The bridged peri-aroylnaphthalene compounds having 1,3-benzendioxy-hinge units were newly synthesized and the spatial organization in
solution was characterized in comparison with isomeric derivatives having 1,2-benzenedioxy-hinge unit and a non-bridged analogue. 1,2-
Benzenedioxy and 1,3-benzendioxy-hinge units, which connect the edge carbon atoms of aroyl groups, afford the distinct difference in
rotation ability of benzene ring of aroyl groups. The sharpness/broadness and the non-equivalency of 1H NMR signals of aromatic protons
demonstrate the highly congested and hinge-depending spatial organization of these bridged peri-aroylnaphthalene molecules.
Furthermore, the significant magnetic field deviation of the signals in 1H NMR spectra proves the presence of effective induced magnetic
field especially for the middle proton at the 2-position of the 1,3-benzenedioxy unit.
Key words: non-coplanarly aromatic ring accumulation, bridged structure, spatial organization in solution, specific magnetic field effect.
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