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
Okamato Y, Brenner W (1964) Organic semiconductors. Reinhold Publishing Corporation, New York
Zaumseil J, Sirringhaus H (2007) Chem Rev 107:1296
Facchetti A (2013) Mater Today 16:123
Sirringhaus H (2014) Adv Mater 26:1319
Coropceanu V, Cornil J, da Silva DA, Olivier Y, Silbey R, Bredas JL (2007) Chem Rev 107:926
Murphy AR, Fréchet JMJ (2007) Chem Rev 107:1066
Facchetti A (2007) Mater Today 10:28
Torruellas WE, Neher D, Zanoni R, Stegeman GI, Kajzar F, Leclerc M (1990) Chem Phys Lett 175:11
Bäuerle P (1998) In: Wegner G, Mullen K (eds) Electronic materials: the oligomer approach. Wiley-VCH, Weinheim
Tour J (1996) Chem Rev 96:537
Shirota Y (2000) J Mater Chem 10:1
Musher JI (1969) Angew Chem Int Ed Engl 8:54
Gillespie RJ, Silvi B (2002) Coord Chem Rev 233–234:53
Dell EJ, Capozzi B, Xia J, Venkataraman L, Campos LM (2015) Nat Chem 7:209
Ghofraniha N, Viola I, Di Maria F, Barbarella G, Gigli G, Leuzzi L, Conti C (2015) Nat Commun 6:6058
Kitamura C, Tanaka S, Yamashita Y (1996) Chem Mater 8:570
Barbarella G, Zambianchi M, Bongini A, Antolini L (1993) Adv Mater 5:834
Barbarella G, Di Maria F (2015) Acc Chem Res 48:2230
Perepichka IF, Perepichka DF (2009) Handbook of thiophene-based materials: applications in organic electronics and photonics. Wiley, Chichester
Roncali J (1992) Chem Rev 92:711
McCullough RD (1998) Adv Mater 10:93
Mishra A, Ma CQ, Bauerle P (2009) Chem Rev 109:1141
Cinar ME, Ozturk T (2015) Chem Rev 115:3036 (and references therein)
Lin Y, Li Y, Zhan X (2012) Chem Soc Rev 41:4245
Lin Y, Zhan X (2016) Acc Chem Res 49:175
Sun Y, Welch GC, Leong WL, Takacs CJ, Bazan GC, Heeger AJ (2012) Nat Mater 11:44
Mazzeo M, Pisignano D, Favaretto L, Barbarella G, Cingolani R, Gigli G (2003) Synth Met 139:671
Hains AW, Ramanan C, Irwin MD, Liu J, Wasielewski MR, Marks TJ (2010) ACS Appl Mater Interfaces 2:175
Kunugi Y, Takimiya K, Negishi N, Otsubo T, Aso Y (2004) J Mater Chem 14:2840
Marseglia EA, Grepioni F, Tedesco E, Braga D (2000) Mol Cryst Liq Cryst Sci Technol Sect A 348:137
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
Nicolas Y, Blanchard P, Levillain E, Allain M, Mercier N, Roncali J (2004) Org Lett 6:273
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
Ma C-Q, Mena-Osteritz E, Debaerdemaeker T, Wienk MM, Janssen RA, Bäuerle P (2007) Angew Chem Int Ed 46:1679
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
Gao JH, Li RJ, Li LQ, Meng Q, Jiang H, Li HX, Hu WP (2007) Adv Mater 19:3008
Mishra A, Bauerle P (2012) Angew Chem Int Ed 51:2020
Noma N, Tsuzuki T, Shirota Y (1995) Adv Mater 7:647
Sakai J, Taima T, Saito K (2008) Org Electron 9:582
Zhang F, Wu D, Xua Y, Feng X (2011) J Mater Chem 21:17590
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
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
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
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
Liu Y, Wan X, Wang F, Zhou J, Long G, Tian J, You J, Yang Y, Chen Y (2011) Adv Energy Mater 1:771
Li Z, He G, Wan X, Liu Y, Zhou J, Long G, Zuo Y, Zhang M, Chen Y (2012) Adv Energy Mater 2:74
Ni W, Wan X, Li M, Wang Y, Chen Y (2015) Chem Commun 51:4936
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
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
Wang Z, Li Z, Liu J, Mei J, Li K, Li Y, Peng Q (2016) ACS Appl Mater Interfaces 8:11639
Steinberger S, Mishra A, Reinold E, Levichkov J, Uhrich C, Pfeiffer M, Bäuerle P (2011) Chem Commun 47:1982
Tamayo AB, Dang X-D, Walker B, Seo JH, Kent T, Nguyen T-Q (2009) Appl Phys Lett 94:103301
Ko EY, Choi S, Park GE, Lee DH, Cho MJ, Choi DH (2016) Synth Met 221:39
Hong MH, Ahn J-S, Nguyen DN, Ngo TT, Lee DH, Cho MJ, Choi DH (2016) J Polym Sci Polym Chem 54:1339
Warnan J, Cabanetos C, Labban AE, Hansen MR, Tassone C, Toney MF, Beaujuge PM (2014) Adv Mater 26:4357
Chen H-Y, Hou J, Zhang S, Liang Y, Yang G, Yang Y, Yu L, Wu Y, Li G (2009) Nat Photon 3:649
Wang C, Dong H, Hu W, Liu Y, Zhu D (2012) Chem Rev 112:2208
Garnier F, Horowitz G, Peng XZ, Fichou D (1991) Synth Met 45:163
Horowitz G, Hajlaoui ME (2000) Adv Mater 12:1046
Halik M, Klauk H, Zschieschang U, Schmid G, Ponomarenko S, Kirchmeyer S, Weber W (2003) Adv Mater 15:917
Deman AL, Tardy J, Nicolas Y, Blanchard P, Roncali J (2004) Synth Met 146:365
Katz HE, Torsi L, Dodabalapur A (1995) Chem Mater 7:2235
Halik M, Klauk H, Zschieschang U, Schmid G, Radlik W, Ponomarenko S, Kirchmeyer S, Weber W (2003) J Appl Phys 93:2977
Usta H, Facchetti A, Marks TJ (2011) Acc Chem Res 44:501
Facchetti A, Mushrush M, Yoon MH, Hutchison GR, Ratner MA, Marks TJ (2004) J Am Chem Soc 126:13859
Yoon MH, DiBenedetto SA, Russell MT, Facchetti A, Marks TJ (2007) Chem Mater 19:4864
Ostroverkhova O (2016) Chem Rev 116:13279
Perepichka IF, Perepichka DF, Meng H, Wudl F (2005) Adv Mater 17:2281
Grimsdale AC, Chan KL, Martin RE, Jokisz PG, Holmes AB (2009) Chem Rev 109:897
Perepichka IF, Perepichka DF, Meng H (2009) In: Perepichka IF, Perepichka DF (eds) Handbook of thiophene-based materials. Wiley, Hoboken
Rasmussen SC, Evenson SJ, McCausland CB (2015) Chem Commun 51:4528
Rasmussen SC (2015) In: Mullen K, Kobayashi S (eds) The encyclopedia of polymeric nanomaterials. Springer, Heidelberg
Becker RS, de Melo JS, Macanita AL, Elisei F (1995) Pure Appl Chem 67:9
Pina J, Burrows HD, Becker RS, Dias FB, Maçanita AL, Seixas de Melo J (2006) J Phys Chem B 110:6499
Egelhaaf H-J, Oelkrug D, Oeter D, Ziegler Ch, Göpel W (1995) J Mol Struct 348:405
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
Wu H-C, Lee W-Y, Lin C-J, Chen W-C (2013) Mat Chem Phys 138:542
Barbarella G, Pudova O, Arbizzani C, Mastragostino M, Bongini A (1998) J Org Chem 63:1742
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
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
Jou J-H, Kumar S, Agrawal A, Lia T-H, Sahooa S (2015) J Mater Chem C 3:2974
Noda T, Shirota Y (1998) J Am Chem Soc 120:9714
Noda T, Ogawa H, Shirota Y (1999) Adv Mater 11:283
Li J, Shan T, Yao M, Gao Y, Han X, Yang B, Lu P (2017) J Mater Chem C 5:2552
Mei J, Leung NLC, Kwok RTK, Lam JWY, Tang BZ (2015) Chem Rev 115:11718
Dikcal F, Ozturk T, Cinar ME (2017) Org Commun 10:56
Kumaresan P, Vegiraju S, Ezhumalai Y, Yau SL, Kim C, Lee W-H, Chen M-C (2014) Polymers 6:2645
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
Cui C, Guo X, Min J, Guo B, Cheng X, Zhang M, Brabec CJ, Li Y (2015) Adv Mater 27:7469
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
Walker B, Kim C, Nguyen T-Q (2011) Chem Mater 23:470
Roncali J (2009) Acc Chem Res 42:1719
Coughlin JE, Henson ZB, Welch GC, Bazan GC (2014) Acc Chem Res 47:257
Chen Y, Wan X, Long G (2013) Acc Chem Res 46:2645
Kim J, Shim HS, Lee H, Choi MS, Kim JJ, Seo Y (2014) J Phys Chem C 118:11559
Skabara PJ (2009) In: Perepichka IF, Perepichka DF (eds) Handbook of thiophene-based materials. Wiley, Chichester
Fernandes SSM, Castro MCR, Mesquita I, Andrade L, Mendes A, Raposo MMM (2017) Dyes Pigments 136:46
Collins SD, Ran NA, Heiber MC, Nguyen T-Q (2017) Adv Energy Mater 7:1602242
Zhou J, Wan X, Liu Y, Long G, Wang F, Li Z, Zuo Y, Li C, Chen Y (2011) Chem Mater 23:4666
van der Poll TS, Love JA, Nguyen T-Q, Bazan GC (2012) Adv Mater 24:3646
Huang Y, Wen W, Mukherjee S, Ade H, Kramer EJ, Bazan GC (2014) Adv Mater 26:4168
Ni W, Li M, Liu F, Wan X, Feng H, Kan B, Zhang Q, Zhang H, Chen Y (2015) Chem Mater 27:6077
Zhou Z, Xu S, Liu W, Zhang C, Hu Q, Liu F, Russell TP, Zhu X (2017) J Mater Chem A 5:3425
Zhang Y, Zhou Z, Hu Q, Liu F, Russell TP, Zhu X (2017) ACS Appl Mater Interfaces 9:6213
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
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
Wang Z, Xu X, Li Z, Feng K, Li K, Li Y, Peng Q (2016) Adv Electron Mater 2:1600061
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
Song HG, Kim YJ, Lee JS, Kim Y-H, Park CE, Kwon S-K (2016) ACS Appl Mater Interfaces 8:34353
Yong W, Zhang M, Xin X, Li Z, Wu Y, Guo X, Yang Z, Hou J (2013) J Mater Chem A 1:14214
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
Tsumura A, Koezuka H, Ando T (1986) Appl Phys Lett 49:1210
Jiang W, Li Y, Wang Z (2013) Chem Soc Rev 42:6113
Ponomarenko SA, Kirchmeyer S, Elschner A, Alpatova NM, Halik M, Klauk H, Zschieschang U, Schmid G (2006) Chem Mater 18:579
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
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
Mori T, Oyama T, Komiyama H, Yasuda T (2017) J Mater Chem C 5:5872
Yang YS, Yasuda T, Kakizoe H, Mieno H, Kino H, Tateyama Y, Adachi C (2013) Chem Commun 49:6483
Yamamoto T, Takimiya K (2007) J Am Chem Soc 129:2224
Kang MJ, Doi I, Mori H, Miyazaki E, Takimiya K, Ikeda M, Kuwabara H (2011) Adv Mater 23:1222
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
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
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
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
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
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
Iino H, Usui T, Hanna J (2015) Nat Commun 6:6828
Takimiya K, Nakano M, Sugino H, Osaka I (2016) Synth Met 217:68
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
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
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
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
Lin G, Qin Y, Zhang J, Guan Y-S, Xu H, Xu W, Zhu D (2016) J Mater Chem C 4:4470
Lim B, Sun H, Lee J, Noh Y-Y (2017) Sci Rep 7:164
Fukutomi Y, Nakano M, Hu J-Y, Osaka I, Takimiya K (2013) J Am Chem Soc 135:11445
Jarosz T, Lapkowski M, Ledwon P (2014) Macromol Rapid Commun 35:1006
Li P, Cui Y, Song C, Zhang H (2016) J Phys Chem C 120:14484
Barbarella G, Favaretto L, Sotgiu G, Antolini L, Gigli G, Cingolani R, Bongini A (2001) Chem Mater 13:4112
Mazzeo M, Vitale V, Sala FD, Anni M, Barbarella G, Fabaretto L, Sotgiu G, Cingolani R, Gigli G (2005) Adv Mater 17:34
Turkoglu G, Cinar ME, Buyruk A, Tekin E, Mucur SP, Kaya K, Ozturk T (2016) J Mater Chem C 4:6045
Park H, Rao Y, Varlan M, Kim J, Ko S-B, Wang S, Kang Y (2012) Tetrahedron 68:9278
Evenson SJ, Pappenfus TM, Delgado MCR, Radke-Wohlers KR, Navarrete JTL, Rasmussen SC (2012) Phys Chem Chem Phys 14:6101
Durben S, Linder T, Baumgartner T (2010) New J Chem 34:1585
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
Yang Z, Mao Z, Xie Z, Zhang Y, Liu S, Zhao J, Xu J, Chi Z, Aldred MP (2017) Chem Soc Rev 46:915
Yook KS, Lee JY (2012) Adv Mater 24:3169
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
Pahlavanlu P, Christensen PR, Therrien JA, Wolf MO (2016) J Phys Chem C 120:70
He X, Shan T, Tang X, Gao Y, Li J, Yang B, Lu P (2016) J Mater Chem C 4:10205
Guo X, Baumgarten M, Müllen K (2013) Prog Polym Sci 38:1832
Mehmood U, Al-Ahmed A, Hussein IA (2016) Renew Sustainable Energy Rev 57:550
Lu L, Zheng T, Wu Q, Schneider AM, Zhao D, Yu L (2015) Chem Rev 115:12666
Yao H, Ye L, Zhang H, Li S, Zhang S, Hou J (2016) Chem Rev 116:7397
Cai Y, Huo L, Sun Y (2017) Adv Mater 29:1605437
Liu C, Wang K, Gong X, Heeger AJ (2016) Chem Soc Rev 45:4848
Gélinas S, Rao A, Kumar A, Smith SL, Chin AW, Clark J, van der Poll TS, Bazan GC, Friend RH (2014) Science 343:512
Zhang M, Guo X, Ma W, Ade H, Hou J (2014) Adv Mater 26:5880
Noh S, Gobalasingham NS, Thompson BC (2016) Macromolecules 49:6835
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
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
Su M-S, Kuo C-Y, Yuan M-C, Jeng US, Su C-J, Wei K-H (2011) Adv Mater 23:3315
Dou L, Chen C-C, Yoshimura K, Ohya K, Chang W-H, Gao J, Liu Y, Richard E, Yang Y (2013) Macromolecules 46:3384
Zhou N, Guo X, Ortiz RP, Li S, Zhang S, Chang RP, Facchetti A, Marks TJ (2012) Adv Mater 24:2242
Cao J, Liao Q, Du X, Chen J, Xiao Z, Zuo Q, Ding L (2013) Energy Environ Sci 6:3224
Li H, Cao J, Zhou Q, Ding L, Wang J (2015) Nano Energy 15:125
Cao JM, Qian L, Lu FT, Zhang JQ, Feng YQ, Qiu XH, Yip HL, Ding LM (2015) Chem Commun 51:11830
Hou JH, Park MH, Zhang SQ, Yao Y, Chen LM, Li JH, Yang Y (2008) Macromolecules 41:6012
Cui C, Wong W-Y (2016) Macromol Rapid Commun 37:287
Liang Y, Xu Z, Xia J, Tsai S-T, Wu Y, Li G, Ray C, Yu L (2010) Adv Mater 22:E135
Zhang C, Zhu X (2017) Acc Chem Res 50:1342
He Z, Zhong C, Su S, Xu M, Wu H, Cao Y (2012) Nat Photon 6:591
Liao S-H, Jhuo H-J, Cheng Y-S, Chen S-A (2013) Adv Mater 25:4766
Qu S, Wang H, Mo D, Chao P, Yang Z, Li L, Tian L, Chen W, He F (2017) Macromolecules 50:4962
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
He Z, Xiao B, Liu F, Wu H, Yang Y, Xiao S, Wang C, Russell TP, Cao Y (2015) Nat Photon 9:174
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
Cui C, Wong W-Y, Li Y (2014) Energy Environ Sci 7:2276
Cui C, He Z, Wu Y, Cheng X, Wu H, Li Y, Cao Y, Wong W-Y (2016) Energy Environ Sci 9:885
Ye L, Zhang S, Zhao W, Yao H, Hou J (2014) Chem Mater 26:3603
Zhang SQ, Ye L, Zhao WC, Yang B, Wang Q, Hou JH (2015) Sci China Chem 58:248
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
Duan C, Gao K, Colberts FJM, Liu F, Meskers SCJ, Wienk MM, Janssen RAJ (2017) Adv Energy Mater 1700519
Cabanetos C, El Labban A, Bartelt JA, Douglas JD, Mateker WR, Fréchet JMJ, McGehee MD, Beaujuge PM (2013) J Am Chem Soc 135:4656
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
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
Bin H, Zhang ZG, Gao L, Chen S, Zhong L, Xue L, Yang C, Li Y (2016) J Am Chem Soc 138:4657
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
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
Gao W, Liu T, Hao M, Wu K, Zhang C, Sun Y, Yang C (2016) Chem Sci 7:6167
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
Truong MA, Nakano K (2016) Bull Chem Soc Jpn 89:1034
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
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
Zhang A, Xiao C, Wu Y, Li C, Ji Y, Li L, Hu W, Wang Z, Ma W, Li W (2016) Macromolecules 49:6431
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
Chen H-J, Liu Z, Zhao Z, Zheng L, Tan S, Yin Z, Zhu C, Liu Y (2016) ACS Appl Mater Interfaces 8:33051
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
Perzon E, Zhang FL, Andersson M, Mammo W, Inganas O, Andersson MR (2007) Adv Mater 19:3308
Wang S, Kappl M, Liebewirth I, Müller M, Kirchhoff K, Pisula W, Müllen K (2012) Adv Mater 24:417
Lee YH, Park S, Oh S, Shin JW, Jung J, Yoo S, Lee MH (2017) ACS Appl Mater Interfaces. doi:10.1021/acsami.7b05615
Ban X, Zhu A, Zhang T, Tong Z, Jiang W, Sun Y (2017) ACS Appl Mater Interfaces. doi:10.1021/acsami.7b04146
Ohmori Y, Uchida M, Muro K, Yoshino K (1991) Solid State Commun 80:605
Tang W, Ke L, Tan L, Lin T, Kietzke T, Chen Z-K (2007) Macromolecules 40:6164
Osken I, Gundogan AS, Tekin E, Eroglu MS, Ozturk T (2013) Macromolecules 46:9202
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
Liu MS, Luo J, Jen AK-Y (2003) Chem Mater 15:3496
Mishra SP, Palai AK, Srivastava R, Kamalasanan MN, Patri M (2009) J Polym Sci Part A Polym Chem 47:6514
Evenson SJ, Mumm MJ, Pokhodnya KI, Rasmussen SC (2011) Macromolecules 44:835
Kostyanovsky VA, Susarova DK, Adam G, Lyubovskaya RN, Troshin PA (2013) Mendeleev Commun 23:26
Zhu Y, Gibbons KM, Kulkarni AP, Jenekhe SA (2007) Macromolecules 40:804
Sundararaman A, Victor M, Varughese R, Jäkle F (2005) J Am Chem Soc 127:13748
Yin X, Guo F, Lalancette RA, Jäkle F (2016) Macromolecules 49:537
Guo F, Yin X, Pammer F, Cheng F, Fernandez D, Lalancette RA, Jäkle F (2014) Macromolecules 47:7831
Mishra SP, Palai AK, Kumar A, Srivastava R, Kamalasanan MN, Patri M (2010) Macromol Chem Phys 211:1890
Sahin O, Cinar ME, Tekin E, Mucur SP, Topal S, Suna G, Eroglu MS, Ozturk T (2017) ChemistrySelect 2:2889
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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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DOI: https://doi.org/10.1007/s41061-017-0174-z