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. Beletskaya^a,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: alexaveron@yandex.ru

DOI: 10.6060/mhc151206a

Macroheterocycles2016 9(1) 65-72

The Pd⁰- and Cu^I-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 Cu^II in the presence of other metals by strong emission quenching caused by copper ions..

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

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