A semiconductive nickel‐‐phosphine coordination polymer**

Fox, Marye Anne; Chandler, Daniel A.

doi:10.1002/adma.19910030709

Cited by 33 publications

(28 citation statements)

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“…Only a relatively small number of primary arylphosphines has been prepared and fully characterized [9 ± 11], and this is particularly true for aromatic hydrocarbons with more than one primary phosphine function [6] [12 ± 23]. For benzene itself, the complete set of primary phosphines has the general formula C 6 H n (PH 2 ) 6Àn comprising a total of 12 species, of which only less than half are known (Fig.…”

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confidence: 99%

“…The synthetic strategies employed are based on previous investigations, mainly the photo-Arbuzov reaction [6] [12] [38]. The methods were adapted to the challenge posed by the multiphosphination of benzene, which was previously accomplished in only isolated cases [6] [12 ± 21].…”

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confidence: 99%

“…The methods were adapted to the challenge posed by the multiphosphination of benzene, which was previously accomplished in only isolated cases [6] [12 ± 21].…”

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confidence: 99%

“…LiAlH 4 Reduction of the three phosphonic acid esters 1 ± 3 in tetrahydrofuran mediated by the addition of stoichiometric quantities of chlorotrimethylsilane [6] [12] gave acceptable yields (46.5, 34.5, and 25.2%, resp.) of the corresponding phosphines 7 ± 9 (Scheme 2).…”

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confidence: 99%

“…Future work will be directed towards the synthesis of even more highly phosphinated benzenes including the elusive (benzenehexayl) hexakis[phosphine] (C 6 (PH 2 ) 6 ). It should be noted that benzenehexathiol C 6 (SH) 6 [48] [49] and hexasilylbenzene C 6 (SiH 3 ) 6 [50] [51] have already been prepared.…”

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(Benzene-1,3,5-triyl)tris[phosphine] (C6H3(PH2)3) and (Benzene-1,3,5-triyl)tris[phosphonic Acid] (C6H3[P(O)(OH)2]3). Absence of Hydrogen Bonding in Solid Primary Phosphines

Reiter

Assmann

Nogai

et al. 2002

HCA

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The prolonged photo-Arbuzov reaction (3 weeks, Hg lamp) of 1,3,5-trichloro-benzene with a large excess of trimethyl phosphite (as a solvent) at 508 gives moderate yields of dimethyl (3,5-dichlorophenyl)phosphonate (1; 14.5%), tetramethyl (5-chloro-1,3-phenylene)bis[phosphonate] (2; 35.4%), and hexamethyl (benzene-1,3,5-triyl)tris[phosphonate] (3; 30.1%). The products can be separated by fractional distillation. Acid hydrolysis of the esters gives almost quantitative yields of the corresponding phosphonic acids 4 ± 6. Reduction of the esters 1 ± 3 by LiAlH 4 in tetrahydrofuran affords the primary phosphines (3,5-dichlorophenyl)phosphine (7; 46.5%), (5-chloro-1,3-phenylene)bis[phosphine] (8; 34.5%) and (benzene-1,3,5-triyl)tris[phosphine] (9; 25.2% yield). In the crude reduction products from 2 (preparation of 8) and from 3 (preparation of 9), (3-chlorophenyl)phosphine and (1,3-phenylene)bis[phosphine], respectively, are observed as by-products. All compounds are characterized by standard analytical, spectroscopic, and (for 1, 7, and 8) structural techniques. The arrangement of the molecules in the crystal structures of 7 and 8 suggest that H-bonding between the primary arylphosphines is virtually insignificant for the packing of the components. This is in marked contrast to the importance of H-bonding for the supramolecular chemistry of arylamines. The new primary polyphosphines and polyphosphonic acids are to be employed in the construction of extended arrays.Introduction. ± Arylphosphines play an important role in many areas of contemporary chemistry. Tertiary phosphines Ar 3 P are the most prominent class of ligands for transition metals, and their complexes are used as homogeneous catalysts in a large variety of reactions [1]. They are also the base chemicals for many reagents in organic synthesis including phosphonium salts [2], phosphonium ylides [2 ± 4], phosphine boranes [2] [5], and phosphine oxides and sulfides [2]. Secondary phosphines Ar 2 PH are less common in catalysts and also as reagents, but their PÀH group offers an additional functionality for the design of more sophisticated substitution patterns and for oxidation products. Finally, primary phosphines ArPH 2 are the least developed series of arylphosphines with still very limited areas of application [6 ± 8]. However, their potential as synthons is even greater owing to two reactive PÀH functions in addition to the nucleophilic/donor center at the P-atom.Only a relatively small number of primary arylphosphines has been prepared and fully characterized [9 ± 11], and this is particularly true for aromatic hydrocarbons with more than one primary phosphine function [6] [12 ± 23]. For benzene itself, the complete set of primary phosphines has the general formula C 6 H n (PH 2 ) 6Àn comprising a total of 12 species, of which only less than half are known (Fig. 1).Current interest in advanced materials with tailored structures and properties has attracted increasing attention to polyphosphinoarenes with a rigid skeleton, on which new structural motifs...

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confidence: 99%

mentioning

confidence: 99%

“…The methods were adapted to the challenge posed by the multiphosphination of benzene, which was previously accomplished in only isolated cases [6] [12 ± 21].…”

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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(Benzene-1,3,5-triyl)tris[phosphine] (C6H3(PH2)3) and (Benzene-1,3,5-triyl)tris[phosphonic Acid] (C6H3[P(O)(OH)2]3). Absence of Hydrogen Bonding in Solid Primary Phosphines

Reiter

Assmann

Nogai

et al. 2002

HCA

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Synthesis of a New Multidentate Phosphane Ligand C6H2(CH2PPh2)4-1,2,4,5 − X-ray Structure of a Dinuclear Ruthenium(II)-Bridged Complex: [{RuCl2(PPh3)}2{C6H2(CH2PPh2)4-1,2,4,5-P,P′,P′′,P′′′}]

Steenwinkel

Kolmschot

Gossage

et al. 1998

Eur. J. Inorg. Chem.

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The tetrakis(phosphane oxide) C6H2{CH2P(O)Ph2}4‐1,2,4,5 (5), has been prepared in high yield from the Arbuzov reaction of C6H2(CH2Br)4‐1,2,4,5 (4), with excess (7 equiv.) of Ph2POEt. Subsequent reduction of 5 with HSiCl3 (12 equiv.) in C6H4Cl2‐1,2 afforded the new tetraphosphane C6H2(CH2PPh2)4‐1,2,4,5 (6), in high yield. The reaction of 6 with [RuCl2(PPh3)4] in CH2Cl2 afforded the green dinuclear ruthenium(II) coordination complex [{RuCl2(PPh3)}2{C6H2‐ (CH2PPh2)4‐1,2,4,5‐P,P′,P′′,P′′′}]·0.5 CH2Cl2 (8), in 39% isolated yield. The solid‐state molecular geometry of 8, determined by X‐ray analysis, shows that the tetraphosphane is ortho‐P,P′‐chelated to each of the two [RuIICl2(PPh3)] units.

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Supramolecular Polymers, Based on Metal‐to‐Ligand Interactions*

2021

Supramolecular Polymers and Assemblies

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A semiconductive nickel‐‐phosphine coordination polymer**

Cited by 33 publications

References 12 publications

(Benzene-1,3,5-triyl)tris[phosphine] (C6H3(PH2)3) and (Benzene-1,3,5-triyl)tris[phosphonic Acid] (C6H3[P(O)(OH)2]3). Absence of Hydrogen Bonding in Solid Primary Phosphines

(Benzene-1,3,5-triyl)tris[phosphine] (C6H3(PH2)3) and (Benzene-1,3,5-triyl)tris[phosphonic Acid] (C6H3[P(O)(OH)2]3). Absence of Hydrogen Bonding in Solid Primary Phosphines

Synthesis of a New Multidentate Phosphane Ligand C6H2(CH2PPh2)4-1,2,4,5 − X-ray Structure of a Dinuclear Ruthenium(II)-Bridged Complex: [{RuCl2(PPh3)}2{C6H2(CH2PPh2)4-1,2,4,5-P,P′,P′′,P′′′}]

Supramolecular Polymers, Based on Metal‐to‐Ligand Interactions*

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