Issue
Korean Journal of Chemical Engineering,
Vol.30, No.8, 1609-1613, 2013
Synthesis and characterization of acrylate copolymer containing fluorescein functional group
We report a novel method to fabricate fluorescent polymer (F-CPA) based on the esterification between acrylate copolymer (CPA) and fluorescein using N, N-dicyclohexylcarbodiimide (DCC)/4-dimethylaminopyridine (DMAP) as catalyst. The resulting copolymer was characterized by Fourier transform-infrared spectroscopy (FT-IR), gel permeation chromatography (GPC), differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), ultravioletvisible spectroscopy (UV-Vis) and fluorescence spectroscopy. In addition, the influences of concentration, solvents, pH and metal cations (Cu2+, Fe3+ and Zn2+) on the fluorescent behaviors of F-CPA are discussed in detail. All those observations suggest that the synthesized F-CPA is an excellent luminescent macromolecular material with simple synthesis method and excellent solubility. Moreover, its sensitive fluorescence response behaviors to solvents, pH and metal cations make it to become a polymer-based probe.
[References]
  1. Tsien RW, Randall, Chem. Eng. News., 72, 34, 1994
  2. Hou XL, Tong XF, Dong WJ, Dong C, Shuang SM, Spectrochim. Acta Part A: Mol. Biomole Spectro., 66, 552, 2007
  3. Guan Y, Zhou W, Yao XH, Zhao MP, Li YZ, Anal. Chim.Acta., 570, 21, 2006
  4. Nakamura Y, Miyatake R, Matsubara, Kiyota H, Ueda M, Tetrahedron., 62, 8805, 2006
  5. Tang YL, He F, Yu MH, Feng FD, An LL, Sun H, Wang S, Li YL, Zhu DB, Macromol. Rapid Commun., 27(6), 389, 2006
  6. Metivier R, Leeay L, Valeur B, Chem. Commun., 8, 996, 2003
  7. Fernandez-Sanchez JF, Segura-Carretero A, Cruces-Blanco C, Talanta., 60, 287, 2003
  8. Geddes CD, Douglas P, Moore CP, Wearc TJ, Egerton PL, Dyes and Pigments., 43, 59, 1999
  9. Niu CG, Guan AL, Zeng GM, Liu YG, Li ZW, Anal.Chim. Acta., 577, 264, 2006
  10. Wu ZQ, Meng LZ, Progress in Fluorescent Polymers., 19, 1381, 2007
  11. Disney MD, Zheng J, Swager TM, Seeberger PH, J. Am. Chem. Soc., 126(41), 13343, 2004
  12. Niu CG, Li ZZ, Anal. Bioanal. Chem., 372, 519, 2002
  13. Santra S, Zhang P, Wang K, Tapec R, Tan W, Anal. Chem., 73, 4988, 2001
  14. Desilva AP, Gunaratne HQ, Gunnlaugsson T, Huxley AJ, Mccoy CP, Rademacher JT, Rice TE, Chem. Rev., 97(5), 1515, 1997
  15. Hung HM, Wang KM, Tan WH, An DL, Yang XH, Angew. Chem. Int. Ed., 43, 5635, 2004
  16. Liu XQ, Du FS, Li ZC, Li FM, Gao QY, Yang GX, Zhang JX, J. Appl. Polym. Sci., 70(6), 1191, 1998
  17. Tao Y, Doat BA, Lam J, Thin Solid Films., 363, 298, 2003
  18. Campo LF, Rodembusch FS, Stefani V, J. Appl. Polym. Sci., 99(5), 2109, 2006
  19. Qaqish RB, Amiji MM, Carbohydr. Polym., 38, 99, 1999
  20. Tommerass K, Strand SP, Tian W, Kenne L, Varum KM, Carbohyder. Res.., 336, 291, 2001
  21. Guo X, Lu JM, Li H, Yao SH, Wang LH, J. Appl. Polym. Sci., 97(5), 2067, 2005
  22. Klok HA, Becker S, Schuch F, Pakula T, Mullen K, Macrom. Chem. Phys., 203, 1106, 2002
  23. Teranishi K, Nishiguchi T, Anal. Biochem., 325, 185, 2004
  24. Yang WC, Schmeer MJ, Yeung ES, Anal. Chem., 77, 4489, 2005
  25. Guan XL, Liu XY, Su ZX, J. Appl. Polym. Sci., 104(6), 3960, 2007
  26. Gao HF, Wang CC, Yang WL, J. Macrom. Sci. Part A., 41, 357, 2004
  27. Cho HK, Lone S, Kim DD, Choi JH, Choi SW, Cho JH, Kim JH, Cheong IW, Polymer, 50(11), 2357, 2009
  28. Nakayama-Ratchford N, Bangsaruntip S, Sun XM, Welsher K, Dai HJ, J. Am. Chem. Soc., 129(9), 2448, 2007
  29. Nese A, Lebedeva NV, Sherwood G, Averick S, Li YC, Gao HF, Peteanu L, Sheiko SS, Matyjaszewski K, Macromolecules, 44(15), 5905, 2011
  30. Yang B, Sun BB, Hebei Chemical Industry., 31, 7, 2008
  31. Rurack K, Spectrochem. Acta Part A., 57, 2161, 2001
  32. Grabchev I, Qian X, Xiao Y, Zhang R, New J. Chem., 26, 920, 2002