Work

Diazulenorubicene as a Non‐benzenoid Isomer of peri ‐Tetracene with Two Sets of 5/7/5 Membered Rings Showing Good Semiconducting Properties

Year: 2023

Type: article

Abstract: 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.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.202304632