The identification and characterization of homoaromatic compounds bearing an interrupted p-system are {fundamental|basic} challenges for the understanding of electronic interactions in organic molecules. {This is|This really is|This can be|That is} {further|additional} hampered by {the fact that|the truth that} no {stable|steady} neutral homoaromatic hydrocarbon is {known|recognized|identified}. We present the preparation of {a new|a brand new} class of neutral homoaromatic compounds, {which are|that are} supported by experimental {evidence|proof} (ring {current|present|existing} observed by NMR spectroscopy, equalization of bond lengths {through|via|by means of|by way of} X-ray structure {analysis|evaluation}) {as well as|in addition to|along with|and also|together with|and} computational {analysis|evaluation} (NICS and ACID). {Furthermore|Moreover|In addition|Additionally}, we show that {one|1|a single|one particular} homoaromatic hydrocarbon {is a|is really a|is actually a|can be a|is often a|is usually a} photoswitch {through|via|by means of|by way of} a reversible photochemical [1,11] sigmatropic rearrangement. We {provide|offer|supply|give|present|deliver} {evidence|proof} that the {local|nearby|neighborhood|regional} 6p homoaromatic state vanishes upon photoswitching to {produce|create|generate|make} a purely {global|international|worldwide} 10p homoaromatic state. These {results|outcomes|final results|benefits} of {stable|steady} and accessible homoaromatic neutral hydrocarbons and their photoswitching behaviour {provide|offer|supply|give|present|deliver} new insights for the understanding and study of homoconjugative interactions in organic molecules, and for the {design|style|design and style} of new responsive molecular {materials|supplies|components}. 6-Bromo-2,3-dihydrobenzofuran structure 1781098-86-9 site PMID:25023702
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