Charge transport and optical properties of cross-conjugated organic molecules: A theoretical study

Organic Electronics

Volumn 15, Issue 7, 2014, Pages 1607-1623

  Nithya, R ^a   Senthilkumar, K ^a  

^a BHARATHIAR UNIVERSITY   (India)

Author keywords

Absorption and emission spectra; Charge transfer integral; Mobility; Site energy; X shaped molecules

Indexed keywords

BENZENE; CARRIER MOBILITY; CHARGE TRANSFER; DICHLOROMETHANE; EMISSION SPECTROSCOPY; EXCITED STATES; INTELLIGENT SYSTEMS; MOLECULES; MONTE CARLO METHODS; OPTICAL PROPERTIES; ORGANIC POLYMERS;

ABSORPTION AND EMISSION SPECTRA; ABSORPTION AND EMISSIONS; CONJUGATED ORGANIC MOLECULES; DENSITY FUNCTIONAL THEORY METHODS; P-TYPE ORGANIC SEMICONDUCTORS; SITE ENERGY; TIME DEPENDENT DENSITY FUNCTIONAL THEORY; TRANSFER INTEGRAL;

DENSITY FUNCTIONAL THEORY;

EID: 84962448540     PISSN: 15661199     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.orgel.2014.04.025     Document Type: Article

References (60)

1. X. Guo, N. Zhou, S.J. Lou, J. Smith, D.B. Tice, J.W. Hennek, R.P. Ortiz, J.T.L. Navarrete, S. Li, J. Strzalka, L.X. Chen, R.P.H. Chang, A. Facchetti, and T.J. Marks Polymer solar cells with enhanced fill factors Nat. Photon. 7 2013 825 833
2. P. Zhang, W. Dou, Z. Ju, L. Yang, X. Tang, W. Liu, and Y. Wu A 9,9′-bianthracene-cored molecule enjoying twisted intramolecular charge transfer to enhance radiative-excitons generation for highly efficient deep-blue OLEDs Org. Electron. 14 2013 915 925
3. C. Wang, H. Dong, W. Hu, Y. Liu, and D. Zhu Semiconducting π-conjugated systems in field-effect transistors: a material odyssey of organic electronics Chem. Rev. 112 2012 2208 2267
4. J. Terao, A. Wadahama, A. Matono, T. Tada, S. Watanabe, S. Seki, T. Fujihara, and Y. Tsuji Design principle for increasing charge mobility of Π-conjugated polymers using regularly localized molecular orbitals Nat. Commun. 4 2013 1691
5. N. Zheng, H. Li, G. Sun, K. Zhong, and B. Yin Synthesis and properties of T-shaped organic conjugates based on 3,6-diarylpyridazine-fused tetrathiafulvalene Org. Biomol. Chem. 11 2013 5100 5108
6. D. Li, H. Wang, J. Kan, W. Lu, Y. Chen, and J. Jiang H-aggregation mode in triple-decker phthalocyaninato-europium semiconductors. Materials design for high-performance air-stable ambipolar organic thin film transistors Org. Electron. 14 2013 2582 2589
7. J.N. Wilson, M. Josowicz, Y.Q. Wang, and U.H.F. Bunz Cruciform pi-systems: hybrid phenylene-ethynylene/phenylene-vinylene oligomers Chem. Commun. 2003 2962 2963 (Pubitemid 38019227)
8. M. Hauck, J. Schonhaber, A.J. Zucchero, K.I. Hardcastle, T.J.J. Muller, and U.H.F. Bunz Phenothiazine cruciforms: synthesis and metallochromic properties J. Org. Chem. 72 2007 6714 6725 (Pubitemid 47434886)
9. H. Uoyama, K.S. Kim, K. Kuroki, J.-Y. Shin, T. Nagata, T. Okujima, H. Yamada, N. Ono, D. Kim, and H. Uno Highly pure synthesis, spectral assignments, and two-photon properties of cruciform porphyrin pentamers fused with benzene units Chem. Eur. J. 16 2010 4063 4074
10. S. Fratiloiu, K. Senthilkumar, F.C. Grozema, H. Christian-Pandya, Z.I. Niazimbetova, Y.J. Bhandari, M.E. Galvin, and L.D.A. Siebbeles Two-dimensional charge delocalization in X-shaped phenylenevinylene oligomers Chem. Mater. 18 2006 2118 2129
11. F.C. Grozema, and L.D.A. Siebbeles Mechanism of charge transport in self-organizing organic materials Int. Rev. Phys. Chem. 27 2008 87 138
12. V. Coropceanu, J.R.M. Cornil, D.A. da Silva Filho, Y. Olivier, R. Silbey, and J.-L. Bredas Charge transport in organic semiconductors Chem. Rev. 107 2007 926 952 (Pubitemid 46736532)
13. T. Sakurai, K. Shi, H. Sato, K. Tashiro, A. Osuka, A. Saeki, S. Seki, S. Tagawa, S. Sasaki, H. Masunaga, K. Osaka, M. Takata, and T. Aida Prominent electron transport property observed for triply fused metalloporphyrin dimer: directed columnar liquid crystalline assembly by amphiphilic molecular design J. Am. Chem. Soc. 130 2008 13812 13813
14. J.-L. Bredas, D. Beljonne, V. Coropceanu, and J. Cornil Charge-transfer and energy-transfer processes in π-conjugated oligomers and polymers: a molecular picture Chem. Rev. 104 2004 4971 5004
15. T. Yamada, F. Suzuki, A. Goto, T. Sato, K. Tanaka, and H. Kaji Revealing bipolar charge-transport property of 4,4′-N,N-dicarbazolylbiphenyl (CBP) by quantum chemical calculations Org. Electron. 12 2011 169 178
16. G.H. Duan, L.J. Wang, H.Y. Zhang, X. Gu, J. Chen, and Y.G. Ma Theoretical study of electronic and charge transport properties of cruciform pi-conjugated 3,6-diphenyl-1,2,4,5-(2′,2″-diphenyl)-benzobisazole Chem. J. Chin. Univ. 31 2010 1029 1033
17. S. Wang, S. Ren, Y. Xiong, M. Wang, X. Gao, and H. Li Benzo[1,2-b:4,5-b′]dithiophene-based cruciforms: syntheses, crystal structures, and charge transport properties ACS Appl. Mater. Interfaces 5 2013 663 671
18. J. Shin, N.S. Kang, K.H. Kim, T.W. Lee, J.-I. Jin, M. Kim, K. Lee, B.K. Ju, J.-M. Hong, and D.H. Choi J-aggregation induced low bandgap anthracene-based conjugated molecule for solution-processed solar cells Chem. Commun. 48 2012 8490 8492
19. K.H. Jung, S.Y. Bae, K.H. Kim, M.J. Cho, K. Lee, Z.H. Kim, D.H. Choi, D.H. Lee, D.S. Chung, and C.E. Park High-mobility anthracene-based X-shaped conjugated molecules for thin film transistors Chem. Commun. 2009 5290 5292
20. K.H. Kim, Z. Chi, M.J. Cho, J.-I. Jin, M.Y. Cho, S.J. Kim, J.-S. Joo, and D.H. Choi Soluble star-shaped molecules based on thiophene derivatives as organic semiconductors for field-effect transistor applications Chem. Mater. 19 2007 4925 4932 (Pubitemid 47582994)
21. D.U. Heo, J.B. Lee, Y.D. Han, J. Joo, H. Lee, H. Lee, and D.H. Choi Self-assembled monolayers made of 6-(5-((6-((5-hexylthiophen-2-yl)ethynyl)-9,10- bis(phenylethynyl)anthracen-2-yl)ethynyl)thiophen-2-yl)hexyl 3-(Triethoxysilyl)Propylcarbamate for Ultrathin Film Transistors Langmuir 28 2012 10948 10955
22. F. He, L.L. Tian, X.Y. Tian, H. Xu, Y.H. Wang, W.J. Xie, M. Hanif, J.L. Xia, F.Z. Shen, B. Yang, F. Li, Y.G. Ma, Y.Q. Yang, and J.C. Shen Diphenylamine-substituted cruciform oligo(phenylene vinylene): enhanced one- and two-photon excited fluorescence in the solid state Adv. Funct. Mater. 17 2007 1551 1557 (Pubitemid 46984715)
23. J.N. Wilson, and U.H.F. Bunz Switching of intramolecular charge transfer in cruciforms: metal ion sensing J. Am. Chem. Soc. 127 2005 4124 4125 (Pubitemid 40463010)
24. P.L. McGrier, K.M. Solntsev, S. Miao, L.M. Tolbert, O.R. Miranda, V.M. Rotello, and U.H.F. Bunz Hydroxycruciforms: amine-responsive fluorophores Chem. Eur. J. 14 2008 4503 4510
25. A.J. Zucchero, P.L. McGrier, and U.H.F. Bunz Cross-conjugated cruciform fluorophores Acc. Chem. Res. 43 2010 397 408
26. J.N. Wilson, K.I. Hardcastle, M. Josowicz, and U.H.F. Bunz Synthesis and electronic properties of bis-styryl substituted trimeric aryleneethynylenes. Comparison of cruciforms with iso-cruciforms Tetrahedron 60 2004 7157 7167 (Pubitemid 39055919)
27. J.N. Wilson, M.D. Smith, V. Enkelmann, and U.H.F. Bunz Cruciform pi-systems: effect of aggregation on emission Chem. Commun. 2004 1700 1701 (Pubitemid 39127842)
28. J. Lim, T.A. Albright, B.R. Martin, and O.S. Miljanic Benzobisoxazole cruciforms: heterocyclic fluorophores with spatially separated frontier molecular orbitals J. Org. Chem. 76 2011 10207 10219
29. C.A. Guido, S. Knecht, J. Kongsted, and B. Mennucci Benchmarking time-dependent density functional theory for excited state geometries of organic molecules in gas-phase and in solution J. Chem. Theory Comput. 9 2013 2209 2220
30. R. Nithya, N. Santhanamoorthi, P. Kolandaivel, and K. Senthilkumar Structural and spectral properties of 4-bromo-1-naphthyl chalcones: a quantum chemical study J. Phys. Chem. A 115 2011 6594 6602
31. R. Nithya, P. Kolandaivel, and K. Senthilkumar Understanding the absorption and emission spectra of borondipyrromethene dye and its substituted analogues Mol. Phys. 110 2012 445 456
32. R. Nithya, M. Sowmiya, P. Kolandaivel, and K. Senthilkumar Structural, optical, and charge transport properties of cyclopentadithiophene derivatives: a theoretical study Struct. Chem. 25 2014 715 731
33. A.A. Vasilev, K. De Mey, I. Asselberghs, K. Clays, B. Champagne, S.E. Angelova, M.I. Spassova, C. Li, and K. Mullen Enhanced intramolecular charge transfer in new type donor-acceptor substituted perylenes J. Phys. Chem. C 116 2012 22711 22719
34. Y. Tawada, T. Tsuneda, S. Yanagisawa, T. Yanai, and K. Hirao A long-range-corrected time-dependent density functional theory J. Chem. Phys. 120 2004 8425
35. H. Iikura, T. Tsuneda, T. Yanai, and K. Hirao A long-range correction scheme for generalized-gradient-approximation exchange functionals J. Chem. Phys. 115 2001 3540
36. T. Yanai, D.P. Tew, and N.C. Handy A new hybrid exchange-correlation functional using the Coulomb-attenuating method (CAM-B3LYP) Chem. Phys. Lett. 393 2004 51 57
37. Y. Zhao, and D.G. Truhlar Density functional for spectroscopy: no long-range self-interaction error, good performance for Rydberg and charge-transfer states, and better performance on average than B3LYP for ground states J. Phys. Chem. A 110 2006 13126 13130 (Pubitemid 46065870)
38. Y. Zhao, and D. Truhlar The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals Theor. Chem. Acc 120 2008 215 241
39. A.D. Becke Density-functional thermochemistry. III. The role of exact exchange J. Chem. Phys. 98 1993 5648 5652
40. C.T. Lee, W. Yang, and R.G. Parr Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys. Rev. B 37 1988 785 789
41. S.H. Vosko, L. Wilk, and M. Nusair Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis Can. J. Phys. 58 1980 1200 1211
42. G. te Velde, F.M. Bickelhaupt, E.J. Baerends, C. Fonseca Guerra, S.J.A. van Gisbergen, J.G. Snijders, and T. Ziegler Chemistry with ADF J. Comput. Chem. 22 2001 931 967 (Pubitemid 32455733)
43. A.D. Becke Density-functional exchange-energy approximation with correct asymptotic behavior Phys. Rev. A 38 1988 3098 3100
44. J.P. Perdew Density-functional approximation for the correlation energy of the inhomogeneous electron gas Phys. Rev. B 33 1986 8822 8824
45. R.A. Marcus, and N. Sutin Electron transfers in chemistry and biology Biochim. Biophys. Acta Rev. Bioenergy 811 1985 265 322 (Pubitemid 15246565)
46. K.V. Mikkelsen, and M.A. Ratner Electron tunneling in solid-state electron-transfer reactions Chem. Rev. 87 1987 113 153
47. K. Senthilkumar, F.C. Grozema, F.M. Bickelhaupt, and L.D.A. Siebbeles Charge transport in columnar stacked triphenylenes: effects of conformational fluctuations on charge transfer integrals and site energies J. Chem. Phys. 119 2003 9809 9817
48. H.L. Tavernier, and M.D. Fayer Distance dependence of electron transfer in DNA: the role of the reorganization energy and free energy J. Phys. Chem. B 104 2000 11541 11550
49. P. Prins, K. Senthilkumar, F.C. Grozema, P. Jonkheijm, A.P.H.J. Schenning, E.W. Meijer, and L.D.A. Siebbeles Charge transport in self-organized Π-stacks of p-phenylene vinylene oligomers J. Phys. Chem. B 109 2005 18267 18274 (Pubitemid 41464160)
50. S. Miertus, E. Scrocco, and J. Tomasi Electrostatic interaction of a solute with a continuum. A direct utilization of AB initio molecular potentials for the prevision of solvent effects Chem. Phys. 55 1981 117 129
51. T. Miteva, L. Palmer, L. Kloppenburg, D. Neher, and U.H.F. Bunz Interplay of Thermochromicity and liquid crystalline behavior in poly(p- phenyleneethynylene)s: π-π interactions or planarization of the conjugated backbone? Macromolecules 33 2000 652 654 (Pubitemid 30563109)
52. V. Lemaur, D.A. da Silva Filho, V. Coropceanu, M. Lehmann, Y. Geerts, J. Piris, M.G. Debije, A.M. van de Craats, K. Senthilkumar, L.D.A. Siebbeles, J.M. Warman, J.-L. Bredas, and J. Cornil Charge transport properties in discotic liquid crystals: a quantum-chemical insight into structure property relationships J. Am. Chem. Soc. 126 2004 3271 3279 (Pubitemid 38380730)
53. S. Ando, J.-I. Nishida, H. Tada, Y. Inoue, S. Tokito, and Y. Yamashita High performance n-type organic field-effect transistors based on π-electronic systems with trifluoromethylphenyl groups J. Am. Chem. Soc. 127 2005 5336 5337 (Pubitemid 40569842)
54. S. Ando, R. Murakami, J.-I. Nishida, H. Tada, Y. Inoue, S. Tokito, and Y. Yamashita N-type organic field-effect transistors with very high electron mobility based on thiazole oligomers with trifluoromethylphenyl groups J. Am. Chem. Soc. 127 2005 14996 14997 (Pubitemid 41547345)
55. J.W. Ponder, TINKER 5.1, Software Tools for Molecular Design, Saint Louis, Washington, 2010.
56. M.N. Gard, A.J. Zucchero, G. Kuzmanich, C. Oelsner, D. Guldi, A. Dreuw, U.H.F. Bunz, and M.A. Garcia-Garibay Cruciforms' polarized emission confirms disjoint molecular orbitals and excited states Org. Lett. 14 2012 1000 1003
57. K. Navamani, G. Saranya, P. Kolandaivel, and K. Senthilkumar Effect of structural fluctuations on charge carrier mobility in thiophene, thiazole and thiazolothiazole based oligomers Phys. Chem. Chem. Phys. 15 2013 17947 17961
58. Y. Geng, H.-B. Li, S.-X. Wu, and Z.-M. Su The interplay of intermolecular interactions, packing motifs and electron transport properties in perylene diimide related materials: a theoretical perspective J. Mater. Chem. 22 2012 20840 20851
59. Y. Li, P. Song, J. Liu, R. Su, and M. Zhao Charge transfer and optoelectronic properties in the triarylamine-based donor-π bridge-acceptor dyes for dye-sensitised solar cells Mol. Simul. 39 2013 521 528
60. J.R. Mannekutla, B.G. Mulimani, and S.R. Inamdar Solvent effect on absorption and fluorescence spectra of coumarin laser dyes: evaluation of ground and excited state dipole moments Spectrochim. Acta Part A 69 2008 419 426 (Pubitemid 351172900)