A novel [2]catenane was synthesised by ring-closing metathesis from a Ca-bisphosphate template. The resulting interlocked structure features two chiral 1,1'-binaphthyl-phosphates, leading to a bifunctional catenane structure. Initial binding studies point at the applicability of such mechanically interlocked bisphosphates as artificial receptors for dicationic guest molecules.

We describe the straightforward synthesis of a series of bis-phosphoric acids (R,R)-1 a-d, featuring two chiral 1,1'-binaphthyl-phosphoric acid units that are tethered by rigid, π-conjugated linkers. The nature of the linker has a profound influence on the properties of the bis-phosphoric acids, such as their self-association behavior and their interaction with metal ions. This led to the identification of one preferred bis-phosphoric acid (R,R)-1 d, which shows selective fluorescence quenching in the presence of ferric ions (Fe ). Thus, (R,R)-1 d could be applied for the detection of Fe , even in the presence of a variety of other metal ions. The chiral nature of the bis-phosphoric acid enables the interaction with Fe to be followed by CD spectroscopy, providing a complementary detection mode with the same probe.

A series of covalently linked bis‐ and trisphosphoric acids was investigated for their application in the stereoselective transfer‐hydrogenation of quinolines. In a combined experimental and theoretical study, it was found that the number and relative positioning of the chiral 1,1′‐binaphthyl‐phosphoric acid groups strongly influences the stereoselectivity of the reaction, based on two competing reaction mechanisms. While a single 3‐monosubstituted phosphoric acid moiety gives rise to little enantioselectivity, correct positioning of two phosphoric acids allows a cooperative mechanism, resulting in significantly higher stereoselectivities.

The synthesis and application of three chiral receptors based on the covalent linkage of 1,1′-binaphthylphosphoric acids is reported. The binding of the lysine enantiomers to the chiral receptors was investigated by DOSY-NMR and NMR titrations, revealing that the bisphosphoric acid 1d acts as a highly stereoselective receptor for binding of D-lysine.