Low symmetry solitaire- and trans-functional porphyrazine/phthalocyanine hybrid complexes: Synthesis, isolation, characterization, and electrochemical and in-situ spectroelectrochemical properties

Abstract

In this work, metal-free and metallo porphyrazine/phthalocyanine hybrids (3a-5b) containing unsymmetrical tert-butyl phenyl and electron withdrawing -NO2 functional groups have been synthesized firstly by direct condensation technique instead of statistical condensation from substituted donor and acceptor precursors; 3,4-Bis(4-tert-butylphenyl)pyrroline-2,5-diimine (1) and 6,7-nitro-1,3,3-tricholoroisoindoline (2). The complexes were characterized by elemental analysis, FT-IR, H-1-NMR, UV-vis and MALDI-TOF spectroscopy. Electrochemical and in situ spectroelectrochemical measurements of the complexes revealed that the attachment of NO2 moieties at the periphery makes a monitorable effect on their redox properties in comparison with those of similar phthalocyanine compounds.