%0 Journal Article %A Liu, Zhiqiang %A Ishibashi, Jacob S. A. %A Darrigan, Clovis %A Dargelos, Alain %A Chrostowska, Anna %A Li, Bo %A Vasiliu, Monica %A Dixon, David A. %A Liu, Shih-Yuan %D 2017 %T The Least Stable Isomer of BN Naphthalene: Toward Predictive Trends for the Optoelectronic Properties of BN Acenes %U https://acs.figshare.com/articles/journal_contribution/The_Least_Stable_Isomer_of_BN_Naphthalene_Toward_Predictive_Trends_for_the_Optoelectronic_Properties_of_BN_Acenes/4903973 %R 10.1021/jacs.7b02661.s001 %2 https://acs.figshare.com/ndownloader/files/8245349 %K structure characterization %K Predictive Trends %K UV-PES %K cyclic voltammetry %K Stable Isomer %K orientational BN isomers %K BN Naphthalene %K cofacial π- stack motif %K BN naphthalene series %K HOMO energy %K Optoelectronic Properties %K BN Acenes %K BN acene compounds %K UV %K BN naphthalene isomers %K four-step sequence %X The 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. %I ACS Publications