Department of Chemistry, Indian Institute of Technology Bombay, Macrocyclic Lab, Lab No. 338, 400076, Mumbai, India.
Chem Rec. 2022 Nov;22(11):e202200144. doi: 10.1002/tcr.202200144. Epub 2022 Jul 27.
The 20π porphyrinoids are immediate higher homologues of 18π porphyrins and differ from porphyrins in aromaticity which in turn affects the structure, properties and chemical reactivities. Research over the years indicated that the 20π porphyrinoids can be stabilized as non-aromatic/anti-aromatic or Mobius aromatic macrocycles using different strategies such as core-modification of porphyrins, non-metal/metal complexation of porphyrins, peripheral modification of porphyrins and expanded porphyrinoids. The structural properties such as aromaticity of the macrocycle can be controlled by choosing the right synthetic strategy. This review will provide an overview of the development in the chemistry of 20π porphyrinoids giving emphasize on the synthesis, structure and electronic properties of these macrocycles which have huge potential for various applications.
20π 卟啉类化合物是 18π 卟啉的直接高同系物,与卟啉在芳香性上有所不同,芳香性又反过来影响结构、性质和化学反应性。多年的研究表明,20π 卟啉类化合物可以通过不同的策略稳定为非芳香/反芳香或莫比乌斯芳香大环,例如卟啉的核修饰、卟啉的非金属/金属络合、卟啉的外围修饰和扩展卟啉类化合物。通过选择正确的合成策略,可以控制大环的结构性质,如芳香性。本文综述了 20π 卟啉类化合物化学的发展,重点介绍了这些大环的合成、结构和电子性质,它们在各种应用中具有巨大的潜力。