Synthesis and electrochemistry of tetrakis(7-coumarinthio-4-methyl)-phthalocyanines, and preparation of their cinnamic acid and sodium cinnamate derivatives

• Published in: Polyhedron 2009-01, Vol.28 (1), p.33-42
• Main Authors: Esenpınar, Aliye Aslı, Özkaya, Ali Rıza, Bulut, Mustafa
• Format: Article
• Language: English
• Subjects: Cinnamic acid; Cobalt; Coumarin ( 2H-1-benzopyran-2-one); Phthalocyanines; Spectroelectrochemistry; Zinc
• ISSN: 0277-5387
• DOI: 10.1016/j.poly.2008.09.021

Novel water soluble free-base, Zn(II) and Co(II) metallo phthalocyanines with four cinnamic acid moieties were prepared from the corresponding tetrakis(7-coumarinthio-4-methyl)-phthalocyanine by the lactone ring opening reaction. The new compounds were purified and characterized by elemental analysis, 1H NMR, Maldi-TOF, FT-IR and UV–Vis spectral data. Cyclic and differential pulse voltammetry and in situ spectroelectrochemistry of the 2,9,16,23-tetrakis(7-coumarinthio-4-methyl) substituted free-base 1a, Zn(II) 1b and Co(II) 1c phthalocyanines, employed as the starting compounds have been studied. This allowed us not only to identify metal- and phthalocyanine ring-based redox processes of the complexes, but also the effect of aggregation on these processes. Novel water soluble free-base, Zn(II) and Co(II) metallo phthalocyanines with four cinnamic acid moieties were prepared from the corresponding tetrakis(7-coumarinthio-4-methyl)-phthalocyanine by the lactone ring opening reaction. The new compounds were purified and characterized by elemental analysis, 1H NMR, Maldi-TOF, FT-IR and UV–Vis spectral data. Cyclic and differential pulse voltammetry and in situ spectroelectrochemistry of the 2,9,16,23-tetrakis(7-coumarinthio-4-methyl) substituted free-base 1a, Zn(II) 1b and Co(II) 1c phthalocyanines, employed as the starting compounds have been studied. This allowed us not only to identify metal- and phthalocyanine ring-based redox processes of the complexes, but also the effect of aggregation on these processes.