Tertiary phosphines: preparation

Musina, E. I.; Balueva, A. S.; Karasik, A. A.

doi:10.1039/9781839166198-00001

Cited by 2 publications

(3 citation statements)

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“…Furthermore, mechanical stimuli induced the selective formation of kinetically and thermodynamically favored host‐guest complexes. Although many high‐molecular‐weight organophosphorus compounds incorporating functional moieties have been reported so far, [18,19] our approach based on self‐assembly in water will pave the way toward expanding the functionalities of organophosphorus compounds, leading to next‐generation supramolecular materials.…”

Section: Discussionmentioning

confidence: 99%

“…These azaylide‐based amphiphiles form 2 nm‐sized spherical micelles and encapsulate various organic dyes in water. This methodology for post‐introducing hydrophilic groups to synthesize amphiphilic molecules is potentially applicable to a wide variety of commercial [18] and known [19] triarylphosphines. Indeed, mixing azide G1 with a highly hydrophobic triarylphosphine such as tri‐2‐naphthylphosphine ( PNp3 ) furnished the corresponding azaylide‐based compound.…”

Section: Introductionmentioning

confidence: 99%

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Transformation of Highly Hydrophobic Triarylphosphines into Amphiphiles via Staudinger Reaction with Hydrophilic Trichlorophenyl Azide

Suzuki,

Akiyama,

Yamashina

et al. 2023

Chemistry A European J

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Owing to its hydrophobic properties and reactivity, triarylphosphines (PAr3) are promising precursors for the development of new amphiphiles. However, an efficient and reliable synthetic method for amphiphiles based on highly hydrophobic PAr3 is still required. Herein, we report a straightforward transformation of highly hydrophobic PAr3 into amphiphiles via the Staudinger reaction. By simply mixing PAr3 and a hydrophilic trichlorophenyl azide containing two hydrophilic chains, amphiphiles bearing a N=P bond (i.e., an azaylide moiety) were quantitatively formed. The obtained azaylide‐based amphiphiles were remarkably water‐soluble, enabling their spontaneous self‐assembly into 2 nm‐sized micelles composed of 4–5 molecules in water with a low critical micelle concentration (up to 0.05 mM or less) due to the effective intermolecular interactions among the hydrophobic surfaces. Although the azaylide moiety is easily hydrolyzed in the presence of water, the azaylide in the amphiphiles displayed notable stability in water even at 60 h, which stems from the LUMO modulation induced by the presence of three electron‐withdrawing chloro groups and two twisted alkoxycarbonyl groups, according to DFT calculations. An amphiphile having a large hydrophobic surface solubilized various hydrophobic organic dyes through efficient intermolecular interactions, resulting in the dyes exhibiting either monomer or excimer emissions in water.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Transformation of Highly Hydrophobic Triarylphosphines into Amphiphiles via Staudinger Reaction with Hydrophilic Trichlorophenyl Azide

Suzuki,

Akiyama,

Yamashina

et al. 2023

Chemistry A European J

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show abstract

“…Phosphorus-containing compounds are ubiquitous in catalysis, 1 particularly as phosphorus( iii )-based ligands in transition metal catalysis. 2,3 However phosphorus( v ) compounds are relatively underexplored as ligands or catalysts.…”

Section: Introductionmentioning

confidence: 99%