Dynamic effects on the charge transport in an organic near-infrared absorber material

Journal of Physical Chemistry C

Volumn 118, Issue 13, 2014, Pages 6537-6547

  Radke, K Sebastian ^a   Scholz, Reinhard ^a   Ortmann, Frank ^a   Leo, Karl ^a,b   Cuniberti, Gianaurelio ^a,b  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

^b CENTER FOR ADVANCING ELECTRONICS DRESDEN CFAED   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON CONDUCTION; ELECTRON TRANSPORT; HIGHEST OCCUPIED MOLECULAR ORBITAL; INTERMOLECULAR COUPLING; INTERNAL REORGANIZATIONS; MOLECULAR DYNAMICS SIMULATIONS; NEAR-INFRARED ABSORBERS; QUANTUM-CHEMICAL CALCULATION;

ELECTRONIC STRUCTURE; HOLE MOBILITY; INFRARED ABSORPTION; MOLECULAR DYNAMICS; QUANTUM CHEMISTRY;

INFRARED DEVICES;

EID: 84898076381     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp408574d     Document Type: Article

References (63)

1. Riede, M.; Lüssem, B.; Leo, K. Organic Semiconductors Compr. Semicond. Sci. Technol. 2011, 4, 448-507
2. Lungenschmied, C.; Dennler, G.; Neugebauer, H.; Sariciftci, S. N.; Glatthaar, M.; Meyer, T.; Meyer, A. Flexible, Long-Lived, Large-Area, Organic Solar Cells Sol. Energy Mater. Sol. Cells 2008, 91, 379-384
3. Brédas, J.-L.; Norton, J. E.; Cornil, J.; Coropceanu, V. Molecular Understanding of Organic Solar Cells: The Challenges Acc. Chem. Res. 2009, 42 (11) 1691-1699
4. Riede, M.; Uhrich, C.; Widmer, J.; Timmreck, R.; Wynands, D.; Schwartz, G.; Guehr, W.-M.; Hildebrandt, D.; Weiss, A.; Hwang, J. Efficient Organic Tandem Solar Cells Based on Small Molecules Adv. Funct. Mater. 2011, 21, 3019-3028
5. Mueller, T.; Gresser, R.; Leo, K.; Riede, M. Organic Solarcell Based on a Novel Infrared Absorbing Aza-Bodipy Dye Sol. Energy Mater. Sol. Cells 2012, 99, 176-181
6. Loudet, A.; Burgess, K. BODIPY Dyes and Their Derivatives: Syntheses and Spectroscopic Properties Chem. Rev. 2007, 107, 4891-4932
7. 2-Azadipyrromethenes Org. Lett. 2006, 8 (16) 3493-3496
8. Zhao, W.; Carreira, E. M. Conformationally Restricted Aza-BODIPY: Highly Fluorescent, Stable Near-Infrared Absorbing Dyes Chem.-Eur. J. 2006, 12, 7254-7263
9. Gresser, R.; Hartmann, H.; Wrackmeyer, M.; Leo, K.; Riede, M. Synthesis of Thiophene-Substituted Aza-BODIPYs and Their Optical and Electrochemical Properties Tetrahedron 2011, 67, 7148-7155
10. Gresser, R.; Hummert, M.; Hartmann, H.; Leo, K.; Riede, M. Synthesis and Characterization of Near-Infrared Absorbing Benzannulated Aza-BODIPY Dyes Chem.-Eur. J. 2011, 17, 2939-2947
11. Donyagina, V. F.; Shimizu, S.; Kobayashi, N.; Lukyanets, E. A. Synthesis of N,N-Difluoroboryl Complexes of 3,30-Diarylazadiisoindolylmethenes Tetrahedron Lett. 2008, 49, 6152-6154
12. Erten-Ela, S.; Yilmaz, M. D.; Icli, B.; Dede, Y.; Icli, S.; Akkaya, E. U. A Panchromatic Boradiazaindacene (BODIPY) Sensitizer for Dye-Sensitized Solar Cells Org. Lett. 2008, 10 (15) 3299-3302
13. Rousseau, T.; Cravino, A.; Bura, T.; Ulrich, G.; Ziessel, R.; Roncali, J. BODIPY Derivatives as Donor Materials for Bulk Heterojunction Solar Cells Chem. Commun. 2009, 1673-1675
14. Kim, B.; Ma, B.; Donuru, V. R.; Liu, H.; Fréchet, J. M. J. Bodipy-Backboned Polymers as Electron Donor in Bulk Heterojunction Solar Cells Chem. Commun. 2010, 46, 4148-4150
15. Meiss, J.; Holzmueller, F.; Gresser, R.; Leo, K.; Riede, M. Near-Infrared Absorbing Semitransparent Organic Solar Cells Appl. Phys. Lett. 2011, 99, 193307
16. Cheng, Y. C.; Silbey, R. J.; da Silva Filho, D. A.; Calbert, J. P.; Cornil, J.; Brédas, J. L. Three-Dimensional Band Structure and Bandlike Mobility in Oligoacene Single Crystals: A Theoretical Investigation J. Chem. Phys. 2003, 118 (8) 3764-3774
17. Ortmann, F.; Bechstedt, F.; Hannewald, K. Charge Transport in Organic Crystals: Interplay of Band Transport, Hopping and Electron-Phonon Scattering New J. Phys. 2010, 12, 023011
18. Troisi, A.; Orlandi, G. Charge-Transport Regime of Crystalline Organic Semiconductors: Diffusion Limited by Thermal Off-Diagonal Electronic Disorder Phys. Rev. Lett. 2006, 96 (8) 086601
19. Troisi, A. Prediction of the Absolute Charge Mobility of Molecular Semiconductors: the Case of Rubrene Adv. Mater. 2007, 19, 2000-2004
20. Picon, J.-D.; Bussac, M. N.; Zuppiroli, L. Quantum Coherence and Carriers Mobility in Organic Semiconductors Phys. Rev. B 2007, 75, 235106
21. Martinelli, N. G.; Olivier, Y.; Athanasopoulos, S.; Delgado, M.-C. R.; Pigg, K. R.; da Silva Filho, D. A.; Sánchez-Carrera, R. S.; Venuti, E.; Della Valle, R. G.; Brédas, J.-L.; Beljonne, D. Influence of Intermolecular Vibrations on the Electronic Coupling in Organic Semiconductors: The Case of Anthracene and Perfluoropentacene Chem. Phys. Chem. 2009, 10, 2265-2273
22. Marcus, R. A. Electron Transfer Reactions in Chemistry. Theory and Experiment Rev. Mod. Phys. 1993, 65 (3) 599-610
23. 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
24. Schrader, M.; Fitzner, R.; Hein, M. P.; Elschner, C.; Baumeier, B.; Leo, K.; Riede, M.; Bäuerle, P.; Andrienko, D. Comparative Study of Microscopic Charge Dynamics in Crystalline Acceptor-Substituted Oligothiophenes J. Am. Chem. Soc. 2012, 134, 6052-6056
25. Zhugayevych, A.; Postupna, O.; Bakus, R. C.; Welch, G. C.; Bazan, G. C.; Tretiak, S. Ab Initio Study of a Molecular Crystal for Photovoltaics: Light Absorption, Exciton and Charge Carrier Transport J. Phys. Chem. C 2013, 117, 4920-4930
26. VandeVondele, J.; Krack, M.; Mohamed, F.; Parrinello, M.; Chassaing, T.; Hutter, J. QUICKSTEP: Fast and Accurate Density Functional Calculations Using a Mixed Gaussian and Plane Waves Approach Comput. Phys. Commun. 2005, 167, 103-128
27. Krack, M.; Parrinello, M. High Performance Computing in Chemistry NIC Ser. 2004, 25, 29-51
28. Goedecker, S.; Teter, M.; Hutter, J. Separable Dual-Space Gaussian Pseudopotentials Phys. Rev. B 1996, 54 (3) 1703-1710
29. Hartwigsen, C.; Goedecker, S.; Hutter, J. Relativistic Separable Dual-Space Gaussian Pseudopotentials from H to Rn Phys. Rev. B 1998, 58 (7) 3641-3662
30. Krack, M. Pseudopotentials for H to Kr Optimized for Gradient-Corrected Exchange-Correlation Functionals Theor. Chem. Acc. 2005, 114, 145-152
31. VandeVondele, J.; Hutter, J. Gaussian Basis Sets for Accurate Calculations on Molecular Systems in Gas and Condensed Phases J. Chem. Phys. 2007, 127, 114105
32. Becke, A. D. A. New Mixing of Hartree-Fock and Local Densityfunctional Theories J. Chem. Phys. 1993, 98 (2) 1372-1377
33. Becke, A. D. Density-Functional Exchange-Energy Approximation with Correct Asymptotic Behavior Phys. Rev. A 1988, 38 (6) 3098-3100
34. Becke, A. D. Densityfunctional Thermochemistry. III. The Role of Exact Exchange J. Chem. Phys. 1993, 98 (7) 5648-5652
35. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. Selfconsistent Molecular Orbital Methods. XX. A Basis Set for Correlated Wave Functions J. Chem. Phys. 1980, 72 (1) 650-654
36. Frisch, M. J.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
37. Novikov, S. V. Organic Glasses: Cluster Structure of the Random Energy Landscape Ann. Phys. 2009, 18 (12) 949-953
38. Coropceanu, V.; Cornil, J.; da Silva Filho, D. A.; Olivier, Y.; Silbey, R.; Brédas, J.-L. Charge Transport in Organic Semiconductors Chem. Rev. 2007, 107, 926-952
39. Gisslén, L.; Scholz, R. Crystallochromy of Perylene Pigments: Interference between Frenkel Excitons and Charge-Transfer States Phys. Rev. B 2009, 80, 115309
40. Scott, A. P.; Radom, L. Harmonic Vibrational Frequencies: An Evaluation of Hartree-Fock, MØller-Plesset, Quadratic Configuration Interaction, Density Functional Theory, and Semiempirical Scale Factors J. Phys. Chem. 1996, 100, 16502-16513
41. Pecchia, A.; Gheorghe, M.; Di Carlo, A.; Lugli, P.; Niehaus, T. A.; Frauenheim, Th.; Scholz, R. Role of Thermal Vibrations in Molecular Wire Conduction Phys. Rev. B 2003, 68, 235321
42. Russell, G. A.; Klick, C. C. Configuration Coordinate Curves for F-Centers in Alkali Habde Crystals Phys. Rev. 1956, 101 (5) 1473-1479
43. Scholz, R.; Vragovicc, I.; Kobitski, A. Yu.; Salvan, G.; Kampen, T. U.; Schreiber, M.; Zahn, D. R. T. Spectroscopic Properties of a Prototypic Organic Semiconductor: The Case of PTCDA. Proceedings of International School of Physics E. Fermi, course CXLIX: Organic nanostructures: Science and applications; Agranovich, V. M.,; La Rocca, G. C., Eds.; IOS Press: Amsterdam, 2002; pp 379-403.
44. Scholz, R.; Schreiber, M. Linear Optical Properties of Perylene-based Chromophores Chem. Phys. 2006, 325, 9-21
45. Schönherr, G.; Bässler, H. Dispersive Hopping Transport via Sites Having a Gaussian Distribution of Energies Philos. Mag. B 1981, 44 (1) 47-61
46. Borsenberger, P. M.; Pautmeier, L.; Bässler, H. Charge Transport in Disordered Molecular Solids J. Chem. Phys. 1991, 94 (8) 5447-5454
47. Poelking, C.; Cho, E.; Malafeev, A.; Ivanov, V.; Kremer, K.; Risko, C.; Brédas, J.-L.; Andrienko, D. Characterization of Charge-Carrier Transport in Semicrystalline Polymers: Electronic Couplings Site Energies and Charge-Carrier Dynamics in Poly(bithiophene-alt-thienothiophene) [PBTTT] J. Phys. Chem. C 2013, 117, 1633-1640
48. May, F.; Al-Helwi, M.; Baumeier, B.; Kowalsky, W.; Fuchs, E.; Lennartz, C.; Andrienko, D. Design Rules for Charge-Transport Efficient Host Materials for Phosphorescent OLEDs J. Am. Chem. Soc. 2012, 134, 13818-13822
49. da Silva Filho, D. A.; Kim, E.-G.; Brédas, J.-L. Transport Properties in the Rubrene Crystal: Electronic Coupling and Vibrational Reorganization Energy Adv. Mater. 2005, 17 (8) 1072-1076
50. Anger, F.; Scholz, R.; Adamski, E.; Broch, K.; Gerlach, A.; Sakamoto, Y.; Suzuki, T.; Schreiber, F. Optical Properties of Fully and Partially Fluorinated Rubrene in Films and Solution Appl. Phys. Lett. 2013, 102, 013308
51. Scholz, R.; Gisslén, L.; Himcinschi, C.; Vragovic, I.; Calzado, E. M.; Louis, E.; San Fabián Maroto, E.; Díaz-García, M. A. Asymmetry between Absorption and Photoluminescence Line Shapes of TPD: Spectroscopic Fingerprint of the Twisted Biphenyl Core J. Phys. Chem. A 2009, 113, 315-324
52. Geng, H.; Niu, Y.; Peng, Q.; Shuai, Z.; Coropceanu, V.; Brédas, J.-L. Theoretical Study of Substitution Effects on Molecular Reorganization Energy in Organic Semiconductors J. Chem. Phy. 2011, 135, 104703
53. Kresse, G.; Furthmüller, J. Efficiency of Ab-Initio Total Energy Calculations for Metals and Semiconductors Using a Plane-Wave Basis Set Comput. Mater. Sci. 1996, 6, 15-50
54. Kresse, G.; Furthmüller, J. Efficient Iterative Schemes for Ab Initio Total-Energy Calculations Using a Plane-Wave Basis Set Phys. Rev. B 1996, 54, 11169-11186
55. Monkhorst, H. J.; Pack, J. D. Special Points for Brillouin-Zone Integrations Phys. Rev. B 1976, 13, 5188-5192
56. Kohn, W.; Sham, L. J. Self-Consistent Equations Including Exchange and Correlation Effects Phys. Rev. 1965, 140, A1133-A1138
57. Perdew, J. P.; Zunger, A. Self-Interaction Correction to Density-Functional Approximations for Many-Electron Systems Phys. Rev. B 1981, 23, 5048-5079
58. Ortmann, F.; Hannewald, K.; Bechstedt, F. Ab Initio Studies of Structural, Vibrational, and Electronic Properties of Durene Crystals and Molecules Phys. Rev. B 2007, 75, 195219
59. Gollub, C.; Avdoshenko, S.; Gutierrez, R.; Berlin, Y.; Cuniberti, G. Charge Migration in Organic Materials: Can Propagating Charges Affect the Key Physical Quantities Controlling Their Motion? Isr. J. Chem. 2012, 52 (5) 452-460
60. Unge, M.; Strafström, S. Effect of Long-Range Correlation on the Metal-Insulator Transition in a Disordered Molecular Crystal Phys. Rev. B 2006, 74, 235403
61. Picon, J.-D.; Bussac, M. N.; Zuppiroli, L. Quantum Coherence and Carriers Mobility in Organic Semiconductors Phys. Rev. B 2007, 75, 235106
62. Troisi, A. Dynamic Disorder in Molecular Semiconductors: Charge Transport in Two Dimensions J. Chem. Phys. 2011, 134, 034702
63. Ortmann, F.; Roche, S. Polaron Transport in Organic Crystals: Temperature Tuning of Disorder Effects Phys. Rev. B 2011, 84, 180302