Design and computational characterization of non-fullerene acceptors for use in solution-processable solar cells

Journal of Physical Chemistry A

Volumn 118, Issue 36, 2014, Pages 7939-7951

  Rutledge, Lesley R ^a   McAfee, Seth M ^a   Welch, Gregory C ^a  

^a DALHOUSIE UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CHARACTERIZATION; COMPUTATIONAL CHEMISTRY; ELECTRON AFFINITY; ELECTRON TRANSPORT PROPERTIES; ELECTRONIC PROPERTIES; ELECTRONS; ENERGY GAP; HETEROJUNCTIONS; MOLECULES; OPTICAL PROPERTIES; SYNTHESIS (CHEMICAL);

ELECTRON ACCEPTOR MATERIALS; ELECTRON PROPERTIES; ELECTRON-DEFICIENT; HETEROJUNCTION SOLAR CELLS; HOMO AND LUMO ENERGIES; INTRINSIC DIPOLE MOMENT; ORGANIC SOLAR CELL; SOLUTION PROCESSABLE;

SOLAR CELLS;

EID: 84907270520     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp505867y     Document Type: Article

References (109)

1. Su, Y.-W.; Lan, S.-C.; Wei, K.-H. Organic Photovoltaics Mater. Today 2012, 15, 554-562
2. Kippelen, B.; Brédas, J.-L. Organic Photovoltaics Energy Environ. Sci. 2009, 2, 251-261
3. Li, G.; Zhu, R.; Yang, Y. Polymer Solar Cells Nat. Photonics 2012, 6, 153-161
4. Søndergaard, R.; Hösel, M.; Angmo, D.; Larsen-Olsen, T. T.; Krebs, F. C. Roll-to-Roll Fabrication of Polymer Solar Cells Mater. Today 2012, 15, 36-49
5. Kaltenbrunner, M.; White, M. S.; Glowacki, E. D.; Sekitani, T.; Someya, T.; Sariciftci, N. S.; Bauer, S. Ultrathin and Lightweight Organic Solar Cells with High Flexibility Nat. Commun. 2011, 3, 770 10.1038/ncomms1772
6. Brabec, C. J.; Sariciftci, N. S.; Hummelen, J. C. Plastic Solar Cells Adv. Funct. Mater. 2001, 11, 15-26
7. Guo, X.; Zhou, N.; Lou, S. J.; Smith, J.; Tice, D. B.; Hennek, J. W.; Ortiz, R. P.; López Navarrete, J. T.; Li, S.; Strzalka, J. Polymer Solar Cells with Enhanced Fill Factors Nat. Photonics 2013, 7, 825-833
8. 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, 593-597
9. Small, C. E.; Chen, S.; Subbiah, J.; Amb, C. M.; Tsang, S.-W.; Lai, T.-H.; Reynolds, J. R.; So, F. High-Efficiency Inverted Dithienogermole-Thienopyrrolodione-Based Polymer Solar Cells Nat. Photonics 2012, 6, 115-120
10. You, J.; Dou, L.; Yoshimura, K.; Kato, T.; Ohya, K.; Moriarty, T.; Emery, K.; Chen, C.-C.; Gao, J.; Li, G. A Polymer Tandem Solar Cell with 10.6% Power Conversion Efficiency Nat. Commun. 2013, 4, 1446
11. Walker, B.; Kim, C.; Nguyen, T.-C. Small Molecule Solution-Processed Bulk Heterojunction Solar Cells Chem. Mater. 2011, 23, 470-482
12. Sonar, P.; Lim, J. P. F.; Chan, K. L. Organic Non-Fullerene Acceptors for Organic Photovoltaics Energy Environ. Sci. 2011, 4, 1558-1574
13. Facchetti, A. Polymer Donor-Polymer Acceptor (All-Polymer) Solar Cells Mater. Today 2013, 16, 123-132
14. Sharenko, A.; Proctor, C. M.; van der Poll, T. S.; Henson, Z. B.; Nguyen, T.-Q.; Bazan, G. C. A High-Performing Solution-Processed Small Molecule: Perylene Diimide Bulk Heterojunction Solar Cell Adv. Mater. 2013, 25, 4403-4406
15. Hudhomme, P. An Overview of Molecular Acceptors for Organic Solar Cells EPJ. Photovoltaics 2013, 4, 40401
16. 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
17. Hains, A. W.; Liang, Z.; Woodhouse, M. A.; Gregg, B. A. Molecular Semiconductors in Organic Photovoltaic Cells Chem. Rev. 2010, 110, 6689-6735
18. Würthner, F.; Meerholz, K. Systems Chemistry Approach in Organic Photovoltaics Chem. - Eur. J. 2010, 16, 9366-9373
19. 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
20. Welch, G. C.; Perez, L. A.; Hoven, C. V.; Zhang, Y.; Dang, X.-D.; Sharenko, A.; Toney, M. F.; Kramer, E. J.; Nguyen, T.-C.; Bazan, G. C. A Modular Molecular Framework for Utility in Small-Molecule Solution-Processed Organic Photovoltaic Devices J. Mater. Chem. 2011, 21, 12700-12709
21. Li, Y.; Guo, Q.; Li, Z.; Pei, J.; Tian, W. Solution Processable D-A Small Molecules for Bulk-Heterojunction Solar Cells Energy Environ. Sci. 2010, 3, 1427-1436
22. Walker, B.; Tamayo, A. B.; Dang, X.-D.; Zalar, P.; Seo, J. H.; Garcia, A.; Tantiwiwat, M.; Nguyen, T.-C. Nanoscale Phase Separation and High Photovoltaic Efficiency in Solution-Processed, Small-Molecule Bulk Heterojunction Solar Cells Adv. Funct. Mater. 2009, 19, 3063-3069
23. Gupta, V.; Kyaw, A. K. K.; Wang, D. H.; Chand, S.; Bazan, G. C.; Heeger, A. J. Barium: An Efficient Cathode Layer for Bulk-heterojunction Solar Cells Sci. Rep. 2013, 3, 1965
24. Zhou, J.; Zuo, Y.; Wan, X.; Long, G.; Zhang, Q.; Ni, W.; Liu, Y.; Li, Z.; He, G.; Li, C. Solution-Processed and High-Performance Organic Solar Cells Using Small Molecules with a Benzodithiophene Unit J. Am. Chem. Soc. 2013, 135, 8484-8487
25. Leong, W. L.; Welch, G. C.; Seifter, J.; Seo, J. H.; Bazan, G. C.; Heeger, A. J. Understanding the Role of Thermal Processing in High Performance Solution Processed Small Molecule Bulk Heterojunction Solar Cells Adv. Energy Mater. 2012, 3, 356-363
26. Sun, Y.; Welch, G. C.; Leong, W. L.; Takacs, C. J.; Bazan, G. C.; Heeger, A. J. Solution-Processed Small-Molecule Solar Cells with 6.7% Efficiency Nat. Mater. 2012, 11, 44-48
27. Zhou, J.; Wan, X.; Liu, Y.; Zuo, Y.; Li, Z.; He, G.; Long, G.; Ni, W.; Li, C.; Su, X. Small Molecules Based on Benzo[1,2-b:4,5-b']dithiophene Unit for High-Performance Solution-Processed Organic Solar Cells J. Am. Chem. Soc. 2012, 134, 16345-16351
28. Bürckstümmer, H.; Tulyakova, E. V.; Deppisch, M.; Lenze, M. R.; Kronenberg, N. M.; Gsänger, M.; Stolte, M.; Meerholz, K.; Würthner, F. Efficient Solution-Processed Bulk Heterojunction Solar Cells by Antiparallel Supramolecular Arrangement of Dipolar Donor-Acceptor Dyes Angew. Chem., Int. Ed. 2011, 50, 11628-11632
29. Liu, Y.; Wan, X.; Wang, F.; Zhou, J.; Long, G.; Tian, J.; Chen, Y. High-Performance Solar Cells using a Solution-Processed Small Molecule Containing Benzodithiophene Unit Adv. Mater. 2011, 23, 5387-5391
30. Liu, Y.; Wan, X.; Wang, F.; Zhou, J.; Long, G.; Tian, J.; You, J.; Yang, Y.; Chen, Y. Spin-Coated Small Molecules for High Performance Solar Cells Adv. Energy Mater. 2011, 1, 771-775
31. Wei, G.; Wang, S.; Sun, K.; Thompson, M. E.; Forrest, S. R. Solvent-Annealed Crystalline Squaraine: PC70BM (1:6) Solar Cells Adv. Energy Mater. 2011, 1, 184-187
32. Wei, G.; Lunt, R. R.; Sun, K.; Thompson, M. E.; Forrest, S. R. Efficient, Ordered Bulk Heterojunction Nanocrystalline Solar Cells by Annealing of Ultrathin Squaraine Thin Films Nano Lett. 2010, 10, 3555-3559
33. Chochos, C. L.; Tagmatarchis, N.; Gregoriou, V. G. Rational Design on n-Type Organic Materials for High Performance Organic Photovoltaics RSC Adv. 2013, 3, 7160-7181
34. Liu, T.; Troisi, A. What Makes Fullerene Acceptors Special as Electron Acceptors in Organic Solar Cells and How to Replace Them Adv. Mater. 2013, 25, 1038-1041
35. Eftaiha, A. F.; Sun, J.-P.; Hill, I. G.; Welch, G. C. Recent Advances of Non-Fullerene, Small Molecular Acceptors for Solution Processed Bulk Heterojunction Solar Cells J. Mater. Chem. A 2014, 2, 1201-1213
36. Ie, Y.; Sakurai, T.; Jinnai, S.; Karakawa, M.; Okuda, K.; Mori, S.; Aso, Y. Three-Dimensional Electron-Accepting Compounds Containing Perylene Bis(dicarboximide)s as n-Type Organic Photovoltaic Materials Chem. Commun. 2013, 49, 8386-8388
37. Winzenberg, K. N.; Kemppinen, P.; Scholes, F. H.; Collis, G. E.; Shu, Y.; Singh, T. B.; Bilic, A.; Forsyth, C. M.; Watkins, S. E. Indan-1,3-dione Electron-Acceptor Small Molecules for Solution-Processable Solar Cells: A Structure-Property Correlation Chem. Commun. 2013, 49, 6307-6309
38. Zhou, Y.; Dai, Y.-Z.; Zheng, Y.-Q.; Wang, X.-Y.; Wang, J.-Y.; Pei, J. Non-Fullerene Acceptors Containing Fluoranthene-Fused Imides for Solution-Processed Inverted Organic Solar Cells Chem. Commun. 2013, 49, 5802-5804
39. Lin, Y.; Cheng, P.; Li, Y.; Zhan, X. A 3D Star-Shaped Non-Fullerene Acceptor for Solution-Processed Organic Solar Cells with a High Open-Circuit Voltage of 1.18 V Chem. Commun. 2012, 48, 4773-4775
40. Zhou, Y.; Ding, L.; Shi, K.; Dai, Y.-Z.; Ai, N.; Wang, J.; Pei, J. A Non-Fullerene Small Molecule as Efficient Electron Acceptor in Organic Bulk Heterojunction Solar Cells Adv. Mater. 2012, 24, 957-961
41. Ren, G.; Ahmed, E.; Jenekhe, S. A. Non-Fullerene Acceptor-Based Bulk Heterojunction Polymer Solar Cells: Engineering the Nanomorphology via Processing Additives Adv. Energy Mater. 2011, 1, 946-953
42. Schwenn, P. E.; Gui, K.; Nardes, A. M.; Krueger, K. B.; Lee, K. H.; Mutkins, K.; Rubinstein-Dunlop, H.; Shaw, P. E.; Kopidakis, N.; Burn, P. L. A Small Molecule Non-fullerene Electron Acceptor for Organic Solar Cells Adv. Energy Mater. 2011, 1, 73-81
43. Bloking, J. T.; Han, X.; Higgs, A. T.; Kastrop, J. P.; Pandey, L.; Norton, J. E.; Risko, C.; Chen, C. E.; Brédas, J.-L.; McGehee, M. D. Solution-Processed Organic Solar Cells with Power Conversion Efficiencies of 2.5% using Benzothiadiazole/Imide-Based Acceptors Chem. Mater. 2011, 23, 5484-5490
44. Hendsbee, A. D.; Sun, J.-P.; Rutledge, L. R.; Hill, I. G.; Welch, G. C. Electron Deficient Diketopyrrolopyrrole Dyes for Organic Electronics: Synthesis by Direct Arylation, Optoelectronic Characterization, and Charge Carrier Mobility J. Mater. Chem. A 2014, 2, 4198-4207
45. Duan, Y.-A.; Geng, Y.; Li, H.-B.; Jin, J.-L.; Wu, Y.; Su, Z.-M. Theoretical Characterization and Design of Small Molecule Donor Material Containing Naphthodithiophene Central Unit for Efficient Organic Solar Cells J. Comput. Chem. 2013, 34, 1611-1619
46. McCormick, T. M.; Bridges, C. R.; Carrera, E. I.; DiCarmine, P. M.; Gibson, G. L.; Hollinger, J.; Kozycz, L. M.; Seferos, D. S. Conjugated Polymers: Evaluating DFT Methods for More Accurate Orbital Energy Modeling Macromolecules 2013, 46, 3879-3886
47. Köse, M. E. Evaluation of Acceptor Strength in Thiophene Coupled Donor-Acceptor Chromophores for Optimal Design of Organic Photovoltaic Materials J. Phys. Chem. A 2012, 116, 12503-12509
48. Pandey, L.; Risko, C.; Norton, J. E.; Brédas, J.-L. Donor-Acceptor Copolymers of Relevance for Organic Photovoltaics: A Theoretical Investigation of the Impact of Chemical Structure Modifications on the Electronic and Optical Properties Macromolecules 2012, 45, 6405-6414
49. Halls, M. D.; Djurovich, P. J.; Giesen, D. J.; Goldberg, A.; Sommer, J.; McAnally, E.; Thompson, M. E. Virtual Screening of Electron Acceptor Materials for Organic Photovoltaic Applications New J. Phys. 2013, 15, 105029
50. Takacs, C. J.; Sun, Y.; Welch, G. C.; Perez, L. A.; Liu, X.; Wen, W.; Bazan, G. C.; Heeger, A. J. Solar Cell Efficiency, Self-Assembly, and Dipole-Dipole Interactions of Isomorphic Narrow-Band-Gap Molecules J. Am. Chem. Soc. 2012, 134, 16597-16606
51. Lei, T.; Wang, J.-Y.; Pei, J. Roles of Flexible Chains in Organic Semiconducting Materials Chem. Mater. 2014, 26, 594-603
52. 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
53. Po, R.; Bernardi, A.; Calabrese, A.; Carbonera, C.; Corso, G.; Pellegrino, A. From Lab to Fab: How Must the Polymer Solar Cell Materials Design Change?-An Industrial Perspective Energy Environ. Sci. 2014, 7, 925-943
54. Roncali, J.; Leriche, P.; Blanchard, P. Molecular Materials for Organic Photovoltaics: Small is Beautiful Adv. Mater. 2014, 26, 3821-3838
55. Osedach, T. P.; Andrew, T. L.; Bulovic, V. Effect of Synthetic Accessibility on the Commercial Viability of Organic Photovoltaics Energy Environ. Sci. 2013, 6, 711-718
56. Henson, Z. B.; Welch, G. C.; van der Poll, T.; Bazan, G. C. Pyridalthiadiazole-Based Narrow Band Gap Chromophores J. Am. Chem. Soc. 2012, 134, 3766-3779
57. Guo, X.; Quinn, J.; Chen, Z.; Usta, H.; Zheng, Y.; Xia, Y.; Hennek, J. W.; Ortiz, R. P.; Marks, T. J.; Facchetti, A. Dialkoxybithiazole: A New Building Block for Head-to-Head Polymer Semiconductors J. Am. Chem. Soc. 2013, 135, 1986-1996
58. Lee, J. Y.; Lee, S. M.; Song, K. W.; Moon, D. K. Synthesis and Photovoltaic Property of Polymer Semiconductor with Phthalimide Derivative as a Promising Electron Withdrawing Material Eur. Polym. J. 2012, 3, 532-540
59. Zhang, M.; Guo, X.; Zhang, Z.-G.; Li, Y. D-A Copolymers Based on Dithienosilole and Phthalimide for Photovoltaic Materials Polymer 2011, 52, 5464-5470
60. Chen, J.; Shi, M.-M.; Hu, X.-L.; Wang, M.; Chen, H.-Z. Conjugated Polymers Based on Benzodithiophene and Arylene Imides: Extended Absorptions and Tunable Electrochemical Properties Polymer 2010, 51, 2897-2902
61. Xin, H.; Guo, X.; Kim, F. S.; Ren, G.; Watson, M. D.; Jenekhe, S. A. Efficient Solar Cells Based on a New Phthalimide-based Donor-Acceptor Copolymer Semiconductor: Morphology, Charge-Transport, and Photovoltaic Properties J. Mater. Chem. 2009, 19, 5303-5310
62. Kola, S.; Tremblay, N. J.; Yeh, M.-L.; Katz, H. E.; Kirschner, S. B.; Reich, D. H. Synthesis and Characterization of a Pyromellitic Diimide-Based Polymer with C- and N-Main Chain Links: Matrix for Solution-Processable n-Channel Field-Effect Transistors ACS Macro Lett. 2012, 1, 136-140
63. Guo, X.; Watson, M. D. Pyromellitic Diimide-Based Donor-Acceptor Poly(phenylene ethynylene)s Macromolecules 2011, 44, 6711-6716
64. Zheng, Q.; Huang, J.; Sarjeant, A.; Katz, H. E. Pyromellitic Diimides: Minimal Cores for High Mobility n-Channel Transistor Semiconductors J. Am. Chem. Soc. 2008, 130, 14410-14411
65. Hansen, J. G.; Bang, K. S.; Thorup, N.; Becher, J. Donor-Acceptor Macrocycles Incorporating Tetrathiafulvalene and Pyromellitic Diimide: Synthesis and Crystal Structures Eur. J. Org. Chem. 2000, 11, 2135-22144
66. Chen, S.; Zhang, Q.; Zheng, Q.; Tang, C.; Lu, C.-Z. Angular-Shaped Naphthalene Tetracarboxylic Diimides for n-Channel Organic Transistor Semiconductors Chem. Commun. 2012, 48, 1254-1256
67. Zhan, X.; Facchetti, A.; Barlow, S.; Marks, T. J.; Ratner, M. A.; Wasielewski, M. R.; Marder, S. R. Rylene and Related Diimides for Organic Electronics Adv. Mater. 2011, 23, 268-284
68. Polander, L. E.; Tiwari, S. P.; Pandey, L.; Seifried, B. M.; Zhang, Q.; Barlow, S.; Risko, C.; Brédas, J.-L.; Kippelen, B.; Marder, S. R. Solution-Processed Molecular Bis(Naphthalene Diimide) Derivatives with High Electron Mobility Chem. Mater. 2011, 23, 3408-3410
69. Yan, H.; Chen, Z.; Zheng, Y.; Newman, C.; Quinn, J. R.; Dötz, F.; Kastler, M.; Facchetti, A. A High-Mobility Electron-Transporting Polymer for Printed Transistors Nature 2009, 457, 679-686
70. Katz, H. E.; Lovinger, A. J.; Johnson, J.; Kloc, C.; Siegrist, T.; Li, W.; Lin, Y.-Y.; Dodabalapur, A. A Soluble and Air-Stable Organic Semiconductor with High Electron Mobility Nature 2000, 404, 478-481
71. Stalder, R.; Mei, J.; Subbiah, J.; Grand, C.; Estrada, L. A.; So, F.; Reynolds, J. R. n-Type Conjugated Polyisoindigos Macromolecules 2011, 44, 6303-6310
72. Mei, J.; Graham, K. R.; Stalder, R.; Reynolds, J. R. Synthesis of Isoindigo-Based Oligothiophenes for Molecular Bulk Heterojunction Solar Cells Org. Lett. 2010, 12, 660-663
73. Stalder, R.; Mei, J.; Reynolds, J. R. Isoindigo-Based Donor-Acceptor Conjugated Polymers Macromolecules 2010, 43, 8348-8352
74. Mulhouse, F. J.-C.; Binzen, B. U.; Hegenheim, B. F.; Basel, K. H. J.; Rixheim, T. M. G. R. Ketopyrroles as Organic Semiconductors. U.S. Patent 20100297405, October 16, 2008.
75. Oh, J. H.; Kim, J. H.; Kim, Y. T.; Shin, W. S.; Yoon, S. C.; Moon, S. J.; Lee, C.; Kang, I. N.; Hwang, D. H. Synthesis of Fluorene-based Semiconducting Copolymers for Organic Solar Cells J. Nanosci. Nanotechnol. 2012, 12, 4132-4136
76. Wallace, J. U.; Chen, S. H. Fluorene-Based Conjugated Oligomers for Organic Photonics and Electronics Adv. Polym. Sci. 2008, 212, 145-186
77. Chua, L.-L.; Zaumseil, J.; Chang, J.-F.; Ou, E. C.-W.; Ho, P. K.-H.; Sirringhaus, H.; Friend, R. H. General Observation of n-Type Field-Effect Behaviour in Organic Semiconductors Nature 2005, 434, 194-199
78. Fitzner, R.; Reinold, E.; Mishra, A.; Mena-Osteritz, E.; Ziehlke, H.; Körner, C.; Leo, K.; Riede, M.; Weil, M.; Tsaryova, O. Structure-Property Relationships in Acceptor-Substituted Oligothiophenes for Efficient Small Molecule Organic Solar Cells Adv. Funct. Mater. 2011, 21, 897-910
79. Haid, S.; Mishra, A.; Uhrich, C.; Pfeiffer, M.; Bäuerle, P. Dicyanovinylene-Substituted Selenophene-Thiophene Co-oligomers for Small-Molecule Organic Solar Cells Chem. Mater. 2011, 23, 4435-4444
80. Lin, L.-Y.; Chen, Y.-H.; Huang, Z.-Y.; Lin, H.-W.; Chou, S.-H.; Lin, F.; Chen, C.-W.; Liu, Y.-H.; Wong, K.-T. A Low-Energy-Gap Organic Dye for High-Performance Small-Molecule Organic Solar Cells J. Am. Chem. Soc. 2011, 133, 15822-15825
81. Liu, Y.; Wan, X.; Yin, B.; Zhou, J.; Long, G.; Yin, S.; Chen, Y. Efficient Solution Processed Bulk-Heterojunction Solar Cells Based a Donor-Acceptor Oligothiophene J. Mater. Chem. 2010, 20, 2464-2468
82. Shen, S.; Jiang, P.; He, C.; Zhang, J.; Shen, P.; Zhang, Y.; Yi, Y.; Zhang, Z.; Li, Z.; Li, Y. Solution-Processable Organic Molecule Photovoltaic Materials with Bithienyl-Benzodithiophene Central Unit and Indenedione End Groups Chem. Mater. 2013, 25, 2274-2281
83. Bloking, J. T.; Giovenzana, T.; Higgs, A. T.; Ponec, A. J.; Hoke, E. T.; Vandewal, K.; Ko, S.; Bao, Z.; Sellinger, A.; McGehee, M. D. Comparing the Device Physics and Morphology of Polymer Solar Cells Employing Fullerenes and Non-Fullerene Acceptors. Adv. Energy Mater. 2014, 1301426.
84. Hendsbee, A. D.; Macaulay, C. M.; Welch, G. C. Synthesis of an H-aggregated Thiophene-Phthalimide Based Small Molecule via Microwave Assisted Direct Arylation Coupling Reactions Dyes Pigments 2014, 102, 204-209
85. Durso, M.; Gentili, D.; Bettini, C.; Zanelli, A.; Cavallini, M.; Angelis, F. D.; Lobello, M. G.; Biondo, V.; Muccini, M.; Capelli, R. π-Core Tailoring for New High Performance Thieno(bis)imide Based n-Type Molecular Semiconductors Chem. Commun. 2013, 49, 4298-4300
86. Melucci, M.; Zambianchi, M.; Favaretto, L.; Gazzano, M.; Zanelli, A.; Monari, M.; Capelli, R.; Troisi, S.; Toffanin, S.; Muccini, M. Thienopyrrolyl Dione End-Capped Oligothiophene Ambipolar Semiconductors for Thin Film- and Light Emitting Transistors Chem. Commun. 2011, 47, 11840-11842
87. Melucci, M.; Durso, M.; Bettini, C.; Gazzano, M.; Maini, L.; Toffanin, S.; Cavallini, S.; Cavallini, M.; Gentili, D.; Biondo, V. Structure-Property Relationships in Multifunctional Thieno(bis)imide-Based Semiconductors with Different Sized and Shaped N-Alkyl Ends J. Mater. Chem. C 2014, 2, 3448-3456
88. Sun, J.-P.; Hendsbee, A. D.; Eftaiha, A. F.; Macaulay, C.; Rutledge, L. R.; Welch, G. C.; Hill, I. G. Phthalimide-Thiophene-Based Conjugated Organic Small Molecules with High Electron Mobility J. Mater. Chem. C 2014, 2, 2612-2621
89. Lin, Y.; Fan, H.; Li, Y.; Zhan, X. Thiazole-Based Organic Semiconductrs for Organic Electronics Adv. Mater. 2012, 24, 3087-3106
90. Grimm, B.; Risko, C.; Azoulay, J. D.; Brédas, J.-L.; Bazan, G. C. Structural Dependence of the Optical Properties of Narrow Bandgap Semiconductors with Orthogonal Donor-Acceptor Geometries Chem. Sci. 2013, 4, 1807-1819
91. Risko, 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
92. Sokolov, A. N.; Atahan-Evrenk, S.; Mondal, R.; Akkerman, H. B.; Sánchez-Carrera, R. S.; Granados-Focil, S.; Schrier, J.; Mannsfeld, S. C. B.; Zoombelt, A. P.; Bao, Z. From Computational Discovery to Experimental Characterization of a High Hole Mobility Organic Crystal Nat. Commun. 2011, 2, 437 10.1038/ncomms1451
93. Ko, S.; Mondal, R.; Risko, C.; Lee, J. K.; Hong, S.; McGehee, M. D.; Brédas, J.-L.; Bao, Z. Tuning the Optoelectronic Properties of Vinylene-Linked Donor-Acceptor Copolymers for Organic Photovoltaics Macromolecules 2010, 43, 6685-6698
94. López, A. M.; Mateo-Alonso, A.; Prato, M. Materials Chemistry of Fullerene C60 Derivatives J. Mater. Chem. 2011, 21, 1305-1318
95. Kozma, E.; Catellani, M. Perylene Diimides Based Materials for Organic Solar Cells Dyes Pigm. 2013, 98, 160-179
96. Brunetti, F. G.; Kumar, R.; Wudl, F. Organic Electronics From Perylene to Organic Photovoltaics: Painting a Brief History with a Broad Brush J. Mater. Chem. 2010, 20, 2934-2948
97. Larson, B. Y.; Whitaker, J. B.; Wang, X.-B.; Popov, A. A.; Rumbles, G.; Kopidakis, N.; Strauss, S. H.; Boltalina, O. V. Electron Affinity of Phenyl-C61-Butyric Acid Methyl Ester J. Phys. Chem. C 2013, 117, 14958-14964
98. Rienstra-Kiracofe, J. C.; Tschumper, G. S.; Schaefer, H. F., III; Nandi, S.; Ellison, G. B. Atomic and Molecular Electron Affinities: Photoelectron Experiments and Theoretical Computations Chem. Rev. 2002, 102, 231-282
99. Spartan'10 (Version 1.1.0) Wavefunction, Inc.: Irvine, CA.
100. Chai, J. D.; Head-Gordon, M. Systematic Optimization of Long-Range Corrected Hybrid Density Functionals J. Chem. Phys. 2008, 128, 084106
101. Dreuw, A.; Head-Gordon, M. Single-Reference ab initio Methods for the Calculation of Excited States of Large Molecules Chem. Rev. 2005, 105, 4009-4037
102. Dreuw, A.; Head-Gordon, M. Failure of Time-Dependent Density Functional Theory for Long-Range Charge-Transfer Excited States: The Zincbacteriochlorin-Bacterlochlorin and Bacteriochlorophyll-Spheroidene Complexes J. Am. Chem. Soc. 2004, 126, 4007-4016
103. Dreuw, A.; Weisman, J. L.; Head-Gordon, M. Long-Range Charge-Transfer Excited States in Time-Dependent Density Functional Theory Require Non-Local Exchange J. Chem. Phys. 2003, 119, 2943-2946
104. Sobolewski, A. L.; Domcke, W. Ab Initio Study of the Excited-State Coupled Electron-Proton-Transfer Process in the 2-Aminopyridine Dimer Chem. Phys. 2003, 294, 73-83
105. 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, Revision C.01; Gaussian, Inc.: Wallingford CT, 2010.
106. Mishra, A.; Ma, C.-Q.; Bäuerle, P. Functional Oligothiophenes: Molecular Design for Multidimensional Nanoarchitectures and Their Applications Chem. Rev. 2009, 109, 1141-1276
107. Shrotriya, V.; Li, G.; Yao, Y.; Moriarty, T.; Emery, K.; Yang, Y. Accurate Measurement and Characterization of Organic Solar Cells Adv. Functional Mater. 2006, 16, 2016-2023
108. Stalder, R.; Mei, J.; Graham, K. R.; Estrada, L. A.; Reynolds, J. R. Isoindigo, a Versatile Electron-Deficient Unit For High-Performance Organic Electronics Chem. Mater. 2014, 26, 664-678
109. Douglas, J. D.; Chen, M. S.; Niskala, J. R.; Lee, O. P.; Yiu, A. T.; Young, E. P.; Fréchet, J. M. J. Solution-Processed, Molecular Photovoltaics that Exploit Hole Transfer from Non-Fullerene, n-Type Materials Adv. Mater. 2014, 26, 4313-4319