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

文献情報

出版日 2023-11-09

DOI 10.1039/D3QO01630G

インパクトファクター 5.281

著者

Irene Paramio

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要旨

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.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry