Fluorescent chemosensors based on a new type of lower rim-dansylated and bridge-substituted calix[4]arenes

被引：8
作者：
Fischer, Conrad [1 ]
Stapf, Manuel [1 ]
Seichter, Wilhelm [1 ]
Weber, Edwin [1 ]
机构：
[1] Tech Univ Bergakad Freiberg, Inst Organ Chem, D-09596 Freiberg, Germany
来源：
SUPRAMOLECULAR CHEMISTRY | 2013年 / 25卷 / 06期
关键词：
fluorogenic calixarenes; dansyl; Cu recognition; chemosensor; crystal structure; CENTER-DOT-HALOGEN; CONFORMATIONAL BEHAVIOR; CRYSTAL-STRUCTURES; ION; CALIXARENES; RECEPTORS; SENSOR; ACID;
D O I：
10.1080/10610278.2013.783918
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The synthesis, structural and chemosensing properties of several lower rim-dansylated calix[4]arenes bearing different methylene bridge substituents are described. Compared to bridge-unsubstituted pendants neither the conformational nor the fluorescence characteristics of the calixarene core are perceptibly influenced by the bridge substituent. X-ray structure as well as NMR measurements indicates the lower rim-propoxylated and-dansylated calixarenes to adopt the cone conformation capable of the complexation of Cu2+ ions at micromolar level. Fluorescent measurements point to selective 1:2 calixarene: Cu2+ complex formation with sensing parameters being of a suitable level to make the use as a potentially immobilisable chemosensor for the detection of Cu2+ ions promising.
引用
收藏
页码：371 / 383
页数：13
相关论文
共 33 条
[1]   Self-assembly of nanosize coordination cages on Si(100) surfaces [J].
Busi, Marco ;
Laurenti, Marco ;
Condorelli, Guglielmo G. ;
Motta, Alessandro ;
Favazza, Maria ;
Fragala, Ignazio L. ;
Montalti, Marco ;
Prodi, Luca ;
Dalcanale, Enrico .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (24) :6891-6898
[2]   Halogen•••halogen versus OH•••O supramolecular interactions in the crystal structures of a series of halogen and methyl substituted cis-9,10-diphenyl-9,10-dihydroanthracene-9, 10-diols [J].
Csöregh, I ;
Brehmer, T ;
Bombicz, P ;
Weber, E .
CRYSTAL ENGINEERING, 2001, 4 (04) :343-357
[3]   Bridge-disubstituted calix[4]arenes obtained via a new preparative route. Synthesis and structural study [J].
Fischer, Conrad ;
Lin, Guisheng ;
Seichter, Wilhelm ;
Weber, Edwin .
TETRAHEDRON, 2011, 67 (31) :5656-5662
[4]   Bridge-substituted calix[4]arenes: syntheses, conformations and application [J].
Fischer, Conrad ;
Gruber, Tobias ;
Seichter, Wilhelm ;
Weber, Edwin .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (11) :4347-4352
[5]   Comparative X-ray structural study of laterally mono-ethyl substituted 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetra-methoxycalix[4]arene and its non-substituted parent compound including guest free and solvated forms. Chemical straightening of guest channels [J].
Fischer, Conrad ;
Lin, Guisheng ;
Bombicz, Petra ;
Seichter, Wilhelm ;
Weber, Edwin .
STRUCTURAL CHEMISTRY, 2011, 22 (02) :433-439
[6]   2-(4-Bromobenzyl)-5,11,17,23-tetra-tert-butyl-25,26,27,28-tetramethoxycalix[4]arene [J].
Fischer, Conrad ;
Lin, Guisheng ;
Seichter, Wilhelm ;
Weber, Edwin .
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 :01704-U3526
[7]   Conformational behaviour and first crystal structures of a calix[4]arene featuring a laterally positioned carboxylic acid function in unsolvated and solvent-complexed forms [J].
Gruber, Tobias ;
Gruner, Margit ;
Fischer, Conrad ;
Seichter, Wilhelm ;
Bombicz, Petra ;
Weber, Edwin .
NEW JOURNAL OF CHEMISTRY, 2010, 34 (02) :250-259
[8]   Calix[4]arenes featuring a direct lower rim attachment of dansyl groups. Synthesis, fluorescence properties and first report on crystal structures [J].
Gruber, Tobias ;
Fischer, Conrad ;
Felsmann, Marika ;
Seichter, Wilhelm ;
Weber, Edwin .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (23) :4904-4917
[9]  
Grundler P., 2007, CHEM SENSORS
[10]   Influence of laterally attached alkyl groups on the conformational behaviour of a basic calix[4]arene: combined NMR, molecular mechanics and X-ray study [J].
Gruner, Margit ;
Fischer, Conrad ;
Gruber, Tobias ;
Weber, Edwin .
SUPRAMOLECULAR CHEMISTRY, 2010, 22 (04) :256-266
1234