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Thiophene-Based Organic Semiconductors

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Abstract

Thiophene-based π-conjugated organic small molecules and polymers are the research subject of significant current interest owing to their potential use as organic semiconductors in material chemistry. Despite simple and similar molecular structures, the hitherto reported properties of thiophene-based organic semiconductors are rather diverse. Design of high performance organic semiconducting materials requires a thorough understanding of inter- and intra-molecular interactions, solid-state packing, and the influence of both factors on the charge carrier transport. In this chapter, thiophene-based organic semiconductors, which are classified in terms of their chemical structures and their structure–property relationships, are addressed for the potential applications as organic photovoltaics (OPVs), organic field-effect transistors (OFETs) and organic light emitting diodes (OLEDs).

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References

  1. Okamato Y, Brenner W (1964) Organic semiconductors. Reinhold Publishing Corporation, New York

    Google Scholar 

  2. Zaumseil J, Sirringhaus H (2007) Chem Rev 107:1296

    Article  CAS  Google Scholar 

  3. Facchetti A (2013) Mater Today 16:123

    Article  CAS  Google Scholar 

  4. Sirringhaus H (2014) Adv Mater 26:1319

    Article  CAS  Google Scholar 

  5. Coropceanu V, Cornil J, da Silva DA, Olivier Y, Silbey R, Bredas JL (2007) Chem Rev 107:926

    Article  CAS  Google Scholar 

  6. Murphy AR, Fréchet JMJ (2007) Chem Rev 107:1066

    Article  CAS  Google Scholar 

  7. Facchetti A (2007) Mater Today 10:28

    Article  CAS  Google Scholar 

  8. Torruellas WE, Neher D, Zanoni R, Stegeman GI, Kajzar F, Leclerc M (1990) Chem Phys Lett 175:11

    Article  CAS  Google Scholar 

  9. Bäuerle P (1998) In: Wegner G, Mullen K (eds) Electronic materials: the oligomer approach. Wiley-VCH, Weinheim

    Google Scholar 

  10. Tour J (1996) Chem Rev 96:537

    Article  CAS  Google Scholar 

  11. Shirota Y (2000) J Mater Chem 10:1

    Article  CAS  Google Scholar 

  12. Musher JI (1969) Angew Chem Int Ed Engl 8:54

    Article  CAS  Google Scholar 

  13. Gillespie RJ, Silvi B (2002) Coord Chem Rev 233–234:53

    Article  Google Scholar 

  14. Dell EJ, Capozzi B, Xia J, Venkataraman L, Campos LM (2015) Nat Chem 7:209

    Article  CAS  Google Scholar 

  15. Ghofraniha N, Viola I, Di Maria F, Barbarella G, Gigli G, Leuzzi L, Conti C (2015) Nat Commun 6:6058

    Article  CAS  Google Scholar 

  16. Kitamura C, Tanaka S, Yamashita Y (1996) Chem Mater 8:570

    Article  CAS  Google Scholar 

  17. Barbarella G, Zambianchi M, Bongini A, Antolini L (1993) Adv Mater 5:834

    Article  CAS  Google Scholar 

  18. Barbarella G, Di Maria F (2015) Acc Chem Res 48:2230

    Article  CAS  Google Scholar 

  19. Perepichka IF, Perepichka DF (2009) Handbook of thiophene-based materials: applications in organic electronics and photonics. Wiley, Chichester

    Book  Google Scholar 

  20. Roncali J (1992) Chem Rev 92:711

    Article  CAS  Google Scholar 

  21. McCullough RD (1998) Adv Mater 10:93

    Article  CAS  Google Scholar 

  22. Mishra A, Ma CQ, Bauerle P (2009) Chem Rev 109:1141

    Article  CAS  Google Scholar 

  23. Cinar ME, Ozturk T (2015) Chem Rev 115:3036 (and references therein)

    Article  CAS  Google Scholar 

  24. Lin Y, Li Y, Zhan X (2012) Chem Soc Rev 41:4245

    Article  CAS  Google Scholar 

  25. Lin Y, Zhan X (2016) Acc Chem Res 49:175

    Article  CAS  Google Scholar 

  26. Sun Y, Welch GC, Leong WL, Takacs CJ, Bazan GC, Heeger AJ (2012) Nat Mater 11:44

    Article  CAS  Google Scholar 

  27. Mazzeo M, Pisignano D, Favaretto L, Barbarella G, Cingolani R, Gigli G (2003) Synth Met 139:671

    Article  CAS  Google Scholar 

  28. Hains AW, Ramanan C, Irwin MD, Liu J, Wasielewski MR, Marks TJ (2010) ACS Appl Mater Interfaces 2:175

    Article  CAS  Google Scholar 

  29. Kunugi Y, Takimiya K, Negishi N, Otsubo T, Aso Y (2004) J Mater Chem 14:2840

    Article  CAS  Google Scholar 

  30. Marseglia EA, Grepioni F, Tedesco E, Braga D (2000) Mol Cryst Liq Cryst Sci Technol Sect A 348:137

    Article  CAS  Google Scholar 

  31. Zhou N, Prabakaran K, Lee B, Chang SH, Harutyunyan B, Guo P, Butler MR, Timalsina A, Bedzyk MJ, Ratner MA, Vegiraju S, Yau S, Wu C-G, Chang RPH, Facchetti A, Chen M-C, Marks TJ (2015) J Am Chem Soc 137:4414

    Article  CAS  Google Scholar 

  32. Nicolas Y, Blanchard P, Levillain E, Allain M, Mercier N, Roncali J (2004) Org Lett 6:273

    Article  CAS  Google Scholar 

  33. Sun X, Liu Y, Chen S, Qiu W, Yu G, Ma Y, Qi T, Zhang H, Xu X, Zhu D (2006) Adv Funct Mater 16:917

    Article  CAS  Google Scholar 

  34. Ma C-Q, Mena-Osteritz E, Debaerdemaeker T, Wienk MM, Janssen RA, Bäuerle P (2007) Angew Chem Int Ed 46:1679

    Article  CAS  Google Scholar 

  35. Li X-C, Sirringhaus H, Garnier F, Holmes AB, Moratti SC, Feeder N, Clegg W, Teat SJ, Friend RH (1998) J Am Chem Soc 120:2206

    Article  CAS  Google Scholar 

  36. Gao JH, Li RJ, Li LQ, Meng Q, Jiang H, Li HX, Hu WP (2007) Adv Mater 19:3008

    Article  CAS  Google Scholar 

  37. Mishra A, Bauerle P (2012) Angew Chem Int Ed 51:2020

    Article  CAS  Google Scholar 

  38. Noma N, Tsuzuki T, Shirota Y (1995) Adv Mater 7:647

    Article  CAS  Google Scholar 

  39. Sakai J, Taima T, Saito K (2008) Org Electron 9:582

    Article  CAS  Google Scholar 

  40. Zhang F, Wu D, Xua Y, Feng X (2011) J Mater Chem 21:17590

    Article  CAS  Google Scholar 

  41. Zhou J, Wan X, Liu Y, Zuo Y, Li Z, He G, Long G, Ni W, Li C, Su X, Chen Y (2012) J Am Chem Soc 134:16345

    Article  CAS  Google Scholar 

  42. Shen S, Jiang P, He C, Zhang J, Shen P, Zhang Y, Yi Y, Zhang Z, Li Z, Li Y (2013) Chem Mater 25:2274

    Article  CAS  Google Scholar 

  43. Wessendorf CD, Schulz GL, Mishra A, Kar P, Ata I, Weidelener M, Urdanpilleta M, Hanisch J, Mena-Osteritz E, Lindén M, Ahlswede E, Bäuerle P (2014) Adv Energy Mater 4:1400266

    Article  CAS  Google Scholar 

  44. 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 (2012) J Am Chem Soc 134:11064

    Article  CAS  Google Scholar 

  45. Liu Y, Wan X, Wang F, Zhou J, Long G, Tian J, You J, Yang Y, Chen Y (2011) Adv Energy Mater 1:771

    Article  CAS  Google Scholar 

  46. Li Z, He G, Wan X, Liu Y, Zhou J, Long G, Zuo Y, Zhang M, Chen Y (2012) Adv Energy Mater 2:74

    Article  CAS  Google Scholar 

  47. Ni W, Wan X, Li M, Wang Y, Chen Y (2015) Chem Commun 51:4936

    Article  CAS  Google Scholar 

  48. Zhang Q, Kan B, Liu F, Long G, Wan X, Chen X, Zuo Y, Ni W, Zhang H, Li M, Hu Z, Huang F, Cao Y, Liang Z, Zhang M, Russell TP, Chen Y (2015) Nat Photon 9:35

    Article  CAS  Google Scholar 

  49. Kan B, Li M, Zhang Q, Liu F, Wan X, Wang Y, Ni W, Long G, Yang X, Feng H, Zuo Y, Zhang M, Huang F, Cao Y, Russell TP, Chen Y (2015) J Am Chem Soc 137:3886

    Article  CAS  Google Scholar 

  50. Wang Z, Li Z, Liu J, Mei J, Li K, Li Y, Peng Q (2016) ACS Appl Mater Interfaces 8:11639

    Article  CAS  Google Scholar 

  51. Steinberger S, Mishra A, Reinold E, Levichkov J, Uhrich C, Pfeiffer M, Bäuerle P (2011) Chem Commun 47:1982

    Article  CAS  Google Scholar 

  52. Tamayo AB, Dang X-D, Walker B, Seo JH, Kent T, Nguyen T-Q (2009) Appl Phys Lett 94:103301

    Article  CAS  Google Scholar 

  53. Ko EY, Choi S, Park GE, Lee DH, Cho MJ, Choi DH (2016) Synth Met 221:39

    Article  CAS  Google Scholar 

  54. Hong MH, Ahn J-S, Nguyen DN, Ngo TT, Lee DH, Cho MJ, Choi DH (2016) J Polym Sci Polym Chem 54:1339

    Article  CAS  Google Scholar 

  55. Warnan J, Cabanetos C, Labban AE, Hansen MR, Tassone C, Toney MF, Beaujuge PM (2014) Adv Mater 26:4357

    Article  CAS  Google Scholar 

  56. Chen H-Y, Hou J, Zhang S, Liang Y, Yang G, Yang Y, Yu L, Wu Y, Li G (2009) Nat Photon 3:649

    Article  CAS  Google Scholar 

  57. Wang C, Dong H, Hu W, Liu Y, Zhu D (2012) Chem Rev 112:2208

    Article  CAS  Google Scholar 

  58. Garnier F, Horowitz G, Peng XZ, Fichou D (1991) Synth Met 45:163

    Article  CAS  Google Scholar 

  59. Horowitz G, Hajlaoui ME (2000) Adv Mater 12:1046

    Article  CAS  Google Scholar 

  60. Halik M, Klauk H, Zschieschang U, Schmid G, Ponomarenko S, Kirchmeyer S, Weber W (2003) Adv Mater 15:917

    Article  CAS  Google Scholar 

  61. Deman AL, Tardy J, Nicolas Y, Blanchard P, Roncali J (2004) Synth Met 146:365

    Article  CAS  Google Scholar 

  62. Katz HE, Torsi L, Dodabalapur A (1995) Chem Mater 7:2235

    Article  CAS  Google Scholar 

  63. Halik M, Klauk H, Zschieschang U, Schmid G, Radlik W, Ponomarenko S, Kirchmeyer S, Weber W (2003) J Appl Phys 93:2977

    Article  CAS  Google Scholar 

  64. Usta H, Facchetti A, Marks TJ (2011) Acc Chem Res 44:501

    Article  CAS  Google Scholar 

  65. Facchetti A, Mushrush M, Yoon MH, Hutchison GR, Ratner MA, Marks TJ (2004) J Am Chem Soc 126:13859

    Article  CAS  Google Scholar 

  66. Yoon MH, DiBenedetto SA, Russell MT, Facchetti A, Marks TJ (2007) Chem Mater 19:4864

    Article  CAS  Google Scholar 

  67. Ostroverkhova O (2016) Chem Rev 116:13279

    Article  CAS  Google Scholar 

  68. Perepichka IF, Perepichka DF, Meng H, Wudl F (2005) Adv Mater 17:2281

    Article  CAS  Google Scholar 

  69. Grimsdale AC, Chan KL, Martin RE, Jokisz PG, Holmes AB (2009) Chem Rev 109:897

    Article  CAS  Google Scholar 

  70. Perepichka IF, Perepichka DF, Meng H (2009) In: Perepichka IF, Perepichka DF (eds) Handbook of thiophene-based materials. Wiley, Hoboken

    Chapter  Google Scholar 

  71. Rasmussen SC, Evenson SJ, McCausland CB (2015) Chem Commun 51:4528

    Article  CAS  Google Scholar 

  72. Rasmussen SC (2015) In: Mullen K, Kobayashi S (eds) The encyclopedia of polymeric nanomaterials. Springer, Heidelberg

    Google Scholar 

  73. Becker RS, de Melo JS, Macanita AL, Elisei F (1995) Pure Appl Chem 67:9

    Article  CAS  Google Scholar 

  74. Pina J, Burrows HD, Becker RS, Dias FB, Maçanita AL, Seixas de Melo J (2006) J Phys Chem B 110:6499

    Article  CAS  Google Scholar 

  75. Egelhaaf H-J, Oelkrug D, Oeter D, Ziegler Ch, Göpel W (1995) J Mol Struct 348:405

    Article  CAS  Google Scholar 

  76. Zen A, Bilge A, Galbrecht F, Alle R, Meerholz K, Grenzer J, Neher D, Scherf U, Farrell T (2006) J Am Chem Soc 128:3914

    Article  CAS  Google Scholar 

  77. Wu H-C, Lee W-Y, Lin C-J, Chen W-C (2013) Mat Chem Phys 138:542

    Article  CAS  Google Scholar 

  78. Barbarella G, Pudova O, Arbizzani C, Mastragostino M, Bongini A (1998) J Org Chem 63:1742

    Article  CAS  Google Scholar 

  79. Barbarella G, Favaretto L, Sotgiu G, Zambianchi M, Bongini A, Arbizzani C, Mastragostino M, Anni M, Gigli G, Cingolani R (2000) J Am Chem Soc 122:11971

    Article  CAS  Google Scholar 

  80. Maria FD, Zangoli M, Palamá IE, Fabiano E, Zanelli A, Monari M, Perinot A, Caironi M, Maiorano V, Maggiore A, Pugliese M, Salatelli E, Gigli G, Viola I, Barbarella G (2016) Adv Funct Mater 26:6970

    Article  CAS  Google Scholar 

  81. Jou J-H, Kumar S, Agrawal A, Lia T-H, Sahooa S (2015) J Mater Chem C 3:2974

    Article  CAS  Google Scholar 

  82. Noda T, Shirota Y (1998) J Am Chem Soc 120:9714

    Article  CAS  Google Scholar 

  83. Noda T, Ogawa H, Shirota Y (1999) Adv Mater 11:283

    Article  CAS  Google Scholar 

  84. Li J, Shan T, Yao M, Gao Y, Han X, Yang B, Lu P (2017) J Mater Chem C 5:2552

    Article  CAS  Google Scholar 

  85. Mei J, Leung NLC, Kwok RTK, Lam JWY, Tang BZ (2015) Chem Rev 115:11718

    Article  CAS  Google Scholar 

  86. Dikcal F, Ozturk T, Cinar ME (2017) Org Commun 10:56

    Article  Google Scholar 

  87. Kumaresan P, Vegiraju S, Ezhumalai Y, Yau SL, Kim C, Lee W-H, Chen M-C (2014) Polymers 6:2645

    Article  CAS  Google Scholar 

  88. Wang K, Liang R-Z, Wolf J, Saleem Q, Babics M, Wucher P, Abdelsamie M, Amassian A, Hansen MR, Beaujuge PM (2016) Adv Funct Mater 26:7103

    Article  CAS  Google Scholar 

  89. Cui C, Guo X, Min J, Guo B, Cheng X, Zhang M, Brabec CJ, Li Y (2015) Adv Mater 27:7469

    Article  CAS  Google Scholar 

  90. Kan B, Zhang Q, Li M, Wan X, Ni W, Long G, Wang Y, Yang X, Feng H, Chen Y (2014) J Am Chem Soc 136:15529

    Article  CAS  Google Scholar 

  91. Walker B, Kim C, Nguyen T-Q (2011) Chem Mater 23:470

    Article  CAS  Google Scholar 

  92. Roncali J (2009) Acc Chem Res 42:1719

    Article  CAS  Google Scholar 

  93. Coughlin JE, Henson ZB, Welch GC, Bazan GC (2014) Acc Chem Res 47:257

    Article  CAS  Google Scholar 

  94. Chen Y, Wan X, Long G (2013) Acc Chem Res 46:2645

    Article  CAS  Google Scholar 

  95. Kim J, Shim HS, Lee H, Choi MS, Kim JJ, Seo Y (2014) J Phys Chem C 118:11559

    Article  CAS  Google Scholar 

  96. Skabara PJ (2009) In: Perepichka IF, Perepichka DF (eds) Handbook of thiophene-based materials. Wiley, Chichester

    Google Scholar 

  97. Fernandes SSM, Castro MCR, Mesquita I, Andrade L, Mendes A, Raposo MMM (2017) Dyes Pigments 136:46

    Article  CAS  Google Scholar 

  98. Collins SD, Ran NA, Heiber MC, Nguyen T-Q (2017) Adv Energy Mater 7:1602242

    Article  CAS  Google Scholar 

  99. Zhou J, Wan X, Liu Y, Long G, Wang F, Li Z, Zuo Y, Li C, Chen Y (2011) Chem Mater 23:4666

    Article  CAS  Google Scholar 

  100. van der Poll TS, Love JA, Nguyen T-Q, Bazan GC (2012) Adv Mater 24:3646

    Article  CAS  Google Scholar 

  101. Huang Y, Wen W, Mukherjee S, Ade H, Kramer EJ, Bazan GC (2014) Adv Mater 26:4168

    Article  CAS  Google Scholar 

  102. Ni W, Li M, Liu F, Wan X, Feng H, Kan B, Zhang Q, Zhang H, Chen Y (2015) Chem Mater 27:6077

    Article  CAS  Google Scholar 

  103. Zhou Z, Xu S, Liu W, Zhang C, Hu Q, Liu F, Russell TP, Zhu X (2017) J Mater Chem A 5:3425

    Article  CAS  Google Scholar 

  104. Zhang Y, Zhou Z, Hu Q, Liu F, Russell TP, Zhu X (2017) ACS Appl Mater Interfaces 9:6213

    Article  CAS  Google Scholar 

  105. Li M, Liu F, Wan X, Ni W, Kan B, Feng H, Zhang Q, Yang X, Wang Y, Zhang Y, Shen Y, Russell TP, Chen Y (2015) Adv Mater 27:6296

    Article  CAS  Google Scholar 

  106. Sun K, Xiao Z, Lu S, Zajaczkowski W, Pisula W, Hanssen E, White JM, Williamson RM, Subbiah J, Ouyang J, Holmes AB, Wong WWH, Jones DJ (2015) Nat Commun 6:6013

    Article  CAS  Google Scholar 

  107. Wang Z, Xu X, Li Z, Feng K, Li K, Li Y, Peng Q (2016) Adv Electron Mater 2:1600061

    Article  CAS  Google Scholar 

  108. Bin H, Yang Y, Zhang Z-G, Ye L, Ghasemi M, Chen S, Zhang Y, Zhang C, Sun C, Xue L, Yang C, Ade H, Li Y (2017) J Am Chem Soc 139:5085

    Article  CAS  Google Scholar 

  109. Song HG, Kim YJ, Lee JS, Kim Y-H, Park CE, Kwon S-K (2016) ACS Appl Mater Interfaces 8:34353

    Article  CAS  Google Scholar 

  110. Yong W, Zhang M, Xin X, Li Z, Wu Y, Guo X, Yang Z, Hou J (2013) J Mater Chem A 1:14214

    Article  CAS  Google Scholar 

  111. Wang J-L, Liu K-K, Yan J, Wu Z, Liu F, Xiao F, Chang Z-F, Wu H-B, Cao Y, Russell TP (2016) J Am Chem Soc 138:7687

    Article  CAS  Google Scholar 

  112. Tsumura A, Koezuka H, Ando T (1986) Appl Phys Lett 49:1210

    Article  CAS  Google Scholar 

  113. Jiang W, Li Y, Wang Z (2013) Chem Soc Rev 42:6113

    Article  CAS  Google Scholar 

  114. Ponomarenko SA, Kirchmeyer S, Elschner A, Alpatova NM, Halik M, Klauk H, Zschieschang U, Schmid G (2006) Chem Mater 18:579

    Article  CAS  Google Scholar 

  115. Xiao K, Liu Y, Qi T, Zhang W, Wang F, Gao J, Qiu W, Ma Y, Cui G, Chen S, Zhan X, Yu G, Qin J, Hu W, Zhu D (2005) J Am Chem Soc 127:13281

    Article  CAS  Google Scholar 

  116. Sun YM, Ma YW, Liu YQ, Lin YY, Wang ZY, Wang Y, Di CG, Xiao K, Chen XM, Qiu WF, Zhang B, Yu G, Hu WP, Zhu DB (2006) Adv Funct Mater 16:426

    Article  CAS  Google Scholar 

  117. Mori T, Oyama T, Komiyama H, Yasuda T (2017) J Mater Chem C 5:5872

    Article  CAS  Google Scholar 

  118. Yang YS, Yasuda T, Kakizoe H, Mieno H, Kino H, Tateyama Y, Adachi C (2013) Chem Commun 49:6483

    Article  CAS  Google Scholar 

  119. Yamamoto T, Takimiya K (2007) J Am Chem Soc 129:2224

    Article  CAS  Google Scholar 

  120. Kang MJ, Doi I, Mori H, Miyazaki E, Takimiya K, Ikeda M, Kuwabara H (2011) Adv Mater 23:1222

    Article  CAS  Google Scholar 

  121. Nakayama K, Hirose Y, Soeda J, Yoshizumi M, Uemura T, Uno M, Li W, Kang MJ, Yamagishi M, Okada Y, Miyazaki E, Nakazawa Y, Nakao A, Takimiya K, Takeya J (2011) Adv Mater 23:1626

    Article  CAS  Google Scholar 

  122. Kang M, Hwang H, Park W-T, Khim D, Yeo J-S, Kim Y, Kim Y-J, Noh Y-Y, Kim D-Y (2017) ACS Appl Mater Interfaces 9:2686

    Article  CAS  Google Scholar 

  123. Yuan Y, Giri G, Ayzner AL, Zoombelt AP, Mannsfeld SC, Chen J, Nordlund D, Toney MF, Huang J, Bao Z (2014) Nat Commun 5:3005

    Google Scholar 

  124. Lee E-K, Lee MY, Choi A, Kim J-Y, Kweon OY, Kim J-H, Jung JY, Shin T-J, Oh JH, Park J-I, Lee SY (2017) Adv Electron Mater 1700142

  125. Roche GH, Tsai Y-T, Clevers S, Thuau D, Castet F, Geerts YH, Moreau JJE, Wantz G, Dautel OJ (2016) J Mater Chem C 4:6742

    Article  CAS  Google Scholar 

  126. Illig S, Eggeman AS, Troisi A, Jiang L, Warwick C, Nikolka M, Schweicher G, Yeates SG, Geerts YH, Anthony JE, Sirringhaus H (2016) Nat Commun 7:10736

    Article  CAS  Google Scholar 

  127. Iino H, Usui T, Hanna J (2015) Nat Commun 6:6828

    Article  CAS  Google Scholar 

  128. Takimiya K, Nakano M, Sugino H, Osaka I (2016) Synth Met 217:68

    Article  CAS  Google Scholar 

  129. Polander LE, Tiwari SP, Pandey L, Seifried BM, Zhang Q, Barlow S, Risko C, Bredas J-L, Kippelen B, Marder SR (2011) Chem Mater 23:3408

    Article  CAS  Google Scholar 

  130. Chen M-C, Vegiraju S, Huang C-M, Huang P-Y, Prabakaran K, Yau SL, Chen W-C, Peng W-T, Chao I, Kim C, Tao Y-T (2014) J Mater Chem C 2:8892

    Article  CAS  Google Scholar 

  131. Youn J, Vegiraju S, Emery JD, Leever BJ, Kewalramani S, Lou SJ, Zhang S, Prabakaran K, Ezhumalai Y, Kim C, Huang P-Y, Stern C, Chang W-C, Bedzyk MJ, Chen LX, Chen M-C, Facchetti A, Marks TJ (2015) Adv Electron Mater 1:1500098

    Article  CAS  Google Scholar 

  132. Vegiraju S, Huang D-Y, Priyanka P, Li Y-S, Luo X-L, Hong S-H, Ni J-S, Tung J-S, Wang C-L, Lien W-C, Yau SL, Liu C-L, Chen M-C (2017) Chem Commun 53:5898

    Article  CAS  Google Scholar 

  133. Lin G, Qin Y, Zhang J, Guan Y-S, Xu H, Xu W, Zhu D (2016) J Mater Chem C 4:4470

    Article  CAS  Google Scholar 

  134. Lim B, Sun H, Lee J, Noh Y-Y (2017) Sci Rep 7:164

    Article  Google Scholar 

  135. Fukutomi Y, Nakano M, Hu J-Y, Osaka I, Takimiya K (2013) J Am Chem Soc 135:11445

    Article  CAS  Google Scholar 

  136. Jarosz T, Lapkowski M, Ledwon P (2014) Macromol Rapid Commun 35:1006

    Article  CAS  Google Scholar 

  137. Li P, Cui Y, Song C, Zhang H (2016) J Phys Chem C 120:14484

    Article  CAS  Google Scholar 

  138. Barbarella G, Favaretto L, Sotgiu G, Antolini L, Gigli G, Cingolani R, Bongini A (2001) Chem Mater 13:4112

    Article  CAS  Google Scholar 

  139. Mazzeo M, Vitale V, Sala FD, Anni M, Barbarella G, Fabaretto L, Sotgiu G, Cingolani R, Gigli G (2005) Adv Mater 17:34

    Article  CAS  Google Scholar 

  140. Turkoglu G, Cinar ME, Buyruk A, Tekin E, Mucur SP, Kaya K, Ozturk T (2016) J Mater Chem C 4:6045

    Article  CAS  Google Scholar 

  141. Park H, Rao Y, Varlan M, Kim J, Ko S-B, Wang S, Kang Y (2012) Tetrahedron 68:9278

    Article  CAS  Google Scholar 

  142. Evenson SJ, Pappenfus TM, Delgado MCR, Radke-Wohlers KR, Navarrete JTL, Rasmussen SC (2012) Phys Chem Chem Phys 14:6101

    Article  CAS  Google Scholar 

  143. Durben S, Linder T, Baumgartner T (2010) New J Chem 34:1585

    Article  CAS  Google Scholar 

  144. Zhan X, Wu Z, Lin Y, Tang S, Yang J, Hu J, Peng Q, Ma D, Li Q, Li Z (2015) J Mater Chem C 3:5903

    Article  CAS  Google Scholar 

  145. Yang Z, Mao Z, Xie Z, Zhang Y, Liu S, Zhao J, Xu J, Chi Z, Aldred MP (2017) Chem Soc Rev 46:915

    Article  CAS  Google Scholar 

  146. Yook KS, Lee JY (2012) Adv Mater 24:3169

    Article  CAS  Google Scholar 

  147. Lin W-C, Huang W-C, Huang M-H, Fan C-C, Lin H-W, Chen L-Y, Liu Y-W, Lin J-S, Chao T-C, Tseng M-R (2013) J Mater Chem C 1:6835

    Article  CAS  Google Scholar 

  148. Pahlavanlu P, Christensen PR, Therrien JA, Wolf MO (2016) J Phys Chem C 120:70

    Article  CAS  Google Scholar 

  149. He X, Shan T, Tang X, Gao Y, Li J, Yang B, Lu P (2016) J Mater Chem C 4:10205

    Article  CAS  Google Scholar 

  150. Guo X, Baumgarten M, Müllen K (2013) Prog Polym Sci 38:1832

    Article  CAS  Google Scholar 

  151. Mehmood U, Al-Ahmed A, Hussein IA (2016) Renew Sustainable Energy Rev 57:550

    Article  CAS  Google Scholar 

  152. Lu L, Zheng T, Wu Q, Schneider AM, Zhao D, Yu L (2015) Chem Rev 115:12666

    Article  CAS  Google Scholar 

  153. Yao H, Ye L, Zhang H, Li S, Zhang S, Hou J (2016) Chem Rev 116:7397

    Article  CAS  Google Scholar 

  154. Cai Y, Huo L, Sun Y (2017) Adv Mater 29:1605437

    Article  CAS  Google Scholar 

  155. Liu C, Wang K, Gong X, Heeger AJ (2016) Chem Soc Rev 45:4848

    Article  CAS  Google Scholar 

  156. Gélinas S, Rao A, Kumar A, Smith SL, Chin AW, Clark J, van der Poll TS, Bazan GC, Friend RH (2014) Science 343:512

    Article  CAS  Google Scholar 

  157. Zhang M, Guo X, Ma W, Ade H, Hou J (2014) Adv Mater 26:5880

    Article  CAS  Google Scholar 

  158. Noh S, Gobalasingham NS, Thompson BC (2016) Macromolecules 49:6835

    Article  CAS  Google Scholar 

  159. Albrecht S, Janietz S, Schindler W, Frisch J, Kurpiers J, Kniepert J, Inal S, Pingel P, Fostiropoulos K, Koch N, Neher D (2012) J Am Chem Soc 134:14932

    Article  CAS  Google Scholar 

  160. Ashraf RS, Meager I, Nikolka M, Kirkus M, Planells M, Schroeder BC, Holliday S, Hurhangee M, Nielsen CB, Sirringhaus H, Mcculloch I (2015) J Am Chem Soc 137:1314

    Article  CAS  Google Scholar 

  161. Su M-S, Kuo C-Y, Yuan M-C, Jeng US, Su C-J, Wei K-H (2011) Adv Mater 23:3315

    Article  CAS  Google Scholar 

  162. Dou L, Chen C-C, Yoshimura K, Ohya K, Chang W-H, Gao J, Liu Y, Richard E, Yang Y (2013) Macromolecules 46:3384

    Article  CAS  Google Scholar 

  163. Zhou N, Guo X, Ortiz RP, Li S, Zhang S, Chang RP, Facchetti A, Marks TJ (2012) Adv Mater 24:2242

    Article  CAS  Google Scholar 

  164. Cao J, Liao Q, Du X, Chen J, Xiao Z, Zuo Q, Ding L (2013) Energy Environ Sci 6:3224

    Article  CAS  Google Scholar 

  165. Li H, Cao J, Zhou Q, Ding L, Wang J (2015) Nano Energy 15:125

    Article  CAS  Google Scholar 

  166. Cao JM, Qian L, Lu FT, Zhang JQ, Feng YQ, Qiu XH, Yip HL, Ding LM (2015) Chem Commun 51:11830

    Article  CAS  Google Scholar 

  167. Hou JH, Park MH, Zhang SQ, Yao Y, Chen LM, Li JH, Yang Y (2008) Macromolecules 41:6012

    Article  CAS  Google Scholar 

  168. Cui C, Wong W-Y (2016) Macromol Rapid Commun 37:287

    Article  CAS  Google Scholar 

  169. Liang Y, Xu Z, Xia J, Tsai S-T, Wu Y, Li G, Ray C, Yu L (2010) Adv Mater 22:E135

    Article  CAS  Google Scholar 

  170. Zhang C, Zhu X (2017) Acc Chem Res 50:1342

    Article  CAS  Google Scholar 

  171. He Z, Zhong C, Su S, Xu M, Wu H, Cao Y (2012) Nat Photon 6:591

    Article  CAS  Google Scholar 

  172. Liao S-H, Jhuo H-J, Cheng Y-S, Chen S-A (2013) Adv Mater 25:4766

    Article  CAS  Google Scholar 

  173. Qu S, Wang H, Mo D, Chao P, Yang Z, Li L, Tian L, Chen W, He F (2017) Macromolecules 50:4962

    Article  CAS  Google Scholar 

  174. Liu Y, Tang D, Zhang K, Huang P, Wang Z, Zhu K, Li Z, Yuan L, Fan J, Zhou Y, Song B (2017) ACS Omega 2:2489

    Article  CAS  Google Scholar 

  175. He Z, Xiao B, Liu F, Wu H, Yang Y, Xiao S, Wang C, Russell TP, Cao Y (2015) Nat Photon 9:174

    Article  CAS  Google Scholar 

  176. Lin Y-C, Su Y-W, Li Y-W, Lin B-H, Chen C-H, Chen H-C, Wu K-H, Yang Y, Wei K-H (2017) J Mater Chem A. doi:10.1039/C7TA04144F

    Google Scholar 

  177. Cui C, Wong W-Y, Li Y (2014) Energy Environ Sci 7:2276

    Article  CAS  Google Scholar 

  178. Cui C, He Z, Wu Y, Cheng X, Wu H, Li Y, Cao Y, Wong W-Y (2016) Energy Environ Sci 9:885

    Article  CAS  Google Scholar 

  179. Ye L, Zhang S, Zhao W, Yao H, Hou J (2014) Chem Mater 26:3603

    Article  CAS  Google Scholar 

  180. Zhang SQ, Ye L, Zhao WC, Yang B, Wang Q, Hou JH (2015) Sci China Chem 58:248

    Article  CAS  Google Scholar 

  181. Subbiah J, Purushothaman B, Chen M, Qin T, Gao M, Vak D, Scholes FH, Chen X, Watkins SE, Wilson GJ, Holmes AB, Wong WW, Jones DJ (2015) Adv Mater 27:702

    Article  CAS  Google Scholar 

  182. Duan C, Gao K, Colberts FJM, Liu F, Meskers SCJ, Wienk MM, Janssen RAJ (2017) Adv Energy Mater 1700519

  183. Cabanetos C, El Labban A, Bartelt JA, Douglas JD, Mateker WR, Fréchet JMJ, McGehee MD, Beaujuge PM (2013) J Am Chem Soc 135:4656

    Article  CAS  Google Scholar 

  184. Liu T, Pan X, Meng X, Liu Y, Wei D, Ma W, Huo L, Sun X, Lee TH, Huang M, Choi H, Kim JY, Choy WCH, Sun Y (2017) Adv Mater 29:1604251

    Article  CAS  Google Scholar 

  185. Pan X, Xiong W, Liu T, Sun X, Huo L, Wei D, Yu M, Han M, Sun Y (2017) J Mater Chem C 5:4471

    Article  CAS  Google Scholar 

  186. Bin H, Zhang ZG, Gao L, Chen S, Zhong L, Xue L, Yang C, Li Y (2016) J Am Chem Soc 138:4657

    Article  CAS  Google Scholar 

  187. Bin H, Zhong L, Yang Y, Gao L, Huang H, Sun C, Li X, Xue L, Zhang Z-G, Zhang Z, Li Y (2017) Adv Energy Mater 1700746

  188. Son HJ, Lu L, Chen W, Xu T, Zheng T, Carsten B, Strzalka J, Darling SB, Chen LX, Yu L (2013) Adv Mater 25:838

    Article  CAS  Google Scholar 

  189. Gao W, Liu T, Hao M, Wu K, Zhang C, Sun Y, Yang C (2016) Chem Sci 7:6167

    Article  CAS  Google Scholar 

  190. Nketia-Yawson B, Lee H-S, Seo D, Yoon Y, Park W-T, Kwak K, Son HJ, Kim BS, Noh Y-Y (2015) Adv Mater 27:3045

    Article  CAS  Google Scholar 

  191. Truong MA, Nakano K (2016) Bull Chem Soc Jpn 89:1034

    Article  CAS  Google Scholar 

  192. He M, Li J, Sorensen M, Zhang F, Hancock R, Fong J, Pozdin V, Smilgies D, Malliaras G (2009) J Am Chem Soc 131:11930

    Article  CAS  Google Scholar 

  193. Yi Z, Ma L, Chen B, Chen D, Chen X, Qin J, Zhan X, Liu Y, Ong WJ, Li J (2013) Chem Mater 25:4290

    Article  CAS  Google Scholar 

  194. Zhang A, Xiao C, Wu Y, Li C, Ji Y, Li L, Hu W, Wang Z, Ma W, Li W (2016) Macromolecules 49:6431

    Article  CAS  Google Scholar 

  195. Li J, Zhao Y, Tan HS, Guo Y, Di C-A, Yu G, Liu Y, Lin M, Lim SH, Zhou Y, Su H, Ong BS (2012) Sci Rep 2:754

    Article  CAS  Google Scholar 

  196. Chen H-J, Liu Z, Zhao Z, Zheng L, Tan S, Yin Z, Zhu C, Liu Y (2016) ACS Appl Mater Interfaces 8:33051

    Article  CAS  Google Scholar 

  197. Bronstein H, Chen Z, Ashraf RS, Zhang W, Du J, Durrant JR, Tuladhar PS, Song K, Watkins SE, Geerts Y, Wienk MM, Janssen RAJ, Anthopoulos T, Sirringhaus H, Heeney M, McCulloch I (2011) J Am Chem Soc 133:3272

    Article  CAS  Google Scholar 

  198. Perzon E, Zhang FL, Andersson M, Mammo W, Inganas O, Andersson MR (2007) Adv Mater 19:3308

    Article  CAS  Google Scholar 

  199. Wang S, Kappl M, Liebewirth I, Müller M, Kirchhoff K, Pisula W, Müllen K (2012) Adv Mater 24:417

    Article  CAS  Google Scholar 

  200. Lee YH, Park S, Oh S, Shin JW, Jung J, Yoo S, Lee MH (2017) ACS Appl Mater Interfaces. doi:10.1021/acsami.7b05615

    Google Scholar 

  201. Ban X, Zhu A, Zhang T, Tong Z, Jiang W, Sun Y (2017) ACS Appl Mater Interfaces. doi:10.1021/acsami.7b04146

    Google Scholar 

  202. Ohmori Y, Uchida M, Muro K, Yoshino K (1991) Solid State Commun 80:605

    Article  Google Scholar 

  203. Tang W, Ke L, Tan L, Lin T, Kietzke T, Chen Z-K (2007) Macromolecules 40:6164

    Article  CAS  Google Scholar 

  204. Osken I, Gundogan AS, Tekin E, Eroglu MS, Ozturk T (2013) Macromolecules 46:9202

    Article  CAS  Google Scholar 

  205. Ohshita J, Kimura K, Lee K-H, Kunai A, Kwak Y-W, Son E-C, Kunugi Y (2007) J Polym Sci Part A Polym Chem 45:4588

    Article  CAS  Google Scholar 

  206. Liu MS, Luo J, Jen AK-Y (2003) Chem Mater 15:3496

    Article  CAS  Google Scholar 

  207. Mishra SP, Palai AK, Srivastava R, Kamalasanan MN, Patri M (2009) J Polym Sci Part A Polym Chem 47:6514

    Article  CAS  Google Scholar 

  208. Evenson SJ, Mumm MJ, Pokhodnya KI, Rasmussen SC (2011) Macromolecules 44:835

    Article  CAS  Google Scholar 

  209. Kostyanovsky VA, Susarova DK, Adam G, Lyubovskaya RN, Troshin PA (2013) Mendeleev Commun 23:26

    Article  CAS  Google Scholar 

  210. Zhu Y, Gibbons KM, Kulkarni AP, Jenekhe SA (2007) Macromolecules 40:804

    Article  CAS  Google Scholar 

  211. Sundararaman A, Victor M, Varughese R, Jäkle F (2005) J Am Chem Soc 127:13748

    Article  CAS  Google Scholar 

  212. Yin X, Guo F, Lalancette RA, Jäkle F (2016) Macromolecules 49:537

    Article  CAS  Google Scholar 

  213. Guo F, Yin X, Pammer F, Cheng F, Fernandez D, Lalancette RA, Jäkle F (2014) Macromolecules 47:7831

    Article  CAS  Google Scholar 

  214. Mishra SP, Palai AK, Kumar A, Srivastava R, Kamalasanan MN, Patri M (2010) Macromol Chem Phys 211:1890

    Article  CAS  Google Scholar 

  215. Sahin O, Cinar ME, Tekin E, Mucur SP, Topal S, Suna G, Eroglu MS, Ozturk T (2017) ChemistrySelect 2:2889

    Article  CAS  Google Scholar 

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Correspondence to Turan Ozturk.

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This article is part of the Topical Collection “Sulfur Chemistry”; edited by Xuefeng Jiang.

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Turkoglu, G., Cinar, M.E. & Ozturk, T. Thiophene-Based Organic Semiconductors. Top Curr Chem (Z) 375, 84 (2017). https://doi.org/10.1007/s41061-017-0174-z

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