Macromolecular Rapid Communications
Macromolecular Rapid Communications
5 years ago

Benzoxazine/Triphenylamine-Based Dendrimers Prepared through Facile One-Pot Mannich Condensations

Benzoxazine/Triphenylamine-Based Dendrimers Prepared through Facile One-Pot Mannich Condensations
Ruey-Chorng Lin, Shiao-Wei Kuo, Mohamed Gamal Mohamed
A series of thermally polymerizable dendrimers of various generations, equipped with triphenylamine (TPA) and benzoxazine (BZ) groups, is synthesized through facile one-pot Mannich condensations of N1,N1-bis(4-aminophenyl)benzene-1,4-diamine (TPA–3NH2, as the core group), 4-(bis(4-aminophenyl)amino)phenol (TPA–2NH2–OH, as the AB2 branching group), and CH2O in 1,4-dioxane. The ratios of the integrated areas in the 1H nuclear magnetic resonance spectra of these dendrimers are consistent with the theoretical numbers of protons, suggesting their successful syntheses. Bathochromic shifts of signals are evident in the UV–vis and photoluminescence spectra upon increasing the generation of the TPA–BZ dendrimers, consistent with an increase in the effective conjugation length. The TPA–BZ dendrimers are able to undergo thermal polymerization and display unique optical physical properties, resulting in thermoset TPA networks after thermal ring-opening polymerization. Dendrimers contain triphenylamine and benzoxazine moieties through facile one-pot Mannich condensations of triphenylamine (TPA)–3NH2 (as the core group), TPA–2NH2–OH (as the AB2 branching group), and CH2O in 1,4-dioxane.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/marc.201700251

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