Studies on the Inclusion Behavior of Amphiphilic p-Sulfonatocalix[4]arene with Ascorbic Acid by Spectrofluorometric Titrations
Yunyou Zhou, Xueping Ding, Xiaoli Fang, Tao Li, Dongbao Tang, Qin Lu
DOI: 10.4236/opj.2011.12009   PDF    HTML     4,053 Downloads   8,512 Views   Citations


The aqueous solution of tetrabutyl ether derivatives of p-sulfonatocalix[4]arene (SC4Bu) and ascorbic acid (AA) complex has been studied based on fluorescence and 1H NMR spectroscopic results. It was found that the fluorescence intensity of SC4Bu quenched regularly upon the addition of AA. A 1:1 stoichiometry for the complexation was established and was verified by Job’s plot. The temperature-dependent inclusion constants were calculated, form which Δ H and ΔS values were calculated. Meanwhile the proposed interaction mechanism of the inclusion complex was discussed based on 1H NMR results. The various factors (ionic strength, and surfactants) effecting the inclusion process were examined in detail.

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Y. Zhou, X. Ding, X. Fang, T. Li, D. Tang and Q. Lu, "Studies on the Inclusion Behavior of Amphiphilic p-Sulfonatocalix[4]arene with Ascorbic Acid by Spectrofluorometric Titrations," Optics and Photonics Journal, Vol. 1 No. 2, 2011, pp. 59-64. doi: 10.4236/opj.2011.12009.

Conflicts of Interest

The authors declare no conflicts of interest.


[1] C. D. Gutsche, “Calixarenes Revisited: Monographs in Supramolecular Chemistry,” Royal Society of Chemistry, Cambridge, 1998.
[2] J. H. Yang, F. Huang, M. Wang, X. Wu and C. X. Sun, “Study on the Molecular Recognitions of Calix[n]arenes to 2,3-Diaminonaphthalene by Using Fluorometric Technique,” Spectrochimica Acta Part A, Vol. 58, No. 8, 2002, pp. 1775-1778. doi:10.1016/S1386-1425(01)00629-1
[3] G. Arena, A. Contino, F. G. Gulino, A. Magri, F. Sansone, D. Sciotto and R. Ungaro, “Complexation of native L-α- Aminoacids by Water Soluble Calix[4]arenas,” Tetrahedron Letters, Vol. 40, No. 8, 1999, pp. 1597-1600. doi:10.1016/S0040-4039(98)02654-9
[4] F. Sansone, S. Barboso, A. Casnati, D. Sciotto and R. Ungaro, Tetrahedron Letters, Vol. 40, No. 25, 1999, pp. 4741-4744. doi:10.1016/S0040-4039(99)00838-2
[5] K. M. Hwang, Y. M. Qi, S. Y. Liu, T. C. Lee, W. Choy and J. Chen, US Patent 5 409 959, 1995.
[6] K. M. Hwang, Y. M. Qi, S. Y. Liu, W. Choy and J. Chen, US Patent 5 441 983, 1995.
[7] J. L. Atwood, R. J. Bridges, R. K. Juneja, K. Ravindra and A. K. Singh, US Patent 748 764, 1996.
[8] D. J. S. Humes, A. W. Coleman and E. Aubert-Fouchet, French Patent FR 2 782 007, 1998.
[9] E. Da Silva, P. Shahgaldian and A. W. Coleman, “Haemolytic Properties of Some Water-Soluble Para- Sulphonato-Calix[n]arenas,” Internationalt International Journal of Pharmaceutics, Vol. 273, No. 1-2, 2004, pp. 57-62. doi:10.1016/j.ijpharm.2003.12.008
[10] J. S. Millership, “A Preliminary Investigation Of The Solution Complexation of 4-Sulphonic Calix[n]arenas with Testosterone,” Journal of Inclusion Phenomena and Macrocyclic Chemistry, Vol. 39, No. 3-4, 2001, pp. 327-331. doi:10.1023/A:1011196217714
[11] Y. Y. Zhou, Q. Lu, C. Liu, S. K. She and L. Wang, “Study on the Inclusion Behavior of p-Sulphon Atocalix[4]arene with 9-Amino-Acridine by Spectrofluore Metric Titrations,” Spectrochim Acta Part A, Vol. 63, No. 2, 2006, pp. 423-426. doi:10.1016/j.saa.2005.04.056
[12] Y. Y. Zhou, Q. Lu, C. Liu, S. K. She and L. Wang, “A novel Spectrofluorimetric Method for Determination of Lomefloxacin Based on Supramolecular Inclusion Complex between it and p-Sulfonated Calix[4]arene,” Analytica Chimica Acta, Vol. 552, No. 1-2, 2005, pp. 152-159. doi:10.1016/j.aca.2005.07.038
[13] Q. Lu, J. S. Gu, H. P. Yu, C. Liu, L. Wang and Y. Y. Zhou, “Study on the Inclusion Interaction of p-Sulfonated Calix[n]arenas with Vitamin K3 Using Methylene Blue as a Spectral Probe,” Spectrochimica Acta Part A, Vol. 68, No. 1, 2007, pp. 15-20. doi:10.1016/j.saa.2006.10.044
[14] C. Martin, “The Parkinson’s Puzzle,” Chemistry in Britain, Vol. 34, No. 99, 1998, pp. 40-42.
[15] A. Heinz, H. Przuntek, G. Winterer and A. Pietzcker, “Clinical Aspects and Follow-up of Dopamine-Induced Psychoses in Continuous Dopaminergic Therapy and Their Implications for the Dopamine Hypothesis of Schizophrenic Symptoms,” Nervenarzt, Vol. 66, No. 9, 1995, pp. 662-669.
[16] J. Yang, R. Gadi, R. Paulino and T. Thomson, “Total Phenolics, Ascorbic Acid, And Antioxidant Capacity of Noni (Morinda citrifolia L.) Juice and Powder as Affected by Illumination During Storage,” Food Chemistry, Vol. 122, No. 3, 2010, pp. 627-632. doi:10.1016/j.foodchem.2010.03.022
[17] C. Carr and B. Feri, “Toward a New Recommended Dietary Allowance for Vitamin C Based on Antioxidant and Health Effects in Humans,” The Americal Journal of Clinical Nutrition, Vol. 69, No. 6, 1999, pp. 1086-1107.
[18] S. Shinkai, S. Mori, H. Koreishi, T. Tsubaki and O. Manabe, “Hexasulfonated Calix[ 6larene Derivatives: A New Class of Catalysts, Surfactants, and Host Molecules,” Journal of the American Chemical Society, Vol. 108, No. 9, 1986, pp. 2409-2416. doi:10.1021/ja00269a045
[19] Y. Liu, B. H. Han and Y. T. Chen, “Molecular Recognition and Complexation Thermodynamics of Dye Guest Molecules by Modified Cyclodextrins and Calixarenesulfonates,” The Journal of Physical Chemistry B, Vol. 106, No. 18, 2002, pp. 4678-4687. doi:10.1021/jp015603r
[20] Y. Y Zhou, H. W. Xu, L. Wu, C. Liu, Q. Lu and L. Wang, “Spectrofluorimetric Study on the Inclusion Interaction Between Vitamin K3 with p-(p-Sulfonated Benzeneazo) Calix[6]arene and Determination of VK3,” Spectro- chimica Acta Part A, Vol. 71, No. 2, 2008, pp. 597-602. |doi:10.1016/j.saa.2007.11.036
[21] M. Catarina, et al., “Multimodal Molecular Encapsulation of Nicardipine Hydrochloride by β-Cyclodextrin, Hydroxypropyl-Β-Cyclodextrin and Triacetyl-Β-Cyclo- dextrin in Solution. Structural Studies by 1H NMR and ROESY Experiments,” European Journal of Pharmaceutical Sciences, Vol. 18, No. 5, 2003, pp. 285-296. doi:10.1016/S0928-0987(03)00025-3
[22] A. L. Thakkarand P. V. Demarco, “Cycloheptaamylose Inclusion Complexes Of Barbiturates: Correlation Be- tween Proton Magnetic Resonance and Solubility Studies,” Journal of Pharmaceutical Sciences, Vol. 60, No. 4, 1971, pp. 652-653. doi:10.1002/jps.2600600444
[23] S. Shinkai, “Calixarenes—The Third Generation Of Supramolecules,” Tetrahedron, Vol. 49, No. 40, 1993, pp. 8933-8968. doi:10.1016/S0040-4020(01)91215-3
[24] Y. Y. Zhou, C. Liu, H. W. Xu, H. P. Yu, Q. Lu and L. Wang, “Study on the Fluorescence Behavior of p-Sulfonated Calix[4,6]arene in Cationic Surfactant Cetyltrimethylammonium Bromide Solution and Its Analytical Application,” Spectrochimica Acta Part A, Vol. 66, No. 4-5, 2007, pp. 919-923. doi:10.1016/j.saa.2006.04.031
[25] C. Liu, Z. Fu, H. P. Yu, H. W. Xu, L. Wang and Y. Y. Zhou, “Spectrofluorimetric Study on the Inclusion Behavior of p-Sulfonated Calix[6]arene with Cetyltrimethylammonium Bromide and Analytical Application,” Journal of Luminescence, Vol. 126, No. 2, 2007, pp. 747-752. doi:10.1016/j.jlumin.2006.11.006

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