In:
Angewandte Chemie, Wiley, Vol. 135, No. 39 ( 2023-09-25)
Kurzfassung:
Non‐benzenoid polycyclic aromatic hydrocarbons (PAHs) have received a lot of attention because of their unique optical, electronic, and magnetic properties, but their synthesis remains challenging. Herein, we report a non‐benzenoid isomer of peri ‐tetracene, diazulenorubicene (DAR), with two sets of 5/7/5 membered rings synthesized by a (3+2) annulation reaction. Compared with the precursor containing only 5/7 membered rings, the newly formed five membered rings switch the aromaticity of the original heptagon/pentagon from antiaromatic/aromatic to non‐aromatic/antiaromatic respectively, modify the intermolecular packing modes, and lower the LUMO levels. Notably, compound 2 b (DAR‐TMS) shows p ‐type semiconducting properties with a hole mobility up to 1.27 cm 2 V −1 s −1 . Moreover, further extension to larger non‐benzenoid PAHs with 19 rings was achieved through on‐surface chemistry from the DAR derivative with one alkynyl group.
Materialart:
Online-Ressource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v135.39
DOI:
10.1002/ange.202304632
Sprache:
Englisch
Verlag:
Wiley
Publikationsdatum:
2023
ZDB Id:
505868-5
ZDB Id:
506609-8
ZDB Id:
514305-6
ZDB Id:
505872-7
ZDB Id:
1479266-7
ZDB Id:
505867-3
ZDB Id:
506259-7
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