Microwave-assisted synthesis, electrochemistry and spectroelectrochemistry of phthalocyanines bearing tetra terminal-alkynyl functionalities and click approach

作者: Ozge Koyun , Semih Gorduk , Bahadır Keskin , Ahmet Çetinkaya , Atıf Koca

DOI: 10.1016/J.POLY.2016.03.019

关键词: PhthalimideElectrochemistryZincSubstituentCombinatorial chemistryAlkoxy groupRedoxPhotochemistryClick chemistryConjugated systemChemistry

摘要: Abstract This work provides a successful, easy and efficient process for the preparation of both symmetrically tetra nonperipheral peripheral terminal alkynyl substituted zinc cobalt phthalocyanines (Pcs) click approach. Two different routes, conventional microwave-assisted synthesis, have been used by direct cyclotetramerization reactions. While novel Pcs were synthesized using only method, very fast, method microwaves has also described synthesis ZnPc complexes. In order to develop phthalimide conjugated phthalocyanine, [2,9(10),16(17),23(24)-tetrakis((1-(2-(1,3-dioxoisoindoline-2-yl)ethyl)-1H-1,2,3-triazol-4-yl)ethoxy)phthalocyaninato]zinc(II), was via reaction. The precursors target complexes characterized comprehensively with 1 H NMR, 13 C FT-IR, UV–Vis spectra together elemental mass analyses. Electrochemical properties examined determine effect position substituents. substitution shifted redox processes toward negative potentials, peripherally gave more reversible processes. On other hand, while Pc ring-based electron transfer reactions metal-based reduction oxidation recorded CoPc complex. Moreover phthalimide–triazole substituent on periphery found affect electrochemical

参考文章(65)
Feng Lv, Xujun He, Li Wu, Tianjun Liu, Lactose substituted zinc phthalocyanine: a near infrared fluorescence imaging probe for liver cancer targeting. Bioorganic & Medicinal Chemistry Letters. ,vol. 23, pp. 1878- 1882 ,(2013) , 10.1016/J.BMCL.2012.12.103
Nagao Kobayashi, Tohru Ashida, Tetsuo Osa, Synthesis, Spectroscopy, Electrochemistry, and Spectroelectrochemistry of a Zinc Phthalocyanine with D2hSymmetry Chemistry Letters. ,vol. 21, pp. 2031- 2034 ,(1992) , 10.1246/CL.1992.2031
Amira Hajri, Sarra Touaiti, Bassem Jamoussi, Preparation of Organic Zn-Phthalocyanine-Based Semiconducting Materials and Their Optical and Electrochemical Characterization Advances in Optoelectronics. ,vol. 2013, pp. 1- 7 ,(2013) , 10.1155/2013/321563
Graeme Williams, Sibi Sutty, Richard Klenkler, Hany Aziz, Renewed interest in metal phthalocyanine donors for small molecule organic solar cells Solar Energy Materials and Solar Cells. ,vol. 124, pp. 217- 226 ,(2014) , 10.1016/J.SOLMAT.2014.02.013
W. A. Nevin, M. R. Hempstead, W. Liu, C. C. Leznoff, A. B. P. Lever, Electrochemistry and spectroelectrochemistry of mononuclear and binuclear cobalt phthalocyanines Inorganic Chemistry. ,vol. 26, pp. 570- 577 ,(1987) , 10.1021/IC00251A017
Hüseyin Karaca, Serdar Sezer, Şeniz Özalp-Yaman, Cihangir Tanyeli, Concise synthesis, electrochemistry and spectroelectrochemistry of phthalocyanines having triazole functionality Polyhedron. ,vol. 72, pp. 147- 156 ,(2014) , 10.1016/J.POLY.2014.01.037
Yeliz İpek, Hatice Dinçer, Atıf Koca, Electrode modification based on “click electrochemistry” between terminal-alkynyl substituted cobalt phthalocyanine and 4-azidoaniline Sensors and Actuators B-chemical. ,vol. 193, pp. 830- 837 ,(2014) , 10.1016/J.SNB.2013.12.031
Feng Lv, Xujun He, li Lu, Li Wu, Tianjun Liu, Synthesis, properties and near-infrared imaging evaluation of glucose conjugated zinc phthalocyanine via Click reaction Journal of Porphyrins and Phthalocyanines. ,vol. 16, pp. 77- 84 ,(2012) , 10.1142/S1088424611004361
Uwe Hahn, Tomás Torres, Amphiphilic zinc phthalocyanine dendrimers by the Click Chemistry approach Journal of Porphyrins and Phthalocyanines. ,vol. 15, pp. 364- 372 ,(2011) , 10.1142/S1088424611003161