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

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.

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Publication Details

Journal
Chemical Communications
Published
2025-01-01
DOI
https://doi.org/10.1039/d5cc05480j
Primary Topic
Organoboron and organosilicon chemistry
Type
article
Field-Weighted Citation Impact
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article

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

Fumitaka Ishiwari, K.-M. Chang, Yi‐Hung Liu, Akinori Saeki et al.
Chemical Communications
Organoboron and organosilicon chemistry
article

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

Fumitaka Ishiwari, K.-M. Chang, Yi‐Hung Liu, Akinori Saeki, Jeffrey M. Farrell, Mandala Anitha, Tin‐Hung Lai, To-Jen Chin
article en

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.

Chemical CommunicationsVol. 61(100)
National Taiwan University (TW), Tokyo Metropolitan University (JP), The University of Osaka (JP)
Openalex Percentile: Top 75%
Organoboron and organosilicon chemistry
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