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Synthesis of New Blue Fluorescent Polymerizable 1,8-Naphthalimides and Their Copolymers with Styrene as Sensors for Fe(III) Cations

DOI: 10.1155/2014/793721

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Abstract:

The synthesis, characterization, and functional properties of two new polymerizable 1,8-naphthalimides (MDs) have been described. Their copolymers with styrene designed to act as a fluorescence PET chemosensor have been investigated. The study also reports the influence of different metal cations (Ag+, Mg2+, Cu2+, Sr2+, Co2+, Pb2+, and Fe3+) on the fluorescence intensity of both low and high molecular weight fluorophores. 1. Introduction In the recent years the development of molecular recognition and sensing systems for different analytes has received considerable attention. Fluorescent chemosensors utilised for detection of metal cations and protons in the environment were based on different molecular structures [1, 2]. The fluorescent polymers are very attractive for this purpose. In this case the fluorescent sensor units can be covalently bonded to the polymer chain, thus showing very similar effect to their monomeric sensor units [3]. The functional characteristics of polymer chemosensors can be expressed either by conformational changes of macromolecules or by the collective transport properties. Recently, new polymerizable 1,8-naphthalimide molecules to sensitive protons or metal cations have been synthesized and their functional properties are investigated. Due to the presence of a polymerizable group they can react with some commercial monomers, allowing copolymers with a green or blue fluorescence to be obtained. It was demonstrated that the copolymers of these polymerizable sensors can be used as homogeneous and heterogeneous photoinduced electron transfer (PET) fluorescent sensors sensitive to metal cations [4–9]. In all cases 1,8-naphthalimides are enough thermo- and water resistible so the polymers can be used for ion determination in solution without contaminating it. The scientific tasks on development of polymeric systems for detection of environment pollutants will be focused on finding such polymeric systems which have specific chemical, physical, and mechanical properties as transparency, resistance to different environment factor and the harmful chemical substances, flexibility, and so forth. In this paper we present the synthesis and functional properties of two new polymerizable 1,8-naphthalimides (MDs) and their copolymer with styrene designed to act as fluorescence chemosensors. The influence of different metal cations on the fluorescence intensity of both low and high molecular weight sensors has been investigated and discussed. 2. Experimental Part 2.1. Materials and Methods 4-Amino-N-allyl-1,8-naphthalimide was synthesized

References

[1]  M. Formica, V. Fusi, L. Giorgi, and M. Micheloni, “New fluorescent chemosensors for metal ions in solution,” Coordination Chemistry Reviews, vol. 256, no. 1-2, pp. 170–192, 2012.
[2]  V. Bojinov and N. Georgiev, “Molecular sensors and molecular logic gates,” Journal of the University of Chemical Technology and Metallurgy, vol. 46, no. 1, pp. 3–26, 2011.
[3]  B. Adhikari and S. Majumdar, “Polymers in sensor applications,” Progress in Polymer Science, vol. 29, no. 7, pp. 699–766, 2004.
[4]  I. Grabchev, X. Qian, Y. Xiao, and R. Zhang, “Novel heterogeneous PET fluorescent sensors selective for transition metal ions or protons: polymers regularly labelled with naphthalimide,” New Journal of Chemistry, vol. 26, no. 7, pp. 920–925, 2002.
[5]  I. Grabchev, J.-M. Chovelon, and V. Bojinov, “New green fluorescent polyvinylcarbazole copolymer with 1,8-naphthalimide side chains as chemosensor for iron cations,” Polymers for Advanced Technologies, vol. 15, no. 7, pp. 382–386, 2004.
[6]  S. Sali, S. Guittonneau, and I. Grabchev, “A novel blue fluorescent chemosensor for metal cations and protons, based on 1,8-naphthalimide and its copolymer with styrene,” Polymers for Advanced Technologies, vol. 17, no. 3, pp. 180–185, 2006.
[7]  I. Grabchev, S. Sali, R. Betcheva, and V. Gregoriou, “New green fluorescent polymer sensors for metal cations and protons,” European Polymer Journal, vol. 43, no. 10, pp. 4297–4305, 2007.
[8]  P. Alaei, S. Rouhani, K. Gharanjig, and J. Ghasemi, “A new polymerizable fluorescent PET chemosensor of fluoride (F?) based on naphthalimide-thiourea dye,” Spectrochimica Acta A, vol. 90, pp. 85–92, 2012.
[9]  V. B. Bojinov, N. I. Georgiev, and N. V. Marinova, “Design and synthesis of highly photostable fluorescence sensing 1,8-naphthalimide-based dyes containing s-triazine UV absorber and HALS units,” Sensors and Actuators B, vol. 148, no. 1, pp. 6–16, 2010.
[10]  T. N. Konstantinova, P. Meallier, and I. Grabchev, “The synthesis of some 1,8-naphthalic anhydride derivatives as dyes for polymeric materials,” Dyes and Pigments, vol. 22, no. 3, pp. 191–198, 1993.
[11]  D. F. Eaton, “Reference materials for fluorescence measurement,” Pure and Applied Chemistry, vol. 60, no. 7, pp. 1107–1114, 1988.
[12]  B. Ramachandram, G. Saroja, N. B. Sankaran, and A. Samanta, “Unusually high fluorescence enhancement of some 1,8-naphthalimide derivatives induced by transition metal salts,” Journal of Physical Chemistry B, vol. 104, no. 49, pp. 11824–11832, 2000.
[13]  I. Grabchev, V. Bojinov, and R. Betcheva, “Spectrophotometric investigation of the copolymerization of styrene or methyl methacrylate with 1,8-naphthalimide dyes,” Journal of Applied Polymer Science, vol. 81, no. 10, pp. 2463–2470, 2001.
[14]  I. Grabchev, “Photophysical characteristics of polymerizable 1,8-naphthalimide dyes and their copolymers with styrene or methylmethacrylate,” Dyes and Pigments, vol. 38, no. 4, pp. 219–226, 1998.
[15]  I. Grabchev, I. Moneva, V. Bojinov, and S. Guittonneau, “Synthesis and properties of fluorescent 1,8-naphthalimide dyes for application in liquid crystal displays,” Journal of Materials Chemistry, vol. 10, no. 6, pp. 1291–1296, 2000.
[16]  H. Shaki, K. Gharanjig, S. Rouhani, and A. Khosravi, “Synthesis and photophysical properties of some novel fluorescent dyes based on naphthalimide derivatives,” Journal of Photochemistry and Photobiology A, vol. 216, no. 1, pp. 44–50, 2010.
[17]  I. Grabchev and T. Philipova, “Fluorescent polyacrylonitrile with 1,8-naphthalimide side chains,” Angewandte Makromolekulare Chemie, vol. 269, pp. 49–53, 1999.

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