Applications of Phosphorus‐Based Materials in Optoelectronics

Duffy, Matthew P.; Bouit, Pierre‐Antoine; Hissler, Muriel

doi:10.1002/9781119235941.ch12

Cited by 17 publications

(28 citation statements)

References 127 publications

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“…From the data in Table 1, four generalizations can be drawn. (1) The yields of phosphine oxides 2 strongly depends on the position, electronic effect of substituents of the arene ring. (2) For para-substituents, electron-donating groups would be expected to facilitate and electron-withdrawing groups to retard the leave of a phenyl group (2a−e, 2j, and 2k−o).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…26 A white solid, yield: 55% (255 mg). 1 General Procedure for the Preparation of Phosphonium Salts 3 and 4. A 0.67 M solution of methyldiphenylphosphine or benzyldiphenylphosphine, arylbromide (1 equiv), and NiBr 2 (6 mol %) in phenol was refluxed for 15 min to 20 h. After the reaction, water (10 mL × 3) was added to azetropically remove phenol by evaporation under reduced pressure.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…47 The synthesis was run on a 2.5 mmol scale for 15 min to give 3b as a white solid in 81% (0.781 g) yield. 1 H NMR (400 MHz, DMSO-d 6 ): δ 3.14 (d, J H−P = 14.6 Hz, 3 H), 3.90 (s, 3 H), 7.32 (dd, J 1H−P = 2.5 Hz, J 2 = 8.9 Hz, 2 H), 7.70 (dd, J 1 = 8.9 Hz, J 2H−P = 12.5 Hz, 2 H), 7.73−7.81 (m, 8 H), 7.84−7.91 (m, 2 H); 13 Methyl(4-phenoxyphenyl)diphenylphosphonium Bromide (3c). The synthesis was run on a 5 mmol scale for 5 h to give 3c as a white solid in 64% (1.440 g) yield.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Aryldiphenylphosphine oxides have been widely used in optoelectronic materials, and as chiral auxiliary and a catalyst in organic synthesis. They are also precursors for the synthesis of aryldiphenylphosphine by reduction. − For the synthesis of aryldiphenylphosphine oxides, there are mainly five methods: (1) the transition metal-catalyzed coupling of diphenylphosphine oxide with aromatic derivatives such as aryl halides or pseudohalides, that is, the Hirao reaction, , aroylhydrazides, and arylboronic acids, (2) the oxidation of aryldiphenylphosphine, , (3) carbophosphinylation of arynes, , (4) the reaction of Ph 2 P(O)Cl with Grignard reagents, , and (5) the alkaline hydrolysis of aryltriphenylphosphonium salts. , Although these methods are available, none solves all challenges of the synthesis of aryldipheylphosphine oxides.…”

Section: Introductionmentioning

confidence: 99%

“…Aryldiphenylphosphine oxides have been widely used in optoelectronic materials, 1 and as chiral auxiliary 2 and a catalyst 3 in organic synthesis. They are also precursors for the synthesis of aryldiphenylphosphine by reduction.…”

Section: ■ Introductionmentioning

confidence: 99%

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Synthesis of Aryldiphenylphosphine Oxides by Quaternization of Tertiary Diphenylphosphines with Aryl Bromides Followed by the Wittig Reaction

Zhong

Huang

2020

ACS Omega

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A two-step method for the synthesis of aryldiphenylphosphine oxides from tertiary diphenylphosphines and aryl bromides is developed. The first step is the quaternization of methyldiphenylphosphine or benzyldiphenylphosphine with aryl bromides. This quaternization can be nickel-catalyzed (metal-free in some cases), and tolerate of a variety of functional groups, furnishing quaternary phosphonium salts in 48−90% yields. The second step is Wittig reactions of these quaternary phosphonium salts with furan-2-carbaldehyde or p-chlorobenzaldehyde to provide aryldiphenylphosphine oxides in 27−90% yields. The use of the Wittig reaction for the synthesis of tertiary phosphine oxides is in contrast to its traditional use for the synthesis of olefins, leaving tertiary phosphine oxide as a byproduct. This quaternization−Wittig method can be applied to synthesize aryldiphenylphosphine oxides that are difficult to access by the alkaline hydrolysis of aryltriphenylphosphonium salts, especially those bearing an electron-deficient aryl group. The ligand-coupling mechanism for the alkaline hydrolysis of (p-acylphenyl)triphenylphosphonim salts is also discussed.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Synthesis of Aryldiphenylphosphine Oxides by Quaternization of Tertiary Diphenylphosphines with Aryl Bromides Followed by the Wittig Reaction

Zhong

Huang

2020

ACS Omega

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Funktionelle polymere Materialien auf der Basis von Hauptgruppen‐Elementen

Vidal

Jäkle

2019

Angewandte Chemie

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In den letzten zehn Jahren wurden enorme Fortschritte bei der Synthese von Polymeren erzielt, die Hauptgruppen‐Elemente enthalten und über die typischen organischen Polymere hinausgehen. Einzigartige Eigenschaften, die sich aus drastischen Unterschieden in Bindung und molekularer Geometrie, elektronischer Struktur und chemischer Reaktivität ergeben, werden in den unterschiedlichsten Anwendungsbereichen genutzt. In dem Aufsatz werden die jüngsten Fortschritte bei Polymeren mit anorganischem Rückgrat hervorgehoben, es wird diskutiert, wie die Lewis‐Säure/Base‐Funktionalisierung von Polymeren zu beispielloser Reaktivität führt, und es werden konjugierte Hybride mit spezifischen elektronischen Strukturen für die Sensorik sowie Anwendungen in Organische‐Elektronik‐Geräten vorgestellt.

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Three‐Component Synthesis of Dioxaphosphorane‐Fused Diphosphacycles Exhibiting Unique Dynamic Fluorescence “On/Off” Properties

Huang

Sun

et al. 2023

Angewandte Chemie

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Rigidly planar polycyclic phosphacycles featuring an internal dioxaphosphorane are promising photofunctional materials. However, the lack of efficient synthetic methods resulted in limited structural diversities which significantly hampered extensive study. Herein, we report a straightforward three-component synthesis of novel dioxaphosphorane-fused diphosphacycles with distinctive photophysical properties. Control experiments and theory calculations were performed to account for a plausible reaction mechanism. We also systematically investigated the structure-property relationships of these unprecedented platforms by combining experiments (X-ray analysis, optical and redox properties) and theoretical computations. Based on their unique structure and properties, a novel fluorescent switch for pH sensing was revealed by a dynamic ringopening/ring-closing process.

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Applications of Phosphorus‐Based Materials in Optoelectronics

Cited by 17 publications

References 127 publications

Synthesis of Aryldiphenylphosphine Oxides by Quaternization of Tertiary Diphenylphosphines with Aryl Bromides Followed by the Wittig Reaction

Synthesis of Aryldiphenylphosphine Oxides by Quaternization of Tertiary Diphenylphosphines with Aryl Bromides Followed by the Wittig Reaction

Funktionelle polymere Materialien auf der Basis von Hauptgruppen‐Elementen

Three‐Component Synthesis of Dioxaphosphorane‐Fused Diphosphacycles Exhibiting Unique Dynamic Fluorescence “On/Off” Properties

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