Synthesis of novel photoactive heterocyclic polyimides containing naphthalene moieties via cycloaddition reactions

1-Naphthylacetic acid (1) was reacted with thionyl chloride and 1-naphthyla cetyl chloride (2) was obtained in a quantitative yield. The reaction of th is acid chloride (2) with isoeugenol (3) was performed in chloroform and a novel isoeugenol ester derivative (4) as a monomer was obtained in a high y ield. The compound (4) was characterized by H-1-NMR, IR, mass, and elementa l analyses and then was used for the preparation of a model compound (6) an d polymerization reactions. 4-Phenyl-1,2,4-triazoline-3,5-dione (PhTD) (5) was allowed to react with compound (4). The reaction is very fast and gives only one double adduct (6) via Diels-Alder and ene pathways in an excellen t yield. The polymerization reactions of the novel monomer (4) with bistria zolinediones [bis-(p-3,5-dioxo-1,2,4-triazolin-4-ylphenyl)methane (7) and 1 ,6-bis-(3,5-dioxo-1,2,4-triazolin-4-yl)hexane] (8) were carried out in N,N- dimethylacetamide (DMAc) at room temperature. The reactions are exothermic and fast and gave novel heterocyclic polyimides containing a naphthalenic p endant group (9) and (10) via repetitive Diels-Alder-ene polyaddition react ions. Stereochemical analysis of the model compound and fluorimetric studie s of the model compound as well as polymers were done conclusively. Excimer formation of the polymers and its effect on fluorescence emission were inv estigated and some structural characterization and physical properties of t hese novel heterocyclic polyimides are reported. (C) 2000 John Wiley & Sons , Inc.