5-diphenylsulfidophosphino-2,2'-bithiophene | 1357142-22-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5-diphenylsulfidophosphino-2,2'-bithiophene
• 英文别名: Diphenyl-sulfanylidene-(5-thiophen-2-ylthiophen-2-yl)-lambda5-phosphane；diphenyl-sulfanylidene-(5-thiophen-2-ylthiophen-2-yl)-λ5-phosphane
• CAS: 1357142-22-3
• 化学式: C₂₀H₁₅PS₃
• 分子量: 382.511
• InChiKey: NCQQHWNKDKMNLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,2'-联二噻吩 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 C₄₈H₄₀Cl₂P₂Pd₂ 、 potassium carbonate 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 20.33h， 生成 5-diphenylsulfidophosphino-2,2'-bithiophene
  参考文献：
  名称：

  芳族ulf盐与二芳基膦通过选择性C-S键断裂的不同C-P交叉偶联

  摘要：

  据报道，芳基噻吨鎓盐与二芳基膦通过不同的C–P交叉偶联，可通过高选择性的C–S键裂解产生各种三芳基膦。在没有催化剂的情况下，芳基噻吨鎓盐与二芳基膦的反应仅通过裂解噻吩骨架的内环C–S键进行膦化开环。在其他条件相同的情况下使用Palladacycle催化剂，则可以通过裂解环外C-S键以更高的速度进行磷酸化反应。

  DOI：

  10.1021/acs.orglett.1c00748

文献信息

• Syntheses, X-ray Crystal Structures, and Optical, Fluorescence, and Nonlinear Optical Characterizations of Diphenylphosphino-Substituted Bithiophenes
  作者：Qun Zhao、Jason L. Freeman、Jianwei Wang、Yuanli Zhang、Tracy P. Hamilton、Christopher M. Lawson、Gary M. Gray

  DOI：10.1021/ic201309k

  日期：2012.2.20

  A series of bithiophene derivatives that are either symmetrically disubstituted with two Ph-2(X)P groups (X = O, S, Se) or monosubstituted with one Ph-2(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 Ph-2(Se)P(C4H2S)(2)P(Se)Ph-2, Ph-2(O)P(C4H2S)(2)H, Ph-2(S)P(C4H2S)(2)H, and Ph-2(O)P(C4H2S)(2)CH2OH exhibit very different solid-state structures depending on the type of intermolecular pi-pi interactions that occur. The compounds have been characterized by electronic absorption and fluorescence studies. Of particular interest is that the quantum yields of Ph-2(O)P(C4H2S)(2)H, Ph-2(O)P(C4H2S)(2)P(O)Ph-2, Ph-2(O)P(C4H2S)(2)CO2Me, and Ph-2(O)P(C4H2S)(2)CH2OH are significantly larger than that of bithiophene (factors of 13, 14, 14, and 2,2, 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 Ph-2(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)(2)H and Ph-2(S)P(C4H2S)(2)H exhibit significantly stronger nonlinear absorption than any previously reported compounds and are promising candidates for use in broadband optical power limiters.
• Diverse C–P Cross-Couplings of Arylsulfonium Salts with Diarylphosphines via Selective C–S Bond Cleavage
  作者：Yun Ye、Jie Zhu、Yinhua Huang

  DOI：10.1021/acs.orglett.1c00748

  日期：2021.3.19

  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

  据报道，芳基噻吨鎓盐与二芳基膦通过不同的C–P交叉偶联，可通过高选择性的C–S键裂解产生各种三芳基膦。在没有催化剂的情况下，芳基噻吨鎓盐与二芳基膦的反应仅通过裂解噻吩骨架的内环C–S键进行膦化开环。在其他条件相同的情况下使用Palladacycle催化剂，则可以通过裂解环外C-S键以更高的速度进行磷酸化反应。