Skip to main content

Fused Thiophenes and Some Oligomers and Polymers Therefrom

  • Chapter
  • First Online:
Thiophenes

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 39))

Abstract

The main methodologies for the synthesis of fused thiophenes (thienothiophenes, dithienothiophenes, and thienoacenes) and some of their oligomers and polymers are described. Such compounds are particularly important in materials chemistry. They have applications in organic light-emitting diodes (OLEDs), organic field effect transistors (OFETs), (dye-sensitized) solar cells, and electrochromic devices (ECDs).

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 229.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD 299.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Katz HE, Bao Z, Gilat SL (2001) Acc Chem Res 34:359

    CAS  Google Scholar 

  2. Kang B, Lee WH, Cho K (2013) Appl Mater Inf 5:2302

    CAS  Google Scholar 

  3. Bundgaard E, Helgesen M, Carlé JE, Krebs FC, Jørgensen M (2013) Macromol Chem Phys 214:1546

    CAS  Google Scholar 

  4. Roncali J (1997) Chem Rev 97:173

    CAS  Google Scholar 

  5. Kertesz M, Choi CH, Yang S (2005) Chem Rev 105:3448

    CAS  Google Scholar 

  6. Skabara PJ (2009) Handbook of thiophene-based materials. In: Perepichka IF, Perepichka DF (eds) Wiley, Chichester, Chap. 3

    Google Scholar 

  7. Mishra A, Ma C-Q, Bäuerle P (2009) Chem Rev 109:1141

    CAS  Google Scholar 

  8. Ozturk T, Ertas E, Mert O (2005) Tetrahedron 61:11055

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  10. Wu Y, Wigglesworth A, Liu P (2013) CIPO application no C88L 65/00 (200601) Publication no CA 2797308/A1 (published June 06 2013)

    Google Scholar 

  11. Ra CS, Yim S, Park G (2008) Bull Korean Chem Soc 29:891

    CAS  Google Scholar 

  12. Ishii A, Nakayama J, Kazami J, Ida Y, Nakamura T, Hoshino M (1991) J Org Chem 56:78

    CAS  Google Scholar 

  13. Litvinov VP (2006) Adv Heterocycl Chem 90:125

    Google Scholar 

  14. Sotzing GA, Invernale MA, Ding Y (2013) US patent application no 13/606829 Publication no US 2013/0235323 A1

    Google Scholar 

  15. Fuller LS, Iddon B, Smith KA (1997) J Chem Soc Perkin Trans 1 22:3465

    Google Scholar 

  16. Faull AW, Hull R (1981) J Chem Soc Perkin Trans 1:1078

    Google Scholar 

  17. Heeney M, Wagner R, Mcculloch I, Tierney S (2005) WIPO PCT application no PCT/EP2005/004271 Publication no WO 2005/111,045 A1

    Google Scholar 

  18. Rutherford DR, Stille JK, Elliott CM, Reichert VR (1992) Macromolecules 25:2294

    CAS  Google Scholar 

  19. He M (2007) US Patent application no 11/711924 Publication no US 2007/0,161,776 A1

    Google Scholar 

  20. Heeney M, Bailey C, Genevicius K, Giles M, Shkunov M, Sparrowe D, Tierney S, Zhang W, McCulloch I (2005) Proc SPIE Int Soc Opt Eng 5940:594007/1

    CAS  Google Scholar 

  21. Hawkins DW, Iddon B, Longthorne DS, Rosyk PJ (1994) J Chem Soc Perkin Trans 1:2735

    Google Scholar 

  22. Prugh JD, Hartman GD, Mallorga PJ, McKeever BM, Michelson SR, Murcko MA, Schwam H, Smith RL, Sondey JM, Springer JP, Sugure FM (1991) J Med Chem 34:1805

    CAS  Google Scholar 

  23. Mazaki Y, Kobayashi K (1989) Tetrahedron Lett 30:3315

    CAS  Google Scholar 

  24. Henssler JT, Matzger AJ (2009) Org Lett 11:3144

    CAS  Google Scholar 

  25. Schroth W, Hintzsche E, Jordan H, Jende T, Spitzner R, Thondorf I (1997) Tetrahedron 53:7509

    CAS  Google Scholar 

  26. Harrowen DC (1983) Tetrahedron Lett 34:5653

    Google Scholar 

  27. Capozzi G, De Sio F, Menichetti S, Nativi C, Pacini PL (1994) Synthesis 521

    Google Scholar 

  28. Capan A, Veisi H, Goren AC, Ozturk T (2012) Macromolecules 45:8228

    CAS  Google Scholar 

  29. Kuszman J, Sohar P, Horvath G (1971) Tetrahedron 27:5055

    Google Scholar 

  30. Choi KS, Saeada K, Dong H, Hoshino M, Nakayama J (1994) Heterocycles 38:143

    CAS  Google Scholar 

  31. Kong H, Jung YK, Cho NS, Kang I-N, Park J-H, Cho S, Shim H-K (2009) Chem Mater 21:2650

    CAS  Google Scholar 

  32. Ito H, Yamamoto T, Yoshimoto N, Tsushima N, Muraoka H, Ogawa S (2013) Heteroatom Chem 24:25

    CAS  Google Scholar 

  33. San Miguel L, Porter WW, Matzger AJ (2007) Org Lett 9:1005

    CAS  Google Scholar 

  34. Leriche P, Raimundo J-M, Turbiez M, Monroche V, Allain M, Sauvage F-X, Roncali J, Frère P, Skabara PJ (2003) J Mater Chem 13:1324

    CAS  Google Scholar 

  35. Nakayama J, Dong H, Sawada K, Ishii A, Kumakura S (1996) Tetrahedron 52:471

    CAS  Google Scholar 

  36. Ahmed MO, Pisula W, Mhaisalkar SG (2012) Molecules 17:12163

    CAS  Google Scholar 

  37. Takamiya K, Ishikawa S, Adachi D, Oku S, Nagamatsu S, Takashima W, Hayase S, Kaneto K (2011) Physics Proc 14:182

    CAS  Google Scholar 

  38. Seidler A, Svoboda J, Dekoj V, Chocholoušová JV, Vacek J, Stará IG, Starý I (2013) Tetrahedron Lett 54:2795

    CAS  Google Scholar 

  39. Liu Y, Liu Q, Zhang X, Ai L, Wang Y, Peng R, Ge Z (2013) New J Chem 37:1189

    CAS  Google Scholar 

  40. Kim H-S, Kim Y-H, Kim T-H, Noh Y-Y, Pyo S, Yi MH, Kim D-Y, Kwon S-K (2007) Chem Mater 19:3561

    CAS  Google Scholar 

  41. Kim KH, Chi Z, Cho MJ, Jin JI, Cho MY, Kim SJ, Joo JS, Choi DH (2007) Chem Mater 19:4925

    CAS  Google Scholar 

  42. Lee B, Seshadri V, Palko H, Sotzing GA (2005) Adv Mater 17:1792

    Google Scholar 

  43. Zhang X, Köhler M, Matzger AJ (2004) Macromolecules 37:6306

    CAS  Google Scholar 

  44. Turbiez M, Frére P, Leriche P, Mercier N, Roncali J (2005) Chem Commun 1161

    Google Scholar 

  45. Poelking C, Cho E, Malafeev A, Ivanov V, Kremer K, Risko C, Brédas J-L, Andrienko D (2013) J Phys Chem C 117:1633

    CAS  Google Scholar 

  46. Schimperna G, Bianci G (2013) WIPO PCT application no PCT/IB2012/053927 Publication no WO 2013/021315 A1 (published Feb 14 2013)

    Google Scholar 

  47. Kawabata K, Takeguchi M, Goto H (2013) Macromolecules 46:2078

    CAS  Google Scholar 

  48. Li Y, Chen L, Chen Y, Li C, Zhang P, Gao L, Yang X, Tu Y, Zhu X (2013) Sol Energy Mater Sol Cells 108:136

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  50. Shahid M, McCarthy-Ward T, Labram J, Rossbauer S, Domingo EB, Watkins SE, Stingelin N, Anthopoulos TD, Heeney M (2012) Chem Sci 3:181

    CAS  Google Scholar 

  51. Wynberg H, Zwanenburg DJ (1967) Tetrahedron Lett 8:761

    Google Scholar 

  52. Huo L, Li Z, Guo X, Wu Y, Zhang M, Ye L, Zhang S, Hou J (2013) J Polym Chem 4:3047

    CAS  Google Scholar 

  53. Dey T, Navarathne D, Invernale MA, Berghorn ID, Sotzing GA (2010) Tetrahedron Lett 51:2089

    CAS  Google Scholar 

  54. Neef CJ, Brotherston ID, Ferraris JP (1999) Chem Mater 11:1957

    CAS  Google Scholar 

  55. Park JH, Seo YG, Yoon DH, Lee Y-S, Lee S-H, Pyo M, Zong K (2010) Eur Polym J 46:1790

    CAS  Google Scholar 

  56. Pomerantz M, Gu X (1997) Synth Met 84:243

    CAS  Google Scholar 

  57. Pomerantz M, Gu X, Zhang SX (2001) Macromolecules 34:1817

    CAS  Google Scholar 

  58. Fukazawa A, Kishi D, Tanaka Y, Seki S, Yamaguchi S (2013) Angew Chem Int Ed 52:12091

    CAS  Google Scholar 

  59. Lee B, Yavuz MS, Sotzing GA (2006) Macromolecules 39:3118

    CAS  Google Scholar 

  60. Lee B, Seshadri V, Sotzing GA (2005) Langmuir 21:10797

    CAS  Google Scholar 

  61. Patra A, Wijsboom YH, Leitus G, Bendikov M (2011) Chem Mater 23:896

    Google Scholar 

  62. Seshadri V, Wu L, Sotzing GA (2003) Langmuir 19:9479

    CAS  Google Scholar 

  63. Yun H-J, Hwang MC, Park SM, Kim R, Chung DS, Kim Y-H, Kwon S-K (2013) ACS Appl Mater Interfaces 5:6045

    CAS  Google Scholar 

  64. Son HJ, Wang W, Xu T, Liang Y, Wu Y, Li G, Yu L (2011) J Am Chem Soc 133:1885

    CAS  Google Scholar 

  65. Liang Y, Feng D, Wu Y, Tsai S-T, Li G, Ray C, Yu L (2009) J Am Chem Soc 131:7792

    CAS  Google Scholar 

  66. 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

    CAS  Google Scholar 

  67. de Jong RLP, Brandsma L (1991) Synth Commun 21:145

    Google Scholar 

  68. James DI, Smith J, Heeney M, Anthopoulos TD, Salleo A, McCulloch I (2012) In: Klauk H (ed) Organic electronics II: more materials and applications, 1st edn. Wiley-VCH Verlag GmbH & Co KGaA Weinheim

    Google Scholar 

  69. Heeney M, Bailey C, Tierney S, Mcculloch I (2006) WIPO PCT application no PCT/EP2005/008045 Publication no WO 2006/021,277 A1

    Google Scholar 

  70. Schneller SW, Petru JD (1974) Synth Commun 4:29

    CAS  Google Scholar 

  71. Gronowitz S, Maltesson B (1972) Acta Chem Scand 26:2982

    CAS  Google Scholar 

  72. Castle SL, Luo J-K, Kudo H, Castle RN, Lee ML (1988) J Heterocycl Chem 25:1363

    CAS  Google Scholar 

  73. Mashraqui SH, Hariharasubrahmanin H, Kumar S (1999) Synthesis 2030

    Google Scholar 

  74. El-Saghier AMM (1993) Bull Chem Soc Jpn 66:2011

    CAS  Google Scholar 

  75. Comel A, Kirsch G (2001) J Heterocycl Chem 38:1167

    CAS  Google Scholar 

  76. Hergué N, Frère P (2007) Org Biomol Chem 5:3442

    Google Scholar 

  77. Heeney M, Bailey C, Genevicius K, Shkunov M, Sparrowe D, Tierney S, McCulloch I (2005) J Am Chem Soc 127:1078

    CAS  Google Scholar 

  78. Dopper JH, Oudman D, Wynberg H (1973) J Am Chem Soc 95:3692

    CAS  Google Scholar 

  79. El-Shafei AK, El-Saghier MM, Sultan AA, Soliman AM (1992) Phosphorus Sulfur Silicon Relat Elem 73:73

    Google Scholar 

  80. Fuchigami T, Kandeel ZE, Nonaka T, Tien HJ (1986) J Chin Chem Soc (Taipei) 33:241

    CAS  Google Scholar 

  81. Cava MP, Lakshmikantham MV (1975) Acc Chem Res 8:139

    CAS  Google Scholar 

  82. Cava MP, Lakshmikantham MV (1984) In: Bird CW, Cheeseman GWH (eds) Comprehensive heterocyclic chemistry, vol 4. Pergamon, New York, p 1037

    Google Scholar 

  83. Beye N, Cava MP (1994) J Org Chem 59:2223

    CAS  Google Scholar 

  84. Nakayama J, Ishii A, Kobayashi Y, Hoshino M (1988) J Chem Soc Chem Commun 959

    Google Scholar 

  85. Cava MP, Pollack NM (1967) J Am Chem Soc 89:3639

    CAS  Google Scholar 

  86. Cava MP, Pollack NM, Dieterle GA (1973) J Am Chem Soc 95:2558

    CAS  Google Scholar 

  87. Cava MP, Husbands GEM (1969) J Am Chem Soc 91:3952

    CAS  Google Scholar 

  88. Cava MP, Behforouz M, Husbands GEM, Srinivasan M (1973) J Am Chem Soc 95:2561

    CAS  Google Scholar 

  89. Ozturk T, Ertas E, Mert O (2010) Chem Rev 110:3419

    CAS  Google Scholar 

  90. Amaresh RR, Lakshmikantham ML, Geng R, Cava MP (2000) Tetrahedron Lett 41:8843

    CAS  Google Scholar 

  91. Amaresh RR, Lakshmikantham ML, Baldwin JW, Cava MP, Metzger RM, Rogers RD (2002) J Org Chem 67:2453

    CAS  Google Scholar 

  92. Yoneda S, Ozaki K, Tsubouchi A, Kojima H, Yanagi K, Minobe M (1985) J Am Chem Soc 107:5801

    CAS  Google Scholar 

  93. Yoneda S, Ozaki K, Tsubouchi A, Kojima H, Yanagi K (1988) J Heterocycl Chem 25:559

    CAS  Google Scholar 

  94. Jørgensen M, Norrman K, Gevorgyan SA, Tromholt T, Andreasen B, Krebs FC (2012) Adv Mater 24:580

    Google Scholar 

  95. De Jong F, Janssen MJ (1971) J Org Chem 36:1645

    Google Scholar 

  96. Ertas E, Ozturk T (2004) Tetrahedron Lett 45:3405

    CAS  Google Scholar 

  97. Osken I, Bildirir H, Ozturk T (2011) Thin Solid Films 519:7707

    CAS  Google Scholar 

  98. Osken I, Sahin O, Gundogan AS, Bildirir H, Capan A, Ertas E, Eroglu MS, Wallis JD, Topal K, Ozturk T (2012) Tetrahedron 68:1216

    CAS  Google Scholar 

  99. Hong W, Yuan H, Li H, Yang X, Gao X, Zhu D (2011) Org Lett 13:1410

    CAS  Google Scholar 

  100. Helberg J, Remonen T (1995) Synth Met 70:1137

    Google Scholar 

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

    CAS  Google Scholar 

  102. Cicoira F, Santato C, Melucci M, Favaretto L, Gazzano M, Muccini M, Barbarella G (2006) Adv Mater 18:169

    CAS  Google Scholar 

  103. Arbizzani C, Catellani M, Mastragostino M, Cerroni MG (1997) J Electroanal Chem 423:23

    CAS  Google Scholar 

  104. Mert O, Sahin E, Ertas E, Ozturk T, Aydin EA, Toppare L (2006) J Electroanal Chem 591:53

    CAS  Google Scholar 

  105. Ates M, Osken I, Ozturk T (2012) J Electrochem Soc 159:E115

    CAS  Google Scholar 

  106. Ozen C, Yurtsever M, Ozturk T (2011) Tetrahedron Lett 67:6275

    CAS  Google Scholar 

  107. Fujitsuka M, Sato T, Segawa H, Shimidzu T (1995) Synth Met 69:309

    CAS  Google Scholar 

  108. Fujitsuka M, Sato T, Shimidzu T, Watanabe A, Ito O (1997) J Phys Chem A 101:1056

    CAS  Google Scholar 

  109. Luzzati S, Basso M, Catellani M, Brabec CJ, Gebeyehu D, Sarifictci NS (2002) Thin Solid Films 403–404:52

    Google Scholar 

  110. Catellani M, Boselli B, Luzzati S, Tripodi C (2002) Thin Solid Films 403–404:66

    Google Scholar 

  111. Neo WT, Cho CM, Song J, Chin JM, Wang X, He C, Chan HSO, Xu J (2013) Eur Polym J 49:2446

    CAS  Google Scholar 

  112. Wang T-L, Shieh Y-T, Yang C-H, Chen Y-Y, Ho T-H, Chen C-H (2013) J Polym Res 20:213

    Google Scholar 

  113. Li J, Ong K-H, Sonar P, Lim S-L, Ng G-M, Wong H-K, Tan H-S, Chen Z-K (2013) Polym Chem 4:804

    CAS  Google Scholar 

  114. Lee C-Y, Kim B, Kim KH, Yoon Y, Lee MW, Choi DH, Ko MJ, Kim H, Lee D-K, Kim K (2013) Synth Met 164:64

    CAS  Google Scholar 

  115. Seah KY, Li J, Ong K-H, Tan H-S, Lim S-L, Wong H-K, Chen Z-K (2013) Polym Chem 4:260

    CAS  Google Scholar 

  116. Li Z, Malenfant P, Tao Y, Ding J (2013) Macromol Chem Phys 214:447

    CAS  Google Scholar 

  117. Balan B, Vijayakumar C, Saeki A, Koizumi Y, Tsujia M, Seki S (2013) Polym Chem 4:2293

    CAS  Google Scholar 

  118. Iyoda M, Miura M, Sasaki S, Kabir SMH, Kuwatani Y, Yoshida M (1997) Tetrahedron Lett 38:4581

    CAS  Google Scholar 

  119. Kabir SMH, Miura M, Sasaki S, Harada G, Kuwatani Y, Yoshida M, Iyoda M (2000) Heterocycles 52:761

    CAS  Google Scholar 

  120. Ohmae T, Nishinaga T, Wu M, Iyoda M (2010) J Am Chem Soc 132:1066

    CAS  Google Scholar 

  121. Taliani C, Ruani G, Zamboni R, Bolognesi A, Catellani M, Destri S, Porzio W, Ostoja P (1989) Synth Met 28:C507

    CAS  Google Scholar 

  122. Bolognesi A, Catellani M, Destri S, Ferro DR, Porzio W, Taliani C, Zamboni R, Ostroga P (1989) Synth Met 28:C527

    CAS  Google Scholar 

  123. Quattrocchi C, Lazzaroni R, Bredas JL, Zamboni R, Taliani C (1993) Synth Met 55–57:4399

    Google Scholar 

  124. Quattrocchi C, Lazzaroni R, Bredas JL, Zamboni R, Taliani C (1993) Macromolecules 26:1260

    CAS  Google Scholar 

  125. Inaoka S, Collard DM (1997) Synth Met 84:193

    CAS  Google Scholar 

  126. Pandya LJ, Tilak BD (1958) Chem Ind 981

    Google Scholar 

  127. Taskiran Cankaya S, Capan A, Cinar ME, Akin E, Topal S, Ozturk T (2013) J Sulfur Chem 34:638

    Google Scholar 

  128. Tan L, Zhang L, Jiang X, Yang X, Wang L, Wang Z, Li L, Hu W, Shuai Z, Li L, Zhu D (2009) Adv Funct Mater 19:272

    CAS  Google Scholar 

  129. Zhang L, Tan L, Wang Z, Hu W, Zhu D (2009) Chem Mater 21:1993

    Google Scholar 

  130. Shi J, Xu L, Li Y, Jia M, Kan Y, Wang H (2013) Org Electron 14:934

    CAS  Google Scholar 

  131. De Jong F, Janssen MJ (1971) J Org Chem 36:1998

    Google Scholar 

  132. Arbizzani C, Catellani M, Cerroni MG, Mastragostino M (1997) Synth Met 84:249

    CAS  Google Scholar 

  133. Arbizzani C, Cerroni MG, Mastragostino M (1999) Sol Energ Mat Sol C 56:205

    CAS  Google Scholar 

  134. Zhang X, Côtè AP, Matzger AJ (2005) J Am Chem Soc 127:10502

    CAS  Google Scholar 

  135. Shaw CM, Zhang X, Miguel LS, Matzger AJ, Martin DC (2013) J Mater Chem C 1:3686

    CAS  Google Scholar 

  136. He M, Zhang F (2007) J Org Chem 72:442

    CAS  Google Scholar 

  137. He M (2013) US Patent application no 12/905,667 Patent no US 8,389,669 B2 (published Mar 5 2013)

    Google Scholar 

  138. He M, Li J, Matthews JR, Niu W, Wallace AL (2013) WIPO PCT patent application no PCT/US 2012/062012 Publication no WO 2013/066732 A1 (published Oct 226 2013)

    Google Scholar 

  139. Okamoto T, Kudoh K, Wakamiya A, Yamaguchi S (2007) Chem Eur J 13:548

    CAS  Google Scholar 

  140. Okamoto T, Kudoh K, Wakamiya A, Yamaguchi S (2005) Org Lett 7:5301

    CAS  Google Scholar 

  141. Yamaguchi S, Xu C, Okamoto T (2006) Pure Appl Chem 78:721

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Turan Ozturk .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2014 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Cinar, M.E., Ozturk, T. (2014). Fused Thiophenes and Some Oligomers and Polymers Therefrom. In: Joule, J. (eds) Thiophenes. Topics in Heterocyclic Chemistry, vol 39. Springer, Cham. https://doi.org/10.1007/7081_2014_129

Download citation

Publish with us

Policies and ethics