School of Science and the Environment, Division of Chemistry and Environmental Science, Manchester Metropolitan University, John Dalton Building, Chester St., Manchester M1 5GD, UK
Mandeep Kaur
School of Science and the Environment, Division of Chemistry and Environmental Science, Manchester Metropolitan University, John Dalton Building, Chester St., Manchester M1 5GD, UK
Sophie L. Benjamin
School of Science and Technology, Nottingham Trent University, Nottingham NG11 8NS, UK
Alan M. Jones
School of Pharmacy, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK
Stuart K. Langley
School of Science and the Environment, Division of Chemistry and Environmental Science, Manchester Metropolitan University, John Dalton Building, Chester St., Manchester M1 5GD, UK
Ryan E. Mewis
School of Science and the Environment, Division of Chemistry and Environmental Science, Manchester Metropolitan University, John Dalton Building, Chester St., Manchester M1 5GD, UK
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.
