Assessment of the aromaticity of borepin rings by spectroscopic,crystallographic and computational methods: a historical overview |
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| Authors: | Reid E Messersmith John D Tovar |
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| Institution: | 1. Department of Chemistry, Johns Hopkins University, Baltimore, MD, USA;2. Department of Materials Science and Engineering, Johns Hopkins University, Baltimore, MD, USA |
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| Abstract: | This review presents a chronological discussion of the evolution of our conceptual and experimental understanding of aromaticity as pertaining to the borepin ring structure. Borepin is the boron‐containing charge‐neutral analogue of the carbocyclic tropylium ion, and many molecular variations involving the borepin motif have been synthesized over the past half century. The aromaticity of the borepin system has been probed with ultraviolet–visible (UV–vis), photoluminescence and infrared (IR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, X‐ray crystallography and computational analysis. Recently, the focus of borepin‐containing compounds has shifted to π‐electron materials, building on the foundation of a firm understanding of the physical organic properties of the borepin motif that will allow for electronic fine‐tuning toward desired applications. Copyright © 2015 John Wiley & Sons, Ltd. |
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| Keywords: | aromaticity borepin π ‐electron materials |
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