Complexation of metals with piperazine-containing azamacrocyclic fluorophores

被引:12
作者
Angelovski, G
Costisella, B
Kolaric, B
Engelhard, M
Eilbracht, P
机构
[1] Max Planck Inst Mol Physiol, Abt Phys Biochem 3, D-44227 Dortmund, Germany
[2] Univ Dortmund, FB Chem Organ Chem 1, D-44227 Dortmund, Germany
[3] Univ Dortmund, FB Chem Gemeinsame Einrichtungen, NMR Spekt, D-44227 Dortmund, Germany
关键词
D O I
10.1021/jo049465o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Azamacrocyclic fluorophores containing piperazine units were synthesized using sequential rhodium-catalyzed regioselective hydroformylation-reductive amination. A piperazine unit is introduced into the macrocycles to act simultaneously as electron donor and binding site. The macrocycles chelate divalent cations, either Zn2+ or Co2+, which considerably enhanced fluorescence. Complexation with Zn2+ was additionally confirmed by NMR.
引用
收藏
页码:5290 / 5294
页数:5
相关论文
共 30 条
[1]   Synthesis of hydroquinone-, biphenol-, and binaphthol-containing aza macroheterocycles via regioselective hydroformylation and reductive amination [J].
Angelovski, G ;
Eilbracht, P .
TETRAHEDRON, 2003, 59 (41) :8265-8274
[2]  
BALZANI V, 1993, SUPRAMOLECULAR PHOTO, P185
[3]   MOLECULAR FLUORESCENT SIGNALING WITH FLUOR SPACER RECEPTOR SYSTEMS - APPROACHES TO SENSING AND SWITCHING DEVICES VIA SUPRAMOLECULAR PHOTOPHYSICS [J].
BISSELL, RA ;
DE SILVA, AP ;
GUNARATNE, HQN ;
LYNCH, PLM ;
MAGUIRE, GEM ;
SANDANAYAKE, KRAS .
CHEMICAL SOCIETY REVIEWS, 1992, 21 (03) :187-195
[4]   ALPHA(1)-ADRENOCEPTOR BLOCKING ACTIVITY OF SOME RING-OPEN ANALOGS OF PRAZOSIN [J].
BOSCHI, D ;
DISTILO, A ;
FRUTTERO, R ;
MEDANA, C ;
SORBA, G ;
GASCO, A .
ARCHIV DER PHARMAZIE, 1994, 327 (10) :661-667
[5]  
Brouwer AJ, 2001, EUR J ORG CHEM, V2001, P1903
[6]   SYNTHESIS AND REACTIVITY OF AZA-CAPPED ENCAPSULATED CO(III) IONS [J].
CREASER, II ;
GEUE, RJ ;
HARROWFIELD, JM ;
HERLT, AJ ;
SARGESON, AM ;
SNOW, MR ;
SPRINGBORG, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (22) :6016-6025
[7]   CHEMICAL COMMUNICATION IN WATER USING FLUORESCENT CHEMOSENSORS [J].
CZARNIK, AW .
ACCOUNTS OF CHEMICAL RESEARCH, 1994, 27 (10) :302-308
[8]   Signaling recognition events with fluorescent sensors and switches [J].
de Silva, AP ;
Gunaratne, HQN ;
Gunnlaugsson, T ;
Huxley, AJM ;
McCoy, CP ;
Rademacher, JT ;
Rice, TE .
CHEMICAL REVIEWS, 1997, 97 (05) :1515-1566
[9]  
DIASPRO A, 2002, CONFOCAL 2 PHOTON MI
[10]  
Dietrich B., 1993, MACROCYCLIC CHEM