Push–pull effect on the electronic, optical and charge transport properties of the benzo[2,3-b]thiophene derivatives as efficient multifunctional materials

Computational and Theoretical Chemistry - Tập 1031 - Trang 76-82 - 2014
Ahmad Irfan1, Abdullah G. Al-Sehemi1,2,3, Mohammad Sultan Al-Assiri4,5
1Department of Chemistry, Faculty of Science, King Khalid University, P.O. Box 9004, Abha, 61413, Saudi Arabia
2Unit of Science and Technology, Faculty of Science, King Khalid University, P.O. Box 9004, Abha 61413, Saudi Arabia
3Center of Excellence for Advanced Materials Research, King Khalid University, P.O. Box 9004, Abha 61413, Saudi Arabia
4Department of Physics, Faculty of Sciences and Arts, Najran University, P.O. Box 1988, Najran 11001, Saudi Arabia
5Promising Centre for Sensors and Electronic Devices (PCSED), Najran University, P.O. Box: 1988, Najran, 11001, Saudi Arabia

Tài liệu tham khảo

Garnier, 1994, All-polymer field-effect transistor realized by printing techniques, Science, 265, 1684, 10.1126/science.265.5179.1684 Burroughes, 1990, Light-emitting diodes based on conjugated polymers, Nature, 347, 539, 10.1038/347539a0 Katz, 2000, A soluble and air-stable organic semiconductor with high electron mobility, Nature, 404, 478, 10.1038/35006603 Sariciftci, 1992, Photoinduced electron transfer from a conducting polymer to buckminsterfullerene, Science, 258, 1474, 10.1126/science.258.5087.1474 Irfan, 2009, Fluorinated derivatives of mer-Alq3: energy decomposition analysis, optical properties, and charge transfer study, Theor. Chem. Acc., 122, 275, 10.1007/s00214-009-0506-3 Torruellas, 1990, Dispersion measurements of the third-order nonlinear susceptibility of polythiophene thin films, Chem. Phys. Lett., 175, 11, 10.1016/0009-2614(90)85510-J Venkataraman, 2006, Dependence of single-molecule junction conductance on molecular conformation, Nature, 442, 904, 10.1038/nature05037 Ernst, 1986, Coordination characteristics of four isomeric.alpha.-diimine ligands..pi. Molecular orbital perturbation calculations for the bidiazines and their correlation with the properties of group 6 metal carbonyl complexes, J. Am. Chem. Soc., 108, 3578, 10.1021/ja00273a005 Hughes, 2005, Electron-transporting materials for organic electroluminescent and electrophosphorescent devices, Mater. Chem., 15, 94, 10.1039/b413249c Galand, 2006, Optimization of narrow band-gap propylenedioxythiophene: cyanovinylene copolymers for optoelectronic applications, Macromolecules, 39, 9132, 10.1021/ma061935o Wu, 2010, Π-Conjugated molecules with fused rings for organic field-effect transistors: design, synthesis and applications, Chem. Soc. Rev., 39, 1489, 10.1039/B813123F Irfan, 2013, Modeling of multifunctional donor-bridge-acceptor 4,6-di(thiophen-2-yl)pyrimidine derivatives: a first principles study, J. Mol. Graph. Model., 44, 168, 10.1016/j.jmgm.2013.06.003 Dufresne, 2007, Preparation, photophysics, and electrochemistry of segmented comonomers consisting of thiophene and pyrimidine units: new monomers for hybrid copolymers, J. Phys. Chem. B, 111, 11407, 10.1021/jp075259j Sanchez-Carrera, 2006, Vibronic coupling in the ground and excited states of oligoacene cations, J. Phys. Chem. B, 110, 18904, 10.1021/jp057462p Wong, 2008, Coumarin dyes for dye-sensitized solar cells: a long-range-corrected density functional study, J. Chem. Phys., 129, 214703, 10.1063/1.3025924 Guillaumont, 2000, Calculation of the absorption wavelength of dyes using time-dependent density-functional theory (TD-DFT), Dyes Pigment, 46, 85, 10.1016/S0143-7208(00)00030-9 Al-Sehemi, 2012, The DFT investigations of the electron injection in hydrazone-based sensitizers, Theor. Chem. Acc., 131, 1199, 10.1007/s00214-012-1199-6 Zhang, 2008, Theoretical studies on the geometrical and electronic structures of N-methyle-3,4-fulleropyrrolidine, J. Mol. Struct. (Theochem), 862, 98, 10.1016/j.theochem.2008.04.035 Irfan, 2009, Push–pull effect on the charge transfer, and tuning of emitting color for disubstituted derivatives of mer-Alq3, Chem. Phys., 364, 39, 10.1016/j.chemphys.2009.08.009 Irfan, 2013, Structural, electronic and charge transfer studies of dianthra[2,3-b:2′,3′-f]thieno[3,2-b]thiophene and its analogues: quantum chemical investigations, J. Mol. Struct., 1049, 198, 10.1016/j.molstruc.2013.06.023 Preat, 2010, Design of new triphenylamine-sensitized solar cells: a theoretical approach, Environ. Sci. Technol., 44, 5666, 10.1021/es100920j Preat, 2009, Enhanced efficiency of organic dye-sensitized solar cells: triphenylamine derivatives, J. Phys. Chem. C, 113, 16821, 10.1021/jp904946a Xu, 2008, New triphenylamine-based dyes for dye-sensitized solar cells, J. Phys. Chem. C, 112, 874, 10.1021/jp076992d Al-Sehemi, 2013, Electronic, optical, and charge transfer properties of donor-bridge-acceptor hydrazone sensitizers, Struct. Chem., 24, 499, 10.1007/s11224-012-0103-2 Irfan, 2012, Quantum chemical study in the direction to design efficient donor-bridge-acceptor triphenylamine sensitizers with improved electron injection, J. Mol. Model., 18, 4893, 10.1007/s00894-012-1488-y Jin, 2012, Theoretical study of coumarin derivatives as chemosensors for fluoride anion, Comput. Theor. Chem., 986, 93, 10.1016/j.comptc.2012.02.018 Irfan, 2012, Quantum chemical investigations aimed at modeling highly efficient zinc porphyrin dye sensitized solar cells, J. Mol. Model., 18, 4199, 10.1007/s00894-012-1421-4 Al-Sehemi, 2012, Synthesis, characterization and DFT study of 4H-benzo[h]chromene derivatives, J. Mol. Struct., 1018, 171, 10.1016/j.molstruc.2012.03.018 Irfan, 2012, Quantum chemical approach toward rational designing of highly efficient oxadiazole based oligomers used in organic field effect transistors, J. Comput. Electron., 11, 374, 10.1007/s10825-012-0417-8 Huong, 2013, Π-conjugated molecules containing naphtho[2,3-b]thiophene and their derivatives: theoretical design for organic semiconductors, J. Phys. Chem. C, 117, 10175, 10.1021/jp401191a Matthews, 1996, Calculation of the photocurrent-potential characteristic for regenerative, sensitized semiconductor electrodes, Sol. Energy Mater. Sol. Cells, 44, 119, 10.1016/0927-0248(96)00036-0 Scalmani, 2006, Geometries and properties of excited states in the gas phase and in solution: theory and application of a time-dependent density functional theory polarizable continuum model, J. Chem. Phys., 124, 094107, 10.1063/1.2173258 Greenham, 1993, Efficient light-emitting diodes based on polymers with high electron affinities, Nature, 365, 628, 10.1038/365628a0 Marcus, 1985, Electron transfers in chemistry and biology, Biochim. Biophys. Acta, 811, 265, 10.1016/0304-4173(85)90014-X Irfan, 2013, Modeling of efficient charge transfer materials of 4,6-di(thiophen-2-yl)pyrimidine derivatives: Quantum chemical investigations, Comput. Mater. Sci. Bredas, 2002, Organic semiconductors: a theoretical characterization of the basic parameters governing charge transport, Proc. Natl. Acad. Sci., 99, 5804, 10.1073/pnas.092143399 Soos, 2004, Polarization in organic molecular crystals and charge-transfer salts, J. Lumin., 110, 332, 10.1016/j.jlumin.2004.08.029 M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, 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, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian 09, Revision A.1; Gaussian Inc., Wallingford, CT, 2009. Hepp, 2003, Light-emitting field-effect transistor based on a tetracene thin film, Phys. Rev. Lett., 91, 157406, 10.1103/PhysRevLett.91.157406 Muccini, 2006, A bright future for organic field-effect transistors, Nat. Mater., 5, 605, 10.1038/nmat1699 Chan, 1970, Dipole moments, charge-transfer parameters, and ionization potentials of the methyl-substituted benzene–tetracyanoethylene complexes, Can. J. Chem., 48, 299, 10.1139/v70-045 Hansch, 1991, A survey of Hammett substituent constants and resonance and field parameters, Chem. Rev., 91, 165, 10.1021/cr00002a004