TY - JOUR
T1 - Novel trans-disubstituted hexaaza-macrocyclic ligands containing pyridine head units: Synthesis, disubstitution and colorimetric properties
AU - Lamelas, Rodrigo
AU - García, Verónica
AU - Liñares, Araceli
AU - Bastida, Rufina
AU - Labisbal, Elena
AU - Fernández-Lodeiro, Adrián
AU - Lodeiro, Carlos
AU - Núñez, Cristina
AU - Valencia, Laura
N1 - Fundacao para a Ciencia e a Tecnologia (SFRH/BD/52528/2014);
Ministerio de Ciencia e Innovacion, Plan Nacional de I+D+i (CTQ2011-24487);
Xunta de Galicia (Spain) - PXIB209028PR ; GRC2015/009;
LAQV/REQUIMTE (UID/QUI/50006/2013);
UCIBIO/REQUIMTE (UID/Multi/04378/2013).
PY - 2016/3/31
Y1 - 2016/3/31
N2 - A trans-N,N′-methylated hexaazamacrocycle precursor L3, derived from the hexadentate polyamine macrocycle L (Py2[18]aneN6), was synthesized for the first time. The crystal structures of the intermediates L1·8H2O and L2I2·H2O showing two trans quaternary nitrogen atoms have also been determined by single-crystal X-ray crystallography. By the alkylation of the trans secondary amines present in L3, two novel macrocyclic molecular probes 1 and 2 linked to two nitrophenylurea and two nitrophenylthiourea groups, respectively, are reported. Crystals of 1·2CDCl3 suitable for single-crystal X-ray diffraction analysis were also obtained. The coordination ability of compounds 1 and 2 toward hydrated nitrate salts of cobalt(II), nickel(II), copper(II), zinc(II) and cadmium(II) was studied. Their responses toward different anions (fluoride (F-), chloride (Cl-), bromide (Br-), iodide (I-), hydroxide (OH-), acetate (AcO-), cyanide (CN-), dihydrogen phosphate (H2PO4-), nitrate (NO3-) and perchlorate (ClO4-)) in DMSO solution were evaluated by UV-vis absorption spectroscopy. The immobilization of probe 1 in cellulose supported systems to evaluate its efficiency in the fast recognition of different anions (F-, AcO-, CN-, H2PO4-) in aqueous phase was also described.
AB - A trans-N,N′-methylated hexaazamacrocycle precursor L3, derived from the hexadentate polyamine macrocycle L (Py2[18]aneN6), was synthesized for the first time. The crystal structures of the intermediates L1·8H2O and L2I2·H2O showing two trans quaternary nitrogen atoms have also been determined by single-crystal X-ray crystallography. By the alkylation of the trans secondary amines present in L3, two novel macrocyclic molecular probes 1 and 2 linked to two nitrophenylurea and two nitrophenylthiourea groups, respectively, are reported. Crystals of 1·2CDCl3 suitable for single-crystal X-ray diffraction analysis were also obtained. The coordination ability of compounds 1 and 2 toward hydrated nitrate salts of cobalt(II), nickel(II), copper(II), zinc(II) and cadmium(II) was studied. Their responses toward different anions (fluoride (F-), chloride (Cl-), bromide (Br-), iodide (I-), hydroxide (OH-), acetate (AcO-), cyanide (CN-), dihydrogen phosphate (H2PO4-), nitrate (NO3-) and perchlorate (ClO4-)) in DMSO solution were evaluated by UV-vis absorption spectroscopy. The immobilization of probe 1 in cellulose supported systems to evaluate its efficiency in the fast recognition of different anions (F-, AcO-, CN-, H2PO4-) in aqueous phase was also described.
KW - Anion sensor
KW - Colorimetric
KW - Disubstitution
KW - Hexaazamacrocycle
KW - Solid support
KW - Urea/thiourea
UR - http://www.scopus.com/inward/record.url?scp=84949575419&partnerID=8YFLogxK
U2 - 10.1016/j.snb.2015.11.090
DO - 10.1016/j.snb.2015.11.090
M3 - Article
AN - SCOPUS:84949575419
SN - 0925-4005
VL - 225
SP - 481
EP - 491
JO - Sensors and Actuators B: Chemical
JF - Sensors and Actuators B: Chemical
ER -