ol5b01042_si_001.pdf (7.5 MB)
G‑Arylated Hydrogen-Bonded Cyclic Tetramer Assemblies with Remarkable Thermodynamic and Kinetic Stability
journal contribution
posted on 2015-06-05, 00:00 authored by Sonia Romero-Pérez, Jorge Camacho-García, Carlos Montoro-García, Ana M. López-Pérez, Alfredo Sanz, María José Mayoral, David González-RodríguezThe preparation and
self-assembly of novel G–C dinucleoside
monomers that are equipped with electron-poor aryl groups at the G-N2 amino group have been studied. Such monomers
associate via Watson–Crick H-bonding into discrete unstrained
tetrameric macrocycles that arise as a thermodynamically and kinetically
stabilized product in a wide variety of experimental conditions, including
very polar solvent environments and low concentrations. G-arylation
produces an increased stability of the cyclic assembly, as a result
of a subtle interplay between enthalpic and entropic effects involving
the solvent coordination sphere.