Issue 1, 2024

Controlling the reactivity of phthalonitriles for the efficient synthesis of chiral phthalocyanines with self-assembly abilities

Abstract

Binaphthol-bridged phthalonitriles are common precursors for the preparation of chiral phthalocyanines (Pcs). However, self-condensation of these phthalonitriles usually leads to the target Pcs in extremely low yields. In this work, we report a smart approach to enhance the reactivity towards self-condensation of binaphthol-bridged phthalonitriles, which relies on the addition of another highly reactive phthalonitrile that initiates the macrocyclization process, but it is eventually released. After optimization of the reaction conditions, ethynyl-containing binaphthyloxy-bridged Zn(II)Pc (AA)2-2 has been obtained in remarkable yields. This Pc synthon has been further endowed with hydrophilic cationic tails, giving the strongly amphiphilic Zn(II)Pc 1, which has shown the ability to form nanostructures in aqueous solutions.

Graphical abstract: Controlling the reactivity of phthalonitriles for the efficient synthesis of chiral phthalocyanines with self-assembly abilities

Supplementary files

Article information

Article type
Research Article
Submitted
05 Oct 2023
Accepted
06 Nov 2023
First published
09 Nov 2023
This article is Open Access
Creative Commons BY-NC license

Org. Chem. Front., 2024,11, 60-66

Controlling the reactivity of phthalonitriles for the efficient synthesis of chiral phthalocyanines with self-assembly abilities

I. Paramio, T. Torres and G. de la Torre, Org. Chem. Front., 2024, 11, 60 DOI: 10.1039/D3QO01630G

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