Zinc-salophen complexes as selective receptors for tertiary amines

被引:88
作者
Cort, Antonella Dalla [1 ]
Mandolini, Luigi
Pasquini, Chiara
Rissanen, Kari
Russo, Luca
Schiaffino, Luca
机构
[1] Univ Roma La Sapienza, Dipartimento Chim, I-00185 Rome, Italy
[2] Univ Roma La Sapienza, CNR, IMC, I-00185 Rome, Italy
[3] Univ Jyvaskyla, Dept Chem, Nanosci Ctr, FIN-40014 Jyvaskyla, Finland
关键词
D O I
10.1039/b700723j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Zinc-salophen compounds 1-3 incorporating in the given order 1,2-diaminobenzene, 2,3-diaminonaphthalene, and 9,10-diaminophenantrene moieties were synthesised. Their binding properties toward a series of tertiary amines were assessed by UV-Vis and fluorescence spectroscopy in chloroform solution. Unprecedented selectivities of quinuclidine vs. triethylamine higher than 10(5) were recorded, thereby revealing the dramatic influence of steric effects on axial coordination of tertiary amines. X-Ray diffraction analyses showed that in the solid state compound 2 is dimeric, but its 1 : 1 quinuclidine complex is monomeric. Strong indications were obtained that both free receptors and their amine adducts are monomeric in dilute chloroform solution.
引用
收藏
页码:1633 / 1638
页数:6
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共 42 条
[1]   Development of a solid-phase microextraction GC-NPD procedure for the determination of free volatile amines in wastewater and sewage-polluted waters [J].
Abalos, M ;
Bayona, JM ;
Ventura, F .
ANALYTICAL CHEMISTRY, 1999, 71 (16) :3531-3537
[2]   Synthesis of photo-luminescent Zn(II) Schiff base complexes and its derivative containing Pd(II) moiety [J].
Chang, KH ;
Huang, CC ;
Liu, YH ;
Hu, YH ;
Chou, PT ;
Lin, YC .
DALTON TRANSACTIONS, 2004, (11) :1731-1738
[3]  
Chichak K, 2002, EUR J INORG CHEM, P357
[4]   LIGAND BINDING BY METALLOPORPHYRINS .3. THERMODYNAMIC FUNCTIONS FOR ADDITION OF SUBSTITUTED PYRIDINES TO NICKEL(II) AND ZINC(II) PORPHYRINS [J].
COLE, SJ ;
CURTHOYS, GC ;
PHILLIPS, JN ;
MAGNUSSO.EA .
INORGANIC CHEMISTRY, 1972, 11 (05) :1024-&
[5]   Photophysical poperties of Schiff-base metal complexes [J].
Cozzi, PG ;
Dolci, LS ;
Garelli, A ;
Montalti, M ;
Prodi, L ;
Zaccheroni, N .
NEW JOURNAL OF CHEMISTRY, 2003, 27 (04) :692-697
[7]   Unprecedented detection of inherent chirality in uranyl-salophen complexes [J].
Dalla Cort, A ;
Mandolini, L ;
Palmieri, G ;
Pasquini, C ;
Schiaffino, L .
CHEMICAL COMMUNICATIONS, 2003, (17) :2178-2179
[8]   A novel ditopic zinc-salophen macrocycle: a potential two-stationed wheel for [2]-pseudorotaxanes [J].
Dalla Cort, Antonella ;
Mandolini, Luigi ;
Pasquini, Chiara ;
Schiaffino, Luca .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (24) :4543-4546
[9]   Thermodynamics of metal-mediated assemblies of porphyrins [J].
Ercolani, Gianfranco .
NON-COVALENT MULTI-PORPHYRIN ASSEMBLIES SYNTHESIS AND PROPERTIES, 2006, 121 :167-215
[10]   Detection of amines and unprotected amino acids in aqueous conditions by formation of highly fluorescent iminium ions [J].
Feuster, EK ;
Glass, TE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (52) :16174-16175