Synthesis of porphyrin-diazacrown ether and porphyrin-cryptand conjugates for fluorescence detection of copper(II) ions
- Authors: Averin A.D.1,2, Yakushev A.A.2, Maloshitskaya O.A.1, Surby S.A.3, Koifman O.I.3, Beletskaya I.P.1,2
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Affiliations:
- Department of Chemistry, M. V. Lomonosov Moscow State University
- A. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences
- Ivanovo State University of Chemistry and Technology
- Issue: Vol 66, No 8 (2017)
- Pages: 1456-1466
- Section: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/241101
- DOI: https://doi.org/10.1007/s11172-017-1908-3
- ID: 241101
Cite item
Abstract
Palladium-catalyzed amination was used for the synthesis of the macrocycles containing trioxadiamine linker and the fragments of either 3,3′-disubstituted biphenyl or 2,7-disubstituted naphthalene. Catalytic macrocyclization gives diazacrown ether-based cryptand with trioxadiamine linker. The synthesized compounds were involved in Pd-catalyzed arylation of zinc meso-(bromophenyl)porphyrin to obtain polymacrocyclic conjugates bearing one or two porphyrin units. The synthesized conjugates were studied as fluorescence sensing material and molecular probes for 18 metal ions. It was found that two of them are very promising fluorescent chemosensors for copper(II) cations.
Keywords
About the authors
A. D. Averin
Department of Chemistry, M. V. Lomonosov Moscow State University; A. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences
Author for correspondence.
Email: averin@org.chem.msu.ru
Russian Federation, 3 Build., 1 Leninskie Gory, Moscow, 119991; 4 Build., 31 Leninsky prosp., Moscow, 119991
A. A. Yakushev
A. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences
Email: averin@org.chem.msu.ru
Russian Federation, 4 Build., 31 Leninsky prosp., Moscow, 119991
O. A. Maloshitskaya
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: averin@org.chem.msu.ru
Russian Federation, 3 Build., 1 Leninskie Gory, Moscow, 119991
S. A. Surby
Ivanovo State University of Chemistry and Technology
Email: averin@org.chem.msu.ru
Russian Federation, 7 Sheremetevskii prosp., Ivanovo, 153000
O. I. Koifman
Ivanovo State University of Chemistry and Technology
Email: averin@org.chem.msu.ru
Russian Federation, 7 Sheremetevskii prosp., Ivanovo, 153000
I. P. Beletskaya
Department of Chemistry, M. V. Lomonosov Moscow State University; A. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences
Email: averin@org.chem.msu.ru
Russian Federation, 3 Build., 1 Leninskie Gory, Moscow, 119991; 4 Build., 31 Leninsky prosp., Moscow, 119991