Aromatic embedding wins over classical hydrogen bonding - a multi-spectroscopic approach for the diphenyl ether-methanol complex
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Updated: Mar 13, 2026

Anionic Polymerization of an Amphiphilic Copolymer for Preparation of Block Copolymer Micelles Stabilized by π-π Stacking Interactions
Published on: October 10, 2016
Chris Medcraft1, Sabrina Zinn1, Melanie Schnell1
1Max-Planck-Institut für Struktur und Dynamik der Materie, Luruper Chaussee 149, D-22761 Hamburg, Germany. melanie.schnell@mpsd.mpg.de and The Hamburg Centre for Ultrafast Imaging (CUI), Luruper Chaussee 149, D-22761 Hamburg, Germany.
Abstract:
Dispersion interactions are omnipresent in intermolecular interactions, but their respective contributions are difficult to predict. Aromatic ethers offer competing docking sites for alcohols: the ether oxygen as a well known hydrogen bond acceptor, but also the aromatic π system. The interaction with two aromatic moieties in diphenyl ether can tip the balance towards π binding. We use a multi-spectroscopic approach to study the molecular recognition, the structure and internal dynamics of the diphenyl ether-methanol complex, employing infrared, infrared-ultraviolet and microwave spectroscopy. We find that the conformer with the hydroxy group of the alcohol binding to one aromatic π cloud and being coordinated by an aromatic C-H bond of the other phenyl group is preferred. Depending on the expansion conditions in the supersonic jet, we observe a second conformer, which exhibits a hydrogen bond to the ether oxygen and is higher in energy.
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