Novel trans-disubstituted hexaaza-macrocyclic ligands containing pyridine head units: Synthesis, disubstitution and colorimetric properties

Rodrigo Lamelas, Verónica García, Araceli Liñares, Rufina Bastida, Elena Labisbal, Adrián Fernández-Lodeiro, Carlos Lodeiro, Cristina Núñez, Laura Valencia

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)481-491
Number of pages11
JournalSensors And Actuators B-Chemical
Volume225
DOIs
Publication statusPublished - 31 Mar 2016

Keywords

  • Anion sensor
  • Colorimetric
  • Disubstitution
  • Hexaazamacrocycle
  • Solid support
  • Urea/thiourea

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