π-Conjugated derivatives containing phosphole rings: synthesis, properties and coordination chemistry

Hissler, Muriel; Lescop, Christophe; Réau, Régis

doi:10.1016/j.crci.2004.11.039

Cited by 15 publications

(8 citation statements)

References 58 publications

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“…[8] Moreover, p-conjugated six-membered phosphorus heterocycles [9][10][11] as well as non-aromatic five-membered rings, such as phospholesa nd their derivatives (e.g.,o xides, sulfides, transition metal complexes), are being extensively investigated as precursors or components of optoelectronic materials,s uch as organicl ight-emitting diodes, organic semiconductors, and organic solar cells. [12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27] Azadiphospholes [28] are aromatic and electron-rich heterocycles, [29,30] which eventually may find applications in organic electronic materials, for example, as electron donors (n-dopants). [31] The relevant syntheticm ethods are rather limited, salts of the anionic four-memberedr ings [II] 2À ,[ III] À ,a nd [IV] À requires reactiono ft he initially formed phosphaketene with as econd equivalento fN a(OCP) leadingt oaformal [2+ +2] cycloaddition.…”

Section: Introductionmentioning

confidence: 99%

“…Another remarkable recent achievement is the activation of dihydrogen by 2,4,6‐tri‐ tert ‐butyl‐1,3,5‐triphosphabenzene, which proceeds without transition metals . Moreover, π‐conjugated six‐membered phosphorus heterocycles as well as non‐aromatic five‐membered rings, such as phospholes and their derivatives (e.g., oxides, sulfides, transition metal complexes), are being extensively investigated as precursors or components of optoelectronic materials, such as organic light‐emitting diodes, organic semiconductors, and organic solar cells …”

Section: Introductionmentioning

confidence: 99%

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A Convenient Synthesis of 1,2,4‐ and 1,3,4‐Azadiphospholes

Suter

Benkő

2016

Chemistry A European J

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A new synthetic route to functionalized neutral and anionic azadiphospholes from easily accessible starting materials is described. Equimolar reaction of Na(OCP) and N-(2,6-dimethylphenyl)pivalimidoyl chloride 2 a cleanly affords the imidoxy-functionalized 1,2,4-azadiphosphole 3 a. Using Na(OCP) and imidoyl chloride in a 2:1 ratio leads to an anionic four-membered ring Na[4 a], which has been structurally characterized. During 16 h at room temperature, Na[4 a] rearranges to the anionic 1,3,4-azadiphospholide Na[5 a] with release of carbon monoxide. Applying the more sterically demanding N-(2,6-diisopropylphenyl)pivalimidoyl chloride allows isolation of the 1,3,4-azadiphospholide Na[5 b] in good yield (>70 %). Possible mechanisms leading to the new isomeric azadiphospholides have been investigated with the aid of high-level composite calculations.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A Convenient Synthesis of 1,2,4‐ and 1,3,4‐Azadiphospholes

Suter

Benkő

2016

Chemistry A European J

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“…19 The area of organophosphorus p-conjugated molecules and polymers with particular emphasis on phosphole-based materials has been reviewed. [20][21][22] In the past year, several reviews in the area of phosphorus-containing dendrimers have been published. Topics covered include their methods of synthesis, 23 their utility in modifying surfaces, 24 the development of water soluble, 25 and metal-containing phosphorus dendrimers.…”

Section: Books and Reviews Of Inorganic Polymer Sciencementioning

confidence: 99%

“…An improved synthesis polysilanes containing n-alkyl groups has been reported. 72 Reproducible yields of 50-83 % were obtained for poly(n-hexylmethylsilane) (22) prepared by the Wurtz coupling of the 21 in THF at room temperature. Interestingly, rate studies demonstrated that the observed degree of polymerization could be correlated to the chain length where there is a maximum probability of backbiting.…”

Section: Polysilanes Polygermanes Polystannanes Polycarbosilanes and ...mentioning

confidence: 99%

Inorganic and organometallic polymers

Gates

2006

Annu. Rep. Prog. Chem., Sect. A: Inorg. Chem.

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This report summarizes the many advances that were made in the area of inorganic polymer science in 2005. Key accomplishments in the synthesis of inorganic polymers include: macromolecules with metal-metal bonds, Pt-Au-containing polymers, highly metallized ferrocene polymers, conjugated phosphole-and silole-containing polymers, and novel metallo-supramolecular macromolecules. Several inorganic and organometallic polymers have been designed for sensor or electro-optical applications. In addition, a number of studies have focused on developing new classes of polyphosphazenes for biomedical applications.

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“…A series of linear p-conjugated compounds incorporating oliogomers derived from phosphole groups has been described. 47 The compounds were also shown to be able to act as ligands to transition metal compounds.…”

Section: Phosphorusmentioning

confidence: 99%

Nitrogen, phosphorus, arsenic, antimony and bismuth

Lynam

2006

Annu. Rep. Prog. Chem., Sect. A: Inorg. Chem.

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This chapter reviews the literature reported during 2005 on the chemistry of nitrogen, phosphorus, arsenic, antimony and bismuth. PreambleOnce again the study of the chemistry of the pnictogens has provided considerable challenges to both synthetic and theoretical chemists. Significant new advances and insights into have been made, of particular note are the developments in the areas of activation of dinitrogen, such as the work of Schrock on molybdenum complexes 1,2 and the discovery of an amido-hydride complex from activation of ammonia. 3 Further highlights include the continued expansion of the use of metal phosphinidene complexes as synthetic reagents for the production of novel phosphoruscontaining materials and the synthesis of several new cationic arsenic-containing species.As in previous years and due to space restrictions this review will not, in general, consider the use of the trivalent elements as ligands, however reviews on ''user friendly'' primary phosphines 4 and how to evaluate the net donor abilities of phosphines 5 have appeared. NitrogenThe activation of dinitrogen remains a major area of interest. The molybdenumcentred reduction of dinitrogen to ammonia remains one of the most impressive methods of nitrogen fixation and a review on this subject has appeared 1 as has a comprehensive study into several aspects of this chemistry. 2 It has been shown that under an atmosphere of N 2 , the dimer [Ta(Z 5 -C 5 Me 4 R)] 2 (m-Cl) 4 (R = Me, Et) disproportionates to give [Ta(Z 5 -C 5 Me 4 R)] 2 (m-Z 1 ,Z 1 -N 2 ) as the nitrogen-containing product. 6 The dinitrogen may be considered to have undergone a four-electron reduction with the tantalum now existing in the (V) oxidation state. In a similar fashion, reduction of [Ti(Z 5 -C 5 Me 5 )Cl 3 ] in the presence of substituted fulvene gives rise to dinuclear species containing a (m-Z 1 , Z 1 -N 2 ) ligand. 7 The reduction of the zirconium complex [NPN]ZrCl 2 (thf) [NPN = PhP(CH 2 SiMe 2 NPh) 2 ] under nitrogen results in the formation of [NPN]Zr(m-Z 2 , Z 2 -N 2 )(thf). 8 A similar reaction with the titanium analogue results in the insertion of dinitrogen into the Ti-PPh bond and formation of 1. Using a related ligand set within the coordination sphere of tantalum, Fryzuk has also shown that it is possible to convert hydrazine to bridging Ta-NH-Ta groups. 9 A reaction of the same precursor with Me 2 NNH 2 results in the formation of a complex containing a bridging nitride ligand. The oxidative addition

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π-Conjugated derivatives containing phosphole rings: synthesis, properties and coordination chemistry

Cited by 15 publications

References 58 publications

A Convenient Synthesis of 1,2,4‐ and 1,3,4‐Azadiphospholes

A Convenient Synthesis of 1,2,4‐ and 1,3,4‐Azadiphospholes

Inorganic and organometallic polymers

Nitrogen, phosphorus, arsenic, antimony and bismuth

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