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An Isosteric Triaza Analogue of a Polycyclic Aromatic Hydrocarbon Monkey Saddle.

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 the 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.

SUBMITTER: Kirschbaum T

PROVIDER: S-EPMC7756504 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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An Isosteric Triaza Analogue of a Polycyclic Aromatic Hydrocarbon Monkey Saddle.

Kirschbaum Tobias T Rominger Frank F Mastalerz Michael M

Chemistry (Weinheim an der Bergstrasse, Germany) 20201012 64

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 the isomerization process of the enantiomers. The aza analogue has a significantly higher inversion barrier ...[more]

PMID: 32539193

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