含联萘基团的手性聚芳醚酮类环状齐聚物修饰电极的制备及其对色氨酸/磷钨杂多酸超分子化合物的手性识别

高等学校化学学报 ›› 2009, Vol. 30 ›› Issue (6): 1235.

含联萘基团的手性聚芳醚酮类环状齐聚物修饰电极的制备及其对色氨酸/磷钨杂多酸超分子化合物的手性识别

杨利国, 金海燕, 王永国, 崔岩, 曹晖, 贲腾, 张万金

吉林大学化学学院, 长春 130012

收稿日期:2008-09-26 出版日期:2009-06-10 发布日期:2009-06-10
通讯作者: 贲腾, 男, 博士, 副教授, 主要从事螺旋状高分子的合成及性质研究. E-mail: tben@jlu.edu.cn
基金资助:
国家自然科学基金(批准号: 50403002, 20854001)资助.

Preparation of Modified Electrode and Chiral Recognition Properties of PAEK Macrocyclic Oligomer Bearing 1,1′-Bi-2-naphthyl Moiety

YANG Li-Guo, JIN Hai-Yan, WANG Yong-Guo, CUI Yan, CAO Hui, BEN Teng*, ZHANG Wan-Jin

College of Chemistry, Jilin University, Changchun 130012, China

Received:2008-09-26 Online:2009-06-10 Published:2009-06-10
Contact: BEN Teng, E-mail: tben@jlu.edu.cn
Supported by:
国家自然科学基金(批准号: 50403002, 20854001)资助.

摘要/Abstract

摘要：

用溶剂诱导的含联萘基团的手性聚芳醚酮类环状齐聚物(S-PENEKC) 制备修饰电极, 利用循环伏安法实现了对D, L, DL-色氨酸/磷钨杂多酸的超分子化合物(D, L, DL-H₃Trp₂-[PW₁₂O₄₀]) 的手性识别.

关键词: 修饰电极, 手性识别, 联萘类刚性环状齐聚物, 手性超分子化合物

Abstract:

Modified electrode of poly(aryl ether ketone) macrocyclic oligomer containing 1,1′-bi-2-naphthyl moiety was successfully prepared, which was used to recognize chiral supramolecules that were derived from tryptophan and tungstophosphoric acid(D, L, DL-H₃Trp₂-[PW₁₂O₄₀]/GC in 1.0 mol/L H₂SO₄) by the cyclic voltammogram method. By means of vibrational circular dichroism spectroscopy, we found that different solvents treatment could alter the plane angle of the two naphthyl groups(i.e., dihedral angle) of S-PENEKC. Therefore, the selectivity of chiral recognition based on S-PENEKC could be achieved by different solvents treatment, which was approved by the results from electrochemical experiments.

Key words: Modified electrode, Chiral recognize, Binaphthyl rigid cyclic oligomer, Chiral supramolecule

TrendMD:

杨利国, 金海燕, 王永国, 崔岩, 曹晖, 贲腾, 张万金. 含联萘基团的手性聚芳醚酮类环状齐聚物修饰电极的制备及其对色氨酸/磷钨杂多酸超分子化合物的手性识别. 高等学校化学学报, 2009, 30(6): 1235.

YANG Li-Guo, JIN Hai-Yan, WANG Yong-Guo, CUI Yan, CAO Hui, BEN Teng*, ....... Preparation of Modified Electrode and Chiral Recognition Properties of PAEK Macrocyclic Oligomer Bearing 1,1′-Bi-2-naphthyl Moiety. Chem. J. Chinese Universities, 2009, 30(6): 1235.

参考文献

[1]Pu L.. Chem. Rev.[J], 1998, 98: 2405—2494
[2]Koovsky′ P., Vyskoil S., Smrina M.. Chem. Rev.[J], 2003, 103: 3213—3245
[3]Telfer S. G., Kuroda R.. Coord. Chem. Rev.[J], 2003, 242: 33—46
[4]Hamilton G. L., Kang E. J., Toste F. D., et al.. Science[J], 2007, 317: 496—499
[5]Murai T., Matsuoka D., Morishita K.. J. Am. Chem. Soc.[J], 2007, 128: 4584—4585
[6]Goh M., Kyotani M., Akagi K.. J. Am. Chem. Soc.[J], 2007, 129: 8519—8527
[7]Helgeson R. C., Mazaleyrat J. P., Cram D. J.. J. Am. Chem. Soc.[J], 1981, 103: 3929—3931
[8]Jiang H., Lin W. B.. J. Am. Chem. Soc.[J], 2003, 125: 8084—8085
[9]Hoger S.. Chem. Eur. J.[J], 2004, 10: 1320—1329
[10]Takahira Y., Sugiura H., Yamaguchi M.. J. Org. Chem.[J], 2006, 71: 763—767
[11]Ema T., Tanida D., Sakai T.. J. Am. Chem. Soc.[J], 2007, 129: 10591—10596
[12]Li Z. B., Liu T. D., Pu L.. J. Org. Chem.[J], 2007, 72: 4340—4343
[13]Kondepudi D. K., Laudadio J., Asakura K.. J. Am. Chem. Soc.[J], 1999, 121: 1448—1451
[14]Wang J. Z., Chen C. H., Wu Z. W., et al.. J. Polym. Sci., Part A: Polym. Chem.[J], 1999, 37: 1957—1967
[15]CAO Hui(曹晖), BEN Teng(贲腾), ZHANG Wan-Jin(张万金), et al.. Chem. J. Chinese Universities(高等学校化学学报)
[J], 2003, 24(9): 1724—1726
[16]Pope M. T., Varga Jr G. M.. Inorg. Chem.[J], 1966, 5: 1249—1254
[17]Keita B., Nadjo L.. J. Electroanal. Chem.[J], 1987, 227: 77—98
[18]Cao H., Ben T., Zhang W. J., et al.. Macromol. Chem. Phys.[J], 2005, 206: 1140—1145
[19]Setnika V., Urbanova′ M., Bou P., et al.. J. Phys. Chem. A.[J], 2001, 105: 8931—8938
[20]Liu S. Q., Shi Z., Dong S. J.. Electroanalysis[J], 1998, 10: 891—896
[21]Wang J.. Analytical Electrochemistry, 3rd Ed.[M], VCH: Wiley, 2006
[22]Wang R. Y., Jia D. Z., Zhang L., et al.. Adv. Funct. Mater.[J], 2006, 16: 687—692
[23]Kortz U., Savelieff M. G, Ghali F. Y. A., et al.. Angew. Chem. Int. Ed.[J], 2002, 41: 4070—4073