160566-49-4

Upstream product

• 65425-96-9 (Z)-β-bromo-β-(trimethylsilyl)styrene 
• 644-97-3 Dichlorophenylphosphine 
• 160566-50-7 (Z)-β,o-dibromo-β-trimethylsilylstyrene 
• 1066-54-2 trimethylsilylacetylene 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 536-74-3 phenylacetylene 
• 38274-16-7 2-bromo-1-(trimethylsilylethynyl)benzene 
• 583-55-1 1-Bromo-2-iodobenzene 

Downstream Products

• 152554-90-0 2-(trimethylsilyl)benzo[b]phosphole P-oxide 
• 1417719-73-3 cis-2,2’-bis(benzo[b]phosphole) P-oxide 
• 1417719-67-5 C₂₈H₂₀P₂ 
• 31236-98-3 1-phenyl-1-benzophosphole 

Relevant academic research and scientific papers

Synthesis of 1-benzometalloles containing group 14, 15, and 16 heavier elements via a common dilithiostyrene intermediate

The Group 14 (Si, Ge, and Sn), Group 15 (P, As, Sb, and Bi), and Group 16 (Se and Te) 2-trimethylsilyl-1-benzometalloles (7) were prepared by the reaction of the corresponding metal reagents with β,o-dilithio-β-trimethyl- silylstyrene intermediate (6), which was derived from phenylacetylene or o- bromoiodobenzene via three steps. The trimethylsilyl group in 7 could be readily removed by treatment with tetrabutylammonium fluoride to give the C- unsubstituted 1-benzometalloles (10).

Synthesis and structure-property relationships of 2,2'-bis(benzo[b] phosphole) and 2,2'-benzo[b]phosphole-benzo[b]heterole hybrid π systems

The first comprehensive study of the synthesis and structure-property relationships of 2,2'-bis(benzo[b]phosphole)s and 2,2'-benzo[b]phosphole- benzo[b]heterole hybrid π systems is reported. 2-Bromobenzo[b]phosphole P-oxide underwent copper-assisted homocoupling (Ullmann coupling) and palladium-catalyzed cross-coupling (Stille coupling) to give new classes of benzo[b]phosphole derivatives. The benzo[b]phosphole-benzo[b]thiophene and -indole derivatives were further converted to P,X-bridged terphenylenes (X=S, N) by a palladium-catalyzed oxidative cycloaddition reaction with 4-octyne through the Cβ-H activation. X-ray analyses of three compounds showed that the benzo[b]phosphole-benzo[b]heterole derivatives have coplanar π planes as a result of the effective conjugation through inter-ring C-C bonds. The π-π* transition energies and redox potentials of the cis and trans isomers of bis(benzo[b]phosphole) P-oxide are very close to each other, suggesting that their optical and electrochemical properties are little affected by the relative stereochemistry at the two phosphorus atoms. The optical properties of the benzo[b]phosphole-benzo[b]heterole hybrids are highly dependent on the benzo[b]heterole subunits. Steady-state UV/Vis absorption/fluorescence spectroscopy, fluorescence lifetime measurements, and theoretical calculations of the non-fused and acetylene-fused benzo[b]phosphole-benzo[b]heterole π systems revealed that their emissive excited states consist of two different conformers in rapid equilibrium.