Adjusting the local arrangement of π-stacked oligothiophenes through hydrogen bonds: A viable route to promote charge transfer

Journal of Physical Chemistry Letters

Volumn 5, Issue 13, 2014, Pages 2320-2324

  Liu, Hongguang ^a   Brémond, Éric ^a   Prlj, Antonio ^a   Gonthier, Jérôme F ^a   Corminboeuf, Clémence ^a  

^a EPFL   (Switzerland)

Author keywords

charge mobility; electronic structure computations; noncovalent interactions; organic electronics; quaterthiophene; stacking

Indexed keywords

ELECTRONIC STRUCTURE; HYDROGEN BONDS; IONS;

CHARGE MOBILITIES; NON-COVALENT INTERACTION; ORGANIC ELECTRONICS; QUATERTHIOPHENE; STRUCTURE COMPUTATION;

CHARGE TRANSFER;

EID: 84903851875     PISSN: None     EISSN: 19487185     Source Type: Journal    
DOI: 10.1021/jz501078s     Document Type: Article

References (53)

1. Henson, Z. B.; Müllen, K.; Bazan, G. C. Design Strategies for Organic Semiconductors beyond the Molecular Formula Nat. Chem. 2012, 4, 699-704
2. Sokolov, A. N.; Atahan-Evrenk, S.; Mondal, R.; Akkerman, H. B.; Sanchez-Carrera, R. S.; Granados-Focil, S.; Schrier, J.; Mannsfeld, S. C. B.; Zoombelt, A. P.; Bao, Z. N. From Computational Discovery to Experimental Characterization of a High Hole Mobility Organic Crystal Nat. Commun. 2011, 2, 437/1-437/8
3. McCulloch, I.; Ashraf, R. S.; Biniek, L.; Bronstein, H.; Combe, C.; Donaghey, J. E.; James, D. I.; Nielsen, C. B.; Schroeder, B. C.; Zhang, W. M. Design of Semiconducting Indacenodithiophene Polymers for High Performance Transistors and Solar Cells Acc. Chem. Res. 2012, 45, 714-722
4. McCulloch, I.; Heeney, M.; Bailey, C.; Genevicius, K.; MacDonald, I.; Shkunov, M.; Sparrowe, D.; Tierney, S.; Wagner, R.; Zhang, W. M. Liquid-Crystalline Semiconducting Polymers with High Charge-Carrier Mobility Nat. Mater. 2006, 5, 328-333
5. 2/Vs for Polymer Thin-Film Transistor J. Appl. Phys. 2009, 105, 024516/1-024516/5
6. Lee, M. J.; Gupta, D.; Zhao, N.; Heeney, M.; McCulloch, I.; Sirringhaus, H. Anisotropy of Charge Transport in a Uniaxially Aligned and Chain-Extended, High-Mobility, Conjugated Polymer Semiconductor Adv. Funct. Mater. 2011, 21, 932-940
7. Elschner, C.; Schrader, M.; Fitzner, R.; Levin, A. A.; Bäuerle, P.; Andrienko, D.; Leo, K.; Riede, M. Molecular Ordering and Charge Transport in a Dicyanovinyl-Substituted Quaterthiophene Thin Film RSC Adv. 2013, 3, 12117-12123
8. 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
9. 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
10. Hotta, S.; Waragai, K. Alkyl-Substituted Oligothiophenes: Crystallographic and Spectroscopic Studies of Neutral and Doped Forms J. Mater. Chem. 1991, 1, 835-842
11. Marseglia, E. A.; Grepioni, F.; Tedesco, E.; Braga, D. Solid State Conformation and Crystal Packing of Methyl-Substituted Quaterthiophenes Mol. Cryst. Liq. Cryst. 2000, 348, 137-151 (Pubitemid 32131000)
12. DiCésare, N.; Belletête, M.; Garcia, E. R.; Leclerc, M.; Durocher, G. Intermolecular Interactions in Conjugated Oligothiophenes. 3. Optical and Photophysical Properties of Quaterthiophene and Substituted Quaterthiophenes in Various Environments J. Phys. Chem. A 1999, 103, 3864-3875 (Pubitemid 129577002)
13. Macchi, G.; Milián Medina, B.; Zambianchi, M.; Tubino, R.; Cornil, J.; Barbarella, G.; Gierschner, J.; Meinardi, F. Spectroscopic Signatures for Planar Equilibrium Geometries in Methyl-Substituted Oligothiophenes Phys. Chem. Chem. Phys. 2009, 11, 984-990
14. Macchi, G.; Botta, C.; Calzaferri, G.; Catti, M.; Cornil, J.; Gierschner, J.; Meinardi, F.; Tubino, R. Weak Forces at Work in Dye-Loaded Zeolite Materials: Spectroscopic Investigation on Cation-Sulfur Interactions Phys. Chem. Chem. Phys. 2010, 12, 2599-2605
15. Williams, D. E.; Xiao, Y. Benzene, Naphthalene and Anthracene Dimers and Their Relation to the Observed Crystal Structures Acta Crystallogr., Sect. A 1993, 49, 1-10
16. Tsuzuki, S.; Honda, K.; Azumi, R. Model Chemistry Calculations of Thiophene Dimer Interactions: Origin of π-Stacking J. Am. Chem. Soc. 2002, 124, 12200-12209 (Pubitemid 35154887)
17. Podeszwa, R.; Bukowski, R.; Szalewicz, K. Potential Energy Surface for the Benzene Dimer and Perturbational Analysis of π-π Interactions J. Phys. Chem. A 2006, 110, 10345-10354 (Pubitemid 44412384)
18. Grimme, S. Do Special Noncovalent π-π Stacking Interactions Really Exist? Angew. Chem., Int. Ed. 2008, 47, 3430-3434
19. Hohenstein, E. G.; Sherrill, C. D. Density Fitting and Cholesky Decomposition Approximations in Symmetry-Adapted Perturbation Theory: Implementation and Application to Probe the Nature of π-π Interactions in Linear Acenes J. Chem. Phys. 2010, 132, 184111/1-184111/10
20. Brédas, J. L.; Calbert, J. P.; da Silva Filho, D. A.; Cornil, J. Organic Semiconductors: A Theoretical Characterization of the Basic Parameters Governing Charge Transport Proc. Natl. Acad. Sci. U. S. A. 2002, 99, 5804-5809 (Pubitemid 34493220)
21. Coropceanu, V.; Cornil, J.; da Silva, D. A.; Olivier, Y.; Silbey, R.; Brédas, J. L. Charge Transport in Organic Semiconductors Chem. Rev. 2007, 107, 926-952 (Pubitemid 46736532)
22. Feng, X. L.; Marcon, V.; Pisula, W.; Hansen, M. R.; Kirkpatrick, J.; Grozema, F.; Andrienko, D.; Kremer, K.; Müllen, K. Towards High Charge-Carrier Mobilities by Rational Design of the Shape and Periphery of Discotics Nat. Mater. 2009, 8, 421-426
23. Moon, H.; Zeis, R.; Borkent, E. J.; Besnard, C.; Lovinger, A. J.; Siegrist, T.; Kloc, C.; Bao, Z. N. Synthesis, Crystal Structure, and Transistor Performance of Tetracene Derivatives J. Am. Chem. Soc. 2004, 126, 15322-15323 (Pubitemid 39577434)
24. Anthony, J. E. Functionalized Acenes and Heteroacenes for Organic Electronics Chem. Rev. 2006, 106, 5028-5048 (Pubitemid 46099388)
25. Wheeler, S. E. Controlling the Local Arrangements of π-Stacked Polycyclic Aromatic Hydrocarbons through Substituent Effects CrystEngComm 2012, 14, 6140-6145
26. Marty, R.; Szilluweit, R.; Sanchez-Ferrer, A.; Bolisetty, S.; Adamcik, J.; Mezzenga, R.; Spitzner, E. C.; Feifer, M.; Steinmann, S. N.; Corminboeuf, C. Hierarchically Structured Microfibers of "Single Stack" Perylene Bisimide and Quaterthiophene Nanowires ACS Nano 2013, 7, 8498-8508
27. Tevis, I. D.; Palmer, L. C.; Herman, D. J.; Murray, I. P.; Stone, D. A.; Stupp, S. I. Self-Assembly and Orientation of Hydrogen-Bonded Oligothiophene Polymorphs at Liquid-Membrane-Liquid Interfaces J. Am. Chem. Soc. 2011, 133, 16486-16494
28. Stone, D. A.; Tayi, A. S.; Goldberger, J. E.; Palmer, L. C.; Stupp, S. I. Self-Assembly and Conductivity of Hydrogen-Bonded Oligothiophene Nanofiber Networks Chem. Commun. 2011, 47, 5702-5704
29. Wall, B. D.; Diegelmann, S. R.; Zhang, S. M.; Dawidczyk, T. J.; Wilson, W. L.; Katz, H. E.; Mao, H. Q.; Tovar, J. D. Aligned Macroscopic Domains of Optoelectronic Nanostructures Prepared via Shear-Flow Assembly of Peptide Hydrogels Adv. Mater. 2011, 23, 5009-5014
30. Balakrishnan, K.; Datar, A.; Naddo, T.; Huang, J. L.; Oitker, R.; Yen, M.; Zhao, J. C.; Zang, L. Effect of Side-Chain Substituents on Self-Assembly of Perylene Diimide Molecules: Morphology Control J. Am. Chem. Soc. 2006, 128, 7390-7398 (Pubitemid 43849142)
31. De Luca, G.; Liscio, A.; Nolde, F.; Scolaro, L. M.; Palermo, V.; Müllen, K.; Samorì, P. Self-Assembly of Discotic Molecules into Mesoscopic Crystals by Solvent-Vapour Annealing Soft Matter 2008, 4, 2064-2070
32. Savage, R. C.; Orgiu, E.; Mativetsky, J. M.; Pisula, W.; Schnitzler, T.; Eversloh, C. L.; Li, C.; Müllen, K.; Samorì, P. Charge Transport in Fibre-Based Perylene-Diimide Transistors: Effect of the Alkyl Substitution and Processing Technique Nanoscale 2012, 4, 2387-2393
33. Gesquière, A.; Abdel-Mottaleb, M. M. S.; De Feyter, S.; De Schryver, F. C.; Schoonbeek, F.; van Esch, J.; Kellogg, R. M.; Feringa, B. L.; Calderone, A.; Lazzaroni, R. Molecular Organization of Bis-Urea Substituted Thiophene Derivatives at the Liquid/Solid Interface Studied by Scanning Tunneling Microscopy Langmuir 2000, 16, 10385-10391 (Pubitemid 32086295)
34. Gsänger, M.; Oh, J. H.; Könemann, M.; Höffken, H. W.; Krause, A. M.; Bao, Z. N.; Würthner, F. A Crystal-Engineered Hydrogen-Bonded Octachloroperylene Diimide with a Twisted Core: An n-Channel Organic Semiconductor Angew. Chem., Int. Ed. 2010, 49, 740-743
35. Zhang, M. X.; Zhao, G. J. Modification of n-Type Organic Semiconductor Performance of Perylene Diimides by Substitution in Different Positions: Two-Dimensional π-Stacking and Hydrogen Bonding ChemSusChem 2012, 5, 879-887
36. Kolhe, N. B.; Devi, R. N.; Senanayak, S. P.; Jancy, B.; Narayan, K. S.; Asha, S. K. Structure Engineering of Naphthalene Diimides for Improved Charge Carrier Mobility: Self-Assembly by Hydrogen Bonding, Good or Bad? J. Mater. Chem. 2012, 22, 15235-15246
37. Sokolov, A. N.; Friščić, T.; Blais, S.; Ripmeester, J. A.; MacGillivray, L. R. Persistent One-Dimensional Face-to-Face π-Stacks within Organic Cocrystals Cryst. Growth Des. 2006, 6, 2427-2428 (Pubitemid 44799865)
38. Sokolov, A. N.; Friščić, T.; MacGillivray, L. R. Enforced Face-to-Face Stacking of Organic Semiconductor Building Blocks within Hydrogen-Bonded Molecular Cocrystals J. Am. Chem. Soc. 2006, 128, 2806-2807
39. Vura-Weis, J.; Ratner, M. A.; Wasielewski, M. R. Geometry and Electronic Coupling in Perylenediimide Stacks: Mapping Structure-Charge Transport Relationships J. Am. Chem. Soc. 2010, 132, 1738-1739
40. Curtis, M. D.; Cao, J.; Kampf, J. W. Solid-State Packing of Conjugated Oligomers: From π-Stacks to the Herringbone Structure J. Am. Chem. Soc. 2004, 126, 4318-4328 (Pubitemid 38453891)
41. Lan, Y. K.; Huang, C. I. Charge Mobility and Transport Behavior in the Ordered and Disordered States of the Regioregular Poly(3-hexylthiophene) J. Phys. Chem. B 2009, 113, 14555-14564
42. Shao, Y.; Molnar, L. F.; Jung, Y.; Kussmann, J.; Ochsenfeld, C.; Brown, S. T.; Gilbert, A. T. B.; Slipchenko, L. V.; Levchenko, S. V.; ONeill, D. P. Advances in Methods and Algorithms in a Modern Quantum Chemistry Program Package Phys. Chem. Chem. Phys. 2006, 8, 3172-3191
43. Perdew, J. P.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple Phys. Rev. Lett. 1996, 77, 3865-3868 (Pubitemid 126631804)
44. Adamo, C.; Barone, V. Toward Reliable Density Functional Methods without Adjustable Parameters: The PBE0 Model J. Chem. Phys. 1999, 110, 6158-6170
45. Steinmann, S. N.; Corminboeuf, C. Comprehensive Benchmarking of a Density-Dependent Dispersion Correction J. Chem. Theory Comput. 2011, 7, 3567-3577
46. Steinmann, S. N.; Piemontesi, C.; Delacht, A.; Corminboeuf, C. Why are the Interaction Energies of Charge-Transfer Complexes Challenging for DFT? J. Chem. Theory Comput. 2012, 8, 1629-1640
47. Steinmann, S. N.; Corminboeuf, C. Exploring the Limits of Density Functional Approximations for Interaction Energies of Molecular Precursors to Organic Electronics J. Chem. Theory Comput. 2012, 8, 4305-4316
48. Zhao, Y.; Truhlar, D. G. The M06 Suite of Density Functionals for Main Group Thermochemistry, Thermochemical Kinetics, Noncovalent Interactions, Excited States, and Transition Elements: Two New Functionals and Systematic Testing of Four M06-Class Functionals and 12 Other Functionals Theor. Chem. Acc. 2008, 120, 215-241
49. Zhao, Y.; Truhlar, D. G. Density Functionals with Broad Applicability in Chemistry Acc. Chem. Res. 2008, 41, 157-167
50. te Velde, G.; Bickelhaupt, F. M.; Baerends, E. J.; Guerra, C. F.; Van Gisbergen, S. J. A.; Snijders, J. G.; Ziegler, T. Chemistry with ADF J. Comput. Chem. 2001, 22, 931-967 (Pubitemid 32455733)
51. Guerra, C. F.; Snijders, J. G.; te Velde, G.; Baerends, E. J. Towards an Order-N DFT Method Theor. Chem. Acc. 1998, 99, 391-403
52. SCM, Theoretical Chemistry. ADF2013; Vrije Universiteit: Amsterdam, The Netherlands, 2013.
53. Valeev, E. F.; Coropceanu, V.; da Silva Filho, D. A.; Salman, S.; Brédas, J. L. Effect of Electronic Polarization on Charge-Transport Parameters in Molecular Organic Semiconductors J. Am. Chem. Soc. 2006, 128, 9882-9886 (Pubitemid 44147973)