1256150-29-4Relevant academic research and scientific papers
Luminescent P-chirogenic copper clusters
Lapprand, Antony,Dutartre, Mathieu,Khiri, Naima,Levert, Etienne,Fortin, Daniel,Rousselin, Yoann,Soldera, Armand,Juge, Sylvain,Harvey, Pierre D.
, p. 7958 - 7967 (2013/08/23)
P-chirogenic clusters of the cubanes [Cu4I4L 4] (L = chiral phosphine) were prepared from (+)- and (-)-ephedrine with L = (S)- or (R)-(R)(Ph)(i-Pr)P (with R = CH3 (seven steps) or C17H35 (1
Organometallic oligomers based on bis(arylacetylide)bis(P-chirogenic phosphine)platinum(II) complexes: Synthesis and photonic properties
Lapprand, Antony,Khiri, Na?ma,Fortin, Daniel,Jugé, Sylvain,Harvey, Pierre D.
, p. 2361 - 2371 (2013/04/10)
A series of P-chirogenic oligomers of the type (- C? - /C - aryl - C? - /C - PtL2 -)n [L = (R)- and (S)-P(Ph)(iPr)(C17H35); aryl = 1,4-benzene, 2,1,3-benzothiadiazole] along the corresponding achiral analogues (L = PBu 3) and model complexes PhC? - /CPtL2C? - /CPh were prepared from the ephedrine strategy and were fully characterized [ 1H, 31P NMR; IR; small-angle X-ray scattering (SAXS); gel permeation chromatography (GPC); thermal gravimetric analysis (TGA); circular dichroism, UV-vis, and luminescence spectroscopy; photophysics, and degree of anisotropy measurements]. From the CD measurements, the chiral environment of the phosphine ligands is modestly felt by the aryl moieties. Concurrently, the TGA shows that the P(C17H35)(Ph)(i-Pr)-containing materials are more stable than those containing the shorter chain ligand PBu3, and exhibits red-shifted absorption and emission bands compared to those including the PBu3 ligands. The presence of the long chain on the phosphorus atoms does not greatly alter the photophysical parameters, notably the emission lifetimes, and fast triplet energy transfer terminal* → central unit has been deduced from the absence of luminescence arising from the terminal units.
Enantiodivergent synthesis of P-chirogenic phosphines
Chaux, Fanny,Frynas, Slawomir,Laureano, Hugo,Salomon, Christine,Morata, Gérald,Auclair, Marie-Laure,Stephan, Michel,Merds, Rachid,Richard, Philippe,Ondel-Eymin, Marie-Jo,Henry, Jean-Christophe,Bayardon, Jér?me,Darcel, Christophe,Jugé, Sylvain
, p. 1213 - 1226 (2011/10/31)
Several approaches for the enantiodivergent synthesis of P-chirogenic mono- and diphosphines are described, using ephedrine methodology and phosphine borane chemistry. Firstly, both enantiomers of a tertiary phosphine can be obtained starting from the same oxazaphospholidine borane complex, prepared from (+)-ephedrine, when changing the order of addition of the organolithium reagents during the synthetic pathway. The second approach is based on the chlorophosphine boranes, which react with an organolithium reagent, to afford the corresponding phosphines with inversion of configuration. In the case where the chlorophosphine borane reacts with the t-butyl lithium reagent, a metal-halogen exchange occurs to afford the corresponding phosphide borane with retention of the configuration. The reaction of the phosphide borane with an alkyl halide leads to the same phosphine, but with the opposite configuration. Another approach depends on the diastereoselective preparation of the starting oxazaphospholidine borane complex from (-)-ephedrine, which leads according the case, to either one or the other enantiomer of a phosphine. Finally, the synthesis of (R,R)- and (S,S)-1,2-bis(methylphenylphosphino)ethane is also demonstrated using both enantiomers of the P-chirogenic diphosphinite diborane, which simultaneously allows the introduction of alkyl- or aryl substituents on the phosphorus atoms. In summary, these approaches show the great efficiency of the "ephedrine methodology" for the enantiodivergent synthesis of P-chirogenic mono- and diphosphines, and bearing alkyl or aryl substituents.
