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Contorted Polycyclic Aromatic Hydrocarbons with Two Embedded Azulene Units
Author(s) -
Yang Xuan,
Rominger Frank,
Mastalerz Michael
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201908643
Subject(s) - azulene , aromaticity , chemistry , polycyclic aromatic hydrocarbon , computational chemistry , photochemistry , molecule , organic chemistry
Polycyclic aromatic hydrocarbons (PAHs) that contain both five‐ and seven‐membered rings are rare, and those where these rings are annulated to each other and build azulene units have, to date, mainly been generated in minute amounts on surfaces. Herein, a rational approach to synthesize soluble contorted PAHs containing two embedded azulene units in the bulk is presented. By stepwise detachment of tert ‐butyl groups, a series of three azulene embedded PAHs with different degrees of contortion has been made to study the impact of curvature on aromaticity and conjugation. Furthermore, the azulene PAHs showed high fluorescence quantum yields in the NIR regime.