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Dalton Trans. 2017 Aug 22;46(33):10802-10808. doi: 10.1039/c7dt01838j.

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

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Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan.


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.


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