Modulating the electronic properties of multimeric thiophene oligomers by utilizing carbon nanotube confinement

Journal of Physical Chemistry C

Volumn 118, Issue 10, 2014, Pages 5510-5522

  Yumura, Takashi ^a   Yamashita, Hiroki ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DENSITY FUNCTIONAL THEORY; ELECTRONIC PROPERTIES; EXCITATION ENERGY; THIOPHENE;

ABSORPTION PROPERTY; DISPERSION CORRECTION; ELECTRONIC TRANSITION; INTERCHAIN COUPLING; INTERCHAIN INTERACTIONS; NANOTUBE CONFINEMENTS; THIOPHENE OLIGOMERS; TIME-DEPENDENT DFT;

CHAINS;

EID: 84896354682     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp5006555     Document Type: Article

References (79)

1. Iijima, S. Helical Microtubules of Graphitic Carbon Nature 1991, 354, 56-58
2. Iijima, S.; Ichihashi, T. Single-shell Carbon Nanotubes of 1-nm Diameter Nature 1993, 363, 603-605
3. Khobystov, A. N.; Britz, D. A.; Briggs, G. A. D. Molecules in Carbon Nanotubes Acc. Chem. Res. 2005, 38, 901-909
4. Takenobu, T.; Takano, T.; Shiraishi, M.; Murakami, Y.; Ata, M.; Kataura, H.; Achiba, Y.; Iwasa, Y. Stable and Controlled Amphoteric Doping by Encapsulation of Organic Molecules Inside Carbon Nanotubes Nat. Mater. 2003, 2, 683-688
5. 2 Polyyne Molecules Inside Chem. Phys. Lett. 2006, 428, 356-360
6. 2 (n = 4-6) Encapsulated in Single-Wall Carbon Nanotubes J. Phys. Chem. C 2007, 111, 5178-5183
7. Fujita, Y.; Bandow, S.; Iijima, S. Formation of Small-diameter Carbon Nanotubes from PTCDA Arranged Inside the Single-Wall Carbon Nanotubes Chem. Phys. Lett. 2005, 413, 410-414
8. Yanagi, Y.; Miyata, Y.; Kataura, H. Highly Stabilized β-Carotene in Carbon Nanotubes Adv. Mater. 2006, 18, 437-441
9. Loi, M. A.; Gao, J.; Cordella, F.; Blondeau, P.; Menna, E.; Bártová, B.; Hébert, C.; Lazar, S.; Botton, G. A.; Milko, M.; Ambrosch-Draxl, C. Encapsulation of Conjugated Oligomers in Single-Walled Carbon Nanotubes: Towards Nanohybrids for Photonic Devices Adv. Mater. 2010, 22, 1635-1639
10. Gao, J.; Blondeau, P.; Salice, P.; Menna, E.; Bártová, B.; Hébert, C.; Leschner, J.; Kaiser, U.; Milko, M.; Ambrosch-Draxl, C.; Loi, M. A. Electronic Interactions between "Pea" and "Pod": The Case of Oligothiophenes Encapsulated in Carbon Nanotubes Small 2011, 7, 1807-1815
11. Alvarez, L.; Almadori, Y.; Arenal, R.; Babaa, R.; Michel, T.; Le Parc, R.; Bantignies, J.-L.; Jousselme, B.; Palacin, S.; Hermet, P.; Sauvajol, J.-L. Charge Transfer Evidence between Carbon Nanotubes and Encapsulated Conjugated Oligomers J. Phys. Chem. C 2011, 115, 11898-11905
12. Kalbáč, M.; Kavan, L.; Gorantla, S.; Gemming, T.; Dunsch, L. Sexithiophene Encapsulated in a Single-Walled Carbon Nanotube: An In Situ Raman Spectroelectrochemical Study of a Peapod Structure Chem.-Eur. J. 2010, 16, 11753-11759
13. Li, L.-J.; Khlobystov, A. N.; Wiltshire, J. G.; Briggs, G. A. D.; Nicholas, R. J. Diameter-selective Encapsulation of Metallocenes in Single-Walled Carbon Nanotubes Nat. Mater. 2005, 4, 481-485
14. Cambré, S.; Wenseleers, W.; Goovaerts, E. Charge Transfer Evidence between Carbon Nanotubes and Encapsulated Conjugated Oligomers J. Phys. Chem. C 2009, 113, 13505-13514
15. Brédas, J. L.; Street, G. B. Polarons, Bipolarons, and Solitons in Conducting Polymers Acc. Chem. Res. 1985, 18, 309-315
16. Swager, T. M. The Molecular Wire Approach to Sensory Signal Amplification Acc. Chem. Res. 1998, 31, 201-207
17. McQuade, D. T.; Pullen, A. E.; Swager, T. M. Conjugated Polymer-Based Chemical Sensors Chem. Rev. 2000, 100, 2537-2574
18. Kertesz, M.; Choi, C. H.; Yang, S. Conjugated Polymers and Aromaticity Chem. Rev. 2005, 105, 3448-3481
19. Chen, Z.; Wannere, C. S.; Corminboeuf, C.; Puchta, R.; Schleyer, P. v. R. Nucleus-Independent Chemical Shifts (NICS) as an Aromaticity Criterion Chem. Rev. 2005, 105, 3842-3888
20. Murphy, A. R.; Frechet, J. M. J. Organic Semiconducting Oligomers for Use in Thin Film Transistors Chem. Rev. 2007, 107, 1066-1096
21. Wang, C.; Dong, H.; Hu, W.; Liu, Y.; Zhu, D. Semiconducting π-Conjugated Systems in Field-Effect Transistors: A Material Odyssey of Organic Electronics Chem. Rev. 2012, 112, 2208-2267
22. McIntosh, G. C.; Tománek, D.; Park, Y. W. Energetics and Electronic Structure of a Polyacetylene Chain Contained in a Carbon Nanotube Phys. Rev. B 2003, 67 (125419) 1-5
23. Orellana, W.; Vásquez, S. O. Endohedral Terthiophene in Zigzag Carbon Nanotubes: Density Functional Calculations Phys. Rev. B 2006, 74 (125419) 1-5
24. Horn, P.; Kertesz, M. Conformational Preferences of β-Carotene in the Confined Spaces inside Carbon Nanotubes J. Phys. Chem. C 2010, 114, 12139-12144
25. Milko, M.; Ambrosch-Draxl, C. Energetics and Structure of Organic Molecules Embedded in Single-Wall Carbon Nanotubes from First Principles: The Example of Benzene Phys. Rev. B 2011, 84 (085437) 1-7
26. Kuwahara, R.; Kudo, Y.; Morisato, T.; Ohno, K. Encapsulation of Carbon Chain Molecules in Single-Walled Carbon Nanotubes J. Phys. Chem. A 2011, 115, 5147-5156
27. Yamashita, H.; Yumura, T. The Role of Weak Bonding in Determining the Structure of Thiophene Oligomers inside Carbon Nanotubes J. Phys. Chem. C 2012, 116, 9681-9690
28. García, G.; Ciofini, I.; Fernández-Gómez, M.; Adamo, C. Confinement Effects on UV-Visible Absorption Spectra: β-Carotene Inside Carbon Nanotube as a Test Case J. Phys. Chem. Lett. 2013, 4, 1239-1243
29. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Gaussian 09, Gaussian, Inc.: Wallingford, CT, 2009.
30. Yumura, T.; Hirahara, K.; Bandow, S.; Yoshizawa, K.; Iijima, S. A Theoretical Study on the Geometrical Features of Finite-length Carbon Nanotubes Capped with Fullerene Hemisphere Chem. Phys. Lett. 2004, 386, 38-43
31. Yumura, T.; Bandow, S.; Yoshizawa, K.; Iijima, S. The Role of Fullerene Hemispheres in Determining Structural Features of Finite-Length Carbon Nanotubes J. Phys. Chem. B 2004, 108, 11426-11434
32. Yumura, T.; Nozaki, D.; Bandow, S.; Yoshizawa, K.; Iijima, S. End-Cap Effects on Vibrational Structures of Finite-length Carbon Nanotubes J. Am. Chem. Soc. 2005, 127, 11769-11776
33. Yumura, T.; Kertesz, M.; Iijima, S. Local Modifications of Single-Wall Carbon Nanotubes Induced by Bond Formation with Encapsulated Fullerenes J. Phys. Chem. B 2007, 111, 1099-1109
34. Yumura, T.; Kertesz, M.; Iijima, S. Confinement Effects on Site-preferences for Cycloadditions into Carbon Nanotubes Chem. Phys. Lett. 2007, 444, 155-160
35. Yumura, T.; Kertesz, M. Roles of Conformational Restrictions of a Bismalonate in the Interactions with a Carbon Nanotube J. Phys. Chem. C 2009, 113, 14184-14194
36. Yumura, T. Chemically Reactive Species Remain Alive inside Carbon Nanotubes: A Density Functional Theory Study Phys. Chem. Chem. Phys. 2011, 13, 337-346
37. Grimme, S. Semiempirical GGA-type Density Functional Constructed with a Long-Range Dispersion Correction J. Comput. Chem. 2006, 27, 1787-1799
38. Grimme, S. Semiempirical Hybrid Density Functional with Perturbative Second-Order Correlation J. Chem. Phys. 2006, 124 (034108) 1-16
39. Becke, A. D. Density-Functional Exchange-Energy Approximation with Correct Asymptotic Behavior Phys. Rev. A 1988, 38, 3098-3100
40. Becke, A. D. Density-Functional Thermochemistry. III. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652
41. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra Using Density Functional Force Fields J. Phys. Chem. 1994, 98, 11623-11627
42. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density Phys. Rev. B 1988, 37, 785-789
43. Vosko, S. H.; Wilk, L.; Nusair, M. Accurate Spin-Dependent Electron Liquid Correlation Energies for Local Spin-Density Calculations: A Critical Analysis Can. J. Phys. 1980, 58, 1200-1211
44. Vázquez-Mayagoitia, A.; David Sherril, C.; Aprá, E.; Sumpter, B. G. An Assessment of Density Functional Methods for Potential Energy Curves of Nonbonded Interactions: The XYG3 and B97-D Approximations J. Chem. Theory Comput. 2010, 6, 727-734
45. Hehre, W. J.; Ditchfield, R.; Pople, J. A. Self-consistent Molecular Orbital Methods. XII. Further Extensions of Gaussian-Type Basis Sets for Use in Molecular Orbital Studies of Organic Molecules J. Chem. Phys. 1972, 56, 2257-2261
46. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. Self-consistent Molecular Orbital Methods. XX. A Basis Set for Correlated Wave Functions J. Chem. Phys. 1980, 72, 650-654
47. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P. v. R. Efficient diffuse function-augmented basis sets for anion calculations. III. The 3-21+G basis set for first-row elements, Li-F J. Comput. Chem. 1983, 4, 294-301
48. Chung, T. C.; Kaufman, J. H.; Heeger, A. J.; Wuld, F. Charge Storage in Doped Poly(thiophene): Optical and Electrochemical Studies Phys. Rev. B 1984, 30, 702-710
49. Tachibana, M.; Tanaka, S.; Yamashita, Y.; Yoshizawa, K. Small Band-Gap Polymers Involving Tricyclic Nonclassical Thiophene as a Building Block J. Phys. Chem. B 2002, 106, 3549-3556
50. Yang, S.; Olishevski, P.; Kertesz, M. Bandgap Calculations for Conjugated Polymers Synth. Met. 2004, 141, 171-177
51. Barbarella, G.; Zambianchi, M.; Bongini, A.; Antolini, L. Crystal Structure of 4,4′,3″,4â€́-Tetramethyl 2,2′:5′,2″:5″,2â€́-Tetrathiophene: A Comparison with the Conformation in Solution Adv. Mater. 1992, 4, 282-285
52. Garnier, F.; Yassar, A.; Hajlaoui, R.; Horowitz, G.; Deloffre, F.; Servet, B.; Ries, S.; Alnot, R. Molecular Engineering of Organic Semiconductors: Design of Self-Assembly Properties in Conjugated Thiophene Oligomers J. Am. Chem. Soc. 1993, 115, 8716-8721
53. Horowitz, G.; Bachet, B.; Yassar, A.; Lang, P.; Demanze, F.; Fave, J.-L.; Garnier, F. Growth and Characterization of Sexithiophene Single Crystals Chem. Mater. 1995, 7, 1337-1341
54. Fichou, D.; Bachet, B.; Demanze, F.; Billy, I.; Horowitz, G.; Garnier, F. Growth and Structural Characterization of the Quasi-2D Single Crystal of α-Octithiophene Adv. Mater. 1996, 8, 500-504
55. Siegrist, T.; Kloc, C.; Laudise, R. A.; Katz, H. E.; Haddon, R. C. Crystal Growth, Structure, and Electronic Band Structure of α-4T Polymorphs Adv. Mater. 1998, 10, 379-382
56. Barbarella, G.; Zambianchi, M.; Antolini, L.; Ostoja, P.; Maccangani, P.; Bongini, A.; Marseglia, E. A.; Tedesco, E.; Gigli, G.; Cingolani, R. Solid-State Conformation, Molecular Packing, and Electrical and Optical Properties of Processable β-Methylated Sexithiophenes J. Am. Chem. Soc. 1999, 121, 8920-8926
57. Katz, H. E.; Bao, Z. The Physical Chemistry of Organic Field-Effect Transistors J. Phys. Chem. B 2000, 104, 671-678
58. Hong, X. M.; Tyson, J. C.; Collard, D. M. Controlling the Macromolecular Architecture of Poly(3-alkylthiophene)s by Alternating Alkyl and Fluoroalkyl Substituents Macromolecules 2000, 33, 3502-3504
59. Pappenfus, T. M.; Chesterfield, R. J.; Frisbie, C. D.; Mann, K. R.; Casado, J.; Raff, J. D.; Miller, L. L. A π-Stacking Terthiophene-Based Quinodimethane Is an n-Channel Conductor in a Thin Film Transistor J. Am. Chem. Soc. 2002, 124, 4184-4185
60. Pappenfus, T. M.; Raff, J. D.; Hukkanen, E. J.; Burney, J. R.; Casado, J.; Drew, S. W.; Miller, L. L.; Mann, K. R. Dinitro and Quinodimethane Derivatives of Terthiophene That Can Be Both Oxidized and Reduced. Crystal Structures, Spectra, and a Method for Analyzing Quinoid Contributions to Structure J. Org. Chem. 2002, 67, 6015-6024
61. Melucci, M.; Gazzano, M.; Barbarella, G.; Cavallini, M.; Biscarini, F.; Maccagnani, P.; Ostoja, P. Multiscale Self-Organization of the Organic Semiconductor α-Quinquethiophene J. Am. Chem. Soc. 2003, 125, 10266-10274
62. Facchetti, A.; Mushrush, M.; Katz, H. E.; Marks, T. J. n-Type Building Blocks for Organic Electronics: A Homologous Family of Fluorocarbon-Substituted Thiophene Oligomers with High Carrier Mobility Adv. Mater. 2003, 15, 33-38
63. Facchetti, A.; Yoon, M.-H.; Stern, C. L.; Hutchison, G. R.; Ratnerm, M. A.; Marks, T. J. Building Blocks for N-Type Molecular and Polymeric Electronics. Perfluoroalkyl- versus Alkyl-Functionalized Oligothiophenes (n Ts; n = 2-6). Systematic Synthesis, Spectroscopy, Electrochemistry, and Solid-State Organization J. Am. Chem. Soc. 2004, 126, 13480-13501
64. Kiriy, N.; Bocharova, V.; Kiriy, A.; Stamm, M.; Krebs, F. C.; Adler, H.-J. Designing Thiophene-Based Azomethine Oligomers with Tailored Properties: Self-assembly and Charge Carrier Mobility Chem. Mater. 2004, 16, 4765-4771
65. Kiriy, N.; Kiriy, A.; Bocharova, V.; Stamm, M.; Richter, S.; Plötner, M.; Fischer, W.-J.; Krebs, F. C.; Senkovska, I.; Adler, H.-J. Conformation, Molecular Packing, and Field Effect Mobility of Regioregular β,β′-Dihexylsexithiophene Chem. Mater. 2004, 16, 4757-4764
66. Hotta, S.; Goto, M.; Azumi, R.; Inoue, M.; Ichikawa, M.; Taniguchi, Y. Crystal Structures of Thiophene/Phenylene Co-Oligomers with Different Molecular Shapes Chem. Mater. 2004, 16, 237-241
67. Letizia, J. A.; Facchetti, A.; Stern, C. L.; Ratner, M. A.; Marks, T. J. High Electron Mobility in Solution-Cast and Vapor-Deposited Phenacyl- Quaterthiophene-Based Field-Effect Transistors: Toward N-Type Polythiophenes J. Am. Chem. Soc. 2005, 127, 13476-13477
68. Chisaka, J.; Lu, M.; Nagamatsu, S.; Chikamatsu, M.; Yoshida, Y.; Goto, M.; Azumi, R.; Yamashita, M.; Yase, K. Structure and Electrical Properties of Unsubstituted Oligothiophenes End-Capped at the β-Position Chem. Mater. 2007, 19, 2694-2701
69. Anthony, J. E.; Brooks, J. S.; Eaton, D. L.; Parkin, S. R. Functionalized Pentacene: Improved Electronic Properties from Control of Solid-State Order J. Am. Chem. Soc. 2001, 123, 9482-9483
70. Ando, S.; Murakami, R.; Nishida, J.; Tada, H.; Inoue, Y.; Tokito, S.; Yamashita, Y. n-Type Organic Field-Effect Transistors with Very High Electron Mobility Based on Thiazole Oligomers with Trifluoromethylphenyl Groups J. Am. Chem. Soc. 2005, 127, 14996-14997
71. Yoon, M.-H.; Facchetti, A.; Stern, C. E.; Marks, T. J. Fluorocarbon-Modified Organic Semiconductors: Molecular Architecture, Electronic, and Crystal Structure Tuning of Arene- versus Fluoroarene-Thiophene Oligomer Thin-Film Properties J. Am. Chem. Soc. 2006, 128, 5792-5801
72. Boys, S. F.; Bernardi, F. The Calculation of Small Molecular Interactions by the Differences of Separate Total Energies. Some Procedures with Reduced Errors Mol. Phys. 1970, 19, 553-566
73. Yumura, T.; Kertesz, M. Cooperative Behaviors in Carbene Additions through Local Modifications of Nanotube Surfaces Chem. Mater. 2007, 19, 1028-1034
74. Cornil, J.; Belionne, D.; Calbret, J.-P.; Brédas, J. L. Interchain Interactions in Organic π-Conjugated Materials: Impact on Electronic Structure, Optical Response, and Charge Transport Adv. Mater. 2001, 13, 1053-1067
75. Brédas, J. L.; Calbert, J. P.; da Silva Filho, D. A.; Cornil, J. A. Organic Semiconductors: A Theoretical Characterization of the Basic Parameters Governing Charge Transport Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5804-5809
76. Hutchison, G. R.; Ratner, M. A.; Marks, T. J. Hopping Transport in Conductive Heterocyclic Oligomers: Reorganization Energies and Substituent Effects J. Am. Chem. Soc. 2005, 127, 2339-2350
77. Hutchison, G. R.; Ratner, M. A.; Marks, T. J. Intermolecular Charge Transfer between Heterocyclic Oligomers. Effects of Heteroatom and Molecular Packing on Hopping Transport in Organic Semiconductors J. Am. Chem. Soc. 2005, 127, 16866-16881
78. Hutchison, G. R.; Ratner, M. A.; Marks, T. J. Electronic Structure and Band Gaps in Cationic Heterocyclic Oligomers. Multidimensional Analysis of the Interplay of Heteroatoms, Substituents, Molecular Length, and Charge on Redox and Transparency Characteristics J. Phys. Chem. B 2005, 109, 3126-3138
79. Koh, S. E.; Risko, C.; da Silva Filho, D. A.; Kwon, O.; Facchetti, A.; Brédas, J. L.; Marks, T. J.; Ratner, M. A. Modeling Electron and Hole Transport in Fluoroarene-Oligothiopene Semiconductors: Investigation of Geometric and Electronic Structure Properties Adv. Funct. Mater. 2008, 18, 332-340