Issue 19, 2022

Access to tetracoordinate boron-doped polycyclic aromatic hydrocarbons with delayed fluorescence and aggregation-induced emission under mild conditions

Abstract

Boron-doped polycyclic aromatic hydrocarbons (PAHs) have attracted ongoing attention in the field of optoelectronic materials due to their unique optical and redox properties. To investigate the effect of tetracoordinate boron in PAHs bearing N-heterocycles (indole and carbazole), a facile approach to four-coordinate boron-doped PAHs was developed, which does not require elevated temperature and pre-synthesized functionalized boron reactants. Five tetracoordinate boron-doped PAHs (NBNN-1–NBNN-5) were synthesized with different functional groups. Two of them (NBNN-1 and NBNN-2) could further undergo oxidative coupling reactions to form fused off-plane tetracoordinate boron-doped PAHs NBNN-1f and NBNN-2f. The investigation of photophysical properties showed that the UV/vis absorption and fluorescence emission are significantly red-shifted compared to those of the three-coordinate boron-doped counterparts. In addition, the emission of NBNN-1–NBNN-3 consisted of prompt fluorescence and delayed fluorescence. The compounds NBNN-1f and NBNN-2f showed aggregation-induced emission.

Graphical abstract: Access to tetracoordinate boron-doped polycyclic aromatic hydrocarbons with delayed fluorescence and aggregation-induced emission under mild conditions

Supplementary files

Article information

Article type
Edge Article
Submitted
25 Mar 2022
Accepted
12 Apr 2022
First published
29 Apr 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022,13, 5597-5605

Access to tetracoordinate boron-doped polycyclic aromatic hydrocarbons with delayed fluorescence and aggregation-induced emission under mild conditions

L. Jiang, Y. Wang, D. Tan, X. Chen, T. Ma, B. Zhang and D. Yang, Chem. Sci., 2022, 13, 5597 DOI: 10.1039/D2SC01722A

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