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Updated: Jun 14, 2025

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
Published on: August 12, 2019
Investigating Bay-Substituted 6,7-Dihydrodibenzo[b,j][4,7]phenanthroline, a Class of Tunable Hindered Rotors:
Yen-Cheng Lu1, Jhih-Syong Jhang2, Chih-Hsiu Lin2
1Department of Chemistry, National Central University, Taoyuan 320317, Taiwan, Republic of China.
Abstract:
We developed a convenient and flexible synthesis of 6,7-dihydrodibenzo[b,j][4,7]phenanthroline derivatives with bay region substituents via Friedländer condensation. Thanks to the mild reaction conditions, unsymmetrical bay-substituted systems also become accessible. The rigid phenanthroline framework holds various functional groups in the bay region in enough proximity for intramolecular interactions to manifest. Measuring the hindered rotational motions in this system unveils subtle structure-property relationships. Most notably, through rotamer distribution, π-π interactions between polycyclic aromatic hydrocarbons were found to scale with the π-surface coverage areas.
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