Fluorescence in complexes based on quinolines-derivatives: a search for better fluorescent probes.
Quinoline-derived fluorescent complexes were designed; synthesized by the reaction of 5-nitro-8-hydroxyquinoline and 5-chloro-8-hydroxyquinoline with Al(3+), Mg(2+), Zn(2+), and Cd(2+) salts (1-8); and characterized. The (1)H NMR spectra of complexes 1 and 5, containing Al(3+), were consistent with an octahedral structure having approximate D3 symmetry, and the results supported the favored facial isomer (fac). Data for complexes 2-4 and 6-8 supported the formation of tetrahedral structures. Intense luminescence was detected for complexes 5-8, even with the naked eye, as indicated by quantum yield values of 0.087, 0.094, 0.051, and 0.021, respectively. Furthermore, in contrast to 5-nitro-8-hydroxyquinoline, the 5-chloro-8-hydroxyquinoline ligand exhibited bands at different energies depending on the coordinated metal, which supported its potential application in ionic and biological probes, as well as in cell imaging.
Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Laboratório de Química de Calixarenos, Espectroscopia Molecular e Catálise, Universidade Federal de São Paulo, Rua Prof. Arthur Riedel, 275, CEP 09972-270, Diadema, SP, Brazil.
Carolina Z P
CZP
Mecca
Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Laboratório de Química de Calixarenos, Espectroscopia Molecular e Catálise, Universidade Federal de São Paulo, Rua Prof. Arthur Riedel, 275, CEP 09972-270, Diadema, SP, Brazil; Fundação do ABC, Faculdade de Medicina, Av. Príncipe de Gales, 821, CEP 09060-650, Santo André, SP, Brazil.
Fernando L A
FLA
Fonseca
Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Laboratório de Química de Calixarenos, Espectroscopia Molecular e Catálise, Universidade Federal de São Paulo, Rua Prof. Arthur Riedel, 275, CEP 09972-270, Diadema, SP, Brazil. Electronic address: ibagatin@unifesp.br.
Izilda A
IA
Bagatin
D000535:Aluminum / Q000737:chemistry; D002104:Cadmium / Q000737:chemistry; D002739:Chloroquinolinols / Q000138:chemical synthesis / Q000737:chemistry*; D056831:Coordination Complexes / Q000138:chemical synthesis / Q000737:chemistry*; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D008274:Magnesium / Q000737:chemistry; D009600:Nitroquinolines / Q000138:chemical synthesis / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D015032:Zinc / Q000737:chemistry
D002739:Chloroquinolinols; D056831:Coordination Complexes; D005456:Fluorescent Dyes; D009600:Nitroquinolines; D002104:Cadmium; C043669:5-chloro-8-hydroxyquinoline; C005308:nitroxoline; D000535:Aluminum; D008274:Magnesium; D015032:Zinc
Coordination complexes; Luminescence; Quinolines