Novel asymmetric phthalocyanine/porphyrazine hybrid complexes

The chemistry of tetrapyrrolic porphyrazine, phthalocyanine and their derivatives has been comprehensively explored by several researchers in the last decade. Especially peripherally-reactive symmetrical and unsymmetrical porphyrazine, phthalocyanine derivatives have the potential to be used in a wide range of high technology applications, such as in electron transfer, magnetic interaction, catalysis, photodynamic theraphy, electrochromic display devices, and as a molecular electronics, or magnetic devices. Despite the fact that symmetrical tetra-, hexa-, octa-and decasubstituted phthalocyanines and related macrocycles are well-known, the synthesis of mono-, and disubstituted phthalocyanine/porphyrazine (Pc/Pz) hybrid macrocycles as well as other unsymmetrical phthalocyanines or porphyrazines continues to be a difficult problem owing to the formation of lots of undesirable compounds and tiring purification steps. The synthesis of unsymmetrical Pc/Pz hybrids has a considerable importance in understanding their nature and applications. In this context, Hoffmann and Barrett have provided examples of hetereatom donors directly bound to the macrocyclic core of the porphyrazine side of the hybride structure. Accordingly, this study has tested and used an alternative synthetic procedure, direct condensation, instead of cross condensation for the preparation of an unsymmetrical free-base and metallo- Pz/Pc hybrids having a solitare- and trans-configurations which bears peripheral nitro, and amino functionality. In this study, we have presented synthesis, characterization and florescence properties of Pc/Pz hybrids bearing nitro and amino functionality. All metal free Pc/Pz hybrids and its metal complexes have been investigated and characterized by UV-vis, IR, 1H-NMR and elementel analysis methods. The flourescence properties of free Pc/Pz hybrids and its metal complexes obtained from 3,4-Bis(4-tert-butylphenyl)pyrroline-2,5-diimine and 6,7-nitro-1,3,3-tricholoroisoindoline have been investigated and compared with the previous reported studies. Keywords: Phthalocyanine, porphyrazine, hybrids, direct condensation, flourescence