Dipyrroethanes/Dipyrroethenes: New Precursors for Porphyrinoids.

IF 8.8 2区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Topics in Current Chemistry Pub Date : 2025-06-02 DOI:10.1007/s41061-025-00506-y

Vratta Grover, Mangalampalli Ravikanth

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引用次数: 0

Abstract

Dipyrroethanes/dipyrroethenes (DPEs) containing two pyrroles connected by two meso sp³/sp² carbons are very useful precursors for the synthesis of very novel porphyrinoids. Dipyrromethanes/dipyrromethenes (DPMs) that consist of two pyrrole rings connected via one meso sp³/sp² carbon are the most popular precursors for the synthesis of several types of porphyrinoids. Dipyrromethanes/dipyrromethenes can be readily prepared by condensing aldehyde and pyrrole under acid-catalyzed conditions, whereas dipyrroethenes (DPEs) require a few skilled synthetic steps to be obtained in good quantities. Especially, dipyrroethenes exist in E/Z-isomeric mixtures but their separation is not required for the synthesis of porphyrinoids. In the last decade, DPEs have been used as key precursors to synthesize contracted porphyrins such as triphyrins(2.1.1), porphyrin isomers such as porphycene(2.0.2.0), and several expanded porphyrins. This review describes different methods available for the synthesis of 5,6-di(alkyl/aryl/heteroaryl) dipyrroethanes/dipyrroethenes and their use in the synthesis of different porphyrinoids ranging from contracted porphyrinoids to expanded porphyrinoids. The structure, reactivity, and physico-chemical properties of various porphyrinoids which were synthesized from DPEs are also discussed.

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二吡咯烷/二吡咯烷：卟啉类化合物的新前体。

含有两个吡咯并由两个介位sp3/sp2碳连接的二吡咯/二吡咯烷（dpe）是合成新型卟啉类化合物非常有用的前驱体。由两个吡咯环通过一个介位sp3/sp2碳连接而成的二吡咯甲烷/二吡咯甲烷（dpm）是合成几种卟啉类化合物最常用的前体。在酸催化的条件下，通过醛和吡咯的缩合可以很容易地制备二吡咯甲烷/二吡咯甲烷，而二吡咯乙烯（dpe）则需要几个熟练的合成步骤才能获得大量。特别是，E/ z异构体混合物中存在二吡罗乙烯，但合成卟啉类化合物不需要分离二吡罗乙烯。在过去的十年中，dpe已被用作合成收缩卟啉如三卟啉（2.1.1）、卟啉异构体如卟啉（2.0.2.0）和几种扩展卟啉的关键前体。综述了5,6-二（烷基/芳基/杂芳基）二吡咯烷/二吡咯烷的不同合成方法及其在各种卟啉类化合物合成中的应用，包括收缩卟啉类化合物和扩张卟啉类化合物。讨论了以dpe为原料合成的各种卟啉类化合物的结构、反应性和理化性质。

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来源期刊

Topics in Current Chemistry Chemistry-General Chemistry

CiteScore

13.70

自引率

1.20%

发文量

期刊介绍： Topics in Current Chemistry is a journal that presents critical reviews of present and future trends in modern chemical research. It covers all areas of chemical science, including interactions with related disciplines like biology, medicine, physics, and materials science. The articles in this journal are organized into thematic collections, offering a comprehensive perspective on emerging research to non-specialist readers in academia or industry. Each review article focuses on one aspect of the topic and provides a critical survey, placing it in the context of the collection. Selected examples highlight significant developments from the past 5 to 10 years. Instead of providing an exhaustive summary or extensive data, the articles concentrate on methodological thinking. This approach allows non-specialist readers to understand the information fully and presents the potential prospects for future developments.