TY - JOUR
T1 - Intramolecular excimer formation and sensing behavior of new fluorimetric probes and their interactions with metal cations and barbituric acids
AU - Lodeiro, C.
AU - Lima, J. C.
AU - Parola, A. J.
AU - Seixas de Melo, J. S.
AU - Capelo, J. L.
AU - Covelo, B.
AU - Tamayo, A.
AU - Pedras, B.
N1 - This work has been supported by the Fundação para a Ciência e a Tecnologia (Project POCI/QUI/55519/2004 FCT-FEDER) (Portugal). BC thanks Caixanova (Spain) by a post-doctoral grant, AT thanks Departament d’Universitats Recerca i Societat de la Informació of the Catalan Government (Spain) by the Grant FI2002-00320.
PY - 2006/5/23
Y1 - 2006/5/23
N2 - A new family of compounds able to promote host-guest interactions with specific molecules (e.g., cyanuric and parabanic acids) and to coordinate metal ions, namely Zn(II) and Cu(II), has been synthesized and fully characterized. The new probes derive from the attachment of two methylaminopyrene units to the carbonyl precursor 2,6-bis(2-formylphenoxymethyl)pyridine. Its signalling properties result from the fluorescence emission properties, which reveal the existence of intramolecular excimer formation. The compounds have showed to be highly sensitive to the solvent and hydrogen ion concentration of the medium. Depending on these, different monomer-to-excimer fluorescence ratio is displayed by the two probes. The compound with a single pyrene unit revealed absence of excimer formation and was used as model compound. The overall results are discussed on the basis of the studied probes as potentially revealing molecular movements, off-on-off fluorescent photoinduced electron transfer (PET), host-guest interactions with specific compounds and of sensing metal ions.
AB - A new family of compounds able to promote host-guest interactions with specific molecules (e.g., cyanuric and parabanic acids) and to coordinate metal ions, namely Zn(II) and Cu(II), has been synthesized and fully characterized. The new probes derive from the attachment of two methylaminopyrene units to the carbonyl precursor 2,6-bis(2-formylphenoxymethyl)pyridine. Its signalling properties result from the fluorescence emission properties, which reveal the existence of intramolecular excimer formation. The compounds have showed to be highly sensitive to the solvent and hydrogen ion concentration of the medium. Depending on these, different monomer-to-excimer fluorescence ratio is displayed by the two probes. The compound with a single pyrene unit revealed absence of excimer formation and was used as model compound. The overall results are discussed on the basis of the studied probes as potentially revealing molecular movements, off-on-off fluorescent photoinduced electron transfer (PET), host-guest interactions with specific compounds and of sensing metal ions.
KW - Barbituric acids
KW - Excimers
KW - Fluorescence
KW - Host-guest interactions
KW - Receptor units
KW - Supramolecular chemistry
UR - http://www.scopus.com/inward/record.url?scp=33645967166&partnerID=8YFLogxK
U2 - 10.1016/j.snb.2005.09.010
DO - 10.1016/j.snb.2005.09.010
M3 - Article
AN - SCOPUS:33645967166
SN - 0925-4005
VL - 115
SP - 276
EP - 286
JO - Sensors and Actuators B: Chemical
JF - Sensors and Actuators B: Chemical
IS - 1
ER -