New Path to Stable Nanographenes

New Path to Stable Nanographenes

Author: Angewandte Chemie International Edition

Peri-acenes with extended zigzag edges can have unique electronic and magnetic properties, but higher peri-acenes generally have poor ambient stability. The introduction of heteroatoms, such as boron or nitrogen (N), to the zigzag edges of peri-acenes can stabilize them thermodynamically.

Xinliang Feng, Technische Universität Dresden, Germany, and colleagues have combined solution-based and surface-assisted synthesis to produce NBN-doped bis– and peri-tetracenes (NBN-BT and NBN-PT, pictured) that are stable in ambient conditions. NBN-BT was prepared via consecutive Suzuki coupling reactions (pictured below), followed by a reduction of the nitro groups and a twofold electrophilic borylation. A photocyclization of NBN-BT in the presence of propylene oxide and iodine then produced NBN-PT.

 

The team found that NBN-BT and NBN-PT can be oxidized to obtain dications, which have similar electronic structures to their all-carbon-based analogues bis-tetracene and peri-tetracene. The work provides a new path for the synthesis of stable zigzag-edged nanographenes with multi-NBN units.


 

 

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