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Porphyrins are widely used for binding of amino acids which usually occurs due to donor-acceptor interaction between NH-groups of amino acid and ZnII atom of metalloporphyrinate.[1,2] In the case of zinc porphyrinates with OH groups the possibility of additional hydrogen bonds formation between the hydroxyl groups of porphyrinate and oxygen atom of amino acid appears. Hydrogen bonds in the resulting molecular complex make it significantly more stable. When porphyrins form hydrogen bonds with amino acids (or with other biological objects) they are considered to be capable of recognizing the given substrates, and the higher the complex stability, the better is the recognizing ability of this porphyrin. This work is devoted to the synthesis of new monohydroxysubstituted zinc porphyrinates with different positions of reactionary centres and investigation of their binding ability towards amino acids. To this end we used synthetic approach on the basis of key 10-arylsubstituted a,c-biladiene dihydrobromides which according to the literature data are widely employed for obtaining of mono-functionalized porphyrins.[3-6] By the method of spectrophotometric titration and 1H NMR spectroscopy a binding ability of the zinc porphyrinates (ZnP) regarding to the methyl esters of ortho(L1), meta(L2), and para(L3) aminobenzoic acids in toluene have been studied.

Synthesis of Monohydroxy-Substituted Diarylporphyrins and Their Binding Ability towards Aminobenzoic Acids