Electrodeposition of Free-Standing
Poly(o-dihydroxybenzene-co-3-methylthiophene)
Films with Tunable Fluorescence Properties
Congcong Liu,
1
Jingkun Xu,
1
Changli Fan,
1
Baoyang Lu,
1
Bin Dong,
2
Guodong Liu
1
1
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University,
Nanchang 330013, China
2
Key Laboratory of Colloid and Interface Chemistry (Shandong University), Ministry of Education,
Jinan 250100, China
Received 18 February 2009; accepted 4 September 2009
DOI 10.1002/app.31381
Published online 3 November 2009 in Wiley InterScience (www.interscience.wiley.com).
ABSTRACT: Electrochemical copolymerization of o-dihy-
droxybenzene (oDHB) and 3-methylthiophene (3MeT) was
successfully achieved in boron trifluoride diethyl etherate
by direct anodic oxidation of the monomer mixtures,
although the oxidation potentials of oDHB and 3MeT were
quite different. The influence of the applied polymeriza-
tion potential on the synthesis of the copolymers was
investigated. The higher applied potential favored the
incorporation of 3MeT units into the copolymers. The
structure and properties of the copolymers were investi-
gated with UV-vis spectroscopy, fluorescence spectros-
copy, FTIR spectroscopy, and thermal analysis. The novel
copolymers had many advantages, including good redox
activity, good thermal stability, and high electrical conduc-
tivity. Additionally, the copolymers fluorescence proper-
ties that were tunable through changes in the feed ratio of
the monomer mixtures.
V
C
2009 Wiley Periodicals, Inc. J Appl
Polym Sci 115: 3273–3281, 2010
Key words: conducting polymers; copolymerization;
electrochemistry
INTRODUCTION
The pursuit of novel conducting polymers is still
one of the main goals in the syntheses and applica-
tions of conducting polymers. Poly(3,4-ethylene-
dioxythiophene) has attracted much attention
among conducting polymers because of its high
conductivity, good processing ability, good mechan-
ical properties, and nice environmental stability.
1
Poly(1,2-methylenedioxybenzene), a poly(3,4-ethyle-
nedioxythiophene) derivative, is of great interest
because of its good properties.
2
o-Dihydroxy-
benzene (oDHB) is a cheaper monomer, whose
structure is similar to 1,2-methylenedioxybenzene
(MDOB). Two electron-donating groups of AOH on
benzene contribute to the polymerization of oDHB.
As a novel conducting polymer, poly(o-dihydroxy-
benzene) (PoDHB), was successfully electrosynthe-
sized by direct anodic oxidation of its monomer,
oDHB, in pur e boron trifluoride diethyl etherate
(BFEE) with good fluorescence properties as a blue-
light-emitting material together with good thermal
stability.
3
However, it also has disadvantages
because it is difficult to electrosynthesize high-qual-
ity, free-standing PoDHB films. It is well known
that copolymerization is an effective method that
can tune the properties of copolymers to be inter-
mediate between those of the individual homopoly-
mers. Therefore, a copolymer containing oDHB
monomer units in the main backbone would be
beneficial for extending the properties of PoDH B.
Poly(3-methylthiophene) (PMeT), an important
derivative of polythiophene, has also been the sub-
ject of intense research because of its high electrical
conductivity
4
(close to 750 S/cm), high tensile
strength, and good flexibility.
5
High-quality, free-
standing PMeT films with good properties can be
easily produced by the direct anodic oxidation of
3-methylthiophene (3MeT) monomer in BFEE.
6
Until now, 3MeT based copolymers have been pre-
pared successfully by the electrochemical oxidation
of mixtures of 3MeT with other corresponding
monomers.
7–15
To the best of our knowledge, the
electrochemical copolymerization of oDHB with
3MeT in BFEE has not been reported so far. It was
of interest to copolymerize oDHB with 3MeT.
In this study, oDHB and 3MeT were copolymer-
ized successfully by the electrochemical oxidation of
the monomer mixture in BFEE. The electrochemistry,
thermal stability, spectroscopic properties, and
Correspondence to: J. Xu (xujingkun@tsinghua.org.cn or
xujingkun@mail.ipc.ac.cn).
Journal of Applied Polymer Science, Vol. 115,3273–3281 (2010)
V
C
2009 Wiley Periodicals, Inc.
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