Syntheses and structures of benzo-bis(1,3,2-diazaboroles) and acenaphtho-1,3,2-diazaboroles

Weber, Lothar; Eickhoff, Daniel; Chrostowska, Anna; Dargelos, Alain; Darrigan, Clovis; Stammler, Hans‐Georg; Neumann, Beate

doi:10.1039/c9dt03818c

Cited by 5 publications

(3 citation statements)

References 83 publications

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“…Due to rapid decomposition at the low concentrations needed for obtaining accurate quantum yield data, we were unable to report these values for the fused-NHBs (this was also observed in Weber's compounds). [10] Elemental analyses were performed on aP erkin-Elmer 2400 Series II analyzer.S imilarly to other reported fused-NHBs, [10] we were unable to obtain C,H,N-values for 3, 4, 8,a nd 11 due to air-and moisture-sensitivity.A ll chemicals were purchased from commercial sources and used directly unless noted otherwise. The 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (IPr•HCl), [34] 4,5,9,10-tetrabromo-2,7-ditert-butylpyrene, [35] and compound 1 [22][23] were prepared according to the literature procedures.…”

Section: General Informationmentioning

confidence: 99%

“…[9] Last year,W eber et al isolated ands tructurally characterized am ethylatedb enzene-fused bis(diazaborole). [10] Notably,t his was the first example of ab enzene-fused bis(diazaborole) that was characterized structurally by X-ray diffraction. However,p hotophysicald ata was unable to be obtainedd ue to rapid decom-positionofU V/vis samples.…”

Section: Introductionmentioning

confidence: 99%

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Planar, Stair‐Stepped, and Twisted: Modulating Structure and Photophysics in Pyrene‐ and Benzene‐Fused N‐Heterocyclic Boranes

Krantz

Weisflog

Frey

et al. 2020

Chemistry A European J

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Because of their rigidity,polycyclic aromatic hydrocarbons (PAHs) have become as ignificant building block in molecular materials chemistry.F usion or doping of boron into PAHs is known to improve the optoelectronic properties by reducing the LUMO energyl evel.H erein, we reporta comprehensive study on the syntheses, structures, and photophysical properties of an ew class of fused N-heterocyclic boranes (NHBs), pyrene-and benzene-linked in a" Janustype" fashion (2-4, 6-9,and 11). Remarkably,these examples of fused NHBs display fluorescent properties, and collectively their emission spans the visible spectrum.T he pyrene-fused NHBs all display blue fluorescence, as the excitationsa re dominated by the pyrene core. In notable contrast, the emission properties of the benzene-fused analogues are highly tunable and are dependent on the electronicso ft he NHB fragments (i.e.,t he functional group directly bound to the boron atoms). Pyrene-fused 2-4 and 11 represent the only molecules in whicht he K-region of pyrene is functionalized with NHB units,a nd while they exhibit distorted (twisted or stair-stepped) pyrene cores, benzene-fused 6-9 are planar. The electronic structure and optical properties of these materials were probed by computational studies, including an evaluation of aromaticity,e lectronic transitions, and molecular orbitals.

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Section: General Informationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Planar, Stair‐Stepped, and Twisted: Modulating Structure and Photophysics in Pyrene‐ and Benzene‐Fused N‐Heterocyclic Boranes

Krantz

Weisflog

Frey

et al. 2020

Chemistry A European J

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“…Group 13 complexes : The synthesis of 2-bromo-N,N′-bis(2′,6′-diisopropylphenyl)acenaphtho-1,3,2-diazaborole, appearing as burgundy red crystalline material, was achieved through the reaction of a diazaborolium salt with fivefold excess of 1% sodium amalgam in toluene 62 . The UV–vis spectrum of the resulting compound in CH 2 Cl 2 showed a broad absorption band ranging from 450 to 600 nm, but exhibited no fluorescence.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, properties, and catalysis of p-block complexes supported by bis(arylimino)acenaphthene ligands

2020

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Bis(arylimino)acenaphthene (Ar-BIAN) ligands have been recognized as robust scaffolds for metal complexes since the 1990 s and most of their coordination chemistry was developed with transition metals. Notably, there have been relatively few reports on complexes comprising main group elements, especially those capitalizing on the redox non-innocence of Ar-BIAN ligands supporting p-block elements. Here we present an overview of synthetic approaches to Ar-BIAN ligands and their p-block complexes using conventional solution-based methodologies and environmentally-benign mechanochemical routes. This is followed by a discussion on their catalytic properties, including comparisons to transition metal counterparts, as well as key structural and electronic properties of p-block Ar-BIAN complexes.

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Boroles

Nguyen

Trang

Dung

et al. 2022

Comprehensive Heterocyclic Chemistry IV

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Syntheses and structures of benzo-bis(1,3,2-diazaboroles) and acenaphtho-1,3,2-diazaboroles

Abstract: 1,3,2-Diazaboroles 4 and 7 with extended π-electron systems were synthesised and characterised by single crystal X-ray diffraction and quantum-chemical calculations.

Cited by 5 publications

References 83 publications

Planar, Stair‐Stepped, and Twisted: Modulating Structure and Photophysics in Pyrene‐ and Benzene‐Fused N‐Heterocyclic Boranes

Planar, Stair‐Stepped, and Twisted: Modulating Structure and Photophysics in Pyrene‐ and Benzene‐Fused N‐Heterocyclic Boranes

Synthesis, properties, and catalysis of p-block complexes supported by bis(arylimino)acenaphthene ligands

Boroles

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