From the journal:

Chemical Communications

Facile π-extension of boron-doped polycyclic aromatic hydrocarbons by frustrated Lewis pair alkynylation

Ke-Wei Chang,a   Ting-Yi Lai,a   To-Jen Chin,a   Mandala Anitha,a   Yi-Hung Liu,a   Fumitaka Ishiwari, ORCID logo cd   Akinori Saeki ORCID logo c  and  Jeffrey M. Farrell ORCID logo *ab  

* Corresponding authors

a Department of Chemistry, National Taiwan University, No. 1, Sec. 4, Roosevelt Rd., Taipei 10617, Taiwan
E-mail: farrell@ntu.edu.tw

b Center for Emerging Materials and Advanced Devices, National Taiwan University, No. 1, Sec. 4, Roosevelt Rd., Taipei 10617, Taiwan

c Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan

d Graduate School of Urban Environmental Sciences, Tokyo Metropolitan University, 1-1 Minamiosawa, Hachioji, Tokyo 192-0297, Japan

Abstract

Despite modest steric demands and a labile substituent, B-brominated boron-doped polycyclic aromatic hydrocarbons (PAHs) can participate in frustrated Lewis pairs. This is exploited for B-alkynylation and functionalization of boron-doped PAHs, enabling deep LUMO levels, solid-state 1D π-stackings, and long-wavelength emissions extending into the near-infrared.

Graphical abstract: Facile π-extension of boron-doped polycyclic aromatic hydrocarbons by frustrated Lewis pair alkynylation

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Article information

DOI
https://doi.org/10.1039/D5CC05480J
Article type
Communication
Submitted
23 Sep 2025
Accepted
23 Oct 2025
First published
05 Nov 2025

Chem. Commun., 2025, Advance Article

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Facile π-extension of boron-doped polycyclic aromatic hydrocarbons by frustrated Lewis pair alkynylation

K. Chang, T. Lai, T. Chin, M. Anitha, Y. Liu, F. Ishiwari, A. Saeki and J. M. Farrell, Chem. Commun., 2025, Advance Article , DOI: 10.1039/D5CC05480J

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