Synthesis and properties of tetra- and octacationicmeso-tetrakis(3-pyridyl)bacteriochlorin derivatives

Author:

Dudkin Semyon V.1,Makarova Elena A.1,Slivka Ludmila K.1,Lukyanets Evgeny A.1

Affiliation:

1. Organic Intermediates and Dyes Institute, B. Sadovaya ¼, 123995 Moscow, Russia

Abstract

The synthesis and properties of new water-soluble tetra- and octacationic derivatives of meso-tetrakis(3-pyridyl)bacteriochlorin are reported. Tetracationic salt was synthesized by quaternization of the pyridine groups of starting bacteriochlorin with 1,4-dibromobutane. Octacationic salts were obtained by treating of tetracationic salt with excess of pyridine or N,N-dimethylaminoethanol. Zinc complexes of water-soluble bacteriochlorin derivatives were prepared by direct metalation of corresponding non-metal compounds with zinc acetylacetonate, unlike to neutral bacteriochlorin which forms zinc complex only by transmetalation of the corresponding cadmium complex. The new bacteriochlorins have strong absorption in red and NIR spectral region. Free-base BCs possess good stability in aqueous solutions as compared to their zinc complexes and efficiently generate singlet oxygen.

Publisher

World Scientific Pub Co Pte Lt

Subject

General Chemistry

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