Understanding electron-withdrawing substituent effect on structural, electronic and charge transport properties of perylene bisimide derivatives

Organic Electronics

Volumn 12, Issue 11, 2011, Pages 1806-1814

  Chai, Shuo ^a,b   Wen, Shu Hao ^a   Han, Ke Li ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Anisotropic mobility; Charge transport; Density functional theory; Electron withdrawing; n Type

Indexed keywords

ANISOTROPY; CARRIER TRANSPORT; CHARGE TRANSFER; DESIGN FOR TESTABILITY; ELECTRON MOBILITY; ELECTRONIC PROPERTIES; ELECTRONS; MOLECULAR ORBITALS; MOLECULES; ORGANIC SOLAR CELLS; POLYCYCLIC AROMATIC HYDROCARBONS; SEMICONDUCTING ORGANIC COMPOUNDS; SOLAR CELLS;

ANISOTROPIC MOBILITY; CONJUGATED STRUCTURES; ELECTRON-WITHDRAWING SUBSTITUENTS; ELECTRONWITHDRAWING; HIGH-PERFORMANCE SEMICONDUCTORS; INTERMOLECULAR INTERACTIONS; MOLECULAR GEOMETRIES; N-TYPE ORGANIC SEMICONDUCTOR;

DENSITY FUNCTIONAL THEORY;

EID: 80051897242     PISSN: 15661199     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.orgel.2011.07.008     Document Type: Article

References (52)

1. Y. Ie, T. Uto, N. Yamamoto, and Y. Aso Dendritic oligothiophene bearing perylene bis(dicarboximide) groups as an active material for photovoltaic device Chem. Commun. 23 2009 1213 1215
2. J.E. Anthony Functionalized acenes and heteroacenes for organic electronics Chem. Rev. 106 2006 5028 5048 (Pubitemid 46099388)
3. M.L. Tang, T. Okamoto, and Z.N. Bao High-performance organic semiconductors: asymmetric linear acenes containing sulphur J. Am. Chem. Soc. 128 2006 16002 16003 (Pubitemid 44936570)
4. M.Y. Kuo, and C.C. Liu Molecular design toward high hole mobility organic semiconductors: Tetraceno [2,3-c] thiophene derivatives of ultrasmall reorganization energies J. Phys. Chem. C 113 2009 16303 16306
5. Z.Y. Yuan, Y. Xiao, and X.H. Qian A design concept of planar conjugated ladder oligomers of perylene bisimides and efficient synthetic strategy via regioselective photocyclization Chem. Commun. 46 2010 2772 2774
6. H.X. Li, R.H. Zheng, and Q.A. Shi Theoretical study on charge carrier mobilities of tetrathiafulvalene derivatives Phys. Chem. Chem. Phys. 13 2011 5642 5650
7. R. Chesterfield, C. Newman, T. Pappenfus, P. Ewbank, M. Haukaas, K. Mann, L. Miller, and C. Frisbie High electron mobility and ambipolar transport in organic thin-film transistors based on a π-stacking quinoidal terthiophene Adv. Mater. 15 2003 1278 1282
8. M.E. Gershenson, V. Podzorov, and A.F. Morpurgo Colloquium: electronic transport in single-crystal organic transistors Rev. Mod. Phys. 78 2006 973 989 (Pubitemid 44496727)
9. D. Braga, and G. Horowitz High-performance organic field-effect transistors Adv. Mater. 21 2009 1473 1486
10. W.Q. Deng, and W.A. Goddard Predictions of hole mobilities in oligoacene organic semiconductors from quantum mechanical calculations J. Phys. Chem. B 108 2004 8614 8621
11. D. Nabok, P. Puschnig, C. Ambrosch-Draxl, O. Werzer, R. Resel, and D.M. Smilgies Crystal and electronic structures of pentacene thin films from grazing-incidence X-ray diffraction and first-principles calculations Phys. Rev. B 76 2007
12. L.B. Roberson, J. Kowalik, L.M. Tolbert, C. Kloc, R. Zeis, X.L. Chi, R. Fleming, and C. Wilkins Pentacene disproportionation during sublimation for field-effect transistors J. Am. Chem. Soc. 127 2005 3069 3075 (Pubitemid 40349888)
13. S.H. Wen, W.Q. Deng, and K.L. Han Revealing quantitative structure-activity relationships of transport properties in acene and acene derivative organic materials Phys. Chem. Chem. Phys. 12 2010 9267 9275
14. H. Klauk, U. Zschieschang, J. Pflaum, and M. Halik Ultralow-power organic complementary circuits Nature 445 2007 745 748 (Pubitemid 46279711)
15. P.F. Baude, D.A. Ender, M.A. Haase, T.W. Kelley, D.V. Muyres, and S.D. Theiss Pentacene-based radio-frequency identification circuitry Appl. Phys. Lett. 82 2003 3964 3966
16. M.-H. Yoon, S.A. DiBenedetto, A. Facchetti, and T.J. Marks Organic thin-film transistors based on carbonyl-functionalized quaterthiophenes: High mobility n-channel semiconductors and ambipolar transport J. Am. Chem. Soc. 127 2005 1348 1349 (Pubitemid 40204490)
17. Y. Ie, M. Nitani, M. Karakawa, H. Tada, and Y. Aso Air-stable n-type organic field-effect transistors based on carbonyl-bridged bithiazole derivatives Adv. Funct. Mater. 20 2010 907 913
18. M.C.R. Delgado, E.G. Kim, D.A. da Silva, and J.L. Brédas Tuning the charge-transport parameters of perylene diimide single crystals via end and/or core functionalization: a density functional theory investigation J. Am. Chem. Soc. 132 2010 3375 3387
19. M. Scholz, R. Schmidt, S. Krause, A. Scholl, F. Reinert, and F. Würthner Electronic structure of epitaxial thin films of bay-substituted perylene bisimide dyes Appl. Phys. A 95 2009 285 290
20. B.L. Liang, Y.X. Zhang, Y.F. Wang, W. Xu, and X.Y. Li Structures and properties of 1,7-disubstituted perylene tetracarboxylic diimides: The substitutional effect study based on density functional theory calculations J. Mater. Chem. 917 2009 133 141
21. F. Pichierri Substitution effects on the frontier orbitals of 3,4,9,10-perylene bis(dicarboximide). A computational quantum chemistry study with insights into the electronic properties of organic semiconductors J. Mol. Struc-Theochem 686 2004 57 63
22. L. Schmidt-Mende, A. Fechtenkotter, K. Mullen, E. Moons, R.H. Friend, and J.D. MacKenzie Self-organized discotic liquid crystals for high-efficiency organic photovoltaics Science 293 2001 1119 1122 (Pubitemid 32758088)
23. Z.Y. Yuan, J. Li, Y. Xiao, Z. Li, and X.H. Qian Core-perfluoroalkylated perylene diimides and naphthalene diimides: versatile synthesis, solubility, electrochemistry, and optical properties J. Org. Chem 75 2010 3007 3016
24. A.L. Briseno, S.C.B. Mannsfeld, C. Reese, J.M. Hancock, Y. Xiong, S.A. Jenekhe, Z. Bao, and Y. Xia Perylenediimide nanowires and their use in fabricating field-effect transistors and complementary inverters Nano Lett. 7 2007 2847 2853 (Pubitemid 47522448)
25. Z.J. Chen, M.G. Debije, T. Debaerdemaeker, P. Osswald, and F. Würthner Tetrachloro-substituted perylene bisimide dyes as promising n-type organic semiconductors: Studies on structural, electrochemical and charge transport properties Chem. Phys. Chem. 5 2004 137 140
26. H.E. Katz, A.J. Lovinger, J. Johnson, C. Kloc, T. Siegrist, W. Li, Y.Y. Lin, and A. Dodabalapur A soluble and air-stable organic semiconductor with high electron mobility Nature 404 2000 478 481 (Pubitemid 30186885)
27. R. Schmidt, M.M. Ling, J.H. Oh, M. Winkler, M. Könemann, Z.N. Bao, and F. Würthner Core-fluorinated rerylene bisimide dyes: Air stable n-channel organic semiconductors for thin film transistors with exceptionally high on-to-off current ratios Adv. Mater. 19 2007 3692 3695 (Pubitemid 350134627)
28. J.H. Oh, S.L. Suraru, W.-Y. Lee, M. Könemann, H.W. Höffken, C. Röger, R. Schmidt, Y. Chung, W.-C. Chen, F. Würthner, and Z. Bao High-performance air-stable n-type organic transistors based on core-chlorinated naphthalene tetracarboxylic diimides Adv. Funct. Mater. 20 2010 2148 2156
29. M.M. Shi, H.Z. Chen, J.Z. Sun, J. Ye, and M. Wang Fluoroperylene diimide: a soluble and air-stable electron acceptor Chem. Commun. 2003 1710 1711 (Pubitemid 36829606)
30. H.Z. Chen, M.M. Ling, X. Mo, M.M. Shi, M. Wang, and Z. Bao Air stable n-channel organic semiconductors for thin film transistors based on fluorinated derivatives of perylene diimides Chem. Mater. 19 2007 816 824 (Pubitemid 46408950)
31. B.A. Jones, M.J. Ahrens, M.H. Yoon, A. Facchetti, T.J. Marks, and M.R. Wasielewski High-mobility air-stable n-type semiconductors with processing versatility: dicyanoperylene-3,4:9,10-bis(dicarboximides) Angew. Chem. Int. Ed. 43 2004 6363 6366 (Pubitemid 40029473)
32. S.H. Wen, A. Li, J.L. Song, W.Q. Deng, K.L. Han, and W.A. Goddard First-principles investigation of anistropic hole mobilities in organic semiconductors J. Phys. Chem. B 113 2009 8813 8819
33. J.-D. Huang, S.-H. Wen, W.-Q. Deng, and K.-L. Han Simulation of hole mobility in α-oligofuran crystals J. Phys. Chem. B 115 2011 2140 2147
34. T. Yamada, T. Sato, K. Tanaka, and H. Kaji Percolation paths for charge transports in N,N′-diphenyl-N,N′-di(m-tolyl)benzidine (TPD) Org. Electron. 11 2010 255 265
35. I. Vilfan Small polaron model of electron motion in organic molecular-crystals Phys. Stat. Sol. B 59 1973 351 360
36. J.J. Kwiatkowski, J. Nelson, H. Li, J.L. Brédas, W. Wenzel, and C. Lennartz Simulating charge transport in tris(8-hydroxyquinoline) aluminium (Alq3) Phys. Chem. Chem. Phys. 10 2008 1852 1858
37. 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. Sonnenberg, J.L. Zheng, 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, N.J. 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, R.A. Gaussian 09, Gaussian, Inc., Wallingford, CT, 2009.
38. V. Coropceanu, J. Cornil, D.A. da Silva, Y. Olivier, R. Silbey, and J.L. Brédas Charge transport in organic semiconductors Chem. Rev. 107 2007 926 952 (Pubitemid 46736532)
39. G.T. Velde, F.M. Bickelhaupt, E.J. Baerends, C.F. Guerra, S.J.A. Van Gisbergen, J.G. Snijders, and T. Ziegler Chemistry with ADF J. Comput. Chem. 22 2001 931 967 (Pubitemid 32455733)
40. R.M. Glaeser, and R.S. Berry Mobilities of electrons and holes in organic molecular solids. Comparison of band and hopping models J. Chem. Phys. 44 1966 3797 3810
41. G.R. Hutchison, M.A. Ratner, and T.J. Marks Effects of heteroatom and molecular packing on hopping transport in organic semiconductors J. Am. Chem. Soc. 127 2005 16866 16881
42. S.T. Bromley, M. Mas-Torrent, P. Hadley, and C. Rovira Importance of intermolecular interactions in assessing hopping mobilities in organic field effect transistors: Pentacene versus dithiophene-tetrathiafulvalene J. Am. Chem. Soc. 126 2004 6544 6545 (Pubitemid 38697342)
43. G.R. Hutchison, M.A. Ratner, and T.J. Marks Hopping transport in conductive heterocyclic oligomers: Reorganization energies and substituent effects J. Am. Chem. Soc. 127 2005 2339 2350 (Pubitemid 40270538)
44. R.A. Marcus On the theory of oxidation-reduction reactions involving electron transfer J. Chem. Phys. 24 1956 966 978
45. R.A. Marcus Theory of oxidation-reduction reactions involving electron transfer.5. Comparison and properties of electrochemical and chemical rate constants J. Phys. Chem. 67 1963 853 857
46. R.A. Marcus Electron-transfer reactions in chemistry - theory and experiment Rev. Mod. Phys. 65 1993 599 610
47. C.R. Newman, C.D. Frisbie, D.A. da Silva Filho, J.-L. Brédas, P.C. Ewbank, and K.R. Mann Introduction to organic thin film transistors and design of n-channel organic semiconductors Chem. Mater. 16 2004 4436 4451
48. B.A. Jones, A. Facchetti, M.R. Wasielewski, and T.J. Marks Theory of oxidation-reduction reactions involving electron transfer.5. Comparison and properties of electrochemical and chemical rate constants J. Am. Chem. Soc. 129 2007 15259 15278
49. R. Schmidt, J.H. Oh, Y.S. Sun, M. Deppisch, A.M. Krause, K. Radacki, H. Braunschweig, M. Konemann, P. Erk, Z.A. Bao, and F. Würthner High-performance air-stable n-channel organic thin film transistors based on halogenated perylene bisimide semiconductors J. Am. Chem. Soc. 131 2009 6215 6228
50. S.H. Wen, W.Q. Deng, and K.L. Han Ultra-low resistance at TTF-TCNQ organic interfaces Chem. Commun. 46 2010 5133 5135
51. V.C. Sundar, J. Zaumseil, V. Podzorov, E. Menard, R.L. Willett, T. Someya, M.E. Gershenson, and J.A. Rogers Elastomeric transistor stamps: reversible probing of charge transport in organic crystals Science 303 2004 1644 1646 (Pubitemid 38338317)
52. S.C.B. Mannsfeld, J. Locklin, C. Reese, M.E. Roberts, A.J. Lovinger, and Z. Bao Probing the anisotropic field-effect mobility of solution-deposited dicyclohexyl-α-quaterthiophene single crystals Adv. Funct. Mater. 17 2007 1617 1622 (Pubitemid 47116533)