Search

A new family of 16‐membered macrocycles comprising two indole (In) and two quinoline (Q) units, coined In2Q2, was synthesized. Each unit is diagonally located and concatenated in a head‐to‐tail fashion, furnishing a non‐flat saddle‐shaped architecture with C2 symmetry. The synthetic protocol utilizing macrocyclic diamide as a pivotal precursor allowed us to access a series of In2Q2 derivatives bearing various substituents on the periphery. The In2Q2 derivatives and their Zn2+ complexes were emissive in both solution phase and solid state. While the entire architecture of In2Q2 is similar to that of quinoline tetramer TEtraQuinoline, a couple of contrasting physicochemical properties were revealed. [ABSTRACT FROM AUTHOR]

A new 15-membered-macrocyclic molecular entity, oxa-TriQuinoline (o-TQ), was designed and synthesized. In o-TQ, three oxygen atoms were joined onto three quinoline units at the 2- and 8-positions in a head-to-tail fashion by three-fold S N Ar reactions, giving rise to the characteristic N 3 O 3 aza-oxa-crown architecture. o-TQ can serve as a new tridentate nitrogen ligand to capture a Cu I cation and adopt a bowl shape, before supramolecular complexation with corannulene and [12]cycloparaphenylene (CPP) occurs through π-π and CH-π interactions. In the presence of the Cu I cation, the non-emissive o-TQ becomes a highly emissive material in the solid state, whereby the emission wavelengths depend on the ancillary ligand on the Cu I cation. The o-TQ/Cu I complex is able to promote carbene catalysis to provide a range of enamines with a gem-difluorinated terminus., (© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)