Abstract
The synthesis, photophysical, singlet oxygen generation, electrochemical and photovoltaic properties of peripheral and axial 1,2,3-triazole group substituted zinc and silicon phthalocyanine complexes with strong absorption in the visible region were described. All novel complexes have been characterized by spectroscopic and electrochemical techniques. All the new compounds are highly soluble in most common organic solvents. The electronic absorption and fluorescence spectral properties of complexes 4 and 5 are investigated. The effects of the triazole group, different metal centers and position of the substituent on the photophysical, electrochemical and photovoltaic properties of the new phthalocyanines were also investigated for the first time in this work. According to the fluorescence measurements, the axially substituted silicon complex (5) showed higher fluorescence quantum yield (ΦF = 0.28) than the peripherally substituted zinc complex (4). In addition, quantum yields for singlet oxygen generation (ΦΔ = 0.32 for silicon complex (4) and ΦΔ = 0.76 for zinc complex (5) in DMSO) were obtained. Electrochemical studies show that complex 5 is present in non-aggregated form as a result of steric hindrance of the axial groups; the LUMO level of this complex is slightly more negative than the conduction band of TiO2 and electron injection might be less effective. Therefore, the power conversion efficiency of 1.30% for a complex 4 based dye-sensitized solar cell (DSSC) is higher than complex 5 (0.90%). Consequently, these zinc and silicon complexes are promising candidates not only for photodynamic therapy but also solar power conversion.
Highlights
Triazole groups, especially 1,2,4-triazoles and 1,2,3-triazoles, are important nitrogen heterocycles that have been widely studied as essential structural features of many of the potent azole fungicides.[1]
1,2,3-triazole groups do not occur naturally, synthetic molecules containing 1,2,3-triazole units exhibit a variety of biological activities, and they have been utilized as starting compounds for the synthesis of many heterocycles
[4.3.0]non-5-ene (DBN) either in n-hexanol or in bulk is most efficient in comparison to another method
Summary
Especially 1,2,4-triazoles and 1,2,3-triazoles, are important nitrogen heterocycles that have been widely studied as essential structural features of many of the potent azole fungicides.[1]. In many applications of phthalocyanines, it is important to have a good understanding of the redox properties of these compounds.[24,25,26] Taking these properties into consideration, it has focused on non-aggregate complexes as a strategy to explain Pcs in conjunction with the 1,2,3-triazole group to study aggregation, photophysical, singlet oxygen generation, electrochemical and photovoltaic properties. There are no studies examining and comparing all the photophysical, singlet oxygen generation, electrochemical and photovoltaic properties of peripheral substituted zinc and axial substituted silicon phthalocyanine complexes. 1,2,3-triazole-substituted silicon and zinc phthalocyanines were designed and prepared
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