Superior anion induced shuttling behaviour exhibited by a halogen bonding two station rotaxane

نویسندگان

  • Timothy A. Barendt
  • Sean W. Robinson
  • Paul D. Beer
چکیده

Two bistable halogen and hydrogen bonding-naphthalene diimide [2]rotaxanes have been prepared and the system incorporating a halogen bond donor anion recognition site is demonstrated to exhibit superior anion induced translational motion of the macrocyclic wheel component relative to the hydrogen bonding analogue. Proton NMR spectroscopy is used to estimate the percentage occupancies of the macrocycle at the respective station and importantly indicates that the halogen bonding rotaxane displays superior positional integrity in competitive protic solvent media as a consequence of strong halogen bond–halide anion binding interactions.

برای دانلود رایگان متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Selective Nitrate Recognition by a Halogen‐Bonding Four‐Station [3]Rotaxane Molecular Shuttle

The synthesis of the first halogen bonding [3]rotaxane host system containing a bis-iodo triazolium-bis-naphthalene diimide four station axle component is reported. Proton NMR anion binding titration experiments revealed the halogen bonding rotaxane is selective for nitrate over the more basic acetate, hydrogen carbonate and dihydrogen phosphate oxoanions and chloride, and exhibits enhanced rec...

متن کامل

Contrasting anion recognition behaviour exhibited by halogen and hydrogen bonding rotaxane hosts.

A rotaxane host system containing a novel halogen bonding (XB) 5-iodo-1,2,3-triazole functionalised pyridinium motif, within its axle component, has been prepared via a ring closing metathesis reaction, using chloride as a template. Proton NMR titration experiments, in competitive 1 : 1 CDCl3-CD3OD solvent media, showed the XB rotaxane selectively bound halides over larger, more basic oxoanions...

متن کامل

Active‐Metal Template Synthesis of a Halogen‐Bonding Rotaxane for Anion Recognition

The synthesis of an all-halogen-bonding rotaxane for anion recognition is achieved by using active-metal templation. A flexible bis-iodotriazole-containing macrocycle is exploited for the metal-directed rotaxane synthesis. Endotopic binding of a Cu(I) template facilitates an active-metal CuAAC iodotriazole axle formation reaction that captures the interlocked rotaxane product. Following copper-...

متن کامل

Chelated charge assisted halogen bonding enhanced halide recognition by a pyridinium-iodotriazolium axle containing [2]rotaxane.

Four halogen and hydrogen bonding rotaxane host systems featuring pyridinium bis-amide-iodotriazole/prototriazole and pyridinium bis-amide-iodotriazolium/prototriazolium axle components have been synthesized by CuAAC-mediated mono-stoppering chloride anion templation and post-rotaxanation methylation reactions. In competitive 45 : 45 : 10 CDCl3-CD3OD-D2O aqueous solvent media, the dicationic ha...

متن کامل

Iodide Recognition and Sensing in Water by a Halogen‐Bonding Ruthenium(II)‐Based Rotaxane

The synthesis and anion-recognition properties of the first halogen-bonding rotaxane host to sense anions in water is described. The rotaxane features a halogen-bonding axle component, which is stoppered with water-solubilizing permethylated β-cyclodextrin motifs, and a luminescent tris(bipyridine)ruthenium(II)-based macrocycle component. (1) H NMR anion-binding titrations in D2 O reveal the ha...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

عنوان ژورنال:

دوره   شماره 

صفحات  -

تاریخ انتشار 2016