte, J. J. E. Moreau, C. Torreilles, F. Serein-Spirau, A. Righi, J. L. Sauvajol, M. Brunet (2000). Synthesis, orientation and optical properties of thiophene–dialkoxyphenylene copolymers, J. Mater. Chem. 10, 927-932.
[9]
A. Azazi, A. Mabrouk, M. Chemek, D. Kreher, K. Alimi (2014). DFT modeling of conjugated copolymers photophysical properties: Towards organic solar cell application, Synthetic Metals 198, 314-322.
[10]
G. Sang, E. Zhou, Y. Huang, Y. Zou, G. Zhao, Y. Li (2009). Incorporation of Thienylene vinylene and Triphenylamine Moieties into Polythiophene Side Chains for All-Polymer Photovoltaic Applications, J. Phys. Chem. C 113, 5879-5885.
[11]
F. C. Grozema, L. P. Candeias, M. Swart, P. Th. van Duijnen, J. Wildeman, G. Hadziioanou, L. D. A. Siebbeles, J. M. Warman (2002). Theoretical and experimental studies of the opto-electronic properties of positively charged oligo (phenylene vinylene) s: Effects of chain length and alkoxy substitution, J. Chem. Phys. 117, 11366-11378.
[12]
A. Irfan, A. G. Al-Sehemi (2014). DFT study of the electronic and charge transfer properties of perfluoroarene–thiophene oligomers, Journal of Saudi Chemical Society 18, 574-580.
[13]
Vinod D. Gupta, Abhinav B. Tathe, Vikas S. Padalkar, Prashant G. Umape, Nagaiyan Sekar (2013). Red emitting solid state fluorescent triphenylamine dyes: Synthesis, photo-physical property and DFT study, Dyes and Pigments 97, 429-439.
[14]
X.M.Hong, H. E. Katz, A. J. Lovinger, Bo-Cheng Wang, K. Raghavachari (2001), Thiophene-Phenylene and Thiophene-Thiazole Oligomeric Semiconductors with High Field-Effect Transistor On/Off Ratios, Chem. Mater.13, 4686-4691.
[15]
D. Shohei1, O.Yasuyuki1, S. Fumio, H. Shu, Y. Hisao (2016). Organic Light-Emitting Diodes with Heterojunction of Thiophene/Phenylene Co-Oligomer Derivatives, Journal of Nanoscience and Nanotechnology, 16, 3194-3199.
[16]
S. Ayachi, S. Ghomrasni, M. Bouachrine, M. Hamidi, K. Alimi (2013). Structure–property relationships of soluble poly (2,5-dibutoxyethoxy-1,4-phenylene-alt-2,5-thienylene) (PBuPT) for organic-optoelectronic devices, Journal of Molecular Structure 1036, 7-18.
[17]
C. R. Newman, C. D. Frisbie, D. A. S. Filho, J. L- Brédas, P. C. Ewbank, K. R. Mann (2004) Chem. Mater. 16, 4436- 4447.
[18]
C. R. Newman, C. D. Frisbie, F. D. A. da Silva, J. L. Bredas, P. C. Ewbank, K. R. Mann (2004). Introduction to Organic Thin Film Transistors and Design of n-Channel Organic Semiconductors, Chem. Mater., 16, 4436-4451.
[19]
L. Yang, J. K. Feng, Y. Liao, A. M. Ren (2007). Theoretical studies on the electronic and optical properties of two blue-emitting fluorene-pyridine-based copolymers, Opt. Mat. 29, 642–650.
[20]
M. Frisch, G. Trucks, H. Schlegel, G. Scuseria, M. Robb, J. Cheeseman, J. Montgomery Jr., T. Vreven, K. Kudin, J. Burant, Gaussian 03, Rev. C. 02, Gaussian Inc., Pittsburgh, PA, 200.
[21]
P. Hohenberg, W. Kohn (1964). Featured in Physics, Inhomogeneous Electron Gas Phys. Rev. Lett. 136, 864-871.
[22]
W. Kohn, L. J. Sham (1965). Self-Consistent Equations Including Exchange and Correlation Effects, Phys. Rev. Lett. 140, 1133-1138.
[23]
G. A. Petersson, A. Bennett, T. G. Tensfeldt, M. A. Al-Laham, W. A. Shirley, J. Mantzaris (1988). A complete basis set model chemistry. I. The total energies of closedshell atoms and hydrides of the first-row atoms, J. Chem. Phys. 89, 2193-2218.
[24]
A. D. Becke (1993). Density-functional thermochemistry. III. The role of exact exchange, J. Chem. Phys. 98, 5648–5652.
[25]
B. Miehlich, A. Savin, H. Stoll, H. Preuss (1989). Results obtained with the correlation energy density functionals of becke and Lee, Yang and Parr, Chemical Physics Letters 157, 200-206.
[26]
C. Lee, W. Yang, R. G. Parr (1988). Development of the Colle–Salvetti correlation-energy formula into a functional of the electron density, Physical Review B 37, 785-789.
[27]
T. Yanai, D. Tew, N. Handy (2004). A new hybrid exchange–correlation functional using the Coulomb-attenuating method (CAM-B3LYP), Chem. Phys. Lett. 393, 51-57.
[28]
M. E. Casida, in: D. P. Chong (Ed.), Recent Advances in Density Functional Methods, Part I, World Scientific, Singapore, 1995, pp. 155-193.
[29]
E. Gross, J. Dobson, M. Petersilka (1996). Density functional theory of time-dependent phenomena, Top. Curr. Chem. 181, 81-72.
[30]
S. Miertus, E. Scrocco, J. Tomasi (1981). Electrostatic interaction of a solute with a continuum. A direct utilizaion of AB initio molecular potentials for the prevision of solvent effects, J. Chem. Phys. 55, 117-129.
[31]
S. Miertus, J. Tomasi (1982). Approximate evaluations of the electrostatic free energy and internal energy changes in solution processes, J. Chem. Phys. 65, 239-245.
[32]
J. B. Foresman, M. Head-Gordon, J. A. Pople, M. J. Frisch (1992). Toward a systematic molecular orbital theory for excited states, J. Phys. Chem., 96, 135-149.
[33]
S. I. Gorelsky, SWizard Program, University of Ottawa, Ottawa, Canada, 2009. http://www.sg-chem.net/.
[34]
S. I. Gorelsky, A. B. P. Lever (2001). Electronic structure and spectra of ruthenium diimine complexes by density functional theory and INDO/S. Comparison of the two methods, J. Organometal. Chem. 635, 187-196.
[35]
J. C. Earles, K. C. Gordon, D. L. Officer, P. Wagner (2007). A Spectroscopic and Computational Study of the Neutral and Radical Cation Species of Conjugated Aryl-Substituted 2,5-Bis (2-thien-2-ylethenyl) thiophene-Based Oligomers, J. Phys. Chem. A 111, 7171-7180.
[36]
P. Wagner, A. M. Ballantyne, K. W. Jolley, D. L. Officer (2006). Synthesis and characterization of novel styryl-substituted oligothienylenevinylenes, Tetrahedron 62, 2190-2199.
[37]
S. Ghomrasni, S. Ayachi, K. Alimi (2015). New acceptor–donor–acceptor (A–D–A) type copolymers for efficient organic photovoltaic devices, Journal of Physics and Chemistry of Solids 76, 105-111.
[38]
J. Zhang, H. B. Li, Y. Geng, S. Z. Wen, R. L. Zhong, Y. Wu, Q. Fu, Z. M. Su (2013). Modification on C219 by coumarin donor toward efficient sensitizer for dye sensitized solar cells: A theoretical study, Dyes Pigm. 99, 127-135.
[39]
R. A. Marcus (1956). On the Theory of Oxidation-Reduction Reactions Involving Electron Transfer. J. Chem. Phys. 24, 966-978.
[40]
R. A. Marcus (1993). Theory and experiment, Rev. Mod. Phys. 65, 599-610.
[41]
B. C. Lin, C. P. Cheng, Z. Q. You, C. P. Hsu (2005). Charge transport properties of tris (8-hydroxyquinolinato) aluminum (III): why it is an electron transporter. J. Am. Chem. Soc., 127, 66-67.
[42]
G. D. Sharma, P. Bala Raju, M. S. Roy (2008). Effect of functional groups of acceptor material on photovoltaic response of bulk hetero-junction organic devices based on tin phthalocyanine (SnPc), Sol. Energ. Mat. Sol. Cells 92, 261-272.
[43]
R. Hirase, M. Ishihara, T. Katagiri, Y. Tanaka, H. Yanagi, S. Hotta (2014). Alkyl mono substituted thiophene/phenylene co-oligomers: Synthesis, thin film preparation, and transistor device characteristics, Organic Electronics 15, 1481-1492.
[44]
M. Turbiez, P. Frère, M. Allain, C. Videlot, J. Ackermann, J. Roncali (2005). Design of Organic Semiconductors: Tuning the Electronic Properties of π-Conjugated Oligothiophenes with the 3,4-Ethylenedioxythiophene (EDOT) Building Block, Chem. Eur. J. 11, 3742-3752.
[45]
O. H. Omar, F. Babudri, G. M. Farinola, F. Naso, A. Operamolla, A. Pedone (2011) Synthesis of d-glucose and l-phenylalanine substituted phenylene-thiophene oligomers, Tetrahedron 67, 486-494.
[46]
S. Kanazawa, M. Ichikawa, T. Koyama, Y. Taniguchi (2006). Self-Waveguided Photoemission and Lasing of Organic Crystalline Wires Obtained by an Improved Expitaxial Growth Method, Chem. Phys. Chem 7. 1881-1884.
[47]
G. A. Petersson, M. A. Al-Laham (1991). A complete basis set model chemistry. II. Open-shell systems and the total energies of the first-row atoms, J. Chem. Phys. 94. 6081-6090.
[48]
R. A. Marcus (1965). On the Theory of Electron-Transfer Reactions. VI. Unified Treatment for Homogeneous and Electrode Reactions, J. Chem. Phys. 43, 679-701.
[49]
M. D. Newton, N. Sutin (1984). Electron Transfer Reactions in Condensed Phases, Annual Rev. Phys. Chem. 35, 437-480.
[50]
R. A. Marcus, N. Sutin (1985). Electron transfers in chemistry and biology, Biochim. Biophys. Acta 811, 265-322.
[51]
P. F. Barbara, T. J. Meyer, M. A. Ratner (1996). Contemporary Issues in Electron Transfer Research, J. Phys. Chem. 100, 13148-13168.
Browse journals by subject