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Synthesis and characterization of new 4‐tolyldiphenylamine derivatives for hole transporting polymers
Author(s) -
Strzelec Krzysztof,
Tsukamoto Nami,
Kook Ha Jae,
Sato Hisaya
Publication year - 2001
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/pi.770
Subject(s) - polymer , aldehyde , monomer , polymer chemistry , condensation polymer , polymerization , materials science , cyclic voltammetry , carbazole , chemistry , electrochemistry , organic chemistry , catalysis , electrode
Abstract New hole transport polymers have been synthesized by condensation polymerization of 4‐tolyldiphenylamine (TDPA) with various types of aldehyde. The reaction conditions have been investigated to yield polymers with high molecular weight. It is found that the molecular weight and yield of the TDPA–aldehyde polymers strongly depend on the electron donor–acceptor nature of the substituent on the aromatic ring of the aldehyde monomer. Structural characterization by 1 H NMR spectroscopy shows that the addition condensation reaction occurs exclusively at the para position of TDPA. The electrochemical and optical properties of polymers have been investigated by cyclic voltammetry and UV–vis spectroscopy. Cyclic voltammograms of all polymers show well‐defined pairs of reduction and oxidation peaks, indicating that the polymers are electrochemically active. All polymers show low conductivities of magnitude 10 −14 S cm −1 . Differential scanning calori‐metry measurements reveal that TDPA–aldehyde polymers exhibit glass transitions in the range 170–230 °C. These polymers possess good solubility and the films show sufficient morphological stability. © 2001 Society of Chemical Industry