Electrochemical and spectroelectrochemical characterizations of new tetra-substituted metallophthalocyanines bearing 4-(
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ORIGINAL PAPER
Electrochemical and spectroelectrochemical characterizations of new tetra‑substituted metallophthalocyanines bearing 4‑(trifluoromethoxy)phenoxy groups on non‑peripheral positions Nazli Farajzadeh1 · Duygu Akyüz2 · Atıf Koca3 · Makbule Burkut Koçak1 Received: 30 March 2020 / Accepted: 22 June 2020 © Springer-Verlag GmbH Austria, part of Springer Nature 2020
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
Keywords Aggregation behavior · Electrochemistry · Phthalocyanine spectroelectrochemistry · 4-(Trifluoromethoxy) phenoxy · Non-peripherally
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00706-020-02657-8) contains supplementary material, which is available to authorized users. * Atıf Koca [email protected]
2
Institute of Chemistry, University of Marmara, Istanbul, Turkey
* Makbule Burkut Koçak [email protected]
3
Department of Chemical Engineering, Engineering Faculty, University of Marmara, Istanbul, Turkey
1
Institute of Chemistry, Technical University of Istanbul, Istanbul, Turkey
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Introduction Phthalocyanine (Pc) and its derivatives include a twodimensional tetrapyrrolici macrocycle with an 18 π-electron conjugated system leading to unique physical and chemical properties [1–3]. Owing to the high-electron transfer abilities of Pcs, possibility, and advantage of their use have been extensively investigated in a wide range of high-tech areas, such as nonlinear optics [4], photodynamic therapy [5], gas sensors [6], and photovoltaic solar cells [7]. It is well known that the utilized materials should have sufficient solubility in differen
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