ChemInform Abstract: In Search of New Organophosphorus Pesticides and Insecticides. Part 1. Synthesis and Anticholinesterase Properties of 4‐(Substituted Phenoxy)dinaphtho(2,1‐d:1′,2′‐f)(1,3,2)dioxaphosphepin‐4‐oxides.

Bull, E. O. J.; Naidu, M. S. R.; Nagaraju, C.

doi:10.1002/chin.199042255

Cited by 2 publications

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“…The two enantiomers of O=PPh(BINOL) were obtained following a modified literature procedure [ 23 ]. In a typical preparation, a solution containing 5.0 mmol (1.432 g) of ( R )- or ( S )-BINOL and 0.7 mL of phenylphosphonic dichloride (0.975 g, 5.0 mmol) in dry toluene (30 mL) was prepared under an inert atmosphere, and then 1.4 mL of triethylamine (10.0 mmol) were slowly added.…”

Section: Methodsmentioning

confidence: 99%

“…Its synthesis, first reported in 1990, was based on the reaction between BINOL and phenylphosphonic dichloride in benzene in the presence of triethylamine as a base. The compound and related species were investigated as possible new organophosphorus pesticides and insecticides [ 23 ]. According to a 2023 Chinese patent [ 24 ], the same product can be obtained from BINOL and diethyl phenylphosphonate in the presence of trifluoromethylsulfonic anhydride, dimethyl sulfoxide, and tetrabutylammonium bromide.…”

Section: Introductionmentioning

confidence: 99%

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Luminescent Behavior of Zn(II) and Mn(II) Halide Derivatives of 4-Phenyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-Oxide and Single-Crystal X-ray Structure Determination of the Ligand

Ferraro,

Castro,

Bortoluzzi

2024

Molecules

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The two enantiomers of chiral phosphonate 4-phenyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-oxide, O=PPh(BINOL), were synthesized from the proper 1,1′-bi-2-naphtol (BINOL) enantiomer and characterized. The structure of the (S)-enantiomer was elucidated by means of single-crystal X-ray diffraction. The reaction with anhydrous ZnBr2 afforded complexes having the general formula [ZnBr2{O=PPh(BINOL)}2] that showed intense fluorescence centered in the near-UV region rationalized on the basis of TD-DFT calculations. The corresponding Mn(II) complexes with the general formula [MnX2{O=PPh(BINOL)}2] (X = Cl, Br) exhibited dual emission upon excitation with UV light, with the relative intensity of the bands dependent upon the choice of the halide. The highest energy transition is comparable with that of the Zn(II) complex, while the lowest energy emission falls in the red region of the spectrum and is characterized by lifetimes in the hundreds of microseconds range. Although the emission at lower energy can also be achieved by direct excitation of the metal center, the luminescence decay curves suggest that the band in the red range is possibly derived from BINOL-centered excited states populated by intersystem crossing.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Luminescent Behavior of Zn(II) and Mn(II) Halide Derivatives of 4-Phenyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepine 4-Oxide and Single-Crystal X-ray Structure Determination of the Ligand

Ferraro,

Castro,

Bortoluzzi

2024

Molecules

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“…Elemental analysis were performed at the Central Drug Research Institute (CDRI), Lucknow, India. 2,2'-dihydroxybinaphthyl 20 (7), bis(2-hydroxy-1napthyl)methane 21 (8), 5,5 ' -dichloro-2,2'-dihydroxybiphenyl sulfide 21 (9) were prepared according to reported procedures.…”

Section: Methodsmentioning

confidence: 99%