Issue 33, 2017

A synthesis of novel expanded porphyrinoids: NiII-induced nitrile cyclization of dicyanovinylene-bis(meso-aryl)dipyrrin

Abstract

NiII-Metallation of dicyanovinylene-bis(meso-aryl)dipyrrin 1 under refluxed toulene conditions resulted in the formation of a bicyclic pyrrolizine ring to afford two isomeric bisNiII expanded porphyrinoid complexes 2a and 2b. Furthermore, acyclic NiII dipyrrin complex 3 was also isolated. The respective structures for 2a, 2b, and 3 were elucidated by X-ray diffraction analysis. Macrocycles 2a and 2b exhibited typical features of aromatic porphyrinoids showing their longest wavelength absorption bands in the near infrared region ranging from 1100 to 1600 nm.

Graphical abstract: A synthesis of novel expanded porphyrinoids: NiII-induced nitrile cyclization of dicyanovinylene-bis(meso-aryl)dipyrrin

Supplementary files

Article information

Article type
Paper
Submitted
20 May 2017
Accepted
16 Jun 2017
First published
16 Jun 2017

Dalton Trans., 2017,46, 10802-10808

A synthesis of novel expanded porphyrinoids: NiII-induced nitrile cyclization of dicyanovinylene-bis(meso-aryl)dipyrrin

N. H. Faialaga, S. Ito, H. Shinokubo, Y. Kim, K. Kim and J. Shin, Dalton Trans., 2017, 46, 10802 DOI: 10.1039/C7DT01838J

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