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Syntheses and properties of amphiphilic zinc(II), nickel(II), and palladium(II) phthalocyanines with eight tri(oxyethylene) chains introduced at non-peripheral $α$ $α$ positions

Department of Chemistry, Graduate School of Natural Science and Technology, Shimane University, 1060 Nishikawatsu, Matsue 690-8504, Japan

E-mail Address: handam@riko.shimane-u.ac.jp

Correspondence to: Makoto Handa, tel: +81-852-32-6418.

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Tomohiro Urata

Department of Chemistry, Graduate School of Natural Science and Technology, Shimane University, 1060 Nishikawatsu, Matsue 690-8504, Japan

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Kai Nakashima

Department of Chemistry, Graduate School of Natural Science and Technology, Shimane University, 1060 Nishikawatsu, Matsue 690-8504, Japan

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Tamotsu Sugimori

Institute of Liberal Arts and Sciences, University of Toyama, Toyama 930-0194, Japan

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Haruo Akashi

Research Institute of Frontier Science and Technology, Okayama University of Science, 1-1 Ridai-cho, Kita-ku, Okayama 700-0005, Japan

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, and

Masahiro Mikuriya

School of Biological and Environmental Sciences, Kwansei Gakuin University, 1 Gakuen Uegahara, Sanda, Hyogo 669-1330, Japan

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https://doi.org/10.1142/S1088424622500948Cited by:0 (Source: Crossref)

Abstract

Amphiphilic zinc(II) (1), nickel(II) (2), and palladium(II) (3) complexes of 1,4,8,11,15,18,22,25-octakis(1,4,7,10-tetraoxaundecyl)phthalocyanine were synthesized and characterized by elemental analysis and MALDI-TOF mass and ¹H NMR spectroscopies. Electronic absorption spectra showed aggregation of the phthalocyanine molecules in $H_{2}$ $H_{2}$ O for 2 and 3, while the monomeric form for 1 in $H_{2}$ $H_{2}$ O, and 1, 2, and 3 in ${CH}_{2} {Cl}_{2}$ ${CH}_{2} {Cl}_{2}$ . The cyclic voltammograms of 1, 2, and 3 in ${CH}_{2} {Cl}_{2}$ ${CH}_{2} {Cl}_{2}$ showed that oxidation of the phthalocyanine ring occurs easily in these complexes. This may be due to the energetically increased HOMO, coming from the deformation of the phthalocyanine ring. Steric hindrance between the $α$ $α$ -introduced 1,4,7,10-tetraoxaundecyl groups (tri(oxyethylene) chains) within the phthalocyanine molecule gives rise to the deformation of the phthalocyanine ring, which decreases the aggregating nature of the present complexes.

Dedicated to Prof. Tomás Torres on the occasion of his 70^th birthday

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