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ISSN 1998-9539

Palladium- and Copper-Catalyzed Amination of Halogenophenyl Substituted Porphyrins for the Synthesis of Porphyrin-Azacrown Ethers Conjugates and Evaluation of Their Sensing Properties

Alexei A. Yakushev,a Alexei D. Averin,a,b@ Olga A. Maloshitskaya,b Sergei A. Syrbu,c Oskar I. Koifman,c and Irina P. Beletskayaa,c

aA.N. Frumkin Institute of Physical Chemistry and Electrochemistry, 119991 Moscow, Russian Federation

bLomonosov Moscow State University, Department of Chemistry, 119991 Moscow, Russian Federation

cIvanovo State University of Chemistry and Technology, 153000 Ivanovo, Russian Federation

@Corresponding author E-mail:


DOI: 10.6060/mhc151206a

Macroheterocycles2016 9(1) 65-72


The Pd0- and CuI-catalyzed amination of meso-(halogenophenyl)substituted porphyrins and their Zn complexes with propane-1,3-diamine and trioxadiamine was carried out to produce mono- and diaminated derivatives. Conditions for the synthesis of bis- and trismacrocyclic porphyrin-azacrown conjugates with trimethylenediamine linkers via Pd0-catalyzed amination reactions were established. The properties of two polymacrocyclic compounds to serve as colorimetric and fluorescent sensors for metal cations were investigated, and trismacrocyclic ligand possessing two 1-aza-18-crown-6 moieties arranged symmetrically around the porphyrin core was found to be selective for CuII in the presence of other metals by strong emission quenching caused by copper ions..




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