Study of the reaction of 1,4-benzoquinone with aniline oligomers and benzidine
- PDF / 908,659 Bytes
- 9 Pages / 595.276 x 790.866 pts Page_size
- 59 Downloads / 153 Views
ORIGINAL PAPER
Study of the reaction of 1,4-benzoquinone with aniline oligomers and benzidine N. A. Durgaryan 1 & N. A. Miraqyan 1 & P. G. Minasyan 1
# The Polymer Society, Taipei 2020
Abstract Polymers and oligomers containing fragments of aniline oligomers and benzidine connected with p-benzoquinone have been synthesized. The UV, NMR and IR spectral data, as well as termal stubilities, of obtained compounds were studied. Some of obtained compounds were oxidized by K2S2O8 using different molar ratio. Electrical conductivities and conductivity activation energies of iodine and hydrochloric acid doped polymers were determined. Keywords Oligomers . 1,4-benzoquinone . Conductivity . Polyaniline
Introduction Recently quinone containing polymers have been intensively studied due to their interesting electrochemical [1] and photoconducting [2] properties. Some biological processes have been understood due to this compounds [3–8]. These polymers are also used for preparation of magnetic [6] and electrode [7] materials. It was shown that polymers containing 1,4-benzoquinoneamine groups exhibit good adhesion to wet or rusty steel and can be used for surface drying [8]. Benzoquinone compounds were also of interest as they could be formed as by product during oxidative polymerization of aniline, some studies were dedicated to the reaction of p-benzoquinone (BQ) with aniline and p-phenylenediamine as well [9, 10]. The reaction of benzoquinone with amines processed by Michael addition reaction resulting firstly 2,5–disubstituted hydroquinone and then after in situ simultaneously oxidation by excess of 1,4-benzoquinone, 2,5–disubstituted1,4-benzoquinone compounds were formed. Recently it has been shown, that this reaction gives opportunity to synthesize conductive polymers containing oligoaniline and aromatic diamine fragments, connected with benzoquinone linkages on the base of cheap and available monomers using industrially available methods. It has been assumed that obtained * N. A. Durgaryan [email protected] 1
Yerevan State University, A.Manoogian 1, 0025 Yerevan, Armenia
polymers could combine the properties of polyaniline and pbenzoquinone groups significantly expanding the range of polyaniline (PANi) applications. Continuing the study where the first members of the row of polymers having structure depicted on Scheme 1 have been synthesized, the presented work has been done in two directions: firstly to synthesize the next members of the row containing three, four and five aniline units, and since it is well known, that high conductivity of PANi is considerably caused by the sequence of quinonediimine and phenylenediamine groups, to synthesize polymers that additionally contain 1,4benzoquinone diimine groups and study the relations between polymer structure and electrical properties.
Results and discussion Synthesis and structural elucidation It has already been established that by the reaction of benzoquinone with aromatic diamines conducting polymers could be synthesized [9–11]. The general method developed for
Data Loading...
