Issue 19, 2024

Contracted porphyrins and calixpyrroles: synthetic challenges and ring-contraction effects

Abstract

Ring-contracted porphyrin analogues, such as subporphyrins and calix[3]pyrroles, have recently attracted considerable attention not only as challenging synthetic targets but also as functional macrocyclic compounds. Although canonical porphyrins and calix[4]pyrrole are selectively generated via acid-catalyzed condensation reactions of pyrrole monomers, their tripyrrolic analogues are always missing under similar conditions. Recent progress in synthesis has shown that strain-controlled approaches using boron(III)-templating, core-modification, or ring tightening provide access to various contracted porphyrins. The tripyrrolic macrocycles are a new class of functional macrocycles exhibiting unique ring-contraction effects, including strong boron chelation and strain-induced ring expansion. This Perspective reviews recent advances in synthetic strategies and the novel ring-contraction effects of subporphyrins, triphyrins(2.1.1), calix[3]pyrroles, and their analogous.

Graphical abstract: Contracted porphyrins and calixpyrroles: synthetic challenges and ring-contraction effects

Article information

Article type
Perspective
Submitted
27 3 2024
Accepted
19 4 2024
First published
24 4 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2024,15, 6994-7009

Contracted porphyrins and calixpyrroles: synthetic challenges and ring-contraction effects

K. Watanabe, N. N. Pati and Y. Inokuma, Chem. Sci., 2024, 15, 6994 DOI: 10.1039/D4SC02028F

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