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Synthesis of Crowned Triazolephthalocyanines
Author(s) -
Cabezón Beatriz,
Quesada Ernesto,
Esperanza Sagrario,
Torres Tomás
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200008)2000:15<2767::aid-ejoc2767>3.0.co;2-2
Subject(s) - chemistry , cyanation , moiety , crown ether , ether , molecule , derivative (finance) , nitrogen atom , combinatorial chemistry , stereochemistry , organic chemistry , ring (chemistry) , ion , financial economics , economics , catalysis
The synthesis of triazolephthalocyanines bearing crown ether and aza‐crown ether substituents is described. Different substituents have been introduced on the nitrogen atom of the aza‐crown moiety to improve the solubility and the intrinsic amphiphilic character of these macrocycles. The crowned triazolephthalocyanines described have been prepared by a statistical procedure, and also by different variations of a stepwise method. Preliminary studies of the aggregation properties of one representative of this new family of compounds have also been carried out. An exhaustive study of the synthesis of the corresponding dicyano derivative precursors of the triazolephthalocyanines is displayed. Two different approaches have been used for this goal: The first one inserts the cyano groups prior to the synthesis of the crown ether moiety, while the second one builds the crown ether part of the molecule in advance of the cyanation process. The incompatibility of the Rosemund‐von‐Braun cyanation conditions and the presence of nitrogen atoms in the molecule is the main difficulty of the synthesis of these precursors.