Article Dans Une Revue Chemistry - A European Journal Année : 2024

A Chiral [2 + 3] Covalent Organic Cage Based on 1,1’‐Bi‐2‐naphthol (BINOL) Units

Midhun Mohan
David-Jérôme Pham
  • Fonction : Auteur
Audrey Fluck
Alain Chaumont
Brice Kauffmann
Laurent Barloy
Pierre Mobian

Résumé

A [2+3] chiral covalent organic cage is produced through a dynamic covalent chemistry approach by mixing two readily available building units, viz. an enantiopure 3,3’-diformyl 2,2’-BINOL compound (A) with a triamino spacer (B). The two enantiomeric (R,R,R) and (S,S,S) forms of the cage C are formed nearly quantitatively thanks to the reversibility of the imine linkage. The X-ray diffraction analysis of cage (S,S,S)-C highlights that the six OH functions of the BINOL fragments are positioned inside the cage cavity. Upon reduction of the imine bonds of cage C, the amine cage D is obtained. The ability of the cage D to host the 1-phenylethylammonium cation (EH+) as a guest is evaluated through UV, CD and DOSY NMR studies. A higher binding constant for (R)-EH+ cation (Ka=1.7 106±10 % M−1) related to (S)-EH+ (Ka=0.9 106±10 % M−1) is determined in the presence of the (R,R,R)-D cage. This enantiopreference is in close agreement with molecular dynamics simulation

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Dates et versions

hal-04523512 , version 1 (27-03-2024)

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Midhun Mohan, David-Jérôme Pham, Audrey Fluck, Simon Chapuis, Alain Chaumont, et al.. A Chiral [2 + 3] Covalent Organic Cage Based on 1,1’‐Bi‐2‐naphthol (BINOL) Units. Chemistry - A European Journal, 2024, 30 (23), pp.e202400458. ⟨10.1002/chem.202400458⟩. ⟨hal-04523512⟩
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