Control of reactivity of phosphine imides by intramolecular coordination with an organoboryl group

Kano, Naokazu; Yanaizumi, Kazuhide; Meng, Xiangtai; Kawashima, Takayuki

doi:10.1002/hc.21033

Cited by 8 publications

(3 citation statements)

References 35 publications

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“…Moreover, the Lewis acidic Ga atoms, adjacent to the P sites, might interact with the Lewis basic N atoms of the phosphine imide to form Ga–N bonds. Molecular examples of phosphine imides displaying such bonding interaction between Lewis basic N and certain Lewis acids, including a triaryl gallium, have been reported. , …”

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“…Molecular examples of phosphine imides displaying such bonding interaction between Lewis basic N and certain Lewis acids, including a triaryl gallium, have been reported. 17,18 Here we present combined scanning tunneling microscopy (STM) and density functional theory (DFT) of the thermally activated surface reaction between perfluorophenyl azides (C 6 F 5 N 3 , PFPA) and GaP(110). Our results provide strong evidence for the formation of covalent molecule−surface bonds in a three-membered-ring configuration (P−N−Ga) featuring both P−N and Ga−N interactions consistent with a Staudinger-type reaction at the GaP(110) surface.…”

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Covalent Functionalization of GaP(110) Surfaces via a Staudinger-Type Reaction with Perfluorophenyl Azide

Ugeda

Bradley²,

Rodrigo³

et al. 2016

J. Phys. Chem. C

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Despite the markedly low chemical reactivity of the nonpolar (110) surfaces of III−V semiconductors, the covalent functionalization of GaP(110) surfaces with perfluorophenyl azide (PFPA) molecules by a Staudinger-type reaction occurs only slightly above room temperature (325 K). Scanning tunneling microscopy observations, combined with density functional theory calculations, support the formation of stable, covalent perfluorophenyl nitride (PFPN) molecule−surface bonds, which can be described as Lewis acidic Ga-stabilized phosphine imides. π−π stacking between aromatic, electron-deficient PFPN units results in compact, commensurate 2D molecular assembly at the surface. PFPA deposition on GaP(110) at room temperature with no additional annealing leads to an intermediate phase consistent with an alternating 1D array of physisorbed and chemisorbed molecular units. This work provides a new route for covalently bonding molecular linkages to the (110) surfaces of III−V semiconductors.

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Covalent Functionalization of GaP(110) Surfaces via a Staudinger-Type Reaction with Perfluorophenyl Azide

Ugeda

Bradley²,

Rodrigo³

et al. 2016

J. Phys. Chem. C

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“…Phosphine imide 1 was lithiated with methyllithium in Et 2 O at room temperature, 9,11,12 and then treated with chlorosilanes to give the corresponding silylated phosphine imides 2a-c in 56, 59 and 64% yields, respectively, from 1 (Scheme 1). Compounds 2a-c are thermally stable at room temperature in contrast to the phosphorus ylide analogue of 2a which was reported to undergo 1,4-silyl migration at 0 1C.…”

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confidence: 99%