title: Facile synthesis and theoretical conformation analysis of a triazine-based double-decker rotor molecule with three anthracene blades.
abstract: The facile synthesis of a rotor-shaped compound with two stacked triazine units, which are symmetrically connected by three anthracene blades through oxygen linkers, is presented. This new double-decker, which is a potential monomer for two-dimensional polymerization, was synthesized by using readily available, cheap building blocks, exploiting the known selectivity difference for the nucleophilic substitution of cyanuric chloride. The crystal structure of a C3h symmetric rotor-shaped compound with 9,10-dihydroanthracene blades, which is a direct precursor to the targeted monomer, and the crystal structure of the new double-decker with the desired C3h symmetry, are also reported. The synthetic efforts were preceded by a computational analysis, which was triggered by the question of conformational stability of the potential monomer. Two stable conformers could be found, and the barrier for the transition path in the gas phase between these conformers was determined by quantum chemical calculations. Exploratory Born-Oppenheimer molecular-dynamics simulations revealed a strong influence of solvent-solute interactions on the stability of the conformers, which resulted in an energetic preference of the C3h symmetric conformation of the double-decker.
authors.affiliation: Laboratory of Polymer Chemistry, ETH Zürich, Vladimir-Prelog-Weg 5, 8093 Zürich (Switzerland).
authors.forename: Max J
authors.initials: MJ
authors.lastname: Kory
authors.forename: Maike
authors.initials: M
authors.lastname: Bergeler
authors.forename: Markus
authors.initials: M
authors.lastname: Reiher
authors.forename: A Dieter
authors.initials: AD
authors.lastname: Schlüter
keywords: Born-Oppenheimer molecular dynamics; cyclophanes; density functional calculations; polymers