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The Least Stable Isomer of BN Naphthalene: Toward Predictive Trends for the Optoelectronic Properties of BN Acenes
journal contribution
posted on 2017-04-19, 00:00 authored by Zhiqiang Liu, Jacob S. A. Ishibashi, Clovis Darrigan, Alain Dargelos, Anna Chrostowska, Bo Li, Monica Vasiliu, David A. Dixon, Shih-Yuan LiuThe least stable
isomer of the parental BN naphthalene series has
been synthesized in a simple four-step sequence. Its experimental
electronic structure characterization via UV-PES, cyclic voltammetry,
and UV–vis spectroscopy in direct comparison with three other
known BN naphthalene isomers has established two guiding principles
for predicting the electronic structures of BN acene compounds: (1)
Orientational BN isomers have similar HOMO–LUMO gaps. (2) For
each pair of orientational BN isomers, the more thermodynamically
stable compound has the lower HOMO energy. Furthermore, we demonstrate
that BN/CC isosterism in the context of BN-9,1-Naph can
impact crystal packing to favor a cofacial π-stack motif.