Open AccessMolecular Recognition in an Aqueous Medium Using Water-Soluble Prismarene Hosts
Author(s) -
Rocco Del Regno,
Giuseppina D. G. Santonoceta,
Paolo Della Sala,
Margherita De Rosa,
Annunziata Soriente,
Carmen Talotta,
Aldo Spinella,
Placido Neri,
Carmelo Sgarlata,
Carmine Gaeta
Publication year - 2022
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.2c00819
Subject(s) - chemistry , random hexamer , pentamer , aqueous solution , water soluble , molecular recognition , ammonium , isothermal titration calorimetry , crystallography , molecule , organic chemistry , biochemistry
The synthesis of water-soluble prism[ n ]arenes ( n = 5 and 6) bearing anionic carboxylato groups on the rims is described. The binding properties of this novel class of water-soluble hosts are studied by nuclear magnetic resonance and calorimetry. The complexation of singly and doubly charged ammonium guests with the more rigid pentamer is enthalpically driven by secondary interactions, while the thermodynamic fingerprint for the larger hexamer reveals driving forces that strongly depend on the guest charge and/or size.