Polythiophenes are among the most widely studied polymeric materials. They are extensively used in organic electronics and in sensory applications. Regioregularity is a key feature that enables a coplanar arrangement of the thiophene rings in the polymer chain, which in turn confers desirable properties such as extended conjugation and high conductivity after doping.We succeeded in the preparation of a regioregular polythiophene that is functionalized with triorganoborane moieties in its side chains by Stille-type polycondensation. The electron-deficient borane moieties can function as electron acceptors, while the empty p orbital on boron facilitates p-delocalization. Studies on the photophysical properties of the polymer revealed energy transfer from the boron-containing side chains to the conjugated polythiophene backbone. Moreover, fluoride binding to the tricoordinate borane moieties led to a pronounced response in the absorption and emission characteristics. Amphiphilic thiophene block copolymers that contain boronic acid functionalities were also prepared using GRIM polymerization techniques. Boronic acid-functionalized polymers have drawn much recent attention because of their strong potential for glucose or RNA sensing, and as self-regulated drug-delivery systems. The synthesis, self-assembly properties and sugar binding behavior of these new polymers will be discussed.

Borane-functionalized polythiophenes for optoelectronic and sensory applications

247th National Meeting (2014)

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