409093-85-2Relevant academic research and scientific papers
Diverse C-P Cross-Couplings of Arylsulfonium Salts with Diarylphosphines via Selective C-S Bond Cleavage
Ye, Yun,Zhu, Jie,Huang, Yinhua
, p. 2386 - 2391 (2021/04/05)
Diverse C-P cross-couplings of arylthianthrenium salts with diarylphosphines producing various triarylphosphines via highly selective C-S bond cleavage are reported. In the absence of catalyst, the reaction of arylthianthrenium salts with diarylphosphines undergoes phosphinative ring opening exclusively via the cleavage of an endocyclic C-S bond of a thianthrene skeleton. The use of a palladacycle catalyst under otherwise the same conditions enables the phosphination via the cleavage of an exocyclic C-S bond with significantly higher speed.
Syntheses, X-ray crystal structures, and optical, fluorescence, and nonlinear optical characterizations of diphenylphosphino-substituted bithiophenes
Zhao, Qun,Freeman, Jason L.,Wang, Jianwei,Zhang, Yuanli,Hamilton, Tracy P.,Lawson, Christopher M.,Gray, Gary M.
experimental part, p. 2016 - 2030 (2012/05/05)
A series of bithiophene derivatives that are either symmetrically disubstituted with two Ph2(X)P groups (X = O, S, Se) or monosubstituted with one Ph2(X)P group (X = O, S, Se) and an organic functional group (H, CHO, CH2OH, CO2Me) have been synthesized. The X-ray crystal structures of Ph2(Se)P(C 4H2S)2P(Se)Ph2, Ph2 (O)P(C4H2S)2H, Ph2(S)P- (C 4H2S)2H, and Ph2(O)P(C 4H2S)2CH2OH exhibit very different solid-state structures depending on the type of intermolecular π-π interactions that occur. The compounds have been characterized by electronic absorption and fluorescence studies. Of particular interest is that the quantum yields of Ph2(O)P(C4H2S)2H, Ph 2(O)P(C4H2S)2P(O)Ph2, Ph2(O)P(C4H2S)2CO2Me, and Ph 2(O)P(C4H2S)2CH2OH are significantly larger than that of bithiophene (factors of 13, 14, 14, and 22, respectively). This behavior is quite different from that of analogously substituted terthiophenes in which substitution results in only modest increases in the quantum yields over that of terthiophene (factors of 0.94, 2.7, 1.3, and 1.5, respectively). DFT studies of the emission process suggest that modifying the Ph2(X)P group affects both the fluorescence and nonradiative rate constants while modifications of the organic substituents primarily affect the nonradiative rate constants. The higher quantum yields of the substituted bithiophenes make them promising for application in organic light-emitting devices (OLED). The optical power limiting (OPL) performances of these Ph 2(X)P-substituted bithiophenes were evaluated by nonlinear transmission measurements in the violet-blue spectral region (430-480 nm) with picosecond laser pulses. The OPL performances are enhanced by heavier X groups and when by higher solubilities. Saturated chloroform solutions of Ph 2(O)P(C4H2S)2H and Ph 2(S)P(C4H2S)2H exhibit significantly stronger nonlinear absorption than any previously reported compounds and are promising candidates for use in broadband optical power limiters.
Novel diphenylphosphine derivatives of 2,2′-bithiophene, 2,2′:5′,2″-terthlophene, 2-(2′-thlenyl)pyndine and 2,6-di-2′-thienylpyridine. Crystal structures of 5,5′-bis(diphenylphosphino)-2,2′-bithiophene, diphenyl{5-[6′-(diphenylphosphino)-2′-pyridyl]-2-thienyl}phosphine and 2,6-bis[5′-(diphenylphosphino)-2′-thienyl]pyridine
Field, John S.,Haines, Raymond J.,Lakoba, Elena I.,Sosabowski, M. Hal
, p. 3352 - 3360 (2007/10/03)
We report the synthesis and characterisation of eight molecules that have in common a diphenylphosphino group bonded to an α-carbon atom of a thienyl or pyridyl ring: 5,5′-bis(diphenylphosphino)-2,2′-bithiophene 1; diphenyl(2,2′-bithienyl-5-yl)phosphine 2; 5,5″-bis(diphenylphosphino)-2,2′:5′,2″-terthiophene 3; diphenyl-(2,2′:5′,2″-terthienyl-5-yl)phosphine 4; diphenyl[5-(2′-pyridyl)-2-thienyl]phosphine 5; diphenyl[6-(2′-thienyl)2-pyridyl]phosphine 6; diphenyl{5-[6′-(diphenylphosphino)-2′-pyridyl]-2-thienyl}phosphine 7; and 2,6-bis[5′-(diphenylphosphino)-2′-thienyl]pyridine 8. Methods used for their synthesis range from lithiation of the parent heterocycle and subsequent reaction with PPh2Cl to the use of coupling reactions catalysed by metal complexes to assemble the molecule from its subunits. The crystal and molecular structures of 1, 7 and 8 have been determined and show that the 2,2′-bithienyl moiety in 1 adopts an s-trans-conformation, while the 2-(2′-thienyl)pyridyl moieties in 7 and 8 adopt s-cis-conformations in the solid state. These compounds represent a new series of ligands that are expected to bond to metals through the phosphorus and/or nitrogen atoms rather than a sulfur atom, in view of the poor donor ability of a thiophene sulfur towards metals.
