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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Thomas, S.W., Joly, G.D. and Swager, T.M., Chem. Rev., 2007, 107: 1339
Thomas, S.W., Gil, C.J. and Wrighton, M.S., J. Phys. Chem., 1995, 99: 4886
Lee, K., “Functionalized conjugated polymers for signal amplifying biosensors and sensor arrays” ProQuest, 2008
McQuade, D.T., Pullen, A.E. and Swager, T.M., Chem. Rev., 2000, 100: 2537
Marsella, M.J. and Swager, T.M., J. Am. Chem. Soc., 1993, 115: 12214
Rochat, S. and Swager, T.M., ACS Appl. Mater. Inter., 2013, 5: 4488
Swager, T.M., Acc. Chem. Res., 1998, 31: 201
Kim, H.N., Guo, Z., Zhu, W., Yoon, J. and Tian, H., Chem. Soc. Rev., 2011, 40: 79
Inzelt, G., “Conducting polymers: a new era in electrochemistry”, Springer Science & Business Media, 2012
Pei, Q. and Yang, Y., J. Am. Chem. Soc., 1996, 118: 7416
Klärner, G., Lee, J.I., Davey, M.H. and Miller, R.D., J. Adv. Mater., 1999, 11: 115
Ouisse, T. and Stephan, O., Org. Electron., 2004, 5: 251
Neher, D., Macromol. Rapid Commun., 2001, 22: 1365
Sun, M.L., Zhong, C.M., Li, F. and Pei, Q.B., Chinese J. Polym. Sci., 2012, 30(4): 503
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
Leclerc, M., J. Polym. Sci., Part A: Polym. Chem., 2001, 39: 2867
Wallace, J.U. and Chen, S.H., "Fluorene-based conjugated oligomers for organic photonics and electronics", Springer Berlin Heidelberg, 2008
Park, M.K., Xia, C., Advincula, R.C., Schütz, P. and Caruso, F., Langmuir, 2001, 17: 7670
Nie, G.M., Li, C.X., Zhang, L. and Wang, L., J. Mater. Chem. B, 2014, 2: 8321
Nie, G.M., Bai, Z.M., Yu, W.Y. and Chen, J., Biomacromolecules, 2013, 14(3): 834
Nie, G.M., Bai, Z.M., Chen, J. and Yu, W.Y., ACS Macro Lett., 2012, 1: 1304
Nie, G.M., Zhang, Y., Guo, Q.F. and Zhang, S.S., Sens. Actuators, B, 2009, 139(2): 592
Pu, K.Y. and Liu, B., Adv. Funct. Mater., 2009, 19: 277
Yu, M.H., He, F., Tang, Y.L., Wang, S., Li, Y.L. and Zhu, D.B., Macromol. Rapid Commun., 2007, 28: 1333
Lv, F.T., Feng, X.L., Tang, H.W., Liu, L.B., Yang, Q. and Wang, S., Adv. Funct. Mater., 2011, 21: 845
Xing, C.F., Shi, Z.Q., Yu, M.H. and Wang, S., Polymer, 2008, 49: 269
Qin, C.J., Cheng, Y.X., Wang, L.X., Jing, X.B. and Wang, F.S., Macromolecules, 2008, 41: 7798
Qin, C.J., Wu, X.F., Tong, H. and Wang, L.X., J. Mater. Chem., 2010, 20: 7957
Qin, C.J., Wong, W.Y. and Wang, L.X., Macromolecules, 2010, 44: 483
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
Zhang, G., Lu, B.Y., Wen, Y.P., Lu, L.M. and Xu, J.K., Sens. Actuators, B, 2012, 171: 786
Carpino, L.A. and Han, G.Y., J. Org. Chem., 1972, 37: 3404
Rault-Berthelot, J., Raoult, E., Tahri-Hassani, J., Deit, H.L. and Simonet, J., Electrochim. Acta, 1999, 44: 3409
Wang, Z., Guo, W.J., Han, J.T., Pei, M.S. and Zhu, X.W., J. Macromol. Sci. B, 2012, 51: 2255
He, Y., Guo, W.J., Pei, M.S. and Zhang, G.Y., Chin. J. Chem., 2012, 30: 985
Scherf, U. and List, E.J.W., Adv. Mater., 2002, 14: 477
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
Fan, C.H., Plaxco, K.W. and Heeger, A.J., J. Am. Chem. Soc., 2002, 124: 5642
Roncali, J., Chem. Rev., 1992, 92: 711
Novák, P., Müller, K. Santhanam, K.S.V. and Haas, O., Chem. Rev., 1997, 97: 207
Chen, W. and Xue, G., Prog. Polym. Sci., 2005, 30: 783
Zhang, S.S., Nie, G.M., Han, X.J., Xu, J.K., Li, M.S. and Cai, T., Electrochim. Acta, 2006, 51: 5738
Nie, G.M. Guo, Q.F., Zhang, Y. and Zhang, S.S., Eur. Polym. J., 2009, 45: 2600
Nie, G.M., Guo, Q.F., Wang, S. and Zhang, S.S., J. Polym. Sci., Part A: Polym. Chem., 2010, 48(8): 1791
Fan, C.L., Xu, J.K., Chen, W. and Dong, B., J. Phys. Chem. C, 2008, 112: 12012
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
Jin, S. and Xue, G., Macromolecules, 1997, 30: 5753
Chen, W. and Xue, G., Prog. Polym. Sci., 2005, 30: 783
Nie, G.M., Yang, H.J., Wang, S. and Li, X.M., Crit. Rev. Solid State Mater. Sci., 2011, 36: 209
Chen, X.W. and Inganäs, O., J. Phys. Chem., 1996, 100: 15202
Zhou, M. and Heinze, J., J. Phys. Chem. B, 1999, 103: 8443
Lu, B.Y., Li, Y.Z. and Xu, J.K., J. Electroanal. Chem., 2010, 643: 67
Fukuda, M., Sawada, K. and Yoshino, K., J. Polym. Sci., Part A: Polym. Chem., 1993, 31: 2465
Nie, G.M., Cai, T., Xu, J.K. and Zhang, S.S., Electrochem. Commun., 2008, 10: 186
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
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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