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Rotational Signatures of Dispersive Stacking in the Formation of Aromatic Dimers
Author(s) -
Fatima Mariyam,
Steber Amanda L.,
Poblotzki Anja,
Pérez Cristóbal,
Zinn Sabrina,
Schnell Melanie
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201812556
Subject(s) - dibenzofuran , heteroatom , chemistry , dimer , intramolecular force , stacking , chemical physics , aromaticity , fluorene , diphenyl ether , computational chemistry , molecule , stereochemistry , organic chemistry , ring (chemistry) , polymer
The aggregation of aromatic species is dictated by inter‐ and intramolecular forces. Not only is characterizing these forces in aromatic growth important for understanding grain formation in the interstellar medium, but it is also imperative to comprehend biological functions. We report a combined rotational spectroscopic and quantum‐chemical study on three homo‐dimers, comprising of diphenyl ether, dibenzofuran, and fluorene, to analyze the influence of structural flexibility and the presence of heteroatoms on dimer formation. The structural information obtained shows clear similarities between the dimers, despite their qualitatively different molecular interactions. All dimers are dominated by dispersion interactions, but the dibenzofuran dimer is also influenced by repulsion between the free electron pairs of the oxygen atoms and the π‐clouds. This study lays the groundwork for understanding the first steps of molecular aggregation in systems with aromatic residues.