Diboron- and digermanium-doped dihydrodibenzohexacenes: Ge–B exchange to access boron-doped extended acenes
Name
d5sc09987k.pdf
Description
Published version
Size
1.09 MB
Format
Adobe PDF
Checksum (MD5)
6fcfe74cac8e3cb26fc802118609c9c4
Author(s)
Kim, Heechan
Peña, Laura F
Espineira-Gutierrez, Adrian
Romero-Nieto, Carlos
Gilliard, Robert J
Date Issued
February 13, 2026
Journal
Chemical Science
Publisher
Royal Society of Chemistry
Citation
Heechan Kim, Laura F. Peña, Adrian Espineira-Gutierrez, Carlos Romero-Nieto, Robert J. Gilliard; Diboron- and digermanium-doped dihydrodibenzohexacenes: Ge–B exchange to access boron-doped extended acenes. Chem. Sci. 2026; 17 (15): 7699–7706.
Version
Final published version
Abstract
Incorporation of main-group atoms into the backbone of polycyclic aromatic hydrocarbons offers an effective strategy to modulate their electronic structures. Boron and germanium doping is particularly attractive for enhancing optoelectronic and electrochemical properties. However, regioselective incorporation of these elements into extended π-conjugated systems remains limited due to synthetic challenges and stability issues. Herein, we report the synthesis of isomeric series of digermanium-(2 and 6) and diboron-(4 and 8) embedded dihydrodibenzohexacenes. The molecular structures of the four compounds were confirmed by single-crystal X-ray diffraction, revealing curved backbones for the digermanium-doped compounds 2 and 6, whereas the diboron analogues 4 and 8 display a planar backbone incorporating two weakly antiaromatic C5B rings. All compounds show efficient photoluminescence in both the solution- and solid-state, spanning the wide spectral regions from blue to orange. Electrochemical studies of 4 and 8 reveal two quasi-reversible reduction processes, with the pseudo-para diboron-substituted isomer 8 exhibiting slightly anodically shifted reduction potentials. These results demonstrate that diboron and digermanium doping provides a promising platform for the development of stable, emissive, and redox-active polycyclic aromatic hydrocarbons.
Terms of Use
Creative Commons Attribution-NonCommercial
Persistent DSpace Link
DOI of Published Version
https://doi.org/10.1039/d5sc09987k
