Confused-Prism[5]arene: a Conformationally Adaptive Host by Stereoselective Opening of the 1,4-Bridged Naphthalene Flap

Paolo Della Sala; Rocco Del Regno; Amedeo Capobianco; Veronica Iuliano; Carmen Talotta; Silvano Geremia; Neal Hickey; Placido Neri; Carmine Gaeta

doi:10.1002/chem.202203030

Confused-Prism[5]arene: a Conformationally Adaptive Host by Stereoselective Opening of the 1,4-Bridged Naphthalene Flap

Chemistry. 2023 Jan 27;29(6):e202203030. doi: 10.1002/chem.202203030. Epub 2022 Dec 5.

Authors

Paolo Della Sala¹, Rocco Del Regno¹, Amedeo Capobianco¹, Veronica Iuliano¹, Carmen Talotta¹, Silvano Geremia², Neal Hickey², Placido Neri¹, Carmine Gaeta¹

Affiliations

¹ Laboratory of Supramolecular Chemistry, Department of Chemistry and Biology "A. Zambelli", University of Salerno, Via Giovanni Paolo II, 84084, Fisciano, Salerno, Italy.
² Centro di Eccellenza in Biocristallografia, Dipartimento di Scienze Chimiche e Farmaceutiche, Università di Trieste, Via L. Giorgieri 1, 34127, Trieste, Italy.

PMID: 36317818
DOI: 10.1002/chem.202203030

Abstract

The confused-prism[5]arene macrocycle (c-PrS[5]^Me ) shows conformational adaptive behavior in the presence of ammonium guests. Upon guest inclusion, the 1,4-bridged naphthalene flap reverses its planar chirality from pS to pR (with reference to the pS(pR)₄ enantiomer). Stereoselective directional threading is also observed in the presence of directional axles, in which up/down stereoisomers of homochiral (pR)₅ -c-PrS[5]^Me pseudorotaxanes are formed.

Keywords: directional; molecular recognition; prismarenes; pseudorotaxanes; stereoselectivity.