Strategies in the synthesis of dibenzo[<i>b,f</i>]heteropines

Maier, D.; Bezuidenhoudt, Barend C. B.; Marais, Charlene

doi:10.3762/bjoc.19.51

Cited by 1 publication

(1 citation statement)

References 75 publications

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“…It appeared that thiepines carrying sterically demanding substituents on the sulfur α-positions as well as annelated analogues show substantially increased lifetimes, owing to steric and electronic effects [ 45 ]. With these criteria in mind, a variety of thermally-stable annelated thiepines were progressively isolated as a result of very diverse synthetic strategies [ 46 – 49 ], which were further applied to the preparation of stable selenepines and tellurepines [ 50 – 53 ].…”

Section: Reviewmentioning

confidence: 99%

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

Okba,

Simón Marqués,

Matsuo

et al. 2024

Beilstein J. Org. Chem.

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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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