Abstract
Two novel phthalonitrile derivatives, bearing two hexyloxy groups and a benzodioxin (or a naphthodioxin) annulated ring, along with their corresponding metal-free phthalocyanines (H2Pc) were prepared. FT-IR, mass, electronic absorption, 1H NMR, and 13C NMR spectroscopy were employed for the characterization of all compounds. The effect of hexadeca substituents on the photophysical properties of metal-free Pcs was investigated. Photophysical properties of H2Pc were studied in tetrahydrofuran (THF). Fluorescent quantum yields of phthalocyanines (Pcs) were calculated and compared with the unsubstituted phthalocyanine. 1,4-Benzoquinone effectively quenched the fluorescence of these compounds in THF. Cyclic and square wave voltammetry methods were applied to metal-free phthalocyanines and Pc-centered oxidation and reduction processes were obtained.
Highlights
Phthalocyanines were first synthesized accidentally, and since they have been used as powerful artificial dyes and pigments in the paper and textile industries
It is known that hexadeca substitution increases the solubility of the macrocycle by reducing aggregation [8,18,19,20,21]
To examine the change in properties induced by the structural variation of appended groups to Pcs, we report here on benzodioxin- or naphthodioxin-substituted Pc derivatives
Summary
Phthalocyanines were first synthesized accidentally, and since they have been used as powerful artificial dyes and pigments in the paper and textile industries. This is because their thermal, chemical, and photochemical properties are excellent [1,2,3,4]. Studies about Pcs with different substituents at α- and β-positions have been published [13,14,15,16,17]. It is known that hexadeca substitution increases the solubility of the macrocycle by reducing aggregation [8,18,19,20,21]
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