Synthesis and Enhanced Properties of Fluorescence-Based Polyurethane Films by Covalently Bonding 1,8-Naphthalimide

Y. Ma; Q.Y. Tang; L.H. Wang; C. Yao

doi:10.14233/ajchem.2014.16233

Issue

Vol. 26 No. 14 (2014): Vol 26 Issue 14

Issue Published : July 5, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis and Enhanced Properties of Fluorescence-Based Polyurethane Films by Covalently Bonding 1,8-Naphthalimide

https://doi.org/10.14233/ajchem.2014.16233

Y. Ma

School of Science, Nanjing University of Technology, Nanjing 211816, P.R. China

Q.Y. Tang

School of Science, Nanjing University of Technology, Nanjing 211816, P.R. China

L.H. Wang

School of Science, Nanjing University of Technology, Nanjing 211816, P.R. China

C. Yao

School of Science, Nanjing University of Technology, Nanjing 211816, P.R. China

Corresponding Author(s) : C. Yao

yaochengnjut@126.com

Asian Journal of Chemistry, Vol. 26 No. 14 (2014): Vol 26 Issue 14
Article Published : July 6, 2014

Abstract

A series of fluorescence-based polyurethane films (AABD-PUs) were synthesized by covalently bonding different amounts of 2-(2-aminoethyl)-6-((2-aminoethyl)amino)-1H-benzo[de]isoquinoline-1,3(2H)-dione (AABD) into polyurethane chains as a chain extender, which was a novel amino-functionalized 1,8-naphthalimide fluorescent dye. The chemical structure of AABD was confirmed by ¹H NMR and FT-IR spectra. The AABD segments content in synthesized AABD-PUs was investigated by ultraviolet visible spectroscopy (UV-visible) and the enhanced properties of AABD-PUs were characterized by fluorescent spectroscopy. It was found that the UV-visible absorption and the fluorescence emission maximum of AABD-PUs showed blue shift in comparison with those of AABD, respectively. The fluorescence intensity of AABD-PUs was observably enhanced due to the changes of micro-circumstance of AABD. Furthermore, the fluorescence of AABD-PUs showed quite good stability, not only for the temperature but also for the fluorescence quencher. Additionally, the fluorophore was fixed permanently into polyurethane chains and was difficult to migrate.

Keywords

Fluorescence Polyurethane Film 1,8-Naphthalimide

Ma, Y., Tang, Q., Wang, L., & Yao, C. (2014). Synthesis and Enhanced Properties of Fluorescence-Based Polyurethane Films by Covalently Bonding 1,8-Naphthalimide. Asian Journal of Chemistry, 26(14), 4307–4312. https://doi.org/10.14233/ajchem.2014.16233

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References

J.H. Kim, K. Park, H.Y. Nam, S. Lee, K. Kim and I.C. Kwon, Prog. Polym. Sci., 32, 1031 (2007); doi:10.1016/j.progpolymsci.2007.05.016.
T. Klingstedt and K.P.R. Nilsson, Biochim. Biophys. Acta, 1810, 286 (2011); doi:10.1016/j.bbagen.2010.05.003.
H.Y. Yang, X.M. Zhang, L.J. Duan, M.Y. Zhang, G.H. Gao and H.X. Zhang, J. Polym. Res., 19, 9973 (2012); doi:10.1007/s10965-012-9973-7.
C.W. Meuse, X.Z. Yang, D.C. Yang and S.L. Hsu, Macromolecules, 25, 925 (1992); doi:10.1021/ma00028a064.
K. Kojio, Y. Mitsui and M. Furukawa, Polymer, 50, 3693 (2009); doi:10.1016/j.polymer.2009.05.030.
Z.D. Shi and X.L. Wang, Polym. Adv. Technol., 20, 1017 (2009); doi:10.1002/pat.1358.
H.N. Kim, Z.Q. Guo, W.H. Zhu, J. Yoon and H. Tian, Chem. Soc. Rev., 40, 79 (2010); doi:10.1039/c0cs00058b.
V.B. Bojinov and D.B. Simeonov, Polym. Degrad. Stab., 95, 43 (2010); doi:10.1016/j.polymdegradstab.2009.10.012.
M.O. Liu, H.-F. Lin, M.-C. Yang, M.-J. Lai, C.-C. Chang, H.-C. Liu, P.-L. Shiao, I.-M. Chen and J.-Y. Chen, Mater. Lett., 60, 2132 (2006); doi:10.1016/j.matlet.2005.12.112.
L. Torini, J.F. Argillier and N. Zydowicz, Macromolecules, 38, 3225 (2005); doi:10.1021/ma047808e.
O. Jaudouin, J.J. Robin, J.M. Lopez-Cuesta, D. Perrin and C. Imbert, Polym. Int., 61, 495 (2012); doi:10.1002/pi.4156.
Y. Zhang, S. Feng, Q. Wu, K. Wang, X. Yi, H. Wang and Y. Pan, Med. Chem. Res., 20, 752 (2011); doi:10.1007/s00044-010-9384-4.
J.E. Rogers and L.A. Kelly, J. Am. Chem. Soc., 121, 3854 (1999); doi:10.1021/ja9841299.
A.M.M. El-Betany and N.B. McKeown, Tetrahedron Lett., 53, 808 (2012); doi:10.1016/j.tetlet.2011.12.009.
H.B. Xiao, M.J. Chen, G.H. Shi, L. Wang, H.Y. Yin and C. Mei, Res. Chem. Intermed., 36, 1021 (2010); doi:10.1007/s11164-010-0214-6.
I. Grabchev, S. Sali, R. Betcheva and V. Gregoriou, Eur. Polym. J., 43, 4297 (2007); doi:10.1016/j.eurpolymj.2007.07.036.
I. Grabchev and V. Bojinov, Polym. Degrad. Stab., 70, l 47 (2000); doi:10.1016/S0141-3910(00)00100-2.
N.Z. Galunov, B.M. Krasovitskii, O.N. Lyubenko, I.G. Yermolenko, L.D. Patsenker and A.O. Doroshenko, J. Lumin., 102-103, 119 (2003); doi:10.1016/S0022-2313(02)00477-5.
X.H. Hu, X.Y. Zhang, J.B. Dai and J. Liu, J. Lumin., 131, 2160 (2011); doi:10.1016/j.jlumin.2011.05.026.
Y.C. Chen, R.R. Chiou, H.L. Huang, Y.Z. Tsai, Y.M. Kuo and D.Y. Chao, J. Appl. Polym. Sci., 97, 455 (2005); doi:10.1002/app.21737.
Y.Y. Zhang and C.H. Zhou, Bioorg. Med. Chem. Lett., 21, 4349 (2011); doi:10.1016/j.bmcl.2011.05.042.
Y. Wang, X. Zhang, B. Han, J. Peng, S. Hou, Y. Huang, H. Sun, M. Xie and Z. Lu, Dyes Pigments, 86, 190 (2010); doi:10.1016/j.dyepig.2010.01.003.
D.J. David and H.B. Staley, Analytical Chemistry of the Polyurethanes, Wiley-Interscience, New York, Vol. 16 (1969).
F.M. Li, S.J. Chen, Z.C. Li and J. Qiu, J. Polym. Sci. Polym. Chem., 34, 1881 (1996); doi:10.1002/(SICI)1099-0518(19960730)34:10<1881::AID-POLA5>3.0.CO;2-S.
J. Qiu, Z.C. Li, Q.Y. Gao, G.-Q. Yao, G.-X. Yang, J.-X. Zhang and F.-M. Li, J. Polym. Sci. Polym. Chem., 34, 3015 (1996); doi:10.1002/(SICI)1099-0518(199610)34:14<3015::AID-POLA19>3.0.CO;2-M.
L. Biczok and H. Linschitz, J. Phys. Chem., 99, 1843 (1995); doi:10.1021/j100007a010.
C. Turro, S.H. Bossmann, Y. Jenkins, J.K. Barton and N.J. Turro, J. Am. Chem. Soc., 117, 9026 (1995); doi:10.1021/ja00140a020.
J. McCall, C. Alexander and M.M. Richter, Anal. Chem., 71, 2523 (1999); doi:10.1021/ac981322c.
A.A.T.C.C. Test Method, 140-2001, Dye and Pigment Migration in a Pad-Dry Process, In: AATCC Technical Manual, American Association of Textile Chemists and Colorists (2006).

References

J.H. Kim, K. Park, H.Y. Nam, S. Lee, K. Kim and I.C. Kwon, Prog. Polym. Sci., 32, 1031 (2007); doi:10.1016/j.progpolymsci.2007.05.016.

T. Klingstedt and K.P.R. Nilsson, Biochim. Biophys. Acta, 1810, 286 (2011); doi:10.1016/j.bbagen.2010.05.003.

H.Y. Yang, X.M. Zhang, L.J. Duan, M.Y. Zhang, G.H. Gao and H.X. Zhang, J. Polym. Res., 19, 9973 (2012); doi:10.1007/s10965-012-9973-7.

C.W. Meuse, X.Z. Yang, D.C. Yang and S.L. Hsu, Macromolecules, 25, 925 (1992); doi:10.1021/ma00028a064.

K. Kojio, Y. Mitsui and M. Furukawa, Polymer, 50, 3693 (2009); doi:10.1016/j.polymer.2009.05.030.

Z.D. Shi and X.L. Wang, Polym. Adv. Technol., 20, 1017 (2009); doi:10.1002/pat.1358.

H.N. Kim, Z.Q. Guo, W.H. Zhu, J. Yoon and H. Tian, Chem. Soc. Rev., 40, 79 (2010); doi:10.1039/c0cs00058b.

V.B. Bojinov and D.B. Simeonov, Polym. Degrad. Stab., 95, 43 (2010); doi:10.1016/j.polymdegradstab.2009.10.012.

M.O. Liu, H.-F. Lin, M.-C. Yang, M.-J. Lai, C.-C. Chang, H.-C. Liu, P.-L. Shiao, I.-M. Chen and J.-Y. Chen, Mater. Lett., 60, 2132 (2006); doi:10.1016/j.matlet.2005.12.112.

L. Torini, J.F. Argillier and N. Zydowicz, Macromolecules, 38, 3225 (2005); doi:10.1021/ma047808e.

O. Jaudouin, J.J. Robin, J.M. Lopez-Cuesta, D. Perrin and C. Imbert, Polym. Int., 61, 495 (2012); doi:10.1002/pi.4156.

Y. Zhang, S. Feng, Q. Wu, K. Wang, X. Yi, H. Wang and Y. Pan, Med. Chem. Res., 20, 752 (2011); doi:10.1007/s00044-010-9384-4.

J.E. Rogers and L.A. Kelly, J. Am. Chem. Soc., 121, 3854 (1999); doi:10.1021/ja9841299.

A.M.M. El-Betany and N.B. McKeown, Tetrahedron Lett., 53, 808 (2012); doi:10.1016/j.tetlet.2011.12.009.

H.B. Xiao, M.J. Chen, G.H. Shi, L. Wang, H.Y. Yin and C. Mei, Res. Chem. Intermed., 36, 1021 (2010); doi:10.1007/s11164-010-0214-6.

I. Grabchev, S. Sali, R. Betcheva and V. Gregoriou, Eur. Polym. J., 43, 4297 (2007); doi:10.1016/j.eurpolymj.2007.07.036.

I. Grabchev and V. Bojinov, Polym. Degrad. Stab., 70, l 47 (2000); doi:10.1016/S0141-3910(00)00100-2.

N.Z. Galunov, B.M. Krasovitskii, O.N. Lyubenko, I.G. Yermolenko, L.D. Patsenker and A.O. Doroshenko, J. Lumin., 102-103, 119 (2003); doi:10.1016/S0022-2313(02)00477-5.

X.H. Hu, X.Y. Zhang, J.B. Dai and J. Liu, J. Lumin., 131, 2160 (2011); doi:10.1016/j.jlumin.2011.05.026.

Y.C. Chen, R.R. Chiou, H.L. Huang, Y.Z. Tsai, Y.M. Kuo and D.Y. Chao, J. Appl. Polym. Sci., 97, 455 (2005); doi:10.1002/app.21737.

Y.Y. Zhang and C.H. Zhou, Bioorg. Med. Chem. Lett., 21, 4349 (2011); doi:10.1016/j.bmcl.2011.05.042.

Y. Wang, X. Zhang, B. Han, J. Peng, S. Hou, Y. Huang, H. Sun, M. Xie and Z. Lu, Dyes Pigments, 86, 190 (2010); doi:10.1016/j.dyepig.2010.01.003.

D.J. David and H.B. Staley, Analytical Chemistry of the Polyurethanes, Wiley-Interscience, New York, Vol. 16 (1969).

F.M. Li, S.J. Chen, Z.C. Li and J. Qiu, J. Polym. Sci. Polym. Chem., 34, 1881 (1996); doi:10.1002/(SICI)1099-0518(19960730)34:10<1881::AID-POLA5>3.0.CO;2-S.

J. Qiu, Z.C. Li, Q.Y. Gao, G.-Q. Yao, G.-X. Yang, J.-X. Zhang and F.-M. Li, J. Polym. Sci. Polym. Chem., 34, 3015 (1996); doi:10.1002/(SICI)1099-0518(199610)34:14<3015::AID-POLA19>3.0.CO;2-M.

L. Biczok and H. Linschitz, J. Phys. Chem., 99, 1843 (1995); doi:10.1021/j100007a010.

C. Turro, S.H. Bossmann, Y. Jenkins, J.K. Barton and N.J. Turro, J. Am. Chem. Soc., 117, 9026 (1995); doi:10.1021/ja00140a020.

J. McCall, C. Alexander and M.M. Richter, Anal. Chem., 71, 2523 (1999); doi:10.1021/ac981322c.

A.A.T.C.C. Test Method, 140-2001, Dye and Pigment Migration in a Pad-Dry Process, In: AATCC Technical Manual, American Association of Textile Chemists and Colorists (2006).

Issue

Vol. 26 No. 14 (2014): Vol 26 Issue 14

Synthesis and Enhanced Properties of Fluorescence-Based Polyurethane Films by Covalently Bonding 1,8-Naphthalimide

Corresponding Author(s) : C. Yao

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