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Corresponding Author

CHEN Ping(chenping-fs@sohu.com)

Abstract

The p-sulfophenylazo calix[4]arene was synthesized through the diazotization-coupling reaction between calix[4]arene and p-aminobenzene sulfonic acid. The UV-Vis spectroscopy, Infrared spectroscopy, and nuclear magnetic resonance (NMR) were used to characterize the as-prepared p-sulfophenylazo calix[4]arene. The electrochemical behaviors of p-sulfophenylazo calix[4]arene were investigated by cyclic voltammetry and chronoamperometry using CH3COOH-CH3COONa as a buffer solution. The result shows that the p-sulfophenylazo calix[4]arene exhibited a pair of redox peaks in a scan potential region of -0.5 ~ 1 V. The oxidation and reduction peak potentials were 0.302 V and -0.003 V, respectively, and changed with the scanning rates. In addition, the electrode reaction was studied by various electrochemical methods, and the kinetic parameters have also been obtained. The activation energy was found to be 14.84 kJ•mol-1.

Graphical Abstract

Keywords

sulfophenylazo calix[4]arene, cyclic voltammetry, glassy carbon electrode, electrochemical behavior

Publication Date

2016-02-29

Online Available Date

2015-10-19

Revised Date

2015-10-14

Received Date

2015-06-04

References

[1] Yang C Y, Liu T T, Xu Y M, et al. Fluorescent ion optodes based on calixarene functionized boron dipyrromethene chromoionophore for simultaneous measurement of multi-electrolytes in biological samples[J]. Sensors and Actuactors B: Chemical, 2014, 192: 423-428.

[2] Akceylan E, Yilmaz M. Synthesis of calix[4]arene alkyl amine derivatives as new phase transfer catalysts for esterification reaction[J]. Tetrahedron, 2011, 67(34): 6240-6245.

[3] Lazzarotto M, Ferreira C I, Castellano E E, et al. Highly constrained guests in complexes of p-tert-butyl calix[6]arene dianion: Pentane-1,5-diammonium and choline[J]. Journal of Molecular Structure, 2014, 1067: 88-93.

[4] Ebdellia R, Dkhila S B, Azibc T, et al. Electrical, optical and morphological properties of a new chromogenic calix[4]arene derivative[J]. Synthetic Metals, 2014, 197: 112-118.

[5] Benounis M, Jaffrezic N, Mattelet C, et al. High sensitive surface plasmon resonance (SPR) sensor based on modified calix[4]arene self assembled monolayer for cadmium ions detection[J]. Materials Transactions, 2015, 56(4): 539-544.

[6] Liu Z C(刘智成), Wang H(王红), Yang R(杨睿), et al. Synthesis and application of phosphorous-containing calixarenes and their complexes[J]. Progress Chemistry(化学进展), 2011, 23(8): 1665-1682.

[7] Özk?nal? S. Spectroscopic and thermal properties of newly mixed azocalix[4]arene ester derivatives[J]. Dyes and Pigments, 2014, 107: 81-89.

[8] ?ener ?, ?ener N, Eri?kin S. Synthesis and absorption spectra of some novel hetaryl tetrakis azo calix[4]arene derivatives[J]. Dyes and Pigments, 2013, 96(1): 256-263.

[9] Fan P, Wan L, Shang Y, et al. Spectroscopic investigation of the interaction of water-soluble azo calix[4]arenes with bovine serum albumin[J]. Bioorganic Chemistry, 2015, 58: 88-95.

[10] Chawla H M, Gupta T. Novel bis-calix[4]arene based molecular probe for ferric iron through colorimetric, ratiometric, and fluorescence enhancement response[J]. Tetrahedron Letters, 2015, 56(6): 793-796.

[11] Liu L M(刘丽梅), Zhang D L(张岱良), Chen P(陈平). The study of electro chemical properties of sulfonic calix[4]arene[J]. Journal of Liaoning Shihua University(辽宁石油化工大学学报), 2014, 34(3): 1-4.

[12] Pailleret A, Herzog G, Arrigan D W M. Electrochemical activity of phenolic calixarenes[J]. Electrochemistry communications, 2003, 5(1): 68-72.

[13] Jing A H(景爱华), Zhang S S(张书胜), Ye B X(冶保献). Study on the electrochemistry of sulfonatocalyx[6]arene at glassy carbon electrode[J]. Journal of Tianing Normal University(Natural Science Edition)(天津师范大学学报: 自然科学版), 2003, 23(3): 12-15.

[14] Zhang Y Z(张亚洲), Liu L M(刘丽梅), Chen P(陈平). Synthesis of water-soluble nitrogen containing calixarene[J]. Journal of Petrochemical Universities(石油化工高等学校学报), 2013, 26(3): 13-17.

[15] Qiao Q D(乔庆东), Li Q(李琪). Electrochemical behaviors of ferrocene using cyclic voltammetry[J]. Journal of Liaoning Shihua University(辽宁石油化工大学学报), 2014, 34(3): 5-7.

[16] Li L M(李丽敏), Sun T L(孙天麟), Gao H X(高洪霞). Research on electric chemical property of 4-(2-thiazole)-metaphenylene diahydroxybenzene[J]. Journal of Liaocheng Teachers College(Natural Science Edition)(聊城师院学报:自然科学版),1997, 10(1): 65-70.

[17] Li Y H(李玉红), Liu H X(刘焕新), Xu B(许兵). The culture of tobacco suspension cells and the isolation of organelles[J]. Journal of Capital Normal University(Natural Science Edition)(首都师范大学学报: 自然科学版), 2007, 28(2): 54-57.

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