Abstract

We present the novel 1,4-difunctionalisation of benzocarborane with organometallic groups suitable for cross-coupling and its subsequent insertion for the first time into conjugated polymer backbones. Copolymers with solubilised cyclopentadithiophene and diketopyrrolopyrrole derivatives were prepared by Stille polymerisation in good molecular weight. The physical, material and optoelectronic properties of the resulting polymers were investigated, demonstrating that benzocarborane acts similarly to a stabilised, electron-deficient cis-diene linker. We also report the first polymer field effect transistors incorporating a benzocarborane in the backbone.

Highlights

  • The unusual properties of carboranes make them, in principle, highly attractive species to incorporate into optoelectronically active materials.[1,2,3,4,5,6] Their unusual delocalized three-centre-twoelectron bonding motif confers upon them extremely high temperature stability, pseudoaromaticity and a strong electron withdrawing nature, and has prompted much research into the properties of carborane containing materials.[7,8] For example, carborane containing polysiloxanes have been demonstrated to show dramatically improved thermal and chemical stability over the parent polymers.[9]

  • We report the first polymer field effect transistors incorporating a benzocarborane in the backbone

  • In 2007, Vicente and co-workers reported the synthesis and electrochemical polymerisation of the ortho, meta and para isomers of di(2-thiophenyl)carborane.[10]. They found that the isomer regiochemistry has a profound in uence on polymer properties, with the para isomer exhibiting the highest ionisation potential, widest band gap and lowest conductivity while the ortho isomer had the lowest ionisation potential, smallest band gap and highest conductivity. These results suggested that effective delocalization through the meta and para isomers of carborane was poor

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Summary

Introduction

The unusual properties of carboranes make them, in principle, highly attractive species to incorporate into optoelectronically active materials.[1,2,3,4,5,6] Their unusual delocalized three-centre-twoelectron bonding motif confers upon them extremely high temperature stability, pseudoaromaticity and a strong electron withdrawing nature, and has prompted much research into the properties of carborane containing materials.[7,8] For example, carborane containing polysiloxanes have been demonstrated to show dramatically improved thermal and chemical stability over the parent polymers.[9].

Results
Conclusion

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