Synthesis and Photophysical Properties of Low Symmetrical Porphyrin-Amino Acid Conjugates and Their Zn Complexes

A. Lyubimtsev,^a^@ A. Semeikin,^a N. Zheglova,^a V. Sheinin,^b O. Kulikova,^b and S. Syrbu^b

Dedicated to Professor Oleg Aleksandrovich Golubchikov on the occasion of his 70-th birthday

^aResearch Institute of Macroheterocycles, Ivanovo State University of Chemistry and Technology, 153000 Ivanovo, Russia

^bG.A. Krestov Institute of Solution Chemistry of the Russian Academy of Sciences, 153045 Ivanovo, Russia

^@Corresponding author E-mail: alexlyubimtsev@mail.ru

DOI: 10.6060/mhc171151l

Macroheterocycles 2018 11(1) 103-110

A series unsymmetrical amino acid substituted porphyrins and their Zn-complexes were synthesized and full characterized by ¹H NMR and UV-Vis spectroscopy and MALDI-TOF spectrometry. Starting with meso-tetraphenylporphyrin (H₂TPP) 1, porphyrin 2 with one nitro group was synthesized via regioselective nitration reaction. Reduction of the 5-(4’-nitrophenyl)-10,15,20-tris(phenyl)porphine 2 and coupling of obtained 5-(4’-aminophenyl)-10,15,20-tris(phenyl)porphine 3 with Boc-protected glycine, L-phenylalanine, L- and D-leucine and L-isoleucine gave the porphyrin-amino acid conjugates 4a-e. These free porphyrin ligands 4 were metallized with Zn(II) to form corresponding Zn-complexes 5a-e. Photostability of the ligands 4 and their Zn-complexes 5 and their ability to singlet oxygen generation were studied. All investigated porphyrin-amino acid conjugates show a higher efficiency to generate singlet oxygen than H₂TPP under the same experimental conditions.

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Synthesis and Photophysical Properties of Low Symmetrical Porphyrin-Amino Acid Conjugates and Their Zn Complexes

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