Synthesis of π -conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments

Abstract
The “precursor approach” has proved particularly valuable for the preparation of insoluble and unstable π-conjugated polycyclic compounds (π-CPCs), which cannot be synthesized via in-solution organic chemistry, for their improved processing, as well as for their electronic investigation both at the material and single-molecule scales. This method relies on the synthesis and processing of soluble and stable direct precursors of the target π-CPCs, followed by their final conversion in situ, triggered by thermal activation, photoirradiation or redox control. Beside well-established reactions involving the elimination of carbon-based small molecules, i.e., retro-Diels–Alder and decarbonylation processes, the late-stage extrusion of chalcogen fragments has emerged as a highly promising synthetic tool to access a wider variety of π-conjugated polycyclic structures and thus to expand the potentialities of the “precursor approach” for further improvements of molecular materials’ performances. This review gives an overview of synthetic strategies towards π-CPCs involving the ultimate elimination of chalcogen fragments upon thermal activation, photoirradiation and electron exchange.

Beilstein J. Org. Chem. 2024, 20, 287–305. doi:10.3762/bjoc.20.30

Source: Beilstein Journal of Organic Chemistry - February 15, 2024 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: arenes chalcogens extrusion fused-ring systems precursor approach Review Source Type: research