Synthesis of glycoluril-tetrathiafulvalene molecular clips for electron-deficient neutral guests through a straightforward Diels–Alder strategy

Abstract

An electroactive molecular clip incorporating tetrathiafulvalene (TTF) sidewalls grafted on a glycoluril platform has been synthesized using a straightforward Diels–Alder strategy. This way of attachment to the glycoluril U-shape scaffold afforded a rigidified and closed receptor for which the electron-rich TTF pincers are expected to be at a suitable distance for sandwiching neutral guests through donor–acceptor interactions. The efficient complexation ability of this host architecture toward one molecule of tetracyanoquinodimethane derivative (F₄-TCNQ) in solution has been demonstrated using cyclic voltammetry and UV-Visible titration methods.