Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments - Groupe Nanosciences
Journal Articles Beilstein Journal of Organic Chemistry Year : 2024

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.
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Dates and versions

hal-04636108 , version 1 (05-07-2024)

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Aissam Okba, Pablo Simón Marqués, Kyohei Matsuo, Naoki Aratani, Hiroko Yamada, et al.. Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments. Beilstein Journal of Organic Chemistry, 2024, 20, pp.287-305. ⟨10.3762/bjoc.20.30⟩. ⟨hal-04636108⟩
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