A method for synthesizing partially substituted cucurbit[n]uril

被引:129
作者
Day, AI [1 ]
Arnold, AP [1 ]
Blanch, RJ [1 ]
机构
[1] Univ New S Wales, Univ Coll, Sch Chem, Australian Def Force Acad, Canberra, ACT 2600, Australia
来源
MOLECULES | 2003年 / 8卷 / 01期
关键词
macrocycles; molecular binding; partially substituted;
D O I
10.3390/80100074
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A novel approach to cucurbituril synthesis is described where partial substitution is introduced into cucurbit[n]uril. The identification of homologues (and their substitution) in reaction mixtures is achieved by a combination of ESMS and the use of the molecular probes (guests) 1,4-dioxane and 1,9-octanediamine. A unique symmetrical hexamethylcucurbit[3,3]uril, the major product, was isolated and characterized.
引用
收藏
页码:74 / 84
页数:11
相关论文
共 19 条
[1]   Controlling factors in the synthesis of cucurbituril and its homologues [J].
Day, A ;
Arnold, AP ;
Blanch, RJ ;
Snushall, B .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) :8094-8100
[2]  
Day AI, 2002, ANGEW CHEM INT EDIT, V41, P275, DOI 10.1002/1521-3773(20020118)41:2<275::AID-ANIE275>3.0.CO
[3]  
2-M
[4]   The effects of alkali metal cations on product distributions in cucurbit[n]uril synthesis [J].
Day, AI ;
Blanch, RJ ;
Coe, A ;
Arnold, AP .
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2002, 43 (3-4) :247-250
[5]  
DAY AI, 2000, Patent No. 9923219990507
[6]   DECAMETHYLCUCURBIT[5]URIL [J].
FLINN, A ;
HOUGH, GC ;
STODDART, JF ;
WILLIAMS, DJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (11) :1475-1477
[7]   Synthesis of disubstituted cucurbit[6]uril and its rotaxane derivative [J].
Isobe, H ;
Sato, S ;
Nakamura, E .
ORGANIC LETTERS, 2002, 4 (08) :1287-1289
[8]   Cucurbit[5]uril, decamethylcucurbit[5]uril and cucurbit[6]uril.: Synthesis, solubility and amine complex formation [J].
Jansen, K ;
Buschmann, HJ ;
Wego, A ;
Döpp, D ;
Mayer, C ;
Drexler, HJ ;
Holdt, HJ ;
Schollmeyer, E .
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2001, 39 (3-4) :357-363
[9]   A facile, stereoselective [2+2] photoreaction mediated by cucurbit[8]uril [J].
Jon, SY ;
Ko, YH ;
Park, SH ;
Kim, HJ ;
Kim, K .
CHEMICAL COMMUNICATIONS, 2001, (19) :1938-1939
[10]   Encapsulation of N2, O2, methanol, or acetonitrile by decamethylcucurbit[5]uril(NH4+)2 complexes in the gas phase:: Influence of the guest on "lid" tightness [J].
Kellersberger, KA ;
Anderson, JD ;
Ward, SM ;
Krakowiak, KE ;
Dearden, DV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (45) :11316-11317