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Crystal growth and characterization of fluorinated perylene diimides

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Abstract

One-dimensional crystals of fluorinated perylene diimides were achieved by the self-assembly of them via solvent-nonsolvent exchanging. The π-conjugated fluorinated perylene diimides were assembled into highly-ordered nanostructures of well-defined morphologies in organic solvents due to the π-π interaction between the aromatic cores. It was found that with more introduced F atoms, perylene diimides showed remarkably improved solubility and thus were much easier to grow into crystals, due to the increased polarity induced by the strong electron-withdrawing F group. More importantly, single crystal of N,N′-diperfluorophenyl-3,4,9,10-perylenetetracarboxylic diimide(DPFPP) was obtained, and the unit cell-dimensions of triclinic structure were determined by the selected area electron diffraction( SAED) patterns to be a=0.712 nm, b=1.072 nm, c=2.914 nm, α=97.0°, β=89.6°, γ=93.4°. Owing to most of the longest c-axis orienting nearly vertically to the long axis of the needle crystal, the molecular planes are expected to be vertical to the needle axis.

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References

  1. Sekitani T., Nakajima H., Maeda H., Fukushima T., Aida T., Hata K., Someya T., Nat. Mater., 2009, 8, 494

    Article  CAS  Google Scholar 

  2. Gelinck G. H., Huitema H. E. A., Veenendaal E., Cantatore E., Schrijnemakers L., Putten J. B. P. H., Geuns T. C. T., Beenhakkers M., Giesbers J. B., Huisman B. H., Meijer E. J., Benito E. M., Touwslager F. J., Marsman A. W., Rens B. J. E., Leeuw D. M., Nat. Mater., 2004, 3, 106

    Article  CAS  Google Scholar 

  3. Sekitani T., Yokota T., Zschieschang U., Klauk H., Bauer S., Takeuchi K., Takamiya M., Sakurai T., Someya T., Science, 2009, 326, 1516

    Article  CAS  Google Scholar 

  4. Sokolov A. N., Roberts M. E., Johnson O. B., Cao Y., Bao Z., Adv. Mater., 2010, 22, 2349

    Article  CAS  Google Scholar 

  5. Spijkman M. J., Brondijk J. J., Geuns T. C. T., Smits E. C. P., Cramer T., Zerbetto F., Stoliar P., Biscarini F., Blom P. W. M., Leeuw D. M., Adv. Funct. Mater., 2010, 20, 898

    Article  CAS  Google Scholar 

  6. Qu Y., Hua J., Tian H., Org. Lett., 2010, 12, 3320

    Article  CAS  Google Scholar 

  7. Yamagata T., Kuwabara J., Kanbara T., Tetrahedron Lett., 2010, 51, 1596

    Article  CAS  Google Scholar 

  8. Deng L., Wu W., Guo H., Zhao J., Ji S., Zhang X., Yuan X., Zhang C., J. Org. Chem., 2011, 76, 9294

    Article  CAS  Google Scholar 

  9. You J., Dou L., Yoshimura K., Liu Q. S., Zhu G. S., Sun F. X., Nat. Commun., 2013, 4, 1446

    Article  Google Scholar 

  10. Li Y. F., Acc. Chem. Res., 2012, 45(5), 723

    Article  CAS  Google Scholar 

  11. Lin Y., Li Y. F., Zhan X. W., Chem. Soc. Rev., 2012, 41, 4245

    Article  CAS  Google Scholar 

  12. Sun Y., Welch G. C., Leong W. L., Takacs C. J., Bazan G. C., Heeger A. J., Nat. Mater., 2012, 11, 44

    Article  CAS  Google Scholar 

  13. He Z., Zhong C., Su S., Xu M., Wu H., Cao Y., Nature Photonics, 2012, 6, 591

    Google Scholar 

  14. Sonar P., Ng G. M., Lin T. T., Dodabalapur A., Chen Z. K., Mater. Chem., 2010, 20, 3626

    Article  CAS  Google Scholar 

  15. Karsten B. P., Bijleveld J. C., Janssen R. A. J., Macromol. Rapid Commun., 2010, 31, 1554

    Article  CAS  Google Scholar 

  16. Lin Y., Cheng P., Li Y., Zhan X., Chem. Commun., 2012, 48, 4773

    Article  CAS  Google Scholar 

  17. Walker B., Kim C., Nguyen T. Q., Chem. Mater., 2011, 23, 470

    Article  CAS  Google Scholar 

  18. Hu X. L., Shi M. M., Zuo L. J., Fu L., Dai S. L., Chen H. Z., Acta Chim. Sin., 2011, 69, 673

    CAS  Google Scholar 

  19. Li B., Chem. J. Chinese Universities, 2013, 34(2), 429

    CAS  Google Scholar 

  20. Li H. Y., Tee B. C. K., Giri G., Chung J. W., Lee S. Y., Bao Z., Adv. Mater., 2012, 24, 2588

    Article  CAS  Google Scholar 

  21. Sundar V. C., Zaumseil J., Podzorov V., Menard E., Willett R. L., Someya T., Gershenson M. E., Rogers J. A., Science, 2004, 303, 1644

    Article  CAS  Google Scholar 

  22. Sirringhaus H., Adv. Mater., 2005, 17, 2411

    Article  CAS  Google Scholar 

  23. Wang C. L., Dong H. L., Hu W. P., Liu Y. Q., Zhu D. B., Chem. Rev., 2012, 112, 2208

    Article  CAS  Google Scholar 

  24. Allard S., Forster M., Souharce B., Thiem H., Scherf U., Angew. Chem. Int. Ed., 2008, 47, 4070

    Article  CAS  Google Scholar 

  25. Du S. S., Zhao C. B., Ma Y., Wang W. L., Chem. J. Chinese Universities, 2013, 34(1), 161

    CAS  Google Scholar 

  26. Zang L., Che Y., Moore J. S., Acc. Chem. Res., 2008, 41, 1596

    Article  CAS  Google Scholar 

  27. Li W. S., Saeki A., Yamamoto Y., Fukushima T., Seki S., Ishii N., Kato K., Takata M., Aida T., Chem. Asian J., 2010, 5, 1566

    Article  CAS  Google Scholar 

  28. Li R., Hu W., Liu Y., Zhu D., Acc. Chem. Res., 2010, 43, 529

    Article  CAS  Google Scholar 

  29. Li Z., Xu F., Chin. J. Chem., 2005, 23, 337

    Article  CAS  Google Scholar 

  30. Li H. Y., Giri G., Tok J. B. H., Bao Z., MRS Bull., 2013, 38, 34

    Article  Google Scholar 

  31. Li H. Y., Tee B. C. K., Cha J. J., Cui Y., Chung J. W., Lee S. Y., Bao Z., J. Am. Chem. Soc., 2012, 134, 2760

    Article  CAS  Google Scholar 

  32. Akkerman H. B., Chang A. C., Verploegen E., Bettinger C. J., Toney M. F., Bao Z., Organic Electronics, 2012, 13, 235

    Article  CAS  Google Scholar 

  33. Podzorov V., Menard E., Borissov A., Kiryukhin V., Rogers J. A., Gershenson M. E., Phys. Rev. Lett., 2004, 93, 086602

    Article  CAS  Google Scholar 

  34. Jurchescu O. D., Baas J., Palstra T. T., Appl. Phys. Lett., 2004, 84, 3061

    Article  CAS  Google Scholar 

  35. Hasegawa T., Takeya J., Sci. Technol. Adv. Mater., 2009, 10, 024314

    Article  Google Scholar 

  36. Pfattner R., Mas-Torrent M., Bilotti I., Brillante A., Milita S., Liscio F., Biscarini F., Marszalek T., Ulanski J., Nosal A., Gazicki-Lipman M., Leufgen M., Schmidt G., Molenkamp L. W., Laukhin V., Veciana J., Rovira C., Adv. Mater., 2010, 22, 4198

    Article  CAS  Google Scholar 

  37. Wen Y., Liu Y., Adv. Mater., 2010, 22, 1331

    Article  CAS  Google Scholar 

  38. Anthony J. E., Facchetti A., Heeney M., Marder S. R., Zhan X., Adv. Mater., 2010, 22, 3876

    Article  CAS  Google Scholar 

  39. Che Y., Datar A., Balakrishnan K., Zang L., J. Am. Chem. Soc., 2007, 129, 7234

    Article  CAS  Google Scholar 

  40. Balakrishnan K., Datar A., Naddo T., Huang J., Oitker R., Yen M., Zhao J., Zang L., J. Am. Chem. Soc., 2006, 128, 7390

    Article  CAS  Google Scholar 

  41. Balakrishnan K., Datar A., Oitker R., Chen H., Zuo J. M., Zang L., J. Am. Chem. Soc., 2005, 127, 10496

    Article  CAS  Google Scholar 

  42. Wurthner F., Chem. Commun., 2004, 14, 1564

    Article  Google Scholar 

  43. Newman C. R., Frisbie C. D., da Silva D. A., Bredas J. L., Ewbank P. C., Mann K. R., Chem. Mater., 2004, 16, 4436

    Article  CAS  Google Scholar 

  44. Oh J. H., Lee H. W., Mannsfeld S., Stoltenberg R. M., Jung E., Jin Y. W., Kim J. M., Yoo J. B., Bao Z., PNAS, 2009, 106(15), 6065

    Article  CAS  Google Scholar 

  45. Chen H. Z., Ling M. M., Mo X., Shi M. M., Wang M., Bao Z., Chem. Mater., 2007, 19, 816

    Article  CAS  Google Scholar 

  46. Shi M. M., Chen H. Z., Wang M., Acta Chim. Sin., 2006, 64, 721

    CAS  Google Scholar 

  47. Huang J. C., Yang L. G., Mo X., Shi M. M., Wang M., Chen H. Z., Acta Chim. Sin., 2007, 65, 1051

    CAS  Google Scholar 

  48. Shi M. M., Chen H. Z., Sun J. Z., Ye J., Wang M., Chem. Commun., 2003, 14, 1710

    Article  Google Scholar 

  49. Katz H. E., Johnson J., Lovinge A. J., Li W., J. Am. Chem. Soc., 2000, 122, 7787

    Article  CAS  Google Scholar 

  50. Katz H. E., Lovinger A. J., Johnson J., Kloc C., Siegrist T., Li W., Lin Y. Y., Dodabalapur A., Nature, 2000, 404, 478

    Article  CAS  Google Scholar 

  51. Che Y., Yang X., Loser S., Zang L., Nano Lett., 2008, 8(8), 2219

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. State Key Laboratory of Silicon Materials, Key Laboratory of Macromolecular Synthesis and Functionalization, Ministry of Education, Department of Polymer Science and Engineering, Zhejiang University, Hangzhou, 310027, P. R. China

    Jiachi Huang, Hanying Li, Xiong Mo, Minmin Shi, Mang Wang & Hongzheng Chen

Authors
  1. Jiachi Huang
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  2. Hanying Li
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  3. Xiong Mo
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  4. Minmin Shi
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  5. Mang Wang
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  6. Hongzheng Chen
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Corresponding authors

Correspondence to Hanying Li or Hongzheng Chen.

Additional information

Supported by the National Natural Science Foundation of China(Nos.51222302, 50990063, 91233114), the Natural Science Foundation of Zhejiang Province, China(No.LZ13E030002) and the Fundamental Research Funds for the Central Universities of China(No.2012QNA4025).

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Huang, J., Li, H., Mo, X. et al. Crystal growth and characterization of fluorinated perylene diimides. Chem. Res. Chin. Univ. 30, 63–67 (2014). https://doi.org/10.1007/s40242-013-3294-1

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  • DOI: https://doi.org/10.1007/s40242-013-3294-1

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