Synthesis and physico-chemical properties of a H-cardanol triazole zinc porphyrin conjugate

Abstract

Although a large number of natural and non-natural metalloporphyrins are known, examples with fluorescence and fat-soluble properties are rare. We have achieved the synthesis of a fluorescent and fat-soluble zinc porphyrin incorporating four units of hydrogenated cardanol (H-cardanol). The synthesis is sustainable since the product is derived from cashew-nut shell liquid (CNSL), which is a renewable and bio-waste material. The H-cardanol triazole zinc porphyrin conjugate (HTZPC) was synthesized through applying a copper(I) catalyzed azide–alkyne cycloaddition (CuAAC) reaction between a H-cardanol derived azide and a tetraarylporphyrin derived alkyne. The absorption and emission properties of the hydrocarbon solvent soluble HTZPC were evaluated using UV-vis and fluorescence emission spectra obtained in various solvents. The results were compared with related molecules like a triazole-zinc porphyrin conjugate (TZPC), zinc tetra-C(4)-methoxyphenyl porphyrin (ZP), and a H-cardanol-triazole conjugate (HTC). The results showed that HTZPC undergoes J-type aggregation in both non-polar and highly polar solvents, which is dictated by van der Waals attractive forces between H-cardanol units in polar solvents (e.g. methanol and dimethylformamide) and π–π stacking interactions between porphyrin units in non-polar solvents (hexane). Moreover, the spectra indicated that the triazole units could stabilize the zinc porphyrin via intermolecular coordinate-complex formation. We anticipate that fat-soluble HTZPC could find applications in medical fields (e.g. in the photodynamic therapy of fat tissue).