A ferrocene redox-active triazolium macrocycle that binds and senses chloride

• Nicholas G. White and
• Paul D. Beer

Beilstein J. Org. Chem. 2012, 8, 246–252, doi:10.3762/bjoc.8.25

• demonstrated by 1H NMR titration experiments to bind chloride and benzoate in CD3CN, solely through charge-assisted C–H···anion hydrogen-bonding interactions. The redox-active macrocycle was also shown to sense chloride electrochemically via a cathodic shift of the Epa wave of the ferrocene/ferrocenium redox

• couple. Experimental General Remarks Bis(azide) 1 [12], and TBTA [18] were prepared as described in the literature. Dry dichloromethane and acetonitrile were purged with nitrogen and passed through a MBraun MSP-800 column. Water was deionised and microfiltered in a Milli-Q® Millipore machine