Evaluation of novel fluorescent 1,5-naphthalene-bis(allylcarbonate) monomer used in the formulation of dental composite resins

This study describes the formulation of composite resins with a novel fluorescent monomer, 1,5-naphthalene-bis(allylcarbonate) (1,5NBAC), and the effects of its incorporation on the selected properties of experimental dental resin composites. 1,5NBAC monomer was synthesized via a one-step nucleophilic acyl substitution reaction. The experimental composite resins were formulated by mixing 1,5NBAC, TEGDMA, BisGMA, a photo-initiator system, and inorganic fillers. A composite resin without 1,5NBAC monomer was used as a control. The materials were evaluated based on their flexural strength, elastic modulus, photopolymerization kinetics, double bond conversion, polymerization shrinkage, color alteration, translucency, and fluorescence parameters. MTT assay was used to evaluate cytotoxicity. 1,5NBAC was successfully synthesized in quantitative yield. The results showed that the 1,5NBAC-based composite resin had similar values of flexural strength, elastic modulus, double bond conversion, and polymerization shrinkage than the control ( p > 0.05). The high fluorescence quantum yield of 1,5NBAC allows the fluorescent property in the experimental resin at lower concentrations. Finally, this study showed no statistically significant differences in biocompatibility outcomes. Because of the fluorescence property of the 1,5NBAC monomer, it could be potentially useful in the formulation of resin composites to produce esthetic materials with fluorescence similar to that of teeth.