Oligothiophene semiconductors: Synthesis, characterization, and applications for organic devices

ACS Applied Materials and Interfaces

Volumn 6, Issue 8, 2014, Pages 5327-5343

  Zhang, Lei ^a   Colella, Nicholas S ^a   Cherniawski, Benjamin P ^a   Mannsfeld, Stefan C B ^b   Briseno, Alejandro L ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

^b SLAC NATIONAL ACCELERATOR LABORATORY   (United States)

Author keywords

crystal packing; intermolecular interactions; oligothiophenes; organic device; polymorphism

Indexed keywords

CHAINS; FUNCTIONAL GROUPS; ORGANIC FIELD EFFECT TRANSISTORS; POLYMORPHISM;

CRYSTAL PACKINGS; ELECTRONIC RELATIONSHIP; INTERMOLECULAR INTERACTIONS; OLIGOTHIOPHENES; ORGANIC DEVICES; ORGANIC ELECTRONIC DEVICES; STRUCTURE PROPERTY RELATIONSHIPS; SYNTHESIS AND CHARACTERIZATIONS;

CHARACTERIZATION;

EID: 84899559117     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am4060468     Document Type: Review

References (108)

1. Beaujuge, P. M.; Fréchet, J. M. J. Molecular Design and Ordering Effects in π-Functional Materials for Transistor and Solar Cell Applications J. Am. Chem. Soc. 2011, 133, 20009-20029
2. Heeney, M.; Bailey, C.; Genevicius, K.; Shkunov, M.; Soarrow, D.; Tierney, S.; McCulloch, I. Stable Polythiophene Semiconductor Incorporating Thieno[2,3- b ]thiophene J. Am. Chem. Soc 2005, 127, 1078-1079
3. McCullough, R. D. The Chemistry of Conducting Polythiophenes Adv. Mater 1998, 10, 93-116
4. Electronic Materials: The Oligomer Approach; Müllen, K.; Wenger, G., Eds.; Wiley-VCH: Weinheim, Germany, 1997.
5. Kline, R. J.; McGehee, M. D.; Kadnikova, E. N.; Liu, J. S.; Fréchet, J. M. J. Controlling the Field-Effect Mobility of of Regioregular Polythiophene by Changing the Molecular Weight Adv. Mater. 2003, 15, 1519-1522
6. Prosa, T. J.; Winokur, M. J.; Moulton, J.; Smith, P.; Heeger, A. J. X-Ray Structural Studies of Poly(3-alkylthiophenes): An Example of an Inverse Comb Macromolecules 1992, 25, 4364-4372
7. Meille, S. V.; Romita, V.; Caronna, T.; Lovinger, A. J.; Catellani, M.; Belobrzeckaja, L. Influence of Molecular Weight and Regioregularity on the Polymorphic Behavior of Poly(3- decylthiophenes) Macromolecules 1997, 30, 7898-7905
8. Kline, R. J.; McGehee, M. D.; Kadnikova, E. N.; Liu, J. S.; Fréchet, J. M. J.; Toney, M. F. Dependence of Regioregular Poly(3-hexylthiophene) Film Morphology and Field-Effect Mobility on Molecular Weight Macromolecules 2005, 38, 3312-3319
9. Kline, R. J.; Delongchamp, D. M.; Fischer, D. A.; Lin, E. K.; Richter, L. J.; Chabinyc, M. L.; Toney, M. F.; Heeney, M.; McCulloch, I. Critical Role of Side-Chain Attachment Density on the Order and Device Performance of Polythiophenes Macromolecules 2007, 40, 7960-7965
10. Zen, A.; Pflaum, J.; Hirschmann, S.; Zhuang, W.; Jaiser, F.; Asawapirom, U.; Rabe, J. P.; Scherf, U.; Neher, D. Effect of Molecular Weight and Annealing of Poly(3-hexylthiophene)s on the Performance of Organic Field-Effect Transistors Adv. Funct. Mater. 2004, 14, 757-764
11. Joshi, S.; Grigorian, S.; Pietsch, U.; Pingel, P.; Zen, A.; Neher, D.; Scherf, U. Thickness Dependence of the Crystalline Structure and Hole Mobility in Thin Films of Low Molecular Weight Poly(3-hexylthiophene) Macromolecules 2008, 41, 6800-6808
12. Lim, J. A.; Liu, F.; Ferdous, S.; Muthukumar, M.; Briseno, A. L. Polymer Semiconductor Crystals Mater. Today 2010, 13, 14-24
13. Coffin, R. C.; Peet, J.; Rogers, J.; Bazan, G. C. Streamlined Microwave-Assisted Preparation of Narrow-Bandgap Conjugated Polymers for High-Performance Bulk Heterojunction Solar Cells Nat. Chem. 2009, 1, 657-661
14. Schilinsky, P.; Asawapirom, U.; Scherf, U.; Biele, M.; Brabec, C. J. Influence of the Molecular Weight of Poly(3-hexylthiophene) on the Performance of Bulk Heterojunction Solar Cells Chem. Mater. 2005, 17, 2175-2180
15. Thompson, B. C.; Fréchet, J. M. J. Polymer-Fullerene Composite Solar Cells Angew. Chem., Int. Ed 2008, 47, 58-77
16. Li, G.; Shrotriya, V.; Huang, J. S.; Yao, Y.; Moriarty, K.; Yang, Y. High-Efficiency Solution Processable Polymer Photovoltaic Cells by Self-Organization of Polymer Blends Nat. Mater. 2005, 4, 864-868
17. He, Z.; Zhong, C.; Su, S.; Xu, M.; Wu, H.; Cao, Y. Enhanced Power-Conversion Efficiency in Polymer Solar Cells Using an Inverted Device Structure Nat. Photonics 2012, 6, 591-595
18. Dou, L.; You, J.; Yang, J.; Chen, C.; He, Y.; Murase, S.; Moriarty, T.; Emery, K.; Li, G.; Yang, Y. Tandem Polymer Solar Cells Featuring a Spectrally Matched Low-Bandgap Polymer Nat. Photonics 2012, 6, 180-185
19. Chen, H.; Guo, Y.; Yu, G.; Zhao, Y.; Zhang, J.; Gao, D.; Liu, H.; Liu, Y. Highly π-Extended Copolymers with Diketopyrrolopyrrole Moieties for High-Performance Field-Effect Transistors Adv. Mater. 2012, 24, 4618-4622
20. Lei, T.; Cao, Y.; Zhou, X.; Peng, Y.; Bian, J.; Pei, J. Systematic Investigation of Isoindigo-Based Polymeric Field-Effect Transistors: Design Strategy and Impact of Polymer Symmetry and Backbone Curvature Chem. Mater. 2012, 24, 1762-1770
21. Lei, T.; Cao, Y.; Fan, Y.; Liu, C.; Yuan, S.; Pei, J. High-Performance Air-Stable Organic Field-Effect Transistors: Isoindigo-Based Conjugated Polymers J. Am. Chem. Soc. 2011, 133, 6099-6101
22. Mei, J.; Kim, D. H.; Ayzner, A. L.; Toney, M. F.; Bao, Z. Siloxane-Terminated Solubilizing Side Chains: Bringing Conjugated Polymer Backbones Closer and Boosting Hole Mobilities in Thin-Film Transistors J. Am. Chem. Soc. 2011, 133, 20130-30133
23. Wang, S.; Kiersnowski, A.; Pisula, W.; Müllen, K. Microstructure Evolution and Device Performance in Solution-Processed Polymeric Field-Effect Transistors: The Key Role of the First Monolayer J. Am. Chem. Soc. 2012, 134, 4015-4018
24. Mishra, A.; Ma, C.-Q.; Bäuerle, P. Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications Chem. Rev. 2009, 109, 1141-1276
25. Mena-Osteritz, E.; Meyer, A.; Langeveld-Voss, B. M. W.; Janssen, R. A. J.; Meijer, E. W.; Bäuerle, P. Two-Dimensional Crystals of Poly(3-Alkyl- thiophene)s: Direct Visualization of Polymer Folds in Submolecular Resolution Angew. Chem., Int. Ed. 2000, 39, 2679-2684
26. Bäuerle, P.; Fischer, T.; Bildlingmeier, B.; Stabel, A.; Rabe, J. Oligothiophenes-Yet Longer? Synthesis, Characterization, and Scanning Tunneling Microscopy Images of Homologous, Isomerically Pure Oligo(alkylthiophene)s Angew. Chem. Int. Ed. 1995, 34, 303-307
27. Takimiya, K.; Sakamoto, K.; Otsubo, T.; Kunugi, Y. Thin Film Characteristics and FET Performances of β-Octyl-substituted Long Oligothiophenes Chem. Lett. 2006, 35, 942-943
28. Izumi, T.; Kobashi, S.; Takimiya, K.; Aso, Y.; Otsubo, T. Synthesis and Spectroscopic Properties of a Series of β-Blocked Long Oligothiophenes up to the 96-mer: Revaluation of Effective Conjugation Length J. Am. Chem. Soc. 2003, 125, 5286-5287
29. Wang, Q. L.; Qu, Y.; Tian, H. K.; Geng, Y. H.; Wang, F. S. Iterative Binomial Synthesis of Monodisperse Polyfluorenes up to 64-mers and Their Chain-Length- Dependent Properties Macromolecules 2011, 44, 1256-1260
30. Azumi, R.; Götz, G.; Debaerdemaeker, T.; Bäuerle, P. Coincidence of the Molecular Organization of β-Substituted Oligothiophenes in Two-Dimensional Layers and Three-Dimensional Crystals Chem.-Eur. J. 2000, 6, 735-744
31. Azumi, R.; Mena-Osteritz, E.; Boese, R.; Benet-Buchholz, J.; Bäuerle, P. The Longest Oligothiophene Ever Examined by X-Ray Structure Analysis J. Mater. Chem 2006, 16, 728-735
32. Horowitz, G.; Bachet, B.; Yassar, A.; Lang, P.; Dmanze, F.; Fave, J. L.; Gamier, F. Growth and Characterization of Sexithiophene Single Crystals Chem. Mater 1995, 7, 1337-1341
33. Handbook of Thiophene-Based Materials: Applications in Organic Electronics and Photonics; Perepichka, I. F.; Perepichka, D. F., Eds.; Wiley: Chichester, U.K., 2009.
34. Fitzner, R.; Mena-Osteritz, E.; Mishra, A.; Schulz, G.; Reinold, E.; Weil, M.; Körner, C.; Ziehlke, H.; Elschner, C.; Leo, K.; Riede, M.; Pfeiffer, M.; Uhrich, C.; Bäuerle, P. Correlation of π-Conjugated Oligomer Structure with Film Morphology and Organic Solar Cell Performance J. Am. Chem. Soc. 2012, 134, 11064-11067
35. Dong, S.; Zhang, H.; Yang, L.; Bai, M.; Yao, Y.; Chen, H.; Gan, L.; Yang, T.; Jiang, H.; Hou, S.; Wan, L.; Guo, X. Solution-Crystallized Organic Semiconductors with High Carrier Mobility and Air Stability Adv. Mater. 2012, 24, 5576-5580
36. Mishra, A.; Bäuerle, P. Small Molecule Organic Semiconductors on the Move: Promises for Future Solar Energy Technology Angew. Chem., Int. Ed. 2012, 51, 2020-2067
37. Chen, Y.; Wan, X.; Long, G. High Performance Photovoltaic Applications Using Solution-Processed Small Molecules Acc. Chem. Res. 2013, 46, 2645-2655
38. Usta, H.; Facchetti, A.; Marks, T. J. n -Channel Semiconductor Materials Design for Organic Complementary Circuits Acc. Chem. Re.s 2011, 44, 501-510
39. Osaka, I.; McCullough, R. Advances in Molecular Design and Synthesis of Regioregular Polythiophenes Acc. Chem. Res. 2008, 41, 1202-1214
40. Katz, H.; Bao, Z.; Gilat, S. L. Synthetic Chemistry for Ultrapure, Processable, and High-Mobility Organic Transistor Semiconductors Acc. Chem. Res 2001, 34, 359-369
41. Allard, S.; Forster, M.; Souharce, B.; Thiem, H.; Scherf, U. Organic Semiconductors for Solution-Processable Field-Effect Transistors (OFETs) Angew. Chem., Int. Ed 2008, 47, 4070-4098
42. Barbarella, G.; Zambianchi, M.; Di Toro, R.; Colonna, M.; Iarossi, D.; Goldoni, F.; Bongini, A. Regioselective Oligomerization of 3-(Alkylsulfanyl) thiophenes with Ferric Chloride J. Org. Chem 1996, 61, 8285-8292
43. Wei, Y.; Chan, C.; Tian, J.; Jang, G.; Hsueh, K. Electrochemical Polymerization of Thiophenes in the Presence of Bithiophene or Terthiophene: Kinetics and Mechanism of the Polymerization Chem. Mater. 1991, 3, 888-897
44. Roncali, J. Synthetic Principles for Bandgap Control in Linear π-Conjugated Systems Chem. Rev. 1997, 97, 173-206
45. 2O as a Model Reaction for the Oxidative Polymerization of Thiophene Derivatives Macromolecules 1996, 29, 3370-3375
46. Zhang, F.; Bäuerle, P. A Controlled Approach to Well-Defined Oligothiophenes via Oxidatively Induced Reductive Elimination of Stable Pt(II) Oligothienyl Complexes J. Am. Chem. Soc 2007, 129, 3090-3091
47. Takahashi, M.; Masui, K.; Sekiguchi, H.; Kobayashi, N.; Mori, A.; Funahashi, M.; Tamaoki, N. Palladium-Catalyzed C-H Homocoupling of Bromothiophene Derivatives and Synthetic Application to Well-Defined Oligothiophenes J. Am. Chem. Soc 2006, 128, 10930-10933
48. Masuda, N.; Tanba, S.; Sugie, A.; Monguchi, D.; Koumura, N.; Hara, K.; Mori, A. Stepwise Construction of Head-to-Tail-Type Oligothiophenes via Iterative Palladium-Catalyzed CH Arylation and Halogen Exchange Org. Lett 2009, 11, 2297-2300
49. Tanaka, S.; Tamba, S.; Tanaka, D.; Sugie, A.; Mori, A. Synthesis of Well-Defined Head-to-Tail-Type Oligothiophenes by Regioselective Deprotonation of 3-Substituted Thiophenes and Nickel-Catalyzed Cross-Coupling Reaction J. Am. Chem. Soc 2011, 133, 16734-16737
50. Zhang, L.; Colella, N.; Liu, F.; Trahan, S.; Baral, J.; Winter, H.; Mannsfeld, S.; Briseno, A. Synthesis, Electronic Structure, Molecular Packing/Morphology Evolution, and Carrier Mobilities of Pure Oligo-/Poly(alkylthiophenes) J. Am. Chem. Soc 2013, 135, 844-854
51. Di Maria, F.; Olivelli, P.; Gazzano, M.; Zanelli, A.; Biasiucci, G.; Gigli, G.; Gentili, D.; D'Angelo, P.; Cavallini, M.; Barbarella, G. A Successful Chemical Strategy To Induce Oligothiophene Self-Assembly into Fibers with Tunable Shape and Function J. Am. Chem. Soc 2011, 133, 8654-8661
52. Koch, F.P.V.; Smith, P.; Heeney, M. Fibonacci's Route to Regioregular Oligo(3-hexylthiophene)s J. Am. Chem. Soc. 2013, 135, 13695-13698
53. Rieke, R.; Kim, S.; W, X. Direct Preparation of 3-Thienyl Organometallic Reagents: 3-Thienylzinc and 3-Thienylmagnesium Iodides and 3-Thienylmanganese Bromides and Their Coupling Reactions J. Org. Chem. 1997, 62, 6921-6927
54. Wenz, G.; Mueller, M. A.; Schmidt, M.; Wegner, G. Structure of Poly (diacetylenes) in Solution Macromolecules 1984, 17, 837-850
55. Meier, H.; Stalmach, U.; Kolshorn, H. Effective conjugation length and UV/vis spectra of oligomers Acta Polym. 1997, 48, 379-384
56. Zade, S. S.; Bendikov, M. From Oligomers to Polymer: Convergence in the HOMO-LUMO Gaps of Conjugated Oligomers Org. Lett. 2006, 8, 5243-5246
57. Oliveira, E. F. d.; Lavarda, F. C. Structure of P3HT in the Solid State J. Polym. Sci., Part B: Polym. Phys. 2013, 51, 1350-1354
58. Bidan, G.; De Nicola, A.; Enée, V.; Guillerez, S. Synthesis and UV-Visible Properties of Soluble Regioregular Oligo(3-octylthiophenes), Monomer to Hexamer Chem. Mater. 1998, 10, 1052-1058
59. Fitzner, R.; Reinold, E.; Mishra, A.; Mena-Osteritz, E.; Ziehlke, H.; Körner, C.; Leo, K.; Riede, M.; Weil, M.; Tsaryova, O.; Weiß, A.; Uhrich, C.; Pfeiffer, M.; Bäuerle, P. Dicyanovinyl-Substituted Oligothiophenes: Structure-Property Relationships and Application in Vacuum- Processed Small Molecule Organic Solar Cells Adv. Funct. Mater. 2011, 21, 897-910
60. 60 Adv. Mater. 2006, 18, 2872-2875
61. Fichou, D. Structural Order in Conjugated Oligothiophenes and its Implications on Opto-electronic Devices J. Mater. Chem. 2000, 10, 571-588
62. Tan, L.; Zhang, L.; Jiang, X.; Yang, X.; Wang, L.; Wang, Z.; Li, L.; Hu, W.; Shuai, Z.; Li, L.; Zhu, D. A Densely and Uniformly Packed Organic Semiconductor Based on Annelated β -Trithiophenes for High- Performance Thin Film Transistors Adv. Funct. Mater. 2009, 19, 272-276
63. Zhang, L.; Tan, L.; Wang, Z.; Hu, W.; Zhu, D. High-Performance, Stable Organic Field-Effect Transistors Based on trans -1,2-(Dithieno[2,3- b:3′,2′- d ]thiophene)ethene Chem. Mater 2009, 21, 1993-1999
64. 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
65. 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
66. Akkerman, H. B.; Mannsfeld, S. C. B.; Kaushik, A. P.; Verploegen, E.; Burnier, L.; Zoombelt, A. P.; Saathoff, J. D.; Hong, S.; Atahan-Evrenk, S.; Liu, X.; Aspurn-Guzik, A.; Toney, M. F.; Clancy, P.; Bao, Z. Effects of Odd-Even Side Chain Length of Alkyl-Substituted Diphenylbithiophenes on First Monolayer Thin Film Packing Structure J. Am. Chem. Soc. 2013, 135, 11006-11014
67. Reese, C.; Roberts, M.; Parkin, S. P.; Bao, Z. Tuning Crystalline Solid-State Order and Charge Transport via Building-Block Modification of Oligothiophenes Adv. Mater. 2009, 21, 3678-3681
68. nCN (n = 3-6) Chem. Mater 1997, 9, 981-990
69. Barbarella, G.; Zamhianchi, M.; Di Toro, R.; Colonna, M.; Antolini, L.; Bongini, A. Functionalization of Sexithiophene with Electron-donating Methylsulphanyl Groups Adv. Mater. 1996, 8, 327-331
70. Liao, J.; Benz, M.; LeGoff, E.; Kunutzidis, M. G. Oligothiophenes as Models for Polythiophenes. The Crystal and Molecular Structures of 3″, 4″- Dibutylpentathiophene and 3′, 3″, 4′, 4″-Tetrabutylhexathiophene Adv. Mater. 1994, 6, 135-138
71. Facchetti, A.; Yoon, M.; Stern, C. L.; Hutchison, G. R.; Ratner, M.; Marks, T. J. Building Blocks for N-Type Molecular and Polymeric Electronics. Perfluoroalkyl- versus Alkyl- Functionalized Oligothiophenes (nTs; n = 2-6). Systematic Synthesis, Spectroscopy, Electrochemistry, and Solid-State Organization J. Am. Chem. Soc. 2004, 126, 13480-13501
72. Barbarella, G.; Zambianchi, M.; Bongini, A.; Antonili, L. Crystal Structure of 4,4′,3″,4′-Tetramethyl2,2′:5′, 2″:5″,2′-tetrathiophene: A Comparison with the Conformation in Solution Adv. Mater. 1992, 4, 282-285
73. 13C-NMR, UV, and MMP2 Calculations of Di- and Tetramethyl-quaterthiophenes Adv. Mater. 1991, 3, 494-496
74. Destri, S.; Ferro, D. R.; Khotinal, I. A.; Porzio, W.; Farina, A. Tetrahexylsexithiophene: Crystal Structure and Molecular Mechanics Calculations Macromol. Chem. Phys. 1998, 199, 1973-1979
75. Herrema, J. K.; Wilderman, J.; Van Bolhuis, F.; Hadziioannou, G. Synthesis and Crystal Structures of Two Dialkyl-substituted Sexithiophenes Synth. Met. 1993, 60, 239-248
76. Kurata, T.; Mohri, T.; Takimiya, K.; Otsubo, T. Conductive, Magnetic, and Optical Properties of Sterically Hindered Dodecithiophenes. Evidence for the Coexistence of Bipolaron and π-Dimer Bull. Chem. Soc. Jpn. 2007, 80, 1799-1807
77. Dunitz, J.; Bernstein, J. Disappearing Polymorphs Acc. Chem. Res. 1995, 28, 193-200
78. Mas-Torrent, M.; Rovira, C. Role of Molecular Order and Solid-State Structure in Organic Field-Effect Transistors Chem. Rev. 2011, 111, 4833-4856
79. Desiraju, G. R. Supramolecular Synthons in Crystal Engineering-A New Organic Synthesis Angew. Chem., Int. Ed. 1995, 34, 2311-2327
80. Antolini, L.; Horowitz, G.; Kouki, F.; Garnier, F. Polymorphism in Oligothiophenes with an Even Number of Thiophene Subunits Adv. Mater. 1998, 10, 382-385
81. Barbarella, G.; Zambianchi, M.; del Fresno, M.; Marimon, I.; Antolini, L.; Bongini, A. Conformational Polymorphism of Oligothiophenes: X-ray Structure of the Monoclinic Form of 3, 3′, 4″, 3′- Tetrakis(methylsulfany-l)2, 2′:5″, 2″:5″, 2′-Quaterthiophene Adv. Mater. 1997, 9, 484-487
82. Barbarella, G.; Zambianchi, M.; Antolini, L.; Ostoja, P.; Maccagnai, 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
83. Pan, H.; Liu, P.; Li, Y.; Wu, Y.; Ong, B. S.; Xu, G. Unique Polymorphism of Oligothiophenes Adv. Mater 2007, 19, 3240-3243
84. Elschner, C.; Schrader, M.; Fitzner, R.; Levin, 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
85. Mannebach, E. M.; Spalenka, J. W.; Johnson, P. S.; Cai, Z.; Himpsel, F. J.; Evans, P. G. High Hole Mobility and Thickness-Dependent Crystal Structure in α,ω-Dihexylsexithiophene Single- Monolayer Field-Effect Transistors Adv. Funct. Mater. 2013, 23, 554-564
86. Defaux, M.; Gholamrezaie, F.; Wang, J.; Kreyes, A.; Ziener, U.; Anokhin, D. V.; Ivanov, D. A.; Moser, A.; Neuhold, A.; Salzmann, I.; Resel, R.; de Leeuw, D. M.; Meskers, S. C. J.; Moeller, M.; Mourran, A. Solution-Processable Septithiophene Monolayer Transistor Adv. Mater. 2012, 24, 973-978
87. Wedl, B.; Resel, R.; Leising, G.; Kunert, B.; Salzmann, I.; Oehzelt, M.; Koch, N.; Vollmer, A.; Duhm, S.; Werzer, O.; Gbabode, G.; Sferrazza, M.; Geerts, Y. Crystallisation Kinetics in Thin Films of Dihexyl-terthiophene: The Appearance of Polymorphic Phases RSC Adv. 2012, 2, 4404-4414
88. Zhang, L.; Tan, L.; Hu, W.; Wang, Z. Synthesis, Packing Arrangement and Transistor Performance of Dimers of Dithienothiophenes J. Mater. Chem. 2009, 19, 8216-8222
89. Fitzner, R.; Elschner, C.; Weil, M.; Uhrich, C.; Körner, C.; Riede, M.; Leo, K.; Pfeiffer, M.; Reinold, E.; Menaosteritz, E.; Bäuerle, P. Interrelation between Crystal Packing and Small-Molecule Organic Solar Cell Performance Adv. Mater. 2012, 24, 675-680
90. Yuan, Q.; Mannsfeld, S. C. B.; Tang, M. L.; Roberts, M.; Toney, M. F.; DeLongchamp, D. M.; Bao, Z. Microstructure of Oligofluorene Asymmetric Derivatives in Organic Thin Film Transistors Chem. Mater. 2008, 20, 2763-2772
91. Yuan, Q.; Mannsfeld, S. C. B.; Tang, M. L.; Toney, M. F.; Lüning, J.; Bao, Z. Thin Film Structure of Tetraceno[2,3- b ]thiophene Characterized by Grazing Incidence X-ray Scattering and Near-Edge X-ray Absorption Fine Structure Analysis J. Am. Chem. Soc. 2008, 130, 3502-3508
92. DeLongchamp, D.M.; Kline, R.J.; Lin, E.K.; Fischer, D.A.; Richter, L.J.; Lucas, L.A.; Heeney, M.; McCulloch, I.; Northrup, J. E. High Carrier Mobility Polythiophene Thin Films: Structure Determination by Experiment and Theory Adv. Mater. 2007, 19, 833-837
93. Rivnay, J.; Mannsfeld, S. C. B.; Miller, C. E.; Salleo, A.; Toney, M. F. Quantitative Determination of Organic Semiconductor Microstructure from the Molecular to Device Scale Chem. Rev. 2012, 112, 5488-5519
94. Schuettfort, T.; Watts, B.; Thomsen, L.; Lee, M.; Sirringhaus, H.; McNeill, C. R. Microstructure of Polycrystalline PBTTT Films: Domain Mapping and Structure Formation ACS Nano 2012, 6, 1849-1864
95. Servet, B.; Ries, S.; Trotel, M.; Patrick, A.; Horowitz, G.; Garnier, F. X-ray Determination of the Crystal Structure and Orientation of Vacuum Evaporated Sexithiophene Films Adv. Mater. 1993, 5, 461-464
96. Mannsfeld, S. C. B.; Tang, M. L.; Bao, Z. Thin Film Structure of Triisopropylsilylethynyl-Functionalized Pentacene and Tetraceno[2,3-b]thiophene from Grazing Incidence X-Ray Diffraction Adv. Mater. 2011, 23, 127-131
97. Collins, B. A.; Cochran, J.E.; Yan, H.; Gann, E.; Hub, C.; Fink, R.; Wang, C.; Schuettfort, T.; McNeill, C.R.; Chabinyc, M.L.; Ade, H. Polarized X-Ray Scattering Reveals Non-crystalline Orientational Ordering in Organic Films Nat. Mater. 2012, 11, 536-543
98. Rivnay, J.; Jimison, L. H.; Northrup, J. E.; Toney, M. F.; Noriega, R.; Lu, S. F.; Marks, T. J.; Facchetti, A.; Salleo, A. Large Modulation of Carrier Transport by Grain-boundary Molecular Packing and Microstructure in Organic Thin Films Nat. Mater. 2009, 8, 952-958
99. Pingel, P.; Zen, A.; Neher, D.; Lieberwirth, I.; Wenger, G.; Allard, S.; Scherf, U. Unexpectedly High Field-effect Mobility of a Soluble, Low Molecular Weight Oligoquaterthiophene Fraction with Low Polydispersity Appl. Phys. A: Mater. Sci. Process. 2009, 95, 67-72
100. Gentili, D.; Di Maria, F.; Liscio, F.; Ferlauto, L.; Leonardi, F.; Maini, L.; Gazzano, M.; Milita, S.; Barbarella, G.; Gavallini, M. Targeting Ordered Oligothiophene Fibers with Enhanced Functional Properties by Interplay of Self-assembly and Wet Lithography J. Mater. Chem. 2012, 22, 20852-20856
101. Haid, S.; Mishra, A.; Weil, M.; Uhrich, C.; Pfeiffer, M.; Bäuerle, P. Synthesis and Structure-Property Correlations of Dicyanovinyl-Substituted Oligoselenophenes and their Application in Organic Solar Cells Adv. Funct. Mater 2012, 22, 4322-4333
102. Liu, Y.; Yang, Y.; Chen, C.; Chen, Q.; Dou, L.; Hong, Z.; Li, G.; Yang, Y. Solution-Processed Small Molecules Using Different Electron Linkers for High-Performance Solar Cells Adv. Mater. 2013, 25, 4657-4662
103. Li, Z.; He, G.; Wan, X.; Liu, Y.; Zhou, J.; Long, G.; Zuo, Y.; Zhang, M.; Chen, Y. Solution Processable Rhodanine-Based Small Molecule Organic Photovoltaic Cells with a Power Conversion Efficiency of 6.1% Adv. Energy. Mater. 2012, 2, 74-77
104. Long, G.; Wan, X.; Kan, B.; Liu, Y.; He, G.; Li, Z.; Zhang, Y.; Zhang, Y.; Zhang, Q.; Zhang, M.; Chen, Y. Investigation of Quinquethiophene Derivatives with Different End Groups for High Open Circuit Voltage Solar Cells Adv. Energy. Mater. 2013, 3, 639-646
105. Di Maria, F.; Gazzano, M.; Zanelli, A.; Gigli, G.; Loiudice, A.; Rizzo, A.; Biasiucci, M.; Salatelli, E.; D'Angelo, P.; Barbarella, G. Synthesis and Photovoltaic Properties of Regioregular Head-to-Head Substituted Thiophene Hexadecamers Macromolecules 2012, 45, 8284-8291
106. Risk, C.; McGehee, M. D.; Brédas, J.-L. A Quantum-chemical Perspective into Low Optical-gap Polymers for Highly-efficient Organic Solar Cells Chem. Sci. 2011, 2, 1200-1218
107. Zade, S. S.; Zamoshchik, N.; Bendikov, M. From Short Conjugated Oligomers to Conjugated Polymers. Lessons from Studies on Long Conjugated Oligomers Acc. Chem. Res. 2011, 44, 14-24
108. Sears, J.S.; Chance, R. R.; Brédas, J.-L. Torsion Potential in Polydiacetylene: Accurate Computations on Oligomers Extrapolated to the Polymer Limit J. Am. Chem. Soc. 2010, 132, 13313-13319