A High-Barrier Molecular Balance for Studying Face-to-Face Arene-Arene Interactions in the Solid State and in Solution was written by Chong, Yong S.;Carroll, William R.;Burns, William G.;Smith, Mark D.;Shimizu, Ken D.. And the article was included in Chemistry – A European Journal in 2009.Synthetic Route of C18H11BrO The following contents are mentioned in the article:
An atropisomeric mol. balance was developed to study face-to-face arene-arene interactions. The balance has a large central 1,4,5,8-naphthalenediimide surface that forms intramol. arene-arene interactions with two pendent arms. The balance adopts distinct syn and anti isomers with varying numbers of intramol. interactions. Thus, the strength of the arene-arene interaction could be quant. measured by NMR spectroscopy from the anti/syn ratios. The size of the arene arms was easily varied, which allowed examination of the relation between arene size and strength of the interaction. A nonlinear size dependence was observed in solution with larger arene arms having a disproportionately stronger arene-arene interaction. The intramol. arene-arene interactions were also characterized in the solid state by x-ray crystallog. These studies were facilitated by the kinetic stability of the syn and anti isomers at room temperature due to the high isomerization barrier (ΔG = 27.0 kcal mol-1). Thus, the anti isomer could be selectively isolated and crystallized in its folded conformation. The x-ray structures confirmed that the anti isomers formed two strong intramol. arene-arene interactions with face-to-face geometries. The solid-state structure anal. also reveals that the rigid framework may contribute to the observed nonlinear size trend. The acetate linker is slightly too long, which selectively destabilizes the balances with smaller arene arms. The larger arene arms are able to compensate for the longer linker and form effective intramol. arene-arene interactions. This study involved multiple reactions and reactants, such as 2-Bromo-1-(pyren-1-yl)ethanone (cas: 80480-15-5Synthetic Route of C18H11BrO).
2-Bromo-1-(pyren-1-yl)ethanone (cas: 80480-15-5) belongs to organobromine compounds. Most organobromine compounds, like most organohalide compounds, are relatively nonpolar. In the pharmaceutical industry organo bromine derivatives are used as sedatives, vasodilators, antiseptic agents, and anticancer agents.Synthetic Route of C18H11BrO
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary