In our work, we aim at taking advantage of intramolecular N→B-coordination to tailor the electronic properties of conjugated oligo- and polymers that may serve as electron accepting/electron transporting (n-type) semiconductors in organic electronic applications. The properties of the materials can be modified through choice of the N-heterocyclic component, and by variation of the substituents on boron. We have demonstrated that electronically and structurally diverse molecular structures can be readily generated by strategies involving hydroboration and dipolar [3+2]-cycloaddition. Recently, we have shown that twofold hydroboration of a pyrazine-derived substrate with 9H-BBN or (C6F5)2B-H allows to vary the electron affinity of the resulting borane over a range of ca. 0.6 eV. An investigation of the corresponding radical anions by EPR-spectroscopy, and single crystal analysis corroborated the π-delocalized nature of these radicals. Furthermore, the clean conversion and high yield of this synthetic strategy proved it to be suitable for polymer post-functionalization. In this talk, we will discuss our latest results on the extension of the above work, and on our efforts towards the preparation N→B-ladder polymers by post-functionalization.

Tailoring of electronic properties via intramolecular N→B-coordination in conjugated π-systems

254th National Meeting (2017)

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