Synthesis, characterization and (electro)chemical polymerization of triphenylamine-end-functionalized poly(ε-caprolactone)

• Published in: Polymer international 2010-05, Vol.59 (5), p.624-629
• Main Authors: Bendrea, Anca-Dana, Vacareanu, Loredana, Grigoras, Mircea
• Format: Article
• Language: English
• Subjects: Applied sciences; chemical and electrochemical polymerization; Exact sciences and technology; functionalized ε-caprolactone oligomers; grafted (branched) polytriphenylamine; Organic polymers; Physicochemistry of polymers; Polymerization; Preparation, kinetics, thermodynamics, mechanism and catalysts; triphenylamine end groups
• ISSN: 0959-8103; 1097-0126
• DOI: 10.1002/pi.2738

Triphenylamine‐based oligomers and polymers with linear, hyperbranched, star‐shaped or dendrimer architectures have been synthesized and studied due to their interesting electro‐optical properties. In many cases insoluble materials are obtained. In this study, we report the synthesis of grafted polytriphenylamine by chemical and electrochemical polymerization of triphenylamine‐end‐functionalized poly(ε‐caprolactone). Functionalized ε‐caprolactone oligomers were obtained by ring‐opening polymerization of ε‐caprolactone initiated by 4‐hydroxymethyltriphenylamine/stannous octanoate (tin 2‐ethylhexanoate). The ring‐opening polymerization of ε‐caprolactone using 4‐hydroxymethyltriphenylamine/stannous octanoate as initiating system provided ε‐caprolactone oligomers, with well‐defined molecular weights, containing a triphenylamine terminal group. Chemical and electrochemical coupling oxidation of the triphenylamine ends allowed the formulation of polyarylamines with ε‐caprolactone oligomers as grafts. Graft copolymers with an aryleneamine backbone and short poly(ε‐caprolactone) grafts were obtained by (electro)chemical oxidation of oligomers containing triphenylamine terminal groups. Copyright © 2009 Society of Chemical Industry A practical synthesis of triphenylamine‐end‐functionalized poly(ε‐caprolactone) oligomers and poly [arylamine‐graft‐(ε‐caprolactone)] polymers has been achieved.