Acenes and other such conjugated molecules have been investigated for a number of optoelectronic applications. Though all-carbon acenes are more studied, heteroacenes can access chemical and electronic space complementary to those of the all-carbon systems. We present a systematic investigation of boron- nitrogen-containing acene isosteres with comparisons to all-carbon analogues as well as comparisons among isomers in which the only difference is the placement of the B–N unit within a particular acene scaffold. We synthesized BN isosteres of naphthalene, anthracene, and tetracene, and we utilized powerful characterization techniques such as UV-photoelectron spectroscopy, cyclic voltammetry, and UV-vis absorption spectroscopy to elucidate electronic structure. Finally, using these results in tandem with theory, we arrived at an empirical model for the frontier orbital energies of the BN acenes which takes into consideration the placement of the BN unit within the scaffold.

Systematic experimental investigation of BN acene isosteres

256th National Meeting (2018)

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