Article

Synthesis and unexpected electrochemical behavior of the triphenylamine-based aramids with ortho- and para-trimethyl-protective substituents

  1. Hung-Ju Yen,
  2. Shiue-Ming Guo,
  3. Guey-Sheng Liou*

Article first published online: 24 SEP 2010

DOI: 10.1002/pola.24326

Issue

Journal of Polymer Science Part A: Polymer Chemistry

Journal of Polymer Science Part A: Polymer Chemistry

Volume 48, Issue 23, pages 5271–5281, 1 December 2010

Additional Information

How to Cite

Yen, H.-J., Guo, S.-M. and Liou, G.-S. (2010), Synthesis and unexpected electrochemical behavior of the triphenylamine-based aramids with ortho- and para-trimethyl-protective substituents. J. Polym. Sci. A Polym. Chem., 48: 5271–5281. doi: 10.1002/pola.24326

Author Information

  1. Functional Polymeric Materials Laboratory, Institute of Polymer Science and Engineering, National Taiwan University, No. 1, Sec. 4, Roosevelt Rd., Taipei 10617, Taiwan

*Functional Polymeric Materials Laboratory, Institute of Polymer Science and Engineering, National Taiwan University, No.1, Sec. 4, Roosevelt Rd., Taipei 10617, Taiwan

Publication History

  1. Issue published online: 28 OCT 2010
  2. Article first published online: 24 SEP 2010
  3. Manuscript Accepted: 18 AUG 2010
  4. Manuscript Received: 10 JUL 2010

Funded by

  • National Science Council of the Republic of China

SEARCH

SEARCH BY CITATION

ARTICLE TOOLS

View Full Article with Supporting Information (HTML) Get PDF (2393K)

Keywords:

  • electrochemistry;
  • high performance polymers;
  • UV–vis spectroscopy;
  • polyamides

Abstract

Two series of new organosoluble polyamides with methyl-substituted triphenylamine (MeTPA) units showing anodically electrochromic characteristic were prepared from the phosphorylation polyamidation reaction of two diamine monomers, 4,4′-diamino-2″,4″,6″-trimethyltriphenylamine (Me3TPA-diamine; 2) and 4,4′-diamino-4″-methyltriphenylamine (MeTPA-diamine; 2′), with various dicarboxylic acids, respectively. These polymers were readily soluble in many polar solvents and showed useful levels of thermal stability associated with relatively high glass-transition temperatures (Tg) (314–329 °C) and high char yields (higher than 62% at 800 °C in nitrogen). In addition, the polymer films showed reversible electrochemical oxidation, high coloration efficiency (CE), low switching time, and anodic green electrochromic behavior. The unexpected electrochemical behavior of higher oxidation potential and lower electrochemical stability of Me3TPA-polyamides I than MeTPA corresponding polymers could be attributed to the higher steric hindrance of ortho-substituents in Me3TPA moieties, thus made the resonance stabilization of cation radical much more difficult for the Me3-substituted phenyl ring. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2010

View Full Article with Supporting Information (HTML) Get PDF (2393K)