Carbon nanotubes (CNTs) possess optoelectronic properties that are exceptional for a wide variety of applications. These properties, however, cannot be fully exploited until methods for preparation of single types of CNTs exist because the bandgap of a CNT depends on its surface topology. We aim to prepare CNTs by using cycloparaphenylenes (short fragments of CNTs) as a launching point. Preliminary evidence has shown that cycloparaphenylenes (CPPs) cannot be directly converted into CNTs. By thickening CPPs into aromatic belts, we believe they will serve as superior templates for CNT growth.<br/>The synthetic methodology for the transformation of nanohoops to nanobelts will be presented. Three reactions have been identified that efficiently incorporate belt segments into CPPs. Ring closing metathesis, inspired by Prof. Ben King’s septulene, has been demonstrated to be an efficient phenylene bridging strategy for systems as strained as [6]CPP. An alternative strategy, previously used for the synthesis of coronene&lt;span style="font-size:10.8333px"&gt;,&lt;/span&gt; is alkyne cyclization where an alkyne dressed [8]CPP was effectively converted to a partial belt CPP. Finally, in an attempt to circumvent problems associated with cyclodehydrogenation under Scholl conditions, cyclodehydrochlorination (CDHC) of a 2-chlorophenyl functionalized [12]CPP has been successfully employed at the heels of an incredible implementation of CDHC to build helically coiled graphene nanoribbons.

Synthesis of aromatic belts from cycloparaphenylenes

255th National Meeting (2018)

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