An important key to design molecules with small internal reorganization energy: Strong nonbonding character in frontier orbitals

Journal of Physical Chemistry Letters

Volumn 1, Issue 1, 2010, Pages 116-121

  Chang, Yu Chang ^a   Chao, Ito ^a  

^a INSTITUTE OF CHEMISTRY   (Taiwan)

Author keywords

Electron transport; Hard matter; Optical and electronic devices

Indexed keywords

ELECTRON TRANSPORT; ELECTRON-TRANSFER REACTIONS; ELECTRONIC DEVICE; ENERGY COST; FRONTIER MOLECULAR ORBITALS; FRONTIER ORBITALS; LITERATURE DATA; MOLECULAR DESIGN; MOLECULAR FRAMEWORKS; ORGANIC ELECTRONICS; PHENALENYL; PHTHALOCYANINE DERIVATIVES; REORGANIZATION ENERGIES; SMALL ENERGY; STRUCTURAL REORGANIZATION;

CHEMICAL BONDS; COSTS; ELECTRON TRANSITIONS; ELECTRON TRANSPORT PROPERTIES; ELECTRONIC EQUIPMENT; MOLECULAR ORBITALS; THERMOELECTRIC EQUIPMENT;

MOLECULES;

EID: 77149172309     PISSN: None     EISSN: 19487185     Source Type: Journal    
DOI: 10.1021/jz900042x     Document Type: Article

References (40)

1. Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001.
2. Marcus, R. A. Electron Transfer Reactions in Chemistry:Theory and Experiment (Nobel Lecture). Angew. Chem., Int. Ed. 1993, 32, 1111-1121.
3. Imahori, H.; Tamaki, K.; Guldi, D. M.; Luo, C.; Fujitsuka, M.; Ito, O.; Sakata, Y.; Fukuzumi, S. Modulating Charge Separation and Charge Recombination Dynamics in Porphyr-in-Fullerene Linked Dyads and Triads: Marcus-Normal versus Inverted Region. J. Am. Chem. Soc. 2001, 123, 2607-2617.
4. Fukuzumi, S. Development of Bioinspired Artificial Photo-synthetic Systems. Phys. Chem. Chem. Phys. 2008, 10, 2283-2297.
5. D'Souza, F.; Ito, O. Photoinduced Electron Transfer in Supra-molecular Systems of Fullerenes Functionalized with Ligands Capable of Binding to Zinc Porphyrins and Zinc Phthalocyanines. Coord. Chem. Rev. 2005, 249, 1410-1422.
6. El-Khouly, M. E.; Ito, O.; Smith, P. M.; D'Souza, F. Intermole-cular and Supramolecular Photoinduced Electron Transfer Processes of Fullerene-Porphyrin/Phthalocyanine Systems. J. Photochem. Photobiol. C 2004, 5, 79-104.
7. Troisi, A. Prediction of the Absolute Charge Mobility of Molecular Semiconductors: The Case of Rubrene. Adv. Mater. 2007,19,2000-2004.
8. Cheung, D. L.; Troisi, D. A. Modelling Charge Transport in Organic Semiconductors: From Quantum Dynamics to Soft Matter. Phys. Chem. Chem. Phys. 2008, 10, 5941-5952.
9. da Silva Filho, D. A.; Olivier, Y.; Coropceanu, V.; Bredas, J.-L.; Cornil, J. In Organic Field-Effect Transistors; Bao, Z., Locklin, J., Eds.; Optical Science and Engineering Series; CRC Press: Boca Raton, FL, 2007; Chapter 1, pp 1-26.
10. Tan, H. S.; Kulkarni, S. R.; Cahyadi, T.; Lee, P. S.; Mhaisalkar, S. G.; Kasim, J.; Shen, Z. X.; Zhu, F. R. Solution-Processed Trilayer Inorganic Dielectric for High Performance Flexible Organic Field Effect Transistors. Appl. Phys. Lett. 2008,93, 183503/1-183503/3.
11. Li, L.; Tang, Q.; Li, H.; Yang, X.; Hu, W.; Song, Y.; Shuai, Z.; Xu, W.; Liu, Y.; Zhu, D. An Ultra Closely π-Stacked Organic Semiconductorfor High PerformanceField-Effect Transistors. Adv. Mater. 2007, 19, 2613-2617.
12. Mas-Torrent, M.; Rovira, C. Novel Small Molecules For Organic Field-Effect Transistors: Towards Processability and High Performance. Chem. Soc. Rev. 2008, 37, 827-838.
13. Deng, W.-Q.; Goddard, W. A. Predictions of Hole Mobilities in Oligoacene Organic Semiconductors from Quantum Mechanical Calculations. J. Phys. Chem. B. 2004,108,8614-8621.
14. Norton, J. E.; Bredas, J.-L. Theoretical Characterization of Titanyl Phthalocyanine as a P-Type Organic Semiconductor: Short Intermolecular π-π Interactions Yield Large Electronic Couplings and Hole Transport Bandwidths. J. Chem. Phys. 2008,128, 034701/1-034701/7.
15. Imahori, H.; Mori, Y.; Matano, Y. Nanostructured Artificial Photosynthesis. J. Photochem. Photobiol. C 2003, 4, 51-83
16. Chen, H.-Y.; Chao, I. Effect of Perfluorination on the Charge-Transport Properties of Organic Semiconductors: Density Functional Theory Study of Perfluorinated Pentacene and Sexithiophene. Chem. Phys. Lett. 2005, 401, 539-545.
17. Chen, H.-Y.; Chao, I. Toward the Rational Design of Functionalized Pentacenes: Reduction of the Impact of Functionalization on the Reorganization Energy. ChemPhysChem 2006, 7,2003-2007.
18. Kuo, M.-Y.; Chen, H.-Y.; Chao, I. Cyanation: ProvidingaThree-in-One Advantage for the Design of n-Type Organic Field-Effect Transistors. Chem.;Eur. J. 2007, 13, 4750-4758.
19. Gruhn, N. E.; da Silva Filho, D. A.; Bill, T. G.; Malagoli, M.; Coropceanu, V.; Kahn, A.; Bredas, J.-L. The Vibrational Re-organization Energy in Pentacene: Molecular Influences on Charge Transport. J. Am. Chem. Soc. 2002, 124, 7918-7919.
20. Coropceanu, V.; Malagoli, M.; da Silva Filho, D. A.; Gruhn, N. E.; Bill, T. G.; Bredas, J.-L. Hole-and Electron-Vibrational Couplings in Oligoacene Crystals: Intramolecular Contributions. Phys. Rev. Lett. 2002,89,275503/1-275503/4
21. Kwon, O.; Coropceanu, V.; Gruhn, N. E.; Durivage, J. C.; Laquindanum, J. G.; Katz, H. E.; Cornil, J.; Bredas, J.-L. Characterization of The Molecular Parameters Determining Charge Transport in Anthradithiophene. J. Chem. Phys. 2004, 120,8186-8194.
22. Malagoli, M.; Coropceanu, V.; daSilvaFilho, D.A.; Bredas, J. L. A Multimode Analysis of the Gas-Phase Photoelectron Spectra in Oligoacenes. J. Phem. Chem. 2004, 120, 7490-7496.
23. Haddon, R. C. Quantum Chemical Studies in the Design of Organic Metals III. Odd-Alternant Hydrocarbons-The Phenalenyl (ply) System. Aust. J. Chem. 1975, 28, 2343-2351.
24. Winkler, M.; Houk, K. N. Nitrogen-Rich Oligoacenes: Candidates for n-Channel Organic Semiconductors. J. Am. Chem. Soc. 2007, 129, 1805-1815.
25. Zhang, Y.; Cai, X.; Bian, Y.; Li, X.; Jiang, J. Heteroatom Substitution of Oligothienoacenes: From Good p-Type Semiconductors to Good Ambipolar Semiconductors for Organic Field-Effect Transistors. J. Phys. Chem. C 2008, 112, 5148-5159.
26. Sancho-García, J. C.; Perez-Jimenez, A. J. Charge-Transport Properties of Prototype Molecular Materials for Organic Electronics Based on Graphene Nanoribbons. Phys. Chem. Chem. Phys. 2009, 11, 2741-2746.
27. Hicks, R. G. What's New in Stable Radical Chemistry? Org. Biomol. Chem. 2007, 5, 1321-1338.
28. Itkis, M. E.; Chi, X.; Cordes, A. W.; Haddon, R. C. Magneto-Opto-Electronic Bistability in a Phenalenyl-Based Neutral Radical. Science 2002, 296, 1443-1445.
29. Pal, S. K.; Itkis, M. E.; Tham, F. S.; Reed, R. W.; Oakley, R. T.; Haddon, R. C. Resonating Valence-Bond Ground State in a Phenalenyl-Based Neutral Radical Conductor. Science 2005, 309,281-284.
30. Kamada, K.; Ohta, K.; Kubo, T.; Shimizu, A.; Morita, Y.; Nakasuji, K.; Kishi, R.; Ohta, S.; Furukawa, S.-i.; Takahashi, H.; Nakano, M. Strong Two-Photon Absorption of Singlet Diradical Hydrocarbons. Angew. Chem., Int. Ed. 2007,46, 3544-3546.
31. Chikamatsu, M.; Mikami, T.; Chisaka, J.; Yoshida, Y.; Azumi, R.; Yase, K.; Shimizu, A.; Kubo, T.; Morita, Y.; Nakasuji, K. Ambipolar Organic Field-Effect Transistors Based on a Low Band Gap Semiconductor with Balanced Hole and Electron Mobilities. Appl. Phys. Lett. 2007,91,043506/1-043506/3.
32. Huang, J.; Kertesz, M. Intermolecular Covalent π-π Bonding Interaction Indicated by Bond Distances, Energy Bands, and Magnetism in Biphenalenyl Biradicaloid Molecular Crystal. J. Am. Chem. Soc. 2007, 129, 1634-1643.
33. Zade, S. S.; Bendikov, M. Study of Hopping Transport in Long Oligothiophenes and Oligoselenophenes: Dependence of Reorganization Energy on Chain Length. Chem.;Eur. J. 2008,14,6734-6741.
34. Cai, X.; Zhang, Y.; Qi, D.; Jiang, J. Density Functional Theory Study on the Semiconducting Properties of Metal Phthalo-cyanine Compounds: Effect of Axially Coordinated Ligand. J. Phys. Chem. A 2009, 113, 2500-2506.
35. Liu, W.i-S.; Liu, C.-C.; Kuo, M.-Y. High-Performance p-Channel Organic Semiconducting Candidates Based on Benzo[1,2-k;4,5-k0]difluoranthene Derivatives. Chem.;Eur. J. 2009,15,5896-5900.
36. Kuo, M.-Y.; Liu, C.-C. Molecular Design toward High Hole Mobility Organic Semiconductors: Tetraceno[2,3-c]thio-phene Derivatives of Ultrasmall Reorganization Energies. J. Phys. Chem. C 2009, 113, 16303-16306.
37. Nelsen, S. F.; Blackstock, S. C.; Kim, Y. Estimation of Inner Shell Marcus Terms for Amino Nitrogen Compounds by Molecular Orbital Calculations. J. Am. Chem. Soc. 1987, 109,677-682.
38. Frisch, M. J. et al.; Gaussian 03, revisions D.02 and E.01; Gaussian, Inc.: Wallingford, CT, 2004
39. Dennington, R., II; Keith, T.; Millam, J.; Eppinnett, K.; Hovell, W. L.; Gilliland, R.; GaussView, version 3.09; Semichem, Inc.: Shawnee Mission, KS, 2003.
40. Dennington, R., II; Keith, T.; Millam, J.; Gauss View, version 4.1; Semichem, Inc.: Shawnee Mission, KS, 2007.