Abstract
A cyclam (1,4,8,11-tetraazacyclotetradecane)-based macrocycle bearing two benzyl and two 2-hydroxy-3,5-di-tert-butylbenzyl pendent arms was synthesized and characterized using spectroscopic techniques and single crystal X-ray diffraction. The macrocycle crystallizes in the triclinic space group P-1, with the asymmetric unit containing one-half of the molecule. The structure is stabilized by hydrogen-bonding which exists between the phenolic protons and the nitrogen atoms of the macrocyclic ring. The presence of this hydrogen bonding is observed in the 1H-NMR due to the deshielded nature of the phenolic OH peak (δ 9.99). Cyclic voltammetry of the ligand revealed a single quasi-reversible peak at −0.58 V (Epc = −0.48 V and Epa = −0.68 V), which is due to the electrochemical oxidation of the phenol to the phenoxyl radical.
Highlights
The N-functionalisation of cyclam (1,4,8,11-tetraazacyclotetradecane) to produce macrocyclic ligands continues to be of significant interest due to the very stable complexes that result when complexed to metal ions
Compounds 1–3 were synthesised according to established literature procedures [21]
The structure is stabilized by hydrogen-bonding, which exists between the phenolic protons and the nitrogen atoms of the macrocyclic ring
Summary
The N-functionalisation of cyclam (1,4,8,11-tetraazacyclotetradecane) to produce macrocyclic ligands continues to be of significant interest due to the very stable complexes that result when complexed to metal ions. The ligand should meet the required coordination demand of the metal ion in question in order to maximise stability. Another role of the pendent arm may be to provide an attachment point for a biomolecule to direct the resulting complex towards a certain bio-marker [13]
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
