Porphyrin-Containing Polymacrocycles: Synthesis and Evaluation as Fluorescent Detectors of Metal Cations

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

^aA.N. Frumkin Institute of Physical Chemistry and Electrochemistry RAS, 119991 Moscow, Russia

^bLomonosov Moscow State University, Department of Chemistry, 119991 Moscow, Russia

^cIvanovo State University of Chemistry and Technology, 153000 Ivanovo, Russia

^dG.A. Krestov Institute of Solution Chemistry RAS, 153045 Ivanovo, Russia

^@Corresponding author E-mail: alexaveron@yandex.ru

DOI: 10.6060/mhc180276a

Macroheterocycles 2018 11(2) 135-140

Using Pd(0)-catalyzed amination reaction of zinc 5,15-bis(4-bromophenyl)porphyrinate with diazatrioxamacrocycle – derivative of 3,3’-disubstituted biphenyl – a series of polymacrocyclic compounds was obtained. The investigation of their fluorescence in the presence of 18 metal cations revealed that two of them can act as molecular probes for Cu(II), Al(III) and Cr(III) by the fluorescence quenching. Tri- and tetramacrocyclic compounds of another structure were synthesized by the Pd(0)-catalyzed arylation of cryptands comprising central diazacrown ether moieties using zinc 5-(4-bromophenyl)porphyrinate. One of these compounds was characterized as a fluorescent chemosensor for Cu(II).

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Porphyrin-Containing Polymacrocycles: Synthesis and Evaluation as Fluorescent Detectors of Metal Cations

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