Skip to main content
SpringerLink
Log in

Noncovalent conformational locks in organic semiconductors

  • Mini Reviews
  • Published:
Science China Chemistry Aims and scope Submit manuscript

Abstract

Highly planar conformation is considered to be one of the most important properties for high performance organic semiconductors. Among all kinds strategies for designing highly performing materials, noncovalent conformational locks (NCLs) have been widely used to increase the planarity and rigidity for π-conjugated systems. This review summarizes π-conjugated small molecules and polymers by employing various NCLs for controlling molecular conformation in the past two years. The optoelectronic properties of the conjugated materials, together with their applications on organic field-effect transistors (OFETs) and organic photovoltaics (OPVs) are discussed. Besides, the outlook and challenges in this field are also presented. It is obvious that NCLs play an important role in the design and synthesis of high-performance organic semiconductors.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. He Z, Xiao B, Liu F, Wu H, Yang Y, Xiao S, Wang C, Russell TP, Cao Y. Nat Photon, 2015, 9: 174–179

    Article  CAS  Google Scholar 

  2. Lin H, Chen S, Li Z, Lai JYL, Yang G, McAfee T, Jiang K, Li Y, Liu Y, Hu H, Zhao J, Ma W, Ade H, Yan H. Adv Mater, 2015, 27: 7299–7304

    Article  CAS  PubMed  Google Scholar 

  3. Park SH, Roy A, Beaupré S, Cho S, Coates N, Moon JS, Moses D, Leclerc M, Lee K, Heeger AJ. Nat Photon, 2009, 3: 297–302

    Article  CAS  Google Scholar 

  4. Facchetti A. Mater Today, 2013, 16: 123–132

    Article  CAS  Google Scholar 

  5. Hu Z, Ying L, Huang F, Cao Y. Sci China Chem, 2017, 60: 571–582

    Article  CAS  Google Scholar 

  6. Xue X, Liu T, Meng X, Sun X, Huo L, Ma W, Sun Y. Sci China Chem, 2017, 60: 243–250

    Article  CAS  Google Scholar 

  7. Zhang H, Liu Y, Sun Y, Li M, Ni W, Zhang Q, Wan X, Chen Y. Sci China Chem, 2017, 60: 366–369

    Article  CAS  Google Scholar 

  8. Zhu C, Fang L. Macromol Rapid Commun, 2017, 39: 1700241

    Article  CAS  Google Scholar 

  9. Tsuda A, Osuka A. Science, 2001, 293: 79–82

    Article  CAS  PubMed  Google Scholar 

  10. Samiullah M, Moghe D, Scherf U, Guha S. Phys Rev B, 2010, 82: 205211

    Article  CAS  Google Scholar 

  11. Briseno AL, Mannsfeld SCB, Shamberger PJ, Ohuchi FS, Bao Z, Jenekhe SA, Xia Y. Chem Mater, 2008, 20: 4712–4719

    Article  CAS  Google Scholar 

  12. McCullough RD, Lowe RD, Jayaraman M, Anderson DL. J Org Chem, 1993, 58: 904–912

    Article  CAS  Google Scholar 

  13. Qin R, Li W, Li C, Du C, Veit C, Schleiermacher HF, Andersson M, Bo Z, Liu Z, Inganas O, Wuerfel U, Zhang F. J Am Chem Soc, 2009, 131: 14612–14613

    Article  CAS  PubMed  Google Scholar 

  14. Huang H, Zhou N, Ortiz RP, Chen Z, Loser S, Zhang S, Guo X, Casado J, López Navarrete JT, Yu X, Facchetti A, Marks TJ. Adv Funct Mater, 2014, 24: 2782–2793

    Article  CAS  Google Scholar 

  15. Roncali J. Macromol Rapid Commun, 2007, 28: 1761–1775

    Article  CAS  Google Scholar 

  16. Usta H, Lu G, Facchetti A, Marks TJ. J Am Chem Soc, 2006, 128: 9034–9035

    Article  CAS  PubMed  Google Scholar 

  17. Usta H, Risko C, Wang Z, Huang H, Deliomeroglu MK, Zhukhovitskiy A, Facchetti A, Marks TJ. J Am Chem Soc, 2009, 131: 5586–5608

    Article  CAS  PubMed  Google Scholar 

  18. Huang H, Chen Z, Ponce Ortiz R, Newman C, Usta H, Lou S, Youn J, Noh YY, Baeg KJ, Chen LX, Facchetti A, Marks TJ, Marks T. J Am Chem Soc, 2012, 134: 10966–10973

    Article  CAS  PubMed  Google Scholar 

  19. Jackson NE, Savoie BM, Kohlstedt KL, Olvera de la Cruz M, Schatz GC, Chen LX, Ratner MA. J Am Chem Soc, 2013, 135: 10475–10483

    Article  CAS  PubMed  Google Scholar 

  20. Hayashi K, Ogawa S, Sano S, Shiro M, Yamaguchi K, Sei Y, Nagao Y. Chem Pharm Bull, 2008, 56: 802–806

    Article  CAS  PubMed  Google Scholar 

  21. Sakamoto Y, Komatsu S, Suzuki T. J Am Chem Soc, 2001, 123: 4643–4644

    Article  CAS  PubMed  Google Scholar 

  22. Hergué N, Leriche P, Blanchard P, Allain M, Gallego-Planas N, Frère P, Roncali J. New J Chem, 2008, 32: 932

    Article  CAS  Google Scholar 

  23. Huang H, Yang L, Facchetti A, Marks TJ. Chem Rev, 2017, 117: 10291–10318

    Article  CAS  PubMed  Google Scholar 

  24. Mishra A, Bäuerle P. Angew Chem Int Ed, 2012, 51: 2020–2067

    Article  CAS  Google Scholar 

  25. Sirringhaus H. Adv Mater, 2014, 26: 1319–1335

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  26. Ni W, Wan X, Li M, Wang Y, Chen Y. Chem Commun, 2015, 51: 4936–4950

    Article  CAS  Google Scholar 

  27. Liu Y, Zhang Z, Feng S, Li M, Wu L, Hou R, Xu X, Chen X, Bo Z. J Am Chem Soc, 2017, 139: 3356–3359

    Article  CAS  PubMed  Google Scholar 

  28. Zhang Z, Li M, Liu Y, Zhang J, Feng S, Xu X, Song J, Bo Z. J Mater Chem A, 2017, 5: 7776–7783

    Article  CAS  Google Scholar 

  29. Li S, Zhan L, Liu F, Ren J, Shi M, Li CZ, Russell TP, Chen H. Adv Mater, 2018, 30: 1705208

    Article  CAS  Google Scholar 

  30. Yu S, Chen Y, Yang L, Ye P, Wu J, Yu J, Zhang S, Gao Y, Huang H. J Mater Chem A, 2017, 5: 21674–21678

    Article  CAS  Google Scholar 

  31. Ye P, Chen Y, Wu J, Wu X, Yu S, Xing W, Liu Q, Jia X, Peng A, Huang H. J Mater Chem C, 2017, 5: 12591–12596

    Article  CAS  Google Scholar 

  32. Yang L, Gu W, Yang Y, Hong L, Zhang X, Xiao Y, Wu X, Peng A, Huang H. Small Methods, 2018, 2: 1700330

    Article  CAS  Google Scholar 

  33. Qiu Z, Xu X, Zhang S, Wang P, Wang Y, Pei Y, Peng Q, Liu Y. Dyes Pigments, 2017, 147: 505–513

    Article  CAS  Google Scholar 

  34. Jo JW, Jung JW, Wang HW, Kim P, Russell TP, Jo WH. Chem Mater, 2014, 26: 4214–4220

    Article  CAS  Google Scholar 

  35. Zhang W, Shi K, Huang J, Gao D, Mao Z, Li D, Yu G. Macromolecules, 2016, 49: 2582–2591

    Article  CAS  Google Scholar 

  36. Yum S, An TK, Wang X, Lee W, Uddin MA, Kim YJ, Nguyen TL, Xu S, Hwang S, Park CE, Woo HY. Chem Mater, 2014, 26: 2147–2154

    Article  CAS  Google Scholar 

  37. Lei T, Xia X, Wang JY, Liu CJ, Pei J. J Am Chem Soc, 2014, 136: 2135–2141

    Article  CAS  PubMed  Google Scholar 

  38. Zhang W, Mao Z, Chen Z, Huang J, Wei C, Gao D, Lin Z, Li H, Wang L, Yu G. Polym Chem, 2017, 8: 879–889

    Article  CAS  Google Scholar 

  39. Zhang W, Mao Z, Huang J, Gao D, Yu G. Macromolecules, 2016, 49: 6401–6410

    Article  CAS  Google Scholar 

  40. Lei T, Cao Y, Fan Y, Liu CJ, Yuan SC, Pei J. J Am Chem Soc, 2011, 133: 6099–6101

    Article  CAS  PubMed  Google Scholar 

  41. Wang E, Mammo W, Andersson MR. Adv Mater, 2014, 26: 1801–1826

    Article  CAS  PubMed  Google Scholar 

  42. Yang J, Zhao Z, Geng H, Cheng C, Chen J, Sun Y, Shi L, Yi Y, Shuai Z, Guo Y, Wang S, Liu Y. Adv Mater, 2017, 29: 1702115

    Article  CAS  Google Scholar 

  43. Gao Y, Deng Y, Tian H, Zhang J, Yan D, Geng Y, Wang F. Adv Mater, 2017, 29: 1606217

    Article  CAS  Google Scholar 

  44. Vegiraju S, Chang BC, Priyanka P, Huang DY, Wu KY, Li LH, Chang WC, Lai YY, Hong SH, Yu BC, Wang CL, Chang WJ, Liu CL, Chen MC, Facchetti A. Adv Mater, 2017, 29: 1702414

    Article  CAS  Google Scholar 

  45. Dong T, Lv L, Feng L, Xia Y, Deng W, Ye P, Yang B, Ding S, Facchetti A, Dong H, Huang H. Adv Mater, 2017, 29: 1606025

    Article  CAS  Google Scholar 

  46. Park GE, Choi S, Shin J, Cho MJ, Choi DH. Org Electron, 2016, 34: 157–163

    Article  CAS  Google Scholar 

  47. Zhou Y, Li M, Guo Y, Lu H, Song J, Bo Z, Wang H. ACS Appl Mater Interfaces, 2016, 8: 31348–31358

    Article  CAS  PubMed  Google Scholar 

  48. Shi S, Liao Q, Tang Y, Guo H, Zhou X, Wang Y, Yang T, Liang Y, Cheng X, Liu F, Guo X. Adv Mater, 2016, 28: 9969–9977

    Article  CAS  PubMed  Google Scholar 

  49. Guo X, Kim FS, Jenekhe SA, Watson MD. J Am Chem Soc, 2009, 131: 7206–7207

    Article  CAS  PubMed  Google Scholar 

  50. Guo X, Quinn J, Chen Z, Usta H, Zheng Y, Xia Y, Hennek JW, Ortiz RP, Marks TJ, Facchetti A. J Am Chem Soc, 2013, 135: 1986–1996

    Article  CAS  PubMed  Google Scholar 

  51. Huang J, Tang Y, Gao K, Liu F, Guo H, Russell TP, Yang T, Liang Y, Cheng X, Guo X. Macromolecules, 2016, 50: 137–150

    Article  CAS  Google Scholar 

  52. Li Y, Lee TH, Park SY, Uddin MA, Kim T, Hwang S, Kim JY, Woo HY. Polym Chem, 2016, 7: 4638–4646

    Article  CAS  Google Scholar 

  53. Li Y, Lee TH, Kim J, Park SY, Song S, Hwang S, Kim JY, Woo HY. J Photopol Sci Technol, 2016, 29: 553–559

    Article  CAS  Google Scholar 

  54. Jeon SJ, Nam SJ, Han YW, Lee TH, Moon DK. Polym Chem, 2017, 8: 2979–2989

    Article  CAS  Google Scholar 

  55. Lee J, Ko H, Song E, Kim HG, Cho K. ACS Appl Mater Interfaces, 2015, 7: 21159–21169

    Article  CAS  PubMed  Google Scholar 

  56. Kini GP, Hoang QV, Song CE, Lee SK, Shin WS, So WW, Uddin MA, Woo HY, Lee JC. Polym Chem, 2017, 8: 3622–3631

    Article  CAS  Google Scholar 

  57. Lv L, Wang X, Dong T, Wang X, Wu X, Yang L, Huang H. Mater Chem Front, 2017, 1: 1317–1323

    Article  CAS  Google Scholar 

  58. Rosenfield RE, Parthasarathy R, Dunitz JD. J Am Chem Soc, 1977, 99: 4860–4862

    Article  CAS  Google Scholar 

  59. Pomerantz M, Cheng Y. Tetrahedron Lett, 1999, 40: 3317–3320

    Article  CAS  Google Scholar 

  60. Cheng Y, Qi Y, Tang Y, Zheng C, Wan Y, Huang W, Chen R. J Phys Chem Lett, 2016, 7: 3609–3615

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

This work was supported by the National Natural Science Foundation of China (21774130, 21574135), Beijing Municipal Natural Science Foundation (2162043), the Key Research Program of Frontier Science, Chinese Academy of Sciences (QYZDB-SSW-JSC046), Key Research Program of the Chinese Academy of Sciences (XDPB08-2), One Hundred Talents Program of Chinese Academy of Sciences, and University of Chinese Academy of Sciences.

Author information

Authors and Affiliations

  1. College of Materials Science and Opto-Electronic Technology & Key Laboratory of Vacuum Physic, University of Chinese Academy of Sciences, Beijing, 100049, China

    Simiao Yu, Aidong Peng & Hui Huang

  2. Key Laboratory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM), Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing, 211816, China

    Simiao Yu & Shiming Zhang

Authors
  1. Simiao Yu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Aidong Peng
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Shiming Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hui Huang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Aidong Peng, Shiming Zhang or Hui Huang.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yu, S., Peng, A., Zhang, S. et al. Noncovalent conformational locks in organic semiconductors. Sci. China Chem. 61, 1359–1367 (2018). https://doi.org/10.1007/s11426-018-9315-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11426-018-9315-2

Keywords

Search

Navigation