Polarized absorption in crystalline pentacene: Theory vs experiment

Journal of Physical Chemistry C

Volumn 119, Issue 38, 2015, Pages 22137-22147

  Hestand, N J ^a   Yamagata, H ^a   Xu, Bolei ^a   Sun, Dezheng ^b   Zhong, Yu ^c   Harutyunyan, Avetik R ^d   Chen, Gugang ^d   Dai, Hai Lung ^a   Rao, Yi ^a   Spano, F C ^a  

^a Temple University   (United States)

^b Department of Earth and Environmental Sciences   (United States)

^c Och Spine at New York Presbyterian Hospitals   (United States)

^d Honda R&D Americas Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AGGREGATES; CHARGE TRANSFER; CRYSTALLINE MATERIALS;

COMPLEX MIXTURE; POLARIZED ABSORPTION; POLARIZED ABSORPTION SPECTRA; SPECTRAL LINE SHAPE; TRANSMITTED LIGHT; TWO-PARTICLE STATE; ULTRA-THIN CRYSTALS; VIBRONIC EXCITONS;

EXCITONS;

EID: 84942342237     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/acs.jpcc.5b07163     Document Type: Article

References (69)

1. Zaumseil, J.; Sirringhaus, H. Electron and Ambipolar Transport in Organic Field-Effect Transistors Chem. Rev. 2007, 107, 1296-1323 10.1021/cr0501543
2. Jurchescu, O. D.; Baas, J.; Palstra, T. T. M. Effect of Impurities on the Mobility of Single Crystal Pentacene Appl. Phys. Lett. 2004, 84, 3061-3063 10.1063/1.1704874
3. Dimitrakopoulos, C. D.; Malenfant, P. R. L. Organic Thin Film Transistors for Large Area Electronics Adv. Mater. 2002, 14, 99-117 10.1002/1521-4095(20020116)14:2<99::AID-ADMA99>3.0.CO;2-9
4. Lin, Y. Y.; Gundlach, D. J.; Nelson, S. F.; Jackson, T. N. Stacked Pentacene Layer Organic Thin-Film Transistors with Improved Characteristics IEEE Electron Device Lett. 1997, 18, 606-608 10.1109/55.644085
5. Klauk, H.; Halik, M.; Zschieschang, U.; Schmid, G.; Radlik, W.; Weber, W. High-Mobility Polymer Gate Dielectric Pentacene Thin Film Transistors J. Appl. Phys. 2002, 92, 5259-5263 10.1063/1.1511826
6. Jadhav, P. J.; Brown, P. R.; Thompson, N.; Wunsch, B.; Mohanty, A.; Yost, S. R.; Hontz, E.; Van Voorhis, T.; Bawendi, M. G.; Bulovic, V. et al. Triplet Exciton Dissociation in Singlet Exciton Fission Photovoltaics Adv. Mater. 2012, 24, 6169-6174 10.1002/adma.201202397
7. Smith, M. B.; Michl, J. Recent Advances in Singlet Fission Annu. Rev. Phys. Chem. 2013, 64, 361-386 10.1146/annurev-physchem-040412-110130
8. Smith, M. B.; Michl, J. Singlet Fission Chem. Rev. 2010, 110, 6891-6936 10.1021/cr1002613
9. Burdett, J. J.; Bardeen, C. J. The Dynamics of Singlet Fission in Crystalline Tetracene and Covalent Analogs Acc. Chem. Res. 2013, 46, 1312-1320 10.1021/ar300191w
10. Burdett, J. J.; Bardeen, C. J. Quantum Beats in Crystalline Tetracene Delayed Fluorescence Due to Triplet Pair Coherences Produced by Direct Singlet Fission J. Am. Chem. Soc. 2012, 134, 8597-8607 10.1021/ja301683w
11. Chan, W. L.; Ligges, M.; Zhu, X. Y. The Energy Barrier in Singlet Fission Can Be Overcome through Coherent Coupling and Entropic Gain Nat. Chem. 2012, 4, 840-845 10.1038/nchem.1436
12. Rao, A.; Wilson, M. W. B.; Hodgkiss, J. M.; Albert-Seifried, S.; Bässler, H.; Friend, R. H. Exciton Fission and Charge Generation Via Triplet Excitons in Pentacene/C-60 Bilayers J. Am. Chem. Soc. 2010, 132, 12698-12703 10.1021/ja1042462
13. Congreve, D. N.; Lee, J. Y.; Thompson, N. J.; Hontz, E.; Yost, S. R.; Reusswig, P. D.; Bahlke, M. E.; Reineke, S.; Van Voorhis, T.; Baldo, M. A. External Quantum Efficiency above 100% in a Singlet-Exciton-Fission-Based Organic Photovoltaic Cell Science 2013, 340, 334-337 10.1126/science.1232994
14. Thorsmølle, V. K.; Averitt, R. D.; Demsar, J.; Smith, D. L.; Tretiak, S.; Martin, R. L.; Chi, X.; Crone, B. K.; Ramirez, A. P.; Taylor, A. J. Morphology Effectively Controls Singlet-Triplet Exciton Relaxation and Charge Transport in Organic Semiconductors Phys. Rev. Lett. 2009, 102, 017401 10.1103/PhysRevLett.102.017401
15. Chan, W. L.; Berkelbach, T. C.; Provorse, M. R.; Monahan, N. R.; Tritsch, J. R.; Hybertsen, M. S.; Reichman, D. R.; Gao, J. L.; Zhu, X. Y. The Quantum Coherent Mechanism for Singlet Fission: Experiment and Theory Acc. Chem. Res. 2013, 46, 1321-1329 10.1021/ar300286s
16. Yost, S. R.; Lee, J.; Wilson, M. W. B.; Wu, T.; McMahon, D. P.; Parkhurst, R. R.; Thompson, N. J.; Congreve, D. N.; Rao, A.; Johnson, K. et al. Transferable Model for Singlet-Fission Kinetics Nat. Chem. 2014, 6, 492-497 10.1038/nchem.1945
17. Beljonne, D.; Yamagata, H.; Bredas, J. L.; Spano, F. C.; Olivier, Y. Charge-Transfer Excitations Steer the Davydov Splitting and Mediate Singlet Exciton Fission in Pentacene Phys. Rev. Lett. 2013, 110, 226402 10.1103/PhysRevLett.110.226402
18. Pac, B.; Petelenz, P. Lowest Singlet Exciton in Pentacene: Modern Calculations Versus Classic Experiments ChemPhysChem 2014, 15, 2801-2809 10.1002/cphc.201402148
19. Tiago, M. L.; Northrup, J. E.; Louie, S. G. Ab Initio Calculation of the Electronic and Optical Properties of Solid Pentacene Phys. Rev. B: Condens. Matter Mater. Phys. 2003, 67, 115212 10.1103/PhysRevB.67.115212
20. Ambrosch-Draxl, C.; Nabok, D.; Puschnig, P.; Meisenbichler, C. The Role of Polymorphism in Organic Thin Films: Oligoacenes Investigated from First Principles New J. Phys. 2009, 11, 125010 10.1088/1367-2630/11/12/125010
21. Cudazzo, P.; Gatti, M.; Rubio, A.; Sottile, F. Frenkel Versus Charge-Transfer Exciton Dispersion in Molecular Crystals Phys. Rev. B: Condens. Matter Mater. Phys. 2013, 88, 195152 10.1103/PhysRevB.88.195152
22. Sharifzadeh, S.; Darancet, P.; Kronik, L.; Neaton, J. B. Low-Energy Charge-Transfer Excitons in Organic Solids from First-Principles: The Case of Pentacene J. Phys. Chem. Lett. 2013, 4, 2197-2201 10.1021/jz401069f
23. Petelenz, B.; Petelenz, P.; Shurvell, H. F.; Smith, V. H. Reconsideration of the Electroabsorption Spectra of the Tetracene and Pentacene Crystals Chem. Phys. 1988, 119, 25-39 10.1016/0301-0104(88)80003-X
24. Petelenz, P.; Slawik, M.; Yokoi, K.; Zgierski, M. Z. Theoretical Calculation of the Electroabsorption Spectra of Polyacene Crystals J. Chem. Phys. 1996, 105, 4427-4440 10.1063/1.472295
25. Yamagata, H.; Norton, J.; Hontz, E.; Olivier, Y.; Beljonne, D.; Bredas, J. L.; Silbey, R. J.; Spano, F. C. The Nature of Singlet Excitons in Oligoacene Molecular Crystals J. Chem. Phys. 2011, 134, 204703 10.1063/1.3590871
26. Zimmerman, P. M.; Bell, F.; Casanova, D.; Head-Gordon, M. Mechanism for Singlet Fission in Pentacene and Tetracene: From Single Exciton to Two Triplets J. Am. Chem. Soc. 2011, 133, 19944-19952 10.1021/ja208431r
27. Schuster, R.; Knupfer, M.; Berger, H. Exciton Band Structure of Pentacene Molecular Solids: Breakdown of the Frenkel Exciton Model Phys. Rev. Lett. 2007, 98, 037402 10.1103/PhysRevLett.98.037402
28. Roth, F.; Schuster, R.; Konig, A.; Knupfer, M.; Berger, H. Momentum Dependence of the Excitons in Pentacene J. Chem. Phys. 2012, 136, 204708 10.1063/1.4723812
29. Zanker, V.; Preuss, J. Microspectrometrical Measurements on Single Crystals of Tetracene and Pentacene in Depedence of Thickness and Temperature Z. Angew. Phys. 1969, 27, 363-365
30. Aoki-Matsumoto, T.; Furuta, K.; Yamada, T.; Moriya, H.; Mizuno, K.; Matsui, A. H. Excitonic Photoluminescence in Pentacene Single Crystal Int. J. Mod. Phys. B 2001, 15, 3753-3756 10.1142/S0217979201008585
31. Prikhotko, A. F.; Tsikora, L. I. Spectral Investigations of Pentacene Opt. Spectrosc. USSR 1968, 25, 242
32. Grobosch, M.; Schuster, R.; Pichler, T.; Knupfer, M.; Berger, H. Analysis of the Anisotropy of Excitons in Pentacene Single Crystals Using Reflectivity Measurements and Electron Energy-Loss Spectroscopy Phys. Rev. B: Condens. Matter Mater. Phys. 2006, 74, 155202 10.1103/PhysRevB.74.155202
33. Dressel, M.; Gompf, B.; Faltermeier, D.; Tripathi, A. K.; Pflaum, J.; Schubert, M. Kramers-Kronig-Consistent Optical Functions of Anisotropic Crystals: Generalized Spectroscopic Ellipsometry on Pentacene Opt. Express 2008, 16, 19770-19778 10.1364/OE.16.019770
34. Hinderhofer, A.; Heinemeyer, U.; Gerlach, A.; Kowarik, S.; Jacobs, R. M. J.; Sakamoto, Y.; Suzuki, T.; Schreiber, F. Optical Properties of Pentacene and Perfluoropentacene Thin Films J. Chem. Phys. 2007, 127, 194705 10.1063/1.2786992
35. Faltermeier, D.; Gompf, B.; Dressel, M.; Tripathi, A. K.; Pflaum, J. Optical Properties of Pentacene Thin Films and Single Crystals Phys. Rev. B: Condens. Matter Mater. Phys. 2006, 74, 125416 10.1103/PhysRevB.74.125416
36. Qi, D. C.; Su, H. B.; Bastjan, M.; Jurchescu, O. D.; Palstra, T. M.; Wee, A. T. S.; Rubhausen, M.; Rusydi, A. Observation of Frenkel and Charge Transfer Excitons in Pentacene Single Crystals Using Spectroscopic Generalized Ellipsometry Appl. Phys. Lett. 2013, 103, 113303 10.1063/1.4811758
37. Hoffmann, M.; Soos, Z. G. Optical Absorption Spectra of the Holstein Molecular Crystal for Weak and Intermediate Electronic Coupling Phys. Rev. B: Condens. Matter Mater. Phys. 2002, 66, 024305 10.1103/PhysRevB.66.024305
38. Hoffmann, M.; Schmidt, K.; Fritz, T.; Hasche, T.; Agranovich, V. M.; Leo, K. The Lowest Energy Frenkel and Charge-Transfer Excitons in Quasi-One-Dimensional Structures: Application to Meptcdi and Ptcda Crystals Chem. Phys. 2000, 258, 73-96 10.1016/S0301-0104(00)00157-9
39. Gisslen, L.; Scholz, R. Crystallochromy of Perylene Pigments: Influence of an Enlarged Polyaromatic Core Region Phys. Rev. B: Condens. Matter Mater. Phys. 2011, 83, 155311 10.1103/PhysRevB.83.155311
40. Gisslen, L.; Scholz, R. Crystallochromy of Perylene Pigments: Interference between Frenkel Excitons and Charge-Transfer States Phys. Rev. B: Condens. Matter Mater. Phys. 2009, 80, 115309 10.1103/PhysRevB.80.115309
41. Yamagata, H.; Maxwell, D. S.; Fan, J.; Kittilstved, K. R.; Briseno, A. L.; Barnes, M. D.; Spano, F. C. Hj-Aggregate Behavior of Crystalline 7,8,15,16-Tetraazaterrylene: Introducing a New Design Paradigm for Organic Materials J. Phys. Chem. C 2014, 118, 28842-28854 10.1021/jp509011u
42. Hestand, N. J.; Tempelaar, R.; Knoester, J.; Jansen, T. L. C.; Spano, F. C. Exciton Mobility Control through Sub-Angstrom Packing Modifications in Molecular Crystals Phys. Rev. B: Condens. Matter Mater. Phys. 2015, 91, 195315 10.1103/PhysRevB.91.195315
43. Schlosser, D. W.; Philpott, M. R. ″Singlet Excitons in Crystalline Naphthalene, Anthracene, Tetracene and Pentacene Chem. Phys. 1980, 49, 181-199 10.1016/0301-0104(80)85256-6
44. Philpott, M. R. Optical Reflection Spectroscopy of Organic-Solids Annu. Rev. Phys. Chem. 1980, 31, 97-129 10.1146/annurev.pc.31.100180.000525
45. Laudise, R. A.; Kloc, C.; Simpkins, P. G.; Siegrist, T. Physical Vapor Growth of Organic Semiconductors J. Cryst. Growth 1998, 187, 449-454 10.1016/S0022-0248(98)00034-7
46. Holmes, D.; Kumaraswamy, S.; Matzger, A. J.; Vollhardt, K. P. C. On the Nature of Nonplanarity in the [N]Phenylenes Chem.-Eur. J. 1999, 5, 3399-3412 10.1002/(SICI)1521-3765(19991105)5:11<3399::AID-CHEM3399>3.0.CO;2-V
47. Philpott, M. R. Theory of Coupling of Electronic and Vibrational Excitations in Molecular Crystals and Helical Polymers J. Chem. Phys. 1971, 55, 2039-2054 10.1063/1.1676371
48. Spano, F. C. The Spectral Signatures of Frenkel Polarons in H- and J-Aggregates Acc. Chem. Res. 2010, 43, 429-439 10.1021/ar900233v
49. Spano, F. C. Excitons in Conjugated Oligomer Aggregates, Films, and Crystals Annu. Rev. Phys. Chem. 2006, 57, 217-243 10.1146/annurev.physchem.57.032905.104557
50. Spano, F. C. Absorption and Emission in Oligo-Phenylene Vinylene Nanoaggregates: The Role of Disorder and Structural Defects J. Chem. Phys. 2002, 116, 5877-5891 10.1063/1.1446034
51. Stradomska, A.; Petelenz, P. Intermediate Vibronic Coupling in Sexithiophene Single Crystals. Ii. Three-Particle Contributions J. Chem. Phys. 2009, 131, 044507 10.1063/1.3182852
52. Spano, F. C.; Yamagata, H. Vibronic Coupling in J-Aggregates and Beyond: A Direct Means of Determining the Exciton Coherence Length from the Photoluminescence Spectrum J. Phys. Chem. B 2011, 115, 5133-5143 10.1021/jp104752k
53. Spano, F. C. The Fundamental Photophysics of Conjugated Oligomer Herringbone Aggregates J. Chem. Phys. 2003, 118, 981-994 10.1063/1.1521933
54. Spano, F. C.; Meskers, S. C. J.; Hennebicq, E.; Beljonne, D. Probing Excitation Delocalization in Supramolecular Chiral Stacks by Means of Circularly Polarized Light: Experiment and Modeling J. Am. Chem. Soc. 2007, 129, 7044-7054 10.1021/ja067321g
55. Spano, F. C.; Meskers, S. C. J.; Hennebicq, E.; Beljonne, D. Using Circularly Polarized Luminescence to Probe Exciton Coherence in Disordered Helical Aggregates J. Chem. Phys. 2008, 129, 024704 10.1063/1.2943647
56. Tempelaar, R.; Stradomska, A.; Knoester, J.; Spano, F. C. Anatomy of an Exciton: Vibrational Distortion and Exciton Coherence in H- and J-Aggregates J. Phys. Chem. B 2013, 117, 457-466 10.1021/jp310298n
57. Tsiper, E. V.; Soos, Z. G. Electronic Polarization in Pentacene Crystals and Thin Films Phys. Rev. B: Condens. Matter Mater. Phys. 2003, 68, 085301 10.1103/PhysRevB.68.085301
58. Sebastian, L.; Weiser, G.; Bässler, H. Charge-Transfer Transitions in Solid Tetracene and Pentacene Studied by Electro-Absorption Chem. Phys. 1981, 61, 125-135 10.1016/0301-0104(81)85055-0
59. Coropceanu, V.; Cornil, J.; da Silva Filho, D. A.; Olivier, Y.; Silbey, R.; Bredas, J. L. Charge Transport in Organic Semiconductors Chem. Rev. 2007, 107, 926-952 10.1021/cr050140x
60. Bree, A.; Lyons, L. E. The Intensity of Ultraviolet-Light Absorption by Monocrystals 0.4. Absorption by Naphthacene of Plane-Polarized Light J. Chem. Soc. 1960, 5206-5212 10.1039/jr9600005206
61. Yamagata, H.; Pochas, C. M.; Spano, F. C. Designing J- and H-Aggregates through Wave Function Overlap Engineering: Applications to Poly(3-Hexylthiophene) J. Phys. Chem. B 2012, 116, 14494-14503 10.1021/jp309407r
62. Kasha, M. Energy Transfer Mechanisms and the Molecular Exciton Model for Molecular Aggregates Radiat. Res. 1963, 20, 55-70 10.2307/3571331
63. Sebastian, L.; Weiser, G.; Peter, G.; Bässler, H. Charge-Transfer Transitions in Crystalline Anthracene and Their Role in Photoconductivity Chem. Phys. 1983, 75, 103-114 10.1016/0301-0104(83)85012-5
64. Sharifzadeh, S.; Wong, C. Y.; Wu, H.; Cotts, B. L.; Kronik, L.; Ginsberg, N. S.; Neaton, J. B. Relating the Physical Structure and Optoelectronic Function of Crystalline Tips-Pentacene Adv. Funct. Mater. 2015, 25, 2038-2046 10.1002/adfm.201403005
65. Lim, S.-H.; Bjorklund, T. G.; Spano, F. C.; Bardeen, C. J. Exciton Delocalization and Superradiance in Tetracene Thin Films and Nanoaggregates Phys. Rev. Lett. 2004, 92, 107402 10.1103/PhysRevLett.92.107402
66. Voigt, M.; Langner, A.; Schouwink, P.; Lupton, J. M.; Mahrt, R. F.; Sokolowski, M. Picosecond Time Resolved Photoluminescence Spectroscopy of a Tetracene Film on Highly Oriented Pyrolytic Graphite: Dynamical Relaxation, Trap Emission, and Superradiance J. Chem. Phys. 2007, 127, 114705 10.1063/1.2766944
67. Camposeo, A.; Polo, M.; Tavazzi, S.; Silvestri, L.; Spearman, P.; Cingolani, R.; Pisignano, D. Polarized Superradiance from Delocalized Exciton Transitions in Tetracene Single Crystals Phys. Rev. B: Condens. Matter Mater. Phys. 2010, 81, 033306 10.1103/PhysRevB.81.033306
68. Anger, F.; Osso, J. O.; Heinemeyer, U.; Broch, K.; Scholz, R.; Gerlach, A.; Schreiber, F. Photoluminescence Spectroscopy of Pure Pentacene, Perfluoropentacene, and Mixed Thin Films J. Chem. Phys. 2012, 136, 054701 10.1063/1.3677839
69. Kistler, K. A.; Pochas, C. M.; Yamagata, H.; Matsika, S.; Spano, F. C. Absorption, Circular Dichroism, and Photoluminescence in Perylene Diimide Bichromophores: Polarization-Dependent H- and J-Aggregate Behavior J. Phys. Chem. B 2012, 116, 77-86 10.1021/jp208794t