Phenylpyridyl‐Fused Boroles: A Unique Coordination Mode and Weak B−N Coordination‐Induced Dual Fluorescence

He, Juan; Rauch, Florian; Friedrich, Alexandra; Krebs, Johannes; Krummenacher, Ivo; Bertermann, Rüdiger; Nitsch, Jörn; Braunschweig, Holger; Finze, Maik; Marder, Todd B.

doi:10.1002/ange.202013692

Cited by 10 publications

(2 citation statements)

References 119 publications

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“…The structure of 408 is a dimer in the solid-state but a monomer in CDCl 3 solution. 219 A stepwise route to 407 was also investigated, using B(OMe) 3 as the boron source but in this case the pyridine ring was dearomatized into a dihydropyridine with a tBu group adjacent to nitrogen and a hydrogen the nitrogen (411). The nitrogen of 408 could be alkylated with methyl triflate to generate cationic 409 which has different electronic properties than its neutral precursor.…”

Section: Heteroarene Fused Borolesmentioning

confidence: 99%

“…Dual fluorescence was observed for 408 in a variety of solvents (hexane, CH 2 Cl 2 , THF, and MeCN) attributed to the equilibrium between monomeric 408 and the dimer that was corroborated by variable temperature NMR spectroscopy and photophysical studies. 219 An intense emission band at 520 nm was observed for 408 with a higher quantum yield (∼0.27 in THF, ∼0.21 in MeCN). 81,100 The UV/vis spectrum of methylated cation 409 featured the lowest energy absorption maximum at ∼400 nm in CH 2 Cl 2 , red-shifted by ∼25 nm in comparison neutral 408 due to the enhanced electron accepting ability in the molecule.…”

Section: Heteroarene Fused Borolesmentioning

confidence: 99%

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9-Borafluorenes: Synthesis, Properties, and Reactivity

Bartholome

Tidwell

et al. 2021

Chem. Rev.

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This review covers all aspects of 9-borafluorene chemistry, from the first attempted synthesis in 1960 to the present. This class of molecules consists of a tricyclic system featuring a central antiaromatic BC 4 ring with two fused arene groups. The synthetic routes to all 9-borafluorenes and their adducts are presented. The Lewis acidity and photophysical properties outlined demonstrate potential utility as sensors and in electronic materials. The reactivity of borafluorenes reveals their prospects as reagents for the synthesis of other boron-containing molecules. The appealing traits of 9-borafluorenes have stimulated investigations into analogues that bear different aromatic groups fused to the central BC 4 ring. Finally, we offer our views on the challenges and future of borafluorene chemistry.

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Section: Heteroarene Fused Borolesmentioning

confidence: 99%

Section: Heteroarene Fused Borolesmentioning

confidence: 99%

9-Borafluorenes: Synthesis, Properties, and Reactivity

Bartholome

Tidwell

et al. 2021

Chem. Rev.

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12b,24b‐Diborahexabenzo[a,c,fg,l,n,qr]pentacene: A Low‐LUMO Boron‐Doped Polycyclic Aromatic Hydrocarbon

et al. 2022

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Herein we devise and execute a new synthesis of a pristine boron-doped nanographene. Our target boron-doped nanographene was designed based on DFT calculations to possess a low LUMO energy level and a narrow band gap derived from its precise geometry and B-doping arrangement. Our synthesis of this target, a doubly B-doped hexabenzopentacene (B 2 -HBP), employs six net CÀ H borylations of an alkene, comprising consecutive hydroboration/electrophilic borylation/dehydrogenation and BBr 3 /AlCl 3 /2,6-dichloropyridine-mediated CÀ H borylation steps. As predicted by our calculations, B 2 -HBP absorbs strongly in the visible region and emits in the NIR up to 1150 nm in o-dichlorobenzene solutions. Furthermore, B 2 -HBP possesses a very low LUMO level, showing two reversible reductions at À 1.00 V and À 1.17 V vs. Fc + /Fc. Our methodology is surprisingly selective despite its implementation of unfunctionalized precursors and offers a new approach to the synthesis of pristine B-doped polycyclic aromatic hydrocarbons.

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A Resonating B, N Covalent Bond and Coordination Bond in Aromatic Compounds and Conjugated Polymers

Shao

Liu

et al. 2022

Angewandte Chemie

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We herein report an organoboron compound (SBN-1) based on NÀ B ! N units with a balanced resonance hybrid of B, N single bond (BÀ N) and B, N coordination bond (B ! N). Despite the different chemical environments of the two nitrogen atoms in the NÀ B ! N unit, the single-crystal structure reveals that the two B, N bonds have similar bond lengths of ca. 1.55 Å and are almost equivalent. The resonance nature of the two B, N bonds contributes to the excellent chemical stability and photostability of SBN-1. The NÀ B! N units in SBN-1 show a strong electron-withdrawing capability and large dipole, resulting in a redshifted absorption spectrum, downshifted LUMO/ HOMO energy levels, and drastically altered molecular packing behaviors in solid state. SBN-1 can be used as a building block to construct small band gap conjugated polymers. The resonance of B, N bonds discovered in this work provides new insight into the design of stable organoboron small molecules and polymers for practical applications.

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Phenylpyridyl‐Fused Boroles: A Unique Coordination Mode and Weak B−N Coordination‐Induced Dual Fluorescence

Cited by 10 publications

References 119 publications

9-Borafluorenes: Synthesis, Properties, and Reactivity

9-Borafluorenes: Synthesis, Properties, and Reactivity

12b,24b‐Diborahexabenzo[a,c,fg,l,n,qr]pentacene: A Low‐LUMO Boron‐Doped Polycyclic Aromatic Hydrocarbon

A Resonating B, N Covalent Bond and Coordination Bond in Aromatic Compounds and Conjugated Polymers

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