Syntheses, Crystal Structures and Complexing Properties of 1,3-Distal Calix[4]arene Schiff Bases

高等学校化学研究 ›› 2010, Vol. 26 ›› Issue (1): 38-45.

Syntheses, Crystal Structures and Complexing Properties of 1,3-Distal Calix[4]arene Schiff Bases

LI Liang, GU Wei-wei and YAN Chao-guo*

College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, P. R. China

收稿日期:2009-02-14 修回日期:2009-03-23 出版日期:2010-01-04 发布日期:2010-03-29
通讯作者: YAN Chao-guo. E-mail: cgyan@yzu.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(No.20672091).

Syntheses, Crystal Structures and Complexing Properties of 1,3-Distal Calix[4]arene Schiff Bases

LI Liang, GU Wei-wei and YAN Chao-guo*

College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, P. R. China

Received:2009-02-14 Revised:2009-03-23 Online:2010-01-04 Published:2010-03-29
Contact: YAN Chao-guo. E-mail: cgyan@yzu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.20672091).

摘要/Abstract

摘要：

Novel 1,3-distal p-tert-butylcalix[4]arene Schiff bases were efficiently synthesized in three steps. At first p-tert-butylcalix[4]arene was reacted with N-2-hydroxyethylphthalimide catalyzed by TPP/DEAD or alkylated with ω-haloalkylphthalimide in the system of K₂CO₃/KI/CH₃COCH₃ to give 1,3-distal diphthalimidoalkyl calixarenes, which were in turn hydrazinolyzed to give diaminoalkyl calixarenes. Then with the aid of the condensation of active calixarene amines with salicylaldehyde, 2-hydroxy-1-naphthaldehyde or pyridine-2-carboxaldehyde, a series of 1,3-distal calixarene Schiff bases was prepared in satisfied yields. The single crystal structures and complexing properties of these Schiff bases for transition metal ions were studied.

关键词: Calixarene; Schiff base; Crystal structure; Metal complex; UV spectroscopy

Abstract:

Key words: Calixarene; Schiff base; Crystal structure; Metal complex; UV spectroscopy

LI Liang, GU Wei-wei and YAN Chao-guo*. Syntheses, Crystal Structures and Complexing Properties of 1,3-Distal Calix[4]arene Schiff Bases[J]. 高等学校化学研究, 2010, 26(1): 38-45.

LI Liang, GU Wei-wei and YAN Chao-guo*. Syntheses, Crystal Structures and Complexing Properties of 1,3-Distal Calix[4]arene Schiff Bases[J]. Chemical Research in Chinese Universities, 2010, 26(1): 38-45.

参考文献

[1] Bohmer B., Angew. Chem. Int. Ed. Engl., 1995, 34, 713
[2] Wieser C., Dielman C., Matt D., Coord. Chem. Rev., 1997, 165, 93
[3] Biros S. M., Rebek J. Jr., Chem. Soc. Rev., 2007, 36, 93
[4] Pluth M. D., Raymond K. N., Chem. Soc. Rev., 2007, 36, 161
[5] Lalor R., Baillie-Johnson H., Redshaw C., et al., J. Am. Chem. Soc., 2008, 130, 2892
[6] Hadjoudis E., Mavrids I. M., Chem. Soc. Rev., 2004, 33, 579
[7] Mahon M. F., McGinley J. A., Rooney D., et al., Tetrahedron, 2008, 64, 11058
[8] Creaven B. S., Deasy M., Flood P. M., et al., Inorg. Chem. Commun., 2008, 11, 1215
[9] Liang Z., Liu Z., Gao Y., Tetrahedron Lett., 2007, 48, 3587
[10] Singh N., Kumar M., Hundal G., Tetrahedron, 2004, 60, 5393
[11] Liu Y., Wang H., Wang L. H., et al., Tetrahedron, 2003, 59, 7967
[12] Yilmaz A., Memon S., Yilmaz M., Tetrahedron, 2002, 58, 7735
[13] Tamburini S., Tomasin P., Vigato P. A., et al., Inorg. Chim. Acta, 1997, 254, 209
[14] Amato M., Ballistreri M., Pappalardo A., et al., Eur. J. Org. Chem., 2005, 3562
[15] Tuntulani T., Thavornyutikarn P., Poompradub S., et al., Tetrahe- dron, 2002, 58, 10277
[16] Liu Y., Zhao B. T., Zhang H. Y., et al., J. Chem. Soc., Perkin Trans. 2, 2001, 1219
[17] Gutsche C. D., Dhawan B., Leonis M., et al., Org. Synth., 1990, 68, 238
[18] Halouani H., Dumazet-Bonnamour I., Perrin M., et al., J. Org. Chem., 2004, 69, 6521
[19] Collins E. M., McKervey M. A., Madigan E., et al., J. Chem. Soc., Perkin Trans. 1, 1991, 3137
[20] Casnati A., Massera C., Pelizzi N., et al., Tetrahedron Lett., 2002, 43, 7311
[21] Danila C., Bolte M., Boehmer V., Org. Biomol. Chem., 2005, 3, 172
[22] Zhang W. C., Huang Z. T., Synthesis, 1997, 1073
[23] Dondoni A., Marra A., Scherrmann M. C., et al., Chem. Eur. J., 1997, 3, 1774
[24] Wang J., Gutsche C. D., Struct. Chem., 2001, 12, 267
[25] Bitter I., Csokai V., Tetrahedron Lett., 2003, 44, 2261
[26] Barsobo S., Carrera A. G., Matthews S. E., et al., J. Chem. Soc., Perkin Trans. 2, 1999, 719
[27] Casnati A., Ca N. D., Fontanella M., et al., Eur. J. Org. Chem., 2005, 2338
[28] Gac S. L., Zeng X. S., Reinaud O., et al., Org. Chem., 2005, 70, 1204
[29] Csokai V., Balázs B., Tóth G., et al., Tetrahedron, 2004, 60, 12059

Syntheses, Crystal Structures and Complexing Properties of 1,3-Distal Calix[4]arene Schiff Bases

Syntheses, Crystal Structures and Complexing Properties of 1,3-Distal Calix[4]arene Schiff Bases

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 0

编辑推荐

Metrics

本文评价