Abstract
The postfunctionalization of the main chain alkyne moieties of carbazole containing poly(arylenebutadiynylene)s was attempted by using a high yielding addition reaction between electron rich alkynes and a strong acceptor molecule, tetracyanoethylene (TCNE). After successful postfunctionalization, the polymer band gap decreased due to the intramolecular donor-acceptor interactions. The resulting donor-acceptor alternating polymer showed a very broad charge-transfer band in the visible region as well as redox activities in both anodic and cathodic directions. The optical band gap showed good agreement with the electrochemical band gap. Furthermore, the thermal stability was enhanced after postfunctionalization. These features of the donor-acceptor alternating polymer are expected to be useful for high performance activities in organic solar cell applications.
Highlights
Since the discovery of conducting polyacetylene films, organic conjugated polymers have become an important class of materials for applications in the generation of organic electronic devices [1]
We recently started a new project on the synthesis of donor-acceptor type polymers by a novel postfunctionalization method based on a high yielding addition reaction between electron rich alkynes and strong acceptor molecules, such as tetracyanoethylene (TCNE) [4]
P1 and P3 showed good solubilities in common organic solvents and the molecular weight was determined by Gel permeation chromatography (GPC) using THF as an eluent
Summary
Since the discovery of conducting polyacetylene films, organic conjugated polymers have become an important class of materials for applications in the generation of organic electronic devices [1]. A conventional synthetic method for achieving donor-acceptor type conjugated polymers is based on the metal catalyzed polycondensation between a bifunctional electron donating monomer and a bifunctional electron accepting comonomer [3] This technique is able to strictly control the sequential alternation of donor and acceptor units within a single polymer chain. We recently started a new project on the synthesis of donor-acceptor type polymers by a novel postfunctionalization method based on a high yielding addition reaction between electron rich alkynes and strong acceptor molecules, such as tetracyanoethylene (TCNE) [4]. We apply the high yielding TCNE addition reaction to aromatic polyamines containing main chain alkynes and show for the first time the postfunctional synthesis of purely organic donor-acceptor alternating conjugated polymers [15]
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