A promising approach to new pi-conjugated materials with enhanced properties is to introduce heteroatoms, either embedded into the conjugated backbone or attached at the periphery. Conjugated organoboranes are known for their desirable optical and electronic properties, which have been exploited, for example, in the development of new linear and non-linear optical materials, emission and electron conduction layers in organic light emitting devices (OLEDs), and new probes and sensors for anions.[1]In this presentation we will discuss our recent work on oligomers and polymers that contain highly electron-deficient organoborane moieties.[2] Interaction of the empty p orbital on boron with the organic pi-system results not only in strongly enhanced electron acceptor properties, but also very interesting optical characteristics. We will also discuss our efforts toward regioregular borane-functionalized polythiophenes and the corresponding conjugated organoboron block copolymers.[3][1] a) C. D. Entwistle, T. B. Marder, Chem. Mater. 2004  , 16, 4574 ; b) F. J�kle, Chem. Rev. 2010  , 110, 3985 ; c) N. Matsumi, Y. Chujo, Polym. J. 2008  , 40, 77; d) A. Doshi and F. J�kle, Chapter 1.30 in Jan Reedijk, Kenneth Poeppelmeier, editors. Comprehensive Inorganic Chemistry II, Vol 1. Oxford: Elsevier; 2013, p 861-891; 'Boron-Containing Polymers'.[2] a) P. Chen, R. A. Lalancette, F. J�kle J. Am. Chem. Soc. 2011  , 133, 8802; b) P. Chen and F. J�kle J. Am. Chem. Soc. 2011  , 133, 20142; c) P. Chen, R. A. Lalancette and F. J�kle, Angew. Chem. Int. Ed. 2012  , 51, 7994; d) X. Yin, J. Chen, R. A. Lalancette, F. J�kle, to be submitted.[3] F. Pammer, F. Guo, R. A. Lalancette and F. J�kle Macromolecules 2012  , 45, 6333.

Enhancing the electron-deficient character of p-conjugated materials by borane functionalization

248th National Meeting (2014)

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