Triptycene Boronates, Boranes, and Boron Ate-Complexes: Toward Sterically Hindered Triarylboranes and Trifluoroborates

Mathieu Gama; Xavier Antognini Silva; Thu Hong Doan; Arnaud Osi; Aurélien Chardon; Nikolay Tumanov; Johan Wouters; Guillaume Berionni

doi:10.1002/ejoc.202001672

Triptycene Boronates, Boranes, and Boron Ate-Complexes: Toward Sterically Hindered Triarylboranes and Trifluoroborates

Mathieu Gama, Xavier Antognini Silva, Thu Hong Doan, Arnaud Osi, Aurélien Chardon, Nikolay Tumanov, Johan Wouters, Guillaume Berionni

Research output: Contribution to journal › Article › peer-review

Abstract

We developed two synthetic strategies towards triptycene-derived bulky boranes, boronates, and boron ate-complexes. Starting from borylated or brominated anthracenes and using a Br/Li exchange and [4+2] cycloaddition reaction with in-situ generated benzyne, we produced a series of triptycene boronates and borates with various boron substituents in positions 1 and 9, such as BPin, Bneo, BF₃K and B(Mes)₂. Single-crystal X-ray diffraction analysis and UV-Vis/photoluminescence measurements provided quantitative information on the effect of the triptycene scaffold on the photophysical and electronic properties of the obtained compounds.

Original language	English
Pages (from-to)	1440-1445
Number of pages	6
Journal	European Journal of Organic Chemistry
Volume	2021
Issue number	9
DOIs	https://doi.org/10.1002/ejoc.202001672
Publication status	Published - 5 Mar 2021

Keywords

Lewis acids
Organoboron chemistry
Sterically hindered compounds
Triptycenes

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10.1002/ejoc.202001672

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title = "Triptycene Boronates, Boranes, and Boron Ate-Complexes: Toward Sterically Hindered Triarylboranes and Trifluoroborates",

abstract = "We developed two synthetic strategies towards triptycene-derived bulky boranes, boronates, and boron ate-complexes. Starting from borylated or brominated anthracenes and using a Br/Li exchange and [4+2] cycloaddition reaction with in-situ generated benzyne, we produced a series of triptycene boronates and borates with various boron substituents in positions 1 and 9, such as BPin, Bneo, BF3K and B(Mes)2. Single-crystal X-ray diffraction analysis and UV-Vis/photoluminescence measurements provided quantitative information on the effect of the triptycene scaffold on the photophysical and electronic properties of the obtained compounds.",

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author = "Mathieu Gama and {Antognini Silva}, Xavier and Doan, {Thu Hong} and Arnaud Osi and Aur{\'e}lien Chardon and Nikolay Tumanov and Johan Wouters and Guillaume Berionni",

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doi = "10.1002/ejoc.202001672",

language = "English",

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T1 - Triptycene Boronates, Boranes, and Boron Ate-Complexes

T2 - Toward Sterically Hindered Triarylboranes and Trifluoroborates

AU - Gama, Mathieu

AU - Antognini Silva, Xavier

AU - Doan, Thu Hong

AU - Osi, Arnaud

AU - Chardon, Aurélien

AU - Tumanov, Nikolay

AU - Wouters, Johan

AU - Berionni, Guillaume

PY - 2021/3/5

Y1 - 2021/3/5

N2 - We developed two synthetic strategies towards triptycene-derived bulky boranes, boronates, and boron ate-complexes. Starting from borylated or brominated anthracenes and using a Br/Li exchange and [4+2] cycloaddition reaction with in-situ generated benzyne, we produced a series of triptycene boronates and borates with various boron substituents in positions 1 and 9, such as BPin, Bneo, BF3K and B(Mes)2. Single-crystal X-ray diffraction analysis and UV-Vis/photoluminescence measurements provided quantitative information on the effect of the triptycene scaffold on the photophysical and electronic properties of the obtained compounds.

AB - We developed two synthetic strategies towards triptycene-derived bulky boranes, boronates, and boron ate-complexes. Starting from borylated or brominated anthracenes and using a Br/Li exchange and [4+2] cycloaddition reaction with in-situ generated benzyne, we produced a series of triptycene boronates and borates with various boron substituents in positions 1 and 9, such as BPin, Bneo, BF3K and B(Mes)2. Single-crystal X-ray diffraction analysis and UV-Vis/photoluminescence measurements provided quantitative information on the effect of the triptycene scaffold on the photophysical and electronic properties of the obtained compounds.

KW - Lewis acids

KW - Organoboron chemistry

KW - Sterically hindered compounds

KW - Triptycenes

UR - http://www.scopus.com/inward/record.url?scp=85101061253&partnerID=8YFLogxK

U2 - 10.1002/ejoc.202001672

DO - 10.1002/ejoc.202001672

M3 - Article

AN - SCOPUS:85101061253

SN - 1434-193X

VL - 2021

SP - 1440

EP - 1445

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 9

ER -

Triptycene Boronates, Boranes, and Boron Ate-Complexes: Toward Sterically Hindered Triarylboranes and Trifluoroborates

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Triptycene Boronates, Boranes, and Boron Ate-Complexes: Toward Sterically Hindered Triarylboranes and Trifluoroborates

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Physical Chemistry and characterization(PC2)

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