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Understanding the Structure and Crystallization of Regioregular Poly (3-hexylthiophene) from the Perspective of Epitaxy

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Book cover P3HT Revisited – From Molecular Scale to Solar Cell Devices

Part of the book series: Advances in Polymer Science ((POLYMER,volume 265))

Abstract

Conjugated polymers form a remarkable class of macromolecules with fascinating electronic properties as well as structural features that make them very different from the more classical and flexible polyolefins. In thin films, the structure and the nanomorphology are two important parameters that control solid state properties such as charge transport. Due to the high anisotropy of electronic properties in conjugated polymers, it is essential to control both crystallization and domain orientation over large length scales. This review demonstrates that epitaxial growth is an original method for bringing macromolecules like regioregular poly(3-hexylthiophene) (P3HT) to a high level of order. Various orientation methods based on epitaxy are presented and the peculiar morphological and structural aspects of oriented P3HT, as analyzed by transmission electron microscopy (TEM), are described. The use of TEM on epitaxied layers is shown to shed some new light on the intriguing crystallization, structure, and growth of this key polymer for organic electronic applications.

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References

  1. Heeger AJ (2001) Rev Mod Phys 73:681

    Article  CAS  Google Scholar 

  2. James DI, Smith J, Heeney M, Anthopoulos TD, Salleo A, McCulloch I (2012) Organic semiconductor materials for transistors. In: Klauk H (ed) Organic electronics II: more materials and applications. Wiley-VCH, Weinheim, pp 1–26

    Google Scholar 

  3. Virkar AA, Mannsfeld S, Bao Z, Stingelin N (2010) Adv Mater 22:3857

    Article  CAS  Google Scholar 

  4. Sirringhaus H, Kawase T, Friend RH, Shimoda T, Inbasekaran M, Wu W, Woo EP (2000) Science 290:2123

    Article  CAS  Google Scholar 

  5. Friend RH, Gymer RW, Holmes AB, Burroughes JH, Marks RN, Taliani C, Bradley DDC, Dos Santos DA, Brédas JL, Lögdlund M, Salaneck WR (1999) Nature 397:121

    Article  CAS  Google Scholar 

  6. Sirringhaus H, Brown PJ, Friend RH, Nielsen MM, Bechgaard K, Langeveld-Voss BMW, Spiering AJH, Janssen RAJ, Meijer EW, Herwig P, de Leeuw DM (1999) Nature 401:685

    Article  CAS  Google Scholar 

  7. Nelson J (2002) Curr Opin Solid State Mater Sci 6:87

    Article  CAS  Google Scholar 

  8. Brabec C, Scherff U, Diakonov V (2008) Organic photovoltaics. Wiley, Weinheim

    Book  Google Scholar 

  9. Facchetti A (2010) Chem Mater 23:733

    Article  Google Scholar 

  10. Himmelberger S, Dacuña J, Rivnay J, Jimison LH, McCarthy-Ward T, Heeney M, McCulloch I, Toney MF, Salleo A (2013) Adv Funct Mater 23:2091

    Article  CAS  Google Scholar 

  11. Rivnay J, Mannsfeld SCB, Miller CE, Salleo A, Toney MF (2012) Chem Rev 112:5488

    Article  CAS  Google Scholar 

  12. Lim JA, Liu F, Ferdous S, Muthukumar M, Briseno AL (2010) Mater Today 13:14

    Article  CAS  Google Scholar 

  13. Brinkmann M (2011) J Polym Sci B 49:1218

    Article  CAS  Google Scholar 

  14. Chang JF, Sun B, Breiby DW, Nielsen MN, Sölling TI, Giles M, McCulloch I, Sirringhaus H (2004) Chem Mater 16:4772

    Article  CAS  Google Scholar 

  15. Rivnay J, Steyrleuthner R, Jimison LH, Casadei A, Chen Z, Toney MF, Facchetti A, Neher D, Salleo A (2011) Macromolecules 44:5246

    Article  CAS  Google Scholar 

  16. Chabinyc ML, Toney MF, Kline RJ, McCulloch I, Heeney M (2007) J Am Chem Soc 129:3226

    Article  CAS  Google Scholar 

  17. Yang H, Shine TJ, Yang L, Cho K, Ryu CY, Bao Z (2005) Adv Funct Mater 15:671

    Article  CAS  Google Scholar 

  18. Yang H, LeFevre SW, Ryu C, Bao Z (2007) Appl Phys Lett 90:172116

    Article  Google Scholar 

  19. Crossland EJW, Tremel K, Fischer F, Rahimi K, Reiter G, Steiner U, Ludwigs S (2012) Adv Mater 24:839

    Article  CAS  Google Scholar 

  20. Tremel K, Ludwigs S (2014) Morphology of P3HT in thin films in relation to optical and electrical properties. Adv Polym Sci. doi:10.1007/12_2014_288

    Google Scholar 

  21. Jimison LH, Toney MF, McCulloch I, Heeney M, Salleo A (2009) Adv Mater 21:1568

    Article  CAS  Google Scholar 

  22. Zheng Z, Yim KH, Saifullah MSM, Welland ME, Friend RH, Kim JS, Huck WTS (2007) Nano Lett 7:987

    Article  CAS  Google Scholar 

  23. Lan YK, Huang CI (2009) J Phys Chem B 90:62117

    Google Scholar 

  24. Brabec CJ, Gowrisanker S, Halls JJM, Laird D, Jia S, Williams SP (2010) Adv Mater 22:3839

    Article  CAS  Google Scholar 

  25. Peet J, Heeger AJ, Bazan GC (2009) Acc Chem Res 42:1700

    Article  CAS  Google Scholar 

  26. Ward MD (2001) Chem Rev 101:1697

    Article  CAS  Google Scholar 

  27. Hooks DE, Fritz T, Ward MD (2001) Adv Mater 13:227

    Article  CAS  Google Scholar 

  28. Jiang S, Qian H, Liu W, Wang C, Wang Z, Yan S, Zhu D (2009) Macromolecules 42:9321

    Article  CAS  Google Scholar 

  29. Bunk O, Nielsen MM, Sølling TI, van de Craats AM, Stutzmann N (2003) J Am Chem Soc 125:2252

    Article  CAS  Google Scholar 

  30. Li L, Li CY, Ni C (2006) J Am Chem Soc 128:1692

    Article  CAS  Google Scholar 

  31. Willems J (1955) Naturwissenschaften 42:176

    Article  CAS  Google Scholar 

  32. Fischer EW (1958) Kolloid Z 159:108

    Google Scholar 

  33. Wittmann JC, Lotz B (1981) J Polym Sci Polym Phys 19:1837

    Article  CAS  Google Scholar 

  34. Wittmann JC, Hodge AM, Lotz B (1983) J Polym Sci Polym Phys 21:2495

    Article  CAS  Google Scholar 

  35. Wittmann JC, Lotz B (1990) Prog Polym Sci 15:909

    Article  CAS  Google Scholar 

  36. Kobayashi T (1991) Organic crystals I: characterization. Springer, Berlin

    Google Scholar 

  37. Dorset DL (1995) Structural electron crystallography. Plenum, New York/London

    Book  Google Scholar 

  38. Koutsky JA, Walton AG, Baer E (1967) Polym Lett 5:177

    Article  CAS  Google Scholar 

  39. Rickert SE, Baer E (1978) J Mater Sci Lett 13:451

    Article  CAS  Google Scholar 

  40. Kopp S, Wittmann JC, Lotz B (1994) Polymer 35:916

    Article  CAS  Google Scholar 

  41. Da Costa V, Le Moigne J, Oswald L, Pham TA, Thierry A (1998) Macromolecules 31:1635

    Article  Google Scholar 

  42. Brinkmann M, Contal C, Kayunkid N, Djuriç T, Resel R (2010) Macromolecules 43:7604

    Article  CAS  Google Scholar 

  43. Brinkmann M, Wittmann JC (2006) Adv Mater 18:860

    Article  CAS  Google Scholar 

  44. Brinkmann M, Rannou P (2007) Adv Funct Mater 17:101

    Article  CAS  Google Scholar 

  45. Brinkmann M, Rannou P (2009) Macromolecules 42:1125

    Article  CAS  Google Scholar 

  46. Roiban L, Hartmann L, Ersen O, Fiore A, Reiss P, Djurado D, Chandezon F, Legrand JF, Doyle S, Brinkmann M (2012) Nanoscale 4:7212

    Article  CAS  Google Scholar 

  47. Kayunkid N, Uttiya S, Brinkmann M (2010) Macromolecules 43:4961

    Article  CAS  Google Scholar 

  48. Brinkmann M (2007) Macromolecules 40:7532

    Article  CAS  Google Scholar 

  49. Brinkmann M (2009) L’actualité Chim 326:31

    CAS  Google Scholar 

  50. Hartmann L, Tremel K, Uttiya S, Crossland E, Kayunkid N, Ludwigs S, Vergnat C, Brinkmann M (2011) Adv Funct Mater 21:4047

    Article  CAS  Google Scholar 

  51. Brinkmann M, Gonthier E, Bogen S, Tremmel K, Ludwigs S, Hufnagel M, Sommer M (2012) ACS Nano 6:10319

    Article  CAS  Google Scholar 

  52. Prosa TJ, Winokur MJ, Moulton J, Smith P, Heeger AJ (1992) Macromolecules 25:4364

    Article  CAS  Google Scholar 

  53. Mardalen J, Samuelsen EJ, Gautum OR, Carlsen PH (1992) Synth Met 48:363

    Article  Google Scholar 

  54. Prosa TJ, Winokur MJ, McCullough RD (1996) Macromolecules 29:3654

    Article  CAS  Google Scholar 

  55. Meille SV, Romita V, Caronna T, Lovinger AJ, Castellani M, Belobrzeckaja L (1997) Macromolecules 30:7898

    Article  CAS  Google Scholar 

  56. Tashiro K (1991) J Polym Sci Polym Phys 29:1223

    Article  CAS  Google Scholar 

  57. Tashiro K, Kobayashi M, Kawai T, Yoshino K (1997) Polymer 38:2867

    Article  CAS  Google Scholar 

  58. Lu G, Li L, Yang X (2007) Adv Mater 19:3594

    Article  CAS  Google Scholar 

  59. Lu G, Li L, Yang W (2008) Macromolecules 41:2062

    Article  CAS  Google Scholar 

  60. Buono A, Son NH, Raos G, Gila L, Cominetti A, Catellani M, Meille SV (2010) Macromolecules 43:6772

    Article  CAS  Google Scholar 

  61. Rahimi K, Botiz I, Stingelin N, Kayunkid N, Sommer M, Koch F, Nguyen H, Coulembier O, Dubois P, Brinkmann M, Reiter G (2012) Angew Chem Int Ed 51:11131

    Article  CAS  Google Scholar 

  62. Lotz B, Lovinger AJ, Cais RE (1988) Macromolecules 21:2375

    Article  CAS  Google Scholar 

  63. Cartier L, Okihara T, Lotz B (1998) Macromolecules 31:3303–3310

    Article  CAS  Google Scholar 

  64. Puiggali J, Ikada Y, Tsuji H, Cartier L, Okihara T, Lotz B (2000) Polymer 41:8921

    Article  CAS  Google Scholar 

  65. Dudenko D, Kiersnowski A, Shu J, Pisula W, Sebastiani D, Spiess HW, Hansen MR (2012) Angew Chem Int Ed 51:11068

    Article  CAS  Google Scholar 

  66. Zen A, Saphiannikova M, Neher D, Grenzer J, Grigorian S, Pietsch U, Asawapirom U, Janietz S, Scherf U, Lieberwirth I, Wegner G (2006) Macromolecules 39:2162

    Article  CAS  Google Scholar 

  67. Kline RJ, McGehee MD, Kadnikova EN, Liu J, Fréchet JMJ, Toney MF (2005) Macromolecules 38:3312

    Article  CAS  Google Scholar 

  68. Verilhac JM, LeBlevennec G, Djurado D, Rieutord F, Chouiki M, Travers JP, Pron A (2006) Synth Met 156:815

    Article  CAS  Google Scholar 

  69. Crossland EJW, Rahimi K, Reiter G, Steiner U, Ludwigs S (2011) Adv Funct Mater 21:518

    Article  CAS  Google Scholar 

  70. Mena-Osteriz E, Meyer A, Langeveld-Voss BMW, Janssen RAJ, Meijer EW, Bäuerle P (2000) Angew Chem Int Ed 39:2680

    Google Scholar 

  71. Brinkmann M, Charoenthai N, Traiphol R, Piyakulawat P, Wlosnewski J, Asawapirom U (2009) Macromolecules 42:8298

    Article  CAS  Google Scholar 

  72. Salammal TS, Mikayelyan E, Grigorian S, Pietsch U, Koenen N, Scherf U, Kayunkid N, Brinkmann M (2012) Macromolecules 45:5575

    Article  CAS  Google Scholar 

  73. Biniek L, Leclerc N, Bechara R, Heiser T, Brinkmann M (2013) Macromolecules 46:4014

    Article  CAS  Google Scholar 

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Brinkmann, M., Hartmann, L., Kayunkid, N., Djurado, D. (2014). Understanding the Structure and Crystallization of Regioregular Poly (3-hexylthiophene) from the Perspective of Epitaxy. In: Ludwigs, S. (eds) P3HT Revisited – From Molecular Scale to Solar Cell Devices. Advances in Polymer Science, vol 265. Springer, Berlin, Heidelberg. https://doi.org/10.1007/12_2014_280

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