ja9b12216_si_005.cif (57.25 kB)
Prismarenes: A New Class of Macrocyclic Hosts Obtained by Templation in a Thermodynamically Controlled Synthesis
dataset
posted on 2020-01-14, 19:47 authored by Paolo Della Sala, Rocco Del Regno, Carmen Talotta, Amedeo Capobianco, Neal Hickey, Silvano Geremia, Margherita De Rosa, Aldo Spinella, Annunziata Soriente, Placido Neri, Carmine GaetaThe novel title macrocycles, based
on methylene-bridged 1,5-naphthalene
units, have been obtained by template effect in a thermodynamically
controlled synthesis. In detail, the prism[5]arene 1 or
the prism[6]arene 3 was selectively removed from the
equilibrium mixture by using the complementary ammonium-templating
agent. When only the solvent 1,2-DCE was used, the 1,4-confused derivative 2 was obtained. The prism[5]arene here described shows a deep
π-electron-rich aromatic cavity that exhibits a great affinity
for the quaternary ammonium guests, originating from favorable cation···π
and +NC–H···π interactions.
This recognition motif is the basis of the templated synthesis of
the prism[n]arenes here reported.