Experimental investigation and theoretical calculation of molecular architectures on carbazole for photovoltaics

Journal of Physical Chemistry C

Volumn 117, Issue 19, 2013, Pages 9581-9589

  Wu, Feiyan ^a   Chen, Lie ^a   Wang, Hongming ^a   Chen, Yiwang ^a  

^a NANCHANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1 ,3-BENZOTHIADIAZOLE; EXPERIMENTAL INVESTIGATIONS; EXTENDED CONJUGATION; INTERMOLECULAR INTERACTIONS; MOLECULAR ARCHITECTURE; POWER CONVERSION EFFICIENCIES; THEORETICAL CALCULATIONS; TIME DEPENDENT DENSITY FUNCTIONAL THEORY;

DENSITY FUNCTIONAL THEORY; POLYCYCLIC AROMATIC HYDROCARBONS; TORSIONAL STRESS;

DIMERS;

EID: 84878056417     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp401552f     Document Type: Article

References (46)

1. Thompson, B. C.; Fréchet, J. M. J. Polymer-Fullerene Composite Solar Cells Angew. Chem., Int. Ed. 2008, 47, 58-77
2. Chen, L.-M.; Hong, Z.; Li, G.; Yang, Y. Recent Progress in Polymer Solar Cells: Manipulation of Polymer:Fullerene Morphology and the Formation of Efficient Inverted Polymer Solar Cells Adv. Mater. 2009, 21, 1434-1449
3. Heeger, A. J. Semiconducting Polymers: The Third Generation Chem. Soc. Rev. 2010, 39, 2354-2371
4. Yu, G.; Gao, J.; Hummelen, J.; Wudl, F.; Heeger, A. J. Polymer Photovoltaic Cells: Enhanced Efficiencies via a Network of Internal Donor-Acceptor Heterojunctions Science 1995, 270, 1789-1791 (Pubitemid 126635480)
5. Li, G.; Shrotriya, V.; Huang, J. S.; Yao, Y.; Moriarty, T.; Emery, K.; Yang, Y. High-Efficiency Solution Processable Polymer Photovoltaic Cells by Self-Organization of Polymer Blends Nat. Mater. 2005, 4, 864-868
6. Ma, W. L.; Yang, C. Y.; Gong, X.; Lee, K. H.; Heeger, A. J. Thermally Stable, Efficient Polymer Solar Cells with Nanoscale Control of the Interpenetrating Network Morphology Adv. Funct. Mater. 2005, 15, 1617-1622 (Pubitemid 41454589)
7. He, Z.; Zhong, C.; Huang, X.; Wong, W.; Wu, H.; Chen, L.; Su, S.; Cao, Y. Simultaneous Enhancement of Open-Circuit Voltage, Short-Circuit Current Density, and Fill Factor in Polymer Solar Cells Adv. Mater. 2011, 23, 4636-4643
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, 591-595
9. Lin, H.-W.; Chiu, S.-W.; Lin, L.-Y.; Hung, Z.-Y.; Chen, Y.-H.; Lin, F.; Wong, K.-T. Device Engineering for Highly Efficient Top-Illuminated Organic Solar Cells with Microcavity Structures Adv. Mater. 2012, 24, 2269-2272
10. Li, X.; Choy, W. C. H.; Huo, L.; Xie, F.; Sha, W. E. I.; Ding, B.; Guo, X.; Li, Y.; Hou, J.; You, J. Dual Plasmonic Nanostructures for High Performance Inverted Organic Solar Cells Adv. Mater. 2012, 24, 3046-3052
11. Etzold, F.; Howard, I. A.; Forler, N.; Cho, D. M.; Meister, M.; Mangold, H.; Shu, J.; Hansen, M. R.; Müllen, K.; Laquai, F. The Effect of Solvent Additives on Morphology and Excited-State Dynamics in PCPDTBT:PCBM Photovoltaic Blends J. Am. Chem. Soc. 2012, 134, 10569-10583
12. Verploegen, E.; Miller, C. E.; Schmidt, K.; Bao, Z.; Toney, M. F. Manipulating the Morphology of P3HT-PCBM Bulk Heterojunction Blends with Solvent Vapor Annealing Chem. Mater. 2012, 24, 3923-3931
13. Wang, H.; Cheng, P.; Liu, Y.; Chen, J.; Zhan, X.; Hu, W.; Shuai, Z.; Li, Y.; Zhu, D. A Conjugated Polymer Based on 5,5′-Bibenzo[ c ][1,2,5]thiadiazole for High-Performance Solar Cells J. Mater. Chem. 2012, 22, 3432-3439
14. Havinga, E.; ten Hoeve, W.; Wynberg, H. Alternate Donor-Acceptor Small-Band-Gap Semiconducting Polymers; Polysquaraines and Polycroconaines Synth. Met. 1993, 55, 299-306 (Pubitemid 23681823)
15. Guo, X.; Zhou, N.; Lou, S. J.; Hennek, J. W.; Ponce Ortiz, R.; Butler, M. R.; Boudreault, P. L.; Strzalka, J.; Morin, P. O.; Leclerc, M. Bithiopheneimide-Dithienosilole/Dithienogermole Copolymers for Efficient Solar Cells: Information from Structure-Property-Device Performance Correlations and Comparison to Thieno[3,4- c ]pyrrole-4,6-dione Analogues J. Am. Chem. Soc. 2012, 134, 18427-18439
16. Liang, Y.; Feng, D.; Wu, Y.; Tsai, S.-T.; Li, G.; Ray, C.; Yu, L. Highly Efficient Solar Cell Polymers Developed via Fine-Tuning of Structural and Electronic Properties J. Am. Chem. Soc. 2009, 131, 7792-7799
17. Huo, L.; Hou, J.; Zhang, S.; Chen, H.-Y.; Yang, Y. A Polybenzo[1,2-b:4,5- b ']dithiophene Derivative with Deep HOMO Level and Its Application in High-Performance Polymer Solar Cells Angew. Chem., Int. Ed. 2010, 49, 1500-1503
18. Li, W.; Roelofs, W. S.; Wienk, M. M.; Janssen, R. A. Enhancing the Photocurrent in Diketopyrrolopyrrole-Based Polymer Solar Cells via Energy Level Control J. Am. Chem. Soc. 2012, 134, 13787-13795
19. Amb, C. M.; Chen, S.; Graham, K. R.; Subbiah, J.; Small, C. E.; So, F.; Reynolds, J. R. Dithienogermole as a Fused Electron Donor in Bulk Heterojunction Solar Cells J. Am. Chem. Soc. 2011, 133, 10062-10065
20. Zhou, H.; Yang, L.; Stuart, A. C.; Price, S. C.; Liu, S.; You, W. Development of Fluorinated Benzothiadiazole as a Structural Unit for a Polymer Solar Cell of 7% Efficiency Angew. Chem., Int. Ed. 2011, 123, 3051-3054
21. Son, H. J.; Wang, W.; Xu, T.; Liang, Y.; Wu, Y.; Li, G.; Yu, L. Synthesis of Fluorinated Polythienothiophene- co -benzodithiophenes and Effect of Fluorination on the Photovoltaic Properties J. Am. Chem. Soc. 2011, 133, 1885-1894
22. Chu, T.-Y.; Lu, J.; Beaupré, S.; Zhang, Y.; Pouliot, J.-R.; Wakim, S.; Zhou, J.; Leclerc, M.; Li, Z.; Ding, J. Bulk Heterojunction Solar Cells Using Thieno[3,4- c ]pyrrole-4,6-dione and Dithieno[3,2- b:2′,3′- d ]silole Copolymer with a Power Conversion Efficiency of 7.3% J. Am. Chem. Soc. 2011, 133, 4250-4253
23. Blouin, N.; Michaud, A.; Leclerc, M. A Low-Bandgap Poly(2,7-carbazole) Derivative for Use in High-Performance Solar Cells Adv. Mater. 2007, 19, 2295-2300 (Pubitemid 47409295)
24. Blouin, N.; Michaud, A.; Gendron, D.; Wakim, S.; Blair, E.; Neagu-Plesu, R.; Belleteîte, M.; Durocher, G.; Tao, Y.; Leclerc, M. Toward a Rational Design of Poly(2,7-carbazole) Derivatives for Solar Cells J. Am. Chem. Soc. 2008, 130, 732-742 (Pubitemid 351455587)
25. Park, S. H.; Roy, A.; Beaupre, S.; Cho, S.; Coates, N.; Moon, J. S.; Moses, D.; Leclerc, M.; Lee, K.; Heeger, A. J. Bulk Heterojunction Solar Cells with Internal Quantum Efficiency Approaching 100% Nat. Photonics 2009, 3, 297-302
26. Berton, N.; Ottone, C.; Labet, V.; de Bettignies, R.; Bailly, S.; Grand, A.; Morell, C.; Sadki, S.; Chandezon, F. New Alternating Copolymers of 3,6-Carbazoles and Dithienylbenzothiadiazoles: Synthesis, Characterization, and Application in Photovoltaics Macromol. Chem. Phys. 2011, 212, 2127-2141
27. Fu, Y.; Cha, H.; Lee, G.-Y.; Moon, B. J.; Park, C. E.; Park, T. 3,6-Carbazole Incorporated into Poly[9,9-dioctylfluorene- alt -(bisthienyl)benzothiadiazole]s Improving the Power Conversion Efficiency Macromolecules 2012, 45, 3004-3009
28. Wang, L.; Fu, Y.; Zhu, L.; Cui, G.; Liang, F.; Guo, L.; Zhang, X.; Xie, Z.; Su, Z. Synthesis and Photovoltaic Properties of Low-Bandgap Polymers Based on N -Arylcarbazole Polymer 2011, 52, 1748-1754
29. Jin, E.; Du, C.; Wang, M.; Li, W.; Li, C.; Wei, H.; Bo, Z. Dibenzothiophene-Based Planar Conjugated Polymers for High Efficiency Polymer Solar Cells Macromolecules 2012, 45, 7843-7854
30. Beaupre, S.; Boudreault, P. L. T.; Leclerc, M. Solar-Energy Production and Energy-Efficient Lighting: Photovoltaic Devices and White-Light-Emitting Diodes Using Poly(2,7-fluorene), Poly(2,7-carbazole), and Poly(2,7- dibenzosilole) Derivatives Adv. Mater. 2010, 22, E6-E27
31. Cai, S.; Chen, L.; Zha, D.; Chen, Y. A Novel Planar D-A Alternating Copolymer with D-A Integrated Structures Exhibiting H-aggregate Behaviors for Polymer Solar Cells J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 624-634
32. Zha, D.; Chen, L.; Wu, F.; Wang, H.; Chen, Y. Donor-Acceptor-Integrated Conjugated Polymers Based on Carbazole[3,4- c:5,6- c ]bis[1,2,5]thiadiazole with Tight π-π Stacking for Photovoltaics J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 565-574
33. Chen, H.; He, C.; Yu, G.; Zhao, Y.; Huang, J.; Zhu, M.; Liu, H.; Guo, Y.; Li, Y.; Liu, Y. Phenanthro[1,10,9,8- cdefg ]carbazole-Containing Copolymer for High Performance Thin-Film Transistors and Polymer Solar Cells J. Mater. Chem. 2012, 22, 3696-3698
34. Jiao, C.; Huang, K.-W.; Luo, J.; Zhang, K.; Chi, C.; Wu, J. Bis- N -annulated Quaterrylenebis(dicarboximide) as a New Soluble and Stable Near-Infrared Dye Org. Lett. 2009, 11, 4508-4511
35. Chen, X.-K.; Zou, L.-Y.; Guo, J.-F.; Ren, A.-M. An Efficient Strategy for Designing N-type Organic Semiconductor Materials-Introducing a Six-Membered Imide Ring into Aromatic Diimides J. Mater. Chem. 2012, 22, 6471-6484
36. Kim, J.-H.; Kim, H. U.; Mi, D.; Jin, S.-H.; Shin, W. S.; Yoon, S. C.; Kang, I.-N.; Hwang, D.-H. Introduction of Perylene Units for Enhanced Interchain Interaction in Conjugated Polymers for Organic Photovoltaic Devices Macromolecules 2012, 45, 2367-2376
37. 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 A.01; Gaussian, Inc.: Wallingford, CT, 2009.
38. Cohen, A. J.; Mori-Sánchez, P.; Yang, W. Challenges for Density Functional Theory Chem. Rev. 2012, 112, 289-320
39. Popere, B. C.; Della Pelle, A. M.; Poe, A.; Balaji, G.; Thayumanavan, S. Predictably Tuning the Frontier Molecular Orbital Energy Levels of Panchromatic Low Band Gap BODIPY-Based Conjugated Polymers Chem. Sci. 2012, 3, 3093-3102
40. 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
41. Banerji, N.; Gagnon, E.; Morgantini, P.-Y.; Valouch, S.; Mohebbi, A. R.; Seo, J.-H.; Leclerc, M.; Heeger, A. J. Breaking Down the Problem: Optical Transitions, Electronic Structure, and Photoconductivity in Conjugated Polymer PCDTBT and in Its Separate Building Blocks J. Phys. Chem. C 2012, 116, 11456-11469
42. Zhang, S. S.; Qu, Z. X.; Tao, P.; Brooks, B.; Shao, Y. H.; Chen, X. Y.; Liu, C. G. Quantum Chemical Study of the Ground and Excited State Electronic Structures of Carbazole Oligomers with and without Triarylborane Substitutes J. Phys. Chem. C 2012, 116, 12434-12442
43. Kim, J.; Kwon, Y. S.; Shin, W. S.; Moon, S. J.; Park, T. Carbazole-Based Copolymers: Effects of Conjugation Breaks and Steric Hindrance Macromolecules 2011, 44, 1909-1919
44. Guo, X.; Puniredd, S. R.; Baumgarten, M.; Pisula, W.; Müllen, K. Benzotrithiophene-Based Donor-Acceptor Copolymers with Distinct Supramolecular Organizations J. Am. Chem. Soc. 2012, 134, 8404-8407
45. Ahmed, E.; Subramaniyan, S.; Kim, F. S.; Xin, H.; Jenekhe, S. A. Benzobisthiazole-Based Donor-Acceptor Copolymer Semiconductors for Photovoltaic Cells and Highly Stable Field-Effect Transistors Macromolecules 2011, 44, 7207-7219
46. Zhou, H.; Yang, L.; You, W. Rational Design of High Performance Conjugated Polymers for Organic Solar Cells Macromolecules 2012, 45, 607-632