Abstract

In this study, a series of non-peripherally tetra-substituted phthalocyanines [M = Zn(II), Co(II), and In(III)] was successfully prepared by cyclotetramerization of the phthalonitrile derivative bearing 4-(trifluoromethoxy)phenoxy group at 3-position. All newly synthesized compounds were characterized using spectroscopic methods, such as FT-IR, NMR, and UV–Vis spectroscopy. The effect of concentration on aggregation properties of the resulting phthalocyanines was investigated in different concentrations ranging from 4 × 10⁻⁶ to 14 × 10⁻⁶ M in THF. In addition, the spectral properties of the metallophthalocyanines were studied in various organic solvents. Besides, redox responses of metallophthalocyanines and their electro-optical responses were determined. Although {1(4),8(11),15(18),22(25)-tetrakis[4-(trifluoromethoxy)phenoxy]phthalocyaninato}cobalt(II) showed well-resolved reversible redox peaks depicting the anticipated electron transfer reactions, electrochemical investigation of its zinc(II) and indium(III) chloride analogs resulted in complex redox waves, and their chemical reversibility decreased with the aggregation of the complexes. The influence of the redox processes on the optical responses of metallophthalocyanines was studied with in situ spectroelectrochemistry measurements and the peak assignments and optical responses of the electrogenerated species were determined.

Graphic abstract

中文翻译：

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新的在非外围位置带有4-（三氟甲氧基）苯氧基的四取代金属酞菁的电化学和光谱电化学表征

摘要

在这项研究中，通过环四聚反应带有4-（三氟甲氧基）苯氧基的邻苯二甲腈衍生物，成功制备了一系列非外围四取代的酞菁类化合物[M = Zn（II），Co（II）和In（III）]。在3位。所有新合成的化合物均使用光谱方法进行表征，例如FT-IR，NMR和UV-Vis光谱。在4×10 ^-6至14×10 ^-6的不同浓度下，研究了浓度对所得酞菁聚集性质的影响。 在THF中的M。另外，在各种有机溶剂中研究了金属酞菁的光谱性质。此外，测定了金属酞菁的氧化还原反应及其电光反应。尽管{1（4），8（11），15（18），22（25）-四[4-（三氟甲氧基）苯氧基]酞菁}}钴（II）表现出很好的可分辨氧化还原峰，描述了预期的电子转移反应，对其氯化锌（II）和氯化铟（III）类似物的电化学研究导致了复杂的氧化还原波，并且它们的化学可逆性随着配合物的聚集而降低。

图形摘要