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

Abstract

1‐Naphthylacetic acid (1) was reacted with thionyl chloride and 1‐naphthyl‐ acetyl chloride (2) was obtained in a quantitative yield. The reaction of this 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 yield. The compound (4) was characterized by 1H‐NMR, IR, mass, and elemental analyses and then was used for the preparation of a model compound (6) and 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 excellent yield. The polymerization reactions of the novel monomer (4) with bistriazolinediones [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 pendant group (9) and (10) via repetitive Diels–Alder‐ene polyaddition reactions. Stereochemical analysis of the model compound and fluorimetric studies of the model compound as well as polymers were done conclusively. Excimer formation of the polymers and its effect on fluorescence emission were investigated and some structural characterization and physical properties of these novel heterocyclic polyimides are reported. © 2000 John Wiley & Sons, Inc. J Appl Polym Sci 78: 527–536, 2000

Synthesis of novel heterocyclic polyimides containing trimellitimide acid moieties

“…In previous studies we reported the preparation both of novel optically active and photoactive [21][22][23] polymers and of flame retardant 24 polymers via tandem Diels-Alder-ene polymerization reactions. We also proposed a reasonable mechanism for these types of reactions.…”

“…In previous studies, we introduced a new polymerization technique via Diels-Alder-ene cycloaddition reactions. [21][22][23][24] In this communication, we report the synthesis of novel heterocyclic polyimides containing a trimellitimide acid pendant group.…”

Synthesis of novel polyimides containing side‐chain azo‐2‐naphthol moieties

“…In previous studies, we reported the synthesis of new aliphatic–aromatic polyimides by Diels–Alder‐ene cycloaddition reactions 25–29. In this investigation, we report the synthesis of novel heterocyclic polyimides containing the azo2‐naphthol pendant group.…”

Fluorescent, electroactive, thermally stable triphenylamine‐ and naphthalene‐based polyimides for optoelectronic applications

“…According to the Hammet equation, electron‐donating groups, mainly at the para orientation of the TPA unit, exert a driving force in radical cation formation and stabilize it efficiently . However, electron‐withdrawing substituents have the opposite impact . Naphthalene‐based PIs have also been reported as fluorescent materials.…”