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Wurster's crownophanes: an alternate topology for para-phenylenediamine-based macrocycles |
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| Authors: | John W Sibert Greg R Hundt Andrew L Sargent Vincent Lynch |
| Institution: | aDepartment of Chemistry, The University of Texas at Dallas, PO Box 830688, Richardson, TX 75083-0688, USA bDepartment of Chemistry, East Carolina University, Greenville, NC 27858, USA cDepartment of Chemistry, The University of Texas at Austin, Austin, TX 78712, USA |
| Abstract: | Six redox-active cyclophane/crown hybrid molecules (crownophanes) were prepared via cyclization reactions involving N,N′-dimethyl-p-phenylenediamine and tosylated oligoethylene glycols of varying length. These new host molecules differ from other phenylenediamine-containing crown ethers in that the electron-rich π face is designed to be part of the ligating group. Their electrochemical properties were determined by cyclic voltammetry with a correlation found between macrocyclic architecture and ease of oxidation. The affinity of the smaller crownophanes for cations was studied by cyclic voltammetry with the result that these hosts show no electrochemical response to alkali metal cations, but, dependent on macrocycle size, modest selectivity for alkaline earth metal cations. This stands in contrast to previously reported phenylenediamine-containing crown ethers in which the redox centers are linked to guest ions through a macrocyclic amino group. |
| Keywords: | Cyclophane Crown Crownophane Wurster Redox |
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