An Isosteric Triaza Analogue of a Polycyclic Aromatic Hydrocarbon Monkey Saddle

Chemistry : a European Journal
Michael MastalerzFrank Rominger

Abstract

Since a few years, the interest in negatively curved fused polycyclic aromatic hydrocarbons (PAHs) has significantly increased. Recently, the first chiral negatively curved PAH with the topology of a monkey saddle was introduced. Herein the synthesis of its triaza congener is reported. The influence of this CH↔N exchange on photophysical and electrochemical properties is studied as well as isomerization process of the enantiomers. The aza analogue has a significantly higher inversion barrier, which makes it easier to handle at room temperature. All experimental results are underpinned by theoretical DFT calculations.

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Citations

Aug 11, 2021·Chemistry : a European Journal·Xuan YangMichael Mastalerz
Dec 15, 2021·Chemistry, an Asian Journal·Ranran LiPeng An

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Methods Mentioned

BETA
column chromatography
NMR
X‐ray

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