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Electrosynthesis, characterization and optical sensing application of amino acid functionalized polyfluorene

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Abstract

An amino acid side chain functionalized polyfluorene derivative poly[N-(9-fluorenylmethoxycarbonyl)-glycine] (P9FG) was facilely electrosynthesized and characterized, and the structure, properties and optical sensing application of the obtained polymer were described and discussed. The electropolymerization occurred at C2 and C7 positions of fluorene units, and amino acid side chain groups were not cleaved from polyfluorene backbone in mixed electrolytes of boron trifluoride diethyl etherate and dichloromethane. Thermal analysis demonstrated good thermal stability of P9FG. Fluorescent spectra indicated that P9FG was a good blue light emitting material that could be employed as optical sensors. The soluble P9FG as a turn-off fluorescent sensor could realize the detection of Fe3+, Cu2+ and Cr2O7 2-, respectively. In addition, P9FG as a turn-off ultraviolet sensor could realize the detection of Cu2+ while as turn-on ultraviolet sensors could also realize the determination of Fe3+ and Cr2O7 2-, respectively. All results indicate that P9FG is a promising candidate for optical sensing.

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References

  1. Thomas, S.W., Joly, G.D. and Swager, T.M., Chem. Rev., 2007, 107: 1339

    Article  CAS  Google Scholar 

  2. Thomas, S.W., Gil, C.J. and Wrighton, M.S., J. Phys. Chem., 1995, 99: 4886

    Article  Google Scholar 

  3. Lee, K., “Functionalized conjugated polymers for signal amplifying biosensors and sensor arrays” ProQuest, 2008

    Google Scholar 

  4. McQuade, D.T., Pullen, A.E. and Swager, T.M., Chem. Rev., 2000, 100: 2537

    Article  CAS  Google Scholar 

  5. Marsella, M.J. and Swager, T.M., J. Am. Chem. Soc., 1993, 115: 12214

    Article  CAS  Google Scholar 

  6. Rochat, S. and Swager, T.M., ACS Appl. Mater. Inter., 2013, 5: 4488

    Article  CAS  Google Scholar 

  7. Swager, T.M., Acc. Chem. Res., 1998, 31: 201

    Article  CAS  Google Scholar 

  8. Kim, H.N., Guo, Z., Zhu, W., Yoon, J. and Tian, H., Chem. Soc. Rev., 2011, 40: 79

    Article  CAS  Google Scholar 

  9. Inzelt, G., “Conducting polymers: a new era in electrochemistry”, Springer Science & Business Media, 2012

    Book  Google Scholar 

  10. Pei, Q. and Yang, Y., J. Am. Chem. Soc., 1996, 118: 7416

    Article  CAS  Google Scholar 

  11. Klärner, G., Lee, J.I., Davey, M.H. and Miller, R.D., J. Adv. Mater., 1999, 11: 115

    Article  Google Scholar 

  12. Ouisse, T. and Stephan, O., Org. Electron., 2004, 5: 251

    Article  CAS  Google Scholar 

  13. Neher, D., Macromol. Rapid Commun., 2001, 22: 1365

    Article  CAS  Google Scholar 

  14. Sun, M.L., Zhong, C.M., Li, F. and Pei, Q.B., Chinese J. Polym. Sci., 2012, 30(4): 503

    Article  CAS  Google Scholar 

  15. Liu, W., Sun, M.L., Liu, Q., He, B.L., Ge, H.L., Sun, M., Zhang, Q.J. and Wang, W., Chinese J. Polym. Sci., 2013, 31(11): 1579

    Article  CAS  Google Scholar 

  16. Leclerc, M., J. Polym. Sci., Part A: Polym. Chem., 2001, 39: 2867

    Article  CAS  Google Scholar 

  17. Wallace, J.U. and Chen, S.H., "Fluorene-based conjugated oligomers for organic photonics and electronics", Springer Berlin Heidelberg, 2008

    Book  Google Scholar 

  18. Park, M.K., Xia, C., Advincula, R.C., Schütz, P. and Caruso, F., Langmuir, 2001, 17: 7670

    Article  CAS  Google Scholar 

  19. Nie, G.M., Li, C.X., Zhang, L. and Wang, L., J. Mater. Chem. B, 2014, 2: 8321

    Article  CAS  Google Scholar 

  20. Nie, G.M., Bai, Z.M., Yu, W.Y. and Chen, J., Biomacromolecules, 2013, 14(3): 834

    Article  CAS  Google Scholar 

  21. Nie, G.M., Bai, Z.M., Chen, J. and Yu, W.Y., ACS Macro Lett., 2012, 1: 1304

    Article  CAS  Google Scholar 

  22. Nie, G.M., Zhang, Y., Guo, Q.F. and Zhang, S.S., Sens. Actuators, B, 2009, 139(2): 592

    Article  CAS  Google Scholar 

  23. Pu, K.Y. and Liu, B., Adv. Funct. Mater., 2009, 19: 277

    Article  CAS  Google Scholar 

  24. Yu, M.H., He, F., Tang, Y.L., Wang, S., Li, Y.L. and Zhu, D.B., Macromol. Rapid Commun., 2007, 28: 1333

    Article  CAS  Google Scholar 

  25. Lv, F.T., Feng, X.L., Tang, H.W., Liu, L.B., Yang, Q. and Wang, S., Adv. Funct. Mater., 2011, 21: 845

    Article  CAS  Google Scholar 

  26. Xing, C.F., Shi, Z.Q., Yu, M.H. and Wang, S., Polymer, 2008, 49: 269

    Article  Google Scholar 

  27. Qin, C.J., Cheng, Y.X., Wang, L.X., Jing, X.B. and Wang, F.S., Macromolecules, 2008, 41: 7798

    Article  CAS  Google Scholar 

  28. Qin, C.J., Wu, X.F., Tong, H. and Wang, L.X., J. Mater. Chem., 2010, 20: 7957

    Article  CAS  Google Scholar 

  29. Qin, C.J., Wong, W.Y. and Wang, L.X., Macromolecules, 2010, 44: 483

    Article  Google Scholar 

  30. Zhang, G., Wen, Y.P., Li, Y.Z., Xu, J.K., Guo, C.Q., Lu, B.Y. and Zhu, D.H., J. Fluoresc., 2013, 23: 1053

    Article  CAS  Google Scholar 

  31. Zhang, G., Lu, B.Y., Wen, Y.P., Lu, L.M. and Xu, J.K., Sens. Actuators, B, 2012, 171: 786

    Article  Google Scholar 

  32. Carpino, L.A. and Han, G.Y., J. Org. Chem., 1972, 37: 3404

    Article  CAS  Google Scholar 

  33. Rault-Berthelot, J., Raoult, E., Tahri-Hassani, J., Deit, H.L. and Simonet, J., Electrochim. Acta, 1999, 44: 3409

    Article  CAS  Google Scholar 

  34. Wang, Z., Guo, W.J., Han, J.T., Pei, M.S. and Zhu, X.W., J. Macromol. Sci. B, 2012, 51: 2255

    Article  CAS  Google Scholar 

  35. He, Y., Guo, W.J., Pei, M.S. and Zhang, G.Y., Chin. J. Chem., 2012, 30: 985

    Article  CAS  Google Scholar 

  36. Scherf, U. and List, E.J.W., Adv. Mater., 2002, 14: 477

    Article  CAS  Google Scholar 

  37. Nothofer, H.G., Meisel, A., Miteva, T., Neher, D., Forster, M., Oda, M., Lieser, G., Sainova, D., Yasuda, A., Lupo, D., Knoll, W. and Scherf, U., Macromol. Symp., 2000, 154: 139

    Article  CAS  Google Scholar 

  38. Fan, C.H., Plaxco, K.W. and Heeger, A.J., J. Am. Chem. Soc., 2002, 124: 5642

    Article  CAS  Google Scholar 

  39. Roncali, J., Chem. Rev., 1992, 92: 711

    Article  CAS  Google Scholar 

  40. Novák, P., Müller, K. Santhanam, K.S.V. and Haas, O., Chem. Rev., 1997, 97: 207

    Article  Google Scholar 

  41. Chen, W. and Xue, G., Prog. Polym. Sci., 2005, 30: 783

    Article  CAS  Google Scholar 

  42. Zhang, S.S., Nie, G.M., Han, X.J., Xu, J.K., Li, M.S. and Cai, T., Electrochim. Acta, 2006, 51: 5738

    Article  CAS  Google Scholar 

  43. Nie, G.M. Guo, Q.F., Zhang, Y. and Zhang, S.S., Eur. Polym. J., 2009, 45: 2600

    Article  CAS  Google Scholar 

  44. Nie, G.M., Guo, Q.F., Wang, S. and Zhang, S.S., J. Polym. Sci., Part A: Polym. Chem., 2010, 48(8): 1791

    Article  CAS  Google Scholar 

  45. Fan, C.L., Xu, J.K., Chen, W. and Dong, B., J. Phys. Chem. C, 2008, 112: 12012

    Article  CAS  Google Scholar 

  46. Fan, C.L., Xu, J.K. Chen, W., Lu, B.Y., Miao, H.M., Liu, C.C. and Liu, G.D., J. Phys. Chem. C, 2009, 113: 9900

    Article  CAS  Google Scholar 

  47. Jin, S. and Xue, G., Macromolecules, 1997, 30: 5753

    Article  CAS  Google Scholar 

  48. Chen, W. and Xue, G., Prog. Polym. Sci., 2005, 30: 783

    Article  CAS  Google Scholar 

  49. Nie, G.M., Yang, H.J., Wang, S. and Li, X.M., Crit. Rev. Solid State Mater. Sci., 2011, 36: 209

    Article  CAS  Google Scholar 

  50. Chen, X.W. and Inganäs, O., J. Phys. Chem., 1996, 100: 15202

    Article  CAS  Google Scholar 

  51. Zhou, M. and Heinze, J., J. Phys. Chem. B, 1999, 103: 8443

    Article  CAS  Google Scholar 

  52. Lu, B.Y., Li, Y.Z. and Xu, J.K., J. Electroanal. Chem., 2010, 643: 67

    Article  CAS  Google Scholar 

  53. Fukuda, M., Sawada, K. and Yoshino, K., J. Polym. Sci., Part A: Polym. Chem., 1993, 31: 2465

    Article  CAS  Google Scholar 

  54. Nie, G.M., Cai, T., Xu, J.K. and Zhang, S.S., Electrochem. Commun., 2008, 10: 186

    Article  CAS  Google Scholar 

  55. Xu, J.K., Zhang, Y.J., Hou, J., Wei, Z.H., Pu, S.Z., Zhao, J.Q. and Du, Y.K., Eur. Polym. J., 2006, 42: 1154

    Article  CAS  Google Scholar 

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Correspondence to Jing-kun Xu  (徐景坤) or Yang-ping Wen  (文阳平).

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Zhang, H., Zhang, G., Xu, Jk. et al. Electrosynthesis, characterization and optical sensing application of amino acid functionalized polyfluorene. Chin J Polym Sci 34, 229–241 (2016). https://doi.org/10.1007/s10118-016-1742-3

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  • DOI: https://doi.org/10.1007/s10118-016-1742-3

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