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

作者: Aliye Aslı Esenpınar , Ali Rıza Özkaya , Mustafa Bulut

DOI: 10.1016/J.POLY.2008.09.021

关键词: LactoneProton NMRRedoxPolymer chemistryOrganic chemistryDifferential pulse voltammetryChemistryElectrochemistryPhthalocyanineCinnamic acidZinc

摘要: Abstract 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 lactone ring opening reaction. The new compounds purified characterized elemental analysis, 1H NMR, Maldi-TOF, FT-IR UV–Vis spectral data. Cyclic differential pulse voltammetry in situ spectroelectrochemistry of 2,9,16,23-tetrakis(7-coumarinthio-4-methyl) substituted free-base 1a, 1b 1c phthalocyanines, employed as starting have been studied. This allowed us not only to identify metal- phthalocyanine ring-based redox processes complexes, but also effect aggregation on these processes.

参考文章(37)
H Murray RD, J Mendez, SA Brown, The natural coumarins : occurrence, chemistry, and biochemistry John Wiley & Sons. ,(1982)
C. C. Leznoff, A. B. P. Lever, Phthalocyanines : properties and applications Wiley. ,(1989)
Duygu Kulaç, Mustafa Bulut, Ahmet Altındal, Ali Rıza Özkaya, Bekir Salih, Özer Bekaroğlu, Synthesis and characterization of novel 4-nitro-2-(octyloxy)phenoxy substituted symmetrical and unsymmetrical Zn(II), Co(II) and Lu(III) phthalocyanines Polyhedron. ,vol. 26, pp. 5432- 5440 ,(2007) , 10.1016/J.POLY.2007.08.015
Yong Pan, Wenxing Chen, Sufang Lu, Yifeng Zhang, Novel aqueous soluble cobalt phthalocyanine: synthesis and catalytic activity on oxidation of 2-mercaptoethanol Dyes and Pigments. ,vol. 66, pp. 115- 121 ,(2005) , 10.1016/J.DYEPIG.2004.09.018
Metin Özer, Ahmet Altındal, Ali Rıza Özkaya, Mustafa Bulut, Özer Bekaroğlu, Synthesis, characterization and some properties of novel bis (pentafluorophenyl )methoxyl substituted metal free and metallophthalocyanines Polyhedron. ,vol. 25, pp. 3593- 3602 ,(2006) , 10.1016/J.POLY.2006.07.011
Fang-Fang Ye, Jian-Rong Gao, Wei-Jian Sheng, Jian-Hong Jia, One-pot synthesis of coumarin derivatives Dyes and Pigments. ,vol. 77, pp. 556- 558 ,(2008) , 10.1016/J.DYEPIG.2007.08.005
A. R. ÖZKAYA, E. HAMURYUDAN, Z. A. BAYIR, Ö. BEKAROĞLU, Electrochemical properties of octakis(hydroxyethylthio)‐substituted phthalocyanines Journal of Porphyrins and Phthalocyanines. ,vol. 4, pp. 689- 697 ,(2000) , 10.1002/1099-1409(200011)4:7<689::AID-JPP235>3.0.CO;2-V
Antigoni Kotali, Ioannis S. Lafazanis, Philip A. Harris, A novel and facile synthesis of 7,8-diacylcoumarins Tetrahedron Letters. ,vol. 48, pp. 7181- 7183 ,(2007) , 10.1016/J.TETLET.2007.07.202