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 mar 2024
Accepted
19 abr 2024
First published
24 abr 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

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements