Synthesis, characterization and photovoltaic behavior of platinum acetylide polymers with electron-deficient 9,10-anthraquinone moiety

A new class of soluble, solution-processable platinum(II) acetylide polymers functionalized with electron-deficient 9,10-anthraquinone spacer and their corresponding diplatinum model complexes were synthesized and characterized. The organometallic polymers exhibit good thermal stability and show low-energy broad absorption bands in the visible region. The effect of the presence of thiophene rings along the polymer chain on the optical and photovoltaic properties of these metallated materials was examined. The low-bandgap polymer with thiophene–anthraquinone–thiophene (donor–acceptor–donor) fragment can serve as a good electron donor for fabricating bulk heterojunction polymer solar cells by blending with a methanofullerene electron acceptor. At the same donor:acceptor blend ratio of 1:4, the light-harvesting ability and solar cell efficiency notably increase when the anthraquinone ring is sandwiched by two thiophene units. Photoexcitation of such polymer solar cells results in a photoinduced electron transfer from the π-conjugated metallopolymer to [6,6]-phenyl C61-butyric acid methyl ester with power conversion efficiency up to ∼ 0.35%. For safety concern, these metallopolymers were also tested for possible cytotoxicity and they do not show significant cytotoxic activity on human liver derived cells and skin keratinocytes at reasonable doses, rendering these functional materials safe to use in practical devices.

Low-bandgap platinum metallopolyynes of 9,10-anthraquinone derivatives and their molecular model complexes are reported. Polymer P1 has an optical bandgap of 2.29 eV and the incorporation of electron-deficient anthraquinone spacer on the oligothiophene ring in the main chain furnishes a new π-conjugated donor–acceptor system with strong visible absorption appropriate for organic solar cells.Figure optionsDownload as PowerPoint slide