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

机译：H-腰果酚三唑锌卟啉偶联物的合成及理化性质

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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).
机译：尽管已知大量天然和非天然金属卟啉，但具有荧光和脂溶性的实例很少。我们已经实现了荧光和脂溶性锌卟啉的合成，其中包含四个单元的氢化腰果酚（H-腰果酚）。合成是可持续的，因为该产品源自腰果壳液（CNSL），这是一种可再生的生物废物材料。 H-腰果酚三唑锌卟啉共轭物（HTZPC）是通过在H-腰果酚衍生的叠氮化物和四芳基卟啉衍生的炔烃之间应用铜（I）催化的叠氮化物-炔烃环加成反应（CuAAC）合成的。使用紫外可见光谱和在各种溶剂中获得的荧光发射光谱，评估了可溶于烃溶剂的HTZPC的吸收和发射性质。将结果与相关分子进行比较，例如三唑-锌卟啉共轭物（TZPC），四-C（4）-甲氧基苯基锌卟啉锌（ZP）和H-腰果酚-三唑共轭物（HTC）。结果表明，HTZPC在非极性和高极性溶剂中均经历J型聚集，这取决于极性溶剂中氢腰果酚单元（例如甲醇和二甲基甲酰胺）之间的范德华力和π-π堆积相互作用非极性溶剂（己烷）中的卟啉单元。此外，光谱表明，三唑单元可以通过分子间配位络合物的形成来稳定卟啉锌。我们预计脂溶性HTZPC可以在医学领域中找到应用（例如在脂肪组织的光动力疗法中）。

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