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An Isosteric Triaza Analogue of a Polycyclic Aromatic Hydrocarbon Monkey Saddle
Author(s) -
Kirschbaum Tobias,
Rominger Frank,
Mastalerz Michael
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202002826
Subject(s) - isomerization , saddle , congener , enantiomer , polycyclic aromatic hydrocarbon , hydrocarbon , chemistry , computational chemistry , saddle point , topology (electrical circuits) , stereochemistry , organic chemistry , catalysis , mathematics , geometry , mathematical optimization , combinatorics
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.