Nanographenes (NGs) and graphene nanoribbons (GNRs) are very promising materials for electronic applications. However, NGs and GNRs produced by physical methods do not allow control over size, shape and functionalization of GNRs, leading to undefined electronic and physical properties. Thus, methods to prepare such materials using the solution-phase bottom-up approach have been proposed. Yet, none of them has been proven as efficient for the introduction of electron-rich and electron-poor units on the edges of GNRs, thus limiting the modulation of their electronic properties. In this regard, our group has revisited and used a photochemical method, called the cyclodehydrochlorination reaction (CDHC), for the regioselective, mild and metal-free synthesis of NGs and GNRs from polychlorinated precursors [1,2]. Although this method is very useful for the synthesis of all-phenyl molecules, very few examples have been reported for the synthesis of heterocycle-fused NGs and GNRs. In this presentation, we will show how the CDHC reaction, a (4n+2)pi<br/>electrocyclization reaction, can be used to prepare well-defined linear and helical NGs and GNRs based on electron-rich heterocyclic motifs such as thiophene, pyrrole and ullazine and electron-poor units such as pyridine and benzothiadiazole. We also show how the CDHC reaction has been used to prepare ladder conjugated polymers (CLPs) with both electron-rich and electron-poor units, thus creating a permanent dipole within the polymer backbone. Carbon nanotubes wrapping, field-effect transistor (OFETs) and bulk heterojunction solar cells (BHJSCs) testing of these new materials will also be presented.<br/><br/>

Functionalized graphene nanoribbons as semiconducting materials for organic electronics

255th National Meeting (2018)

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