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AIMS Materials Science, 2017, 4(4): 878-893. doi: 10.3934/matersci.2017.4.878
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A simple route to linear and hyperbranched polythiophenes containing diketopyrrolopyrrole linking groups with improved conversion efficiency
1 Institute of Lighting and Energy Photonics, National Chiao Tung University, 301 Gaofa 3rd Road, Guiren District, Tainan City 71150, Taiwan R.O.C.
2 Department of Physics, Chung-Yuan Christian University, No. 200, Chung-Pei Road, Chungli, Taoyuan City 32023, Taiwan R.O.C.
Received: , Accepted: , Published:
Topical Section: Materials for Energy Systems
References
1. Loewe RS, Khersonsky SM, McCullough RD (1999) A simple method to prepare head-to-tail coupled, regioregular poly(3-alkylthiophenes) using Grignard metathesis. Adv Mater 11: 250–253.
2. Loewe RS, Ewbank PC, Liu J, et al. (2001) Regioregular, head-to-tail coupled poly(3-alkylthiophenes) made easy by the GRIM method: investigation of the reaction and the origin of regioselectivity. Macromolecules 34: 4324–4333.
3. Kim Y, Cook S, Tuladhar SM, et al. (2006) A strong regioregularity effect in self-organizing conjugated polymer films and high-efficiency polythiophene:fullerene solar cells. Nat Mater 5: 197–203.
4. Cheng YJ, Yang SH, Hsu CS (2009) Synthesis of conjugated polymers for organic solar cell applications. Chem Rev 109: 5868–5923.
5. Chang YT, Hsu SL, Chen GY, et al. (2008) Intramolecular donor–acceptor regioregular poly(3-hexylthiophene)s presenting octylphenanthrenyl-imidazole moieties exhibit enhanced charge transfer for heterojunction solar cell applications. Adv Funct Mater 18: 2356–2365.
6. Chang YT, Hsu SL, Su MH, et al. (2009) Intramolecular donor–acceptor regioregular poly(hexylphenanthrenyl-imidazole thiophene) exhibits enhanced hole mobility for heterojunction solar cell applications. Adv Mater 21: 2093–2097.
7. Hou J, Tan Z, Yan Y, et al. (2006) Synthesis and photovoltaic properties of two-dimensional conjugated polythiophenes with bi(thienylenevinylene) side chains. J Am Chem Soc 128: 4911–4916.
8. Li Y, Zou Y (2008) Conjugated polymer photovoltaic materials with broad absorption band and high charge carrier mobility. Adv Mater 20: 2952–2958.
9. Zhang Q, Cirpan A, Russell TP, et al. (2009) Donor–acceptor poly(thiophene-block-perylene diimide) copolymers: synthesis and solar cell fabrication. Macromolecules 42: 1079–1082.
10. Lanzi M, Paganin L, Errani F (2012) Synthesis, characterization and photovoltaic properties of a new thiophene-based double-cable polymer with pendent fullerene group. Polymer 53: 2134–2145.
11. Lanzi M, Salatelli E, Benelli T, et al. (2015) A regioregular polythiophene-fullerene for polymeric solar cells. J Appl Polym Sci 132: 42121.
12. Piereini F, Lanzi M, Nakielski P, et al. (2017) Single-Material Organic Solar Cells Based on Electrospun Fullerene-Grafted Polythiopene Nanofibers. Macromolecules 50: 4972–4981.
13. Zhou E, Tan Z, Yang Y, et al. (2007) Synthesis, hole mobility, and photovoltaic properties of cross-linked polythiophenes with vinylene-terthiophene-vinylene as conjugated bridge. Macromolecules 40: 1831–1837.
14. Tu G, Bilge A, Adamczyk S, et al. (2007) The influence of interchain branches on solid state packing, hole mobility and photovoltaic properties of poly(3-hexylthiophene) (P3HT). Macromol Rapid Comm 28: 1781–1785.
15. Mangold HS, Richter TV, Link S, et al. (2012) Optoelectronic properties of hyperbranched polythiophenes. J Phys Chem B 116: 154–159.
16. Yang SH, Lin TS, Huang YZ, et al. (2014) Synthesis of hyperbranched polythiophenes containing tetrachloroperylene bisimide as bridging moiety for polymer solar cells. Polymer 55: 6058–6068.
17. Li W, Hendriks KH, Roelofs WSC, et al. (2013) Efficient small bandgap polymer solar cells with high fill factors for 300 nm thick films. Adv Mater 25: 3182–3186.
18. Tan H, Deng X, Yu J, et al. (2013) A novel benzo[1,2-b:4,5-b']dithiophene-based conjugated polymer with a pendant diketopyrrolopyrrole unit for high-performance solar cells. Macromolecules 46: 113–118.
19. Kanimozhi C, Balraju P, Sharma GD, et al. (2010) Synthesis of diketopyrrolopyrrole containing copolymers: a study of their optical and photovoltaic properties. J Phys Chem B 114: 3095–3103.
20. Huo L, Hou J, Chen HY, et al. (2009) Bandgap and molecular level control of the low-bandgap polymers based on 3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione toward highly efficient polymer solar cells. Macromolecules 42: 6564–6571.
21. Roncali J (1997) Synthetic principles for bandgap control in linear π-conjugated systems. Chem Rev 97: 173–205.
22. Stefan MC, Javier AE, Osaka I, et al. (2009) Grignard metathesis method (GRIM): toward a universal method for the synthesis of conjugated polymers. Macromolecules 42: 30–32.
23. Chen WC, Chen PY, Yang SH (2017) Solution-processed hybrid light emitting and photovoltaic devices comprising zinc oxide nanorod arrays and tungsten trioxide layers. AIMS Mater Sci 4: 551–560.
24. Huang WJ, Huang PH, Yang SH (2016) PCBM doped with fluorene-based polyelectrolytes as electron transporting layers for improving the performance of planar heterojunction perovskite solar cells. Chem Commun 52: 13572–13575.
25. Nunez CM, Chiou BS, Andrady AL, et al. (2000) Solution Rheology of Hyperbranched Polyesters and Their Blends with Linear Polymers. Macromolecules 33: 1720–1726.
26. Lee JU, Jung JW, Emrick T, et al. (2010) Synthesis of C60-end capped P3HT and its application for high performance of P3HT/PCBM bulk heterojunction solar cells. J Mater Chem 20: 3287–3294.
27. Stevens DM, Qin Y, Hillmyer MA, et al. (2009) Enhancement of the morphology and open circuit voltage in bilayer polymer/fullerene solar cells. J Phys Chem C 113: 11408–11415.
28. Zhao Y, Yuan G, Roche P (1995) A calorimetric study of the phase transitions in poly(3-hexylthiophene). Polymer 36: 2211–2214.
29. Zhao J, Swinnen A, Assche GV, et al. (2009) Phase diagram of P3HT/PCBM blends and its implication for the stability of morphology. J Phys Chem B 113: 1587–1591.
30. Kim Y, Choulis SA, Nelson J, et al. (2005) Device annealing effect in organic solar cells with blends of regioregular poly(3-hexylthiophene) and soluble fullerene. Appl Phys Lett 86: 063502.
31. Liao HC, Chantarat N, Chen SY, et al. (2011) Annealing effect on photovoltaic performance of hybrid P3HT/In-Situ grown CdS nanocrystal solar cells. J Electrochem Soc 158: E67–E72.
32. Li G, Shrotriya V, Yao Y, et al. (2007) Manipulating regioregular poly(3-hexylthiophene): [6,6]-phenyl-C61-butyric acid methyl ester blends-route towards high efficiency polymer solar cells. J Mater Chem 17: 3126–3140.
33. Brown PJ, Thomas DS, Köhler A, et al. (2003) Effect of interchain interactions on the absorption and emission of poly(3-hexylthiophene). Phys Rev B 67: 064203.
34. Noriega R, Rivnay J, Vandewal K, et al. (2013) A general relationship between disorder, aggregation and charge transport in conjugated polymers. Nat Mater 12: 1038–1044.
35. Yao K, Chen L, Li F, et al. (2012) Cooperative assembly donor–acceptor system induced by intermolecular hydrogen bonds leading to oriented nanomorphology for optimized photovoltaic performance. J Phys Chem C 116: 714–721.
36. Kim JY, Lee K, Coates NE, et al. (2007) Efficient tandem polymer solar cells fabricated by all-solution processing. Science 317: 222–225.
37. Scharber MC, Mühlbacher D, Koppe M, et al. (2006) Design rules for donors in bulk-heterojunction solar cells-towards 10% energy-conversion efficiency. Adv Mater 18: 789–794.
38. Zhu R, Jiang CY, Liu B, et al. (2009) Highly efficient nanoporous TiO2-polythiophene hybrid solar cells based on interfacial modification using a metal-free organic dye. Adv Mater 21: 994–1000.
39. Hou J, Chen TL, Zhang S, et al. (2009) An easy and effective method to modulate molecular energy level of poly(3-alkylthiophene) for high-VOC polymer solar cells. Macromolecules 42: 9217–9219.
40. Sekiguchi H, Sekiguchi T (2014) Molecular ordering effect of regioregular poly(3-hexylthiophene) using sulfur K-edge X-ray absorption spectroscopy. Jpn J Appl Phys 53: 02BB07.
41. Chen HY, Hou J, Zhang S, et al. (2009) Polymer solar cells with enhanced open-circuit voltage and efficiency. Nat Photonics 3: 649–653.
42. Huang JS, Chou CY, Lin CF (2014) Enhancing performance of organic-inorganic hybrid solar cells using a fullerene interlayer from all-solution processing. Sol Energ Mat Sol C 6: 466–471.
43. Tan Z, Li L, Cui C, et al. (2012) Solution-processed tungsten oxide as an effective anode buffer layer for high-performance polymer solar cells. J Phys Chem C 116: 18626–18632.
44. Lampande R, Kim GW, Boizot J, et al. (2013) A highly efficient transition metal oxide layer for hole extraction and transport in inverted polymer bulk heterojunction solar cells. J Mater Chem A 1: 6895–6900.
45. Wang F, Tan Z, Li Y (2015) Solution-processable metal oxides/chelates as electrode buffer layers for efficient and stable polymer solar cells. Energ Environ Sci 8: 1059–1091.
46. Ma W, Yang C, Gong X, et al. (2005) Thermally stable, efficient polymer solar cells with nanocontrol of the interpenetrating network morphology. Adv Funct Mater 15: 1617–1622.
47. Li G, Shrotriya V, Yao Y, et al. (2005) Investigation of annealing effects and film thickness dependence of polymer solar cells based on poly(3-hexylthiophene). J Appl Phys 98: 043704.
48. Peet J, Kim Y, Coates NE, et al. (2007) Efficiency enhancement in low-bandgap polymer solar cells by processing with alkane dithiols. Nat Mater 6: 497–500.
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