Novel self-coloured polymers based on new fluorescent naphthalimide derivatives: synthesis, characterisation and photophysical properties

• Published in: Pigment & resin technology 2017-05, Vol.46 (3), p.244-250
• Main Authors: Shaki, Hanieh, Khosravi, Alireza, Gharanjig, Kamaladin
• Format: Article
• Language: English
• Subjects: Dyes; Electrons; Ethanol; Fluorescence; Fourier transforms; NMR; Nuclear magnetic resonance; Polymers; Spectrum analysis; Studies
• ISSN: 0369-9420; 1758-6941
• DOI: 10.1108/PRT-07-2016-0080

Purpose In this study, two novel fluorescent dyes, based on naphthalimide derivatives have been synthesised from acenaphthene as a starting material. The ability of the dyes to graft to polymer chain was then demonstrated. The novel synthesised dyes and self-coloured polymers were characterised by a variety of techniques. Design/methodology/approach The novel dyes were prepared through by halogenation, oxidation, imidation and amination reactions. All steps of these processes were monitored by thin layer chromatography. The fluorescent dyes and their intermediates were characterised by differential scanning calorimeter, fourier transform infrared spectroscopy (FTIR), Proton Nuclear Magnetic Resonance (1H-NMR) and carbon-13 nuclear magnetic resonance (13-CNMR) spectroscopic techniques. The molar extinction coefficients and absorption maximum wavelength were obtained by examining the dyes and polymer solutions in Dimethylformamide (DMF) and toluene solvents. The fluorescency of novel dyes and self-coloured polymers was evaluated. Their quantum yields and Stokes shift values were determined as DMF and toluene solutions. The percentage of the covalently bounded dyes into the polymer chain was calculated. Findings The characterisation of the synthesised dyes and self-coloured polymers verified their structural correctness. The results of reaction dyes with resin demonstrated that the dyes were covalently bonded to the chain of an acrylic polymer (resin) containing carboxylic acid groups giving self-coloured polymers. The extent of fluorescence of the synthesised dyes and their polymers showed that compounds containing functional amino group in C-4 position of naphthalimide ring have high fluorescence properties. Originality/value This study is original. Self-coloured polymers based on acrylic were synthesised by novel naphthalimide dyes with acrylic resin for the first time, successfully. The novel dyes and their self-coloured polymers exhibit good and acceptable fluorescent activity.