5,5'-bis(diphenylphosphino)-2,2'-bithiophene | 409093-84-1

• 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: 5,5'-bis(diphenylphosphino)-2,2'-bithiophene
• 英文别名: bis(5,5'-diphenylphosphino)-2,2'-bithiophene；PT2P；[5-(5-Diphenylphosphanylthiophen-2-yl)thiophen-2-yl]-diphenylphosphane
• CAS: 409093-84-1
• 化学式: C₃₂H₂₄P₂S₂
• 分子量: 534.622
• InChiKey: BEINYDCSTOIYNH-UHFFFAOYSA-N

物化性质

• 沸点：
  637.5±55.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,5'-bis(diphenylphosphino)-2,2'-bithiophene 在 selenium 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到5,5'-bis(diphenylselenidophosphino)-2,2'-bithiophene
  参考文献：
  名称：

  Syntheses, X-ray Crystal Structures, and Optical, Fluorescence, and Nonlinear Optical Characterizations of Diphenylphosphino-Substituted Bithiophenes

  摘要：

  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.

  DOI：

  10.1021/ic201309k
• 作为产物：
  描述：

  2,2'-联二噻吩 、 二苯基氯化膦 在 正丁基锂 作用下， 以 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 14.0h， 生成 5,5'-bis(diphenylphosphino)-2,2'-bithiophene
  参考文献：
  名称：

  前过渡金属化合物及制备方法和应用

  摘要：

  本发明涉烯烃聚合催化剂领域，公开了前过渡金属化合物及制备方法和应用，该化合物具有式(1)或式(2)所示的结构。含有本发明提供的前过渡金属化合物的催化剂具有催化活性高、稳定性好、催化剂成本低的优点。

  公开号：

  CN114426561A

文献信息

• Synthesis and Characterization of Cyclic Oligomeric [<i>cis</i>-Mo(CO)₄(Ph₂P(C₄H₂S)₂PPh₂)]<i>_n</i> and Model Complexes for the Edge and Corners in the Cyclic Oligomer
  作者：R. Dustan Myrex、Clark S. Colbert、Gary M. Gray、Christina H. Duffey

  DOI：10.1021/om030595h

  日期：2004.2.1

  Conducting organometallic polymers are an interesting class of materials because they combine the electronic properties of metals with the simpler processing requirements of organic polymers. In an approach to incorporating poly(thiophene) segments into controlled three-dimensional environments, we have synthesized 5,5‘-bis(diphenylphosphino)-2,2‘-bithiophene, Ph2P(C4H2S)2PPh2, and have reacted this

  导电有机金属聚合物是一类有趣的材料，因为它们将金属的电子特性与有机聚合物的更简单加工要求结合在一起。在将聚噻吩链段纳入受控的三维环境的一种方法中，我们合成了5,5'-双（二苯基膦基）-2,2'-联噻吩，Ph 2 P（C 4 H 2 S）2 PPh 2，并使该配体与Mo（CO）4（nbd）以1：1的比例反应。该反应的产物是环状低聚物，这通过IR光谱中仅存在顺式-Mo（CO）4吸收以及在该光谱中不存在游离膦的共振来表明。31 P 1 H} NMR谱。聚合物在THF中的尺寸排阻色谱法测得该聚合物的M n n值为6.0×10 3，M w值为9.7×10 3。为了更好地理解聚合物的结构特征，对边缘Mo（CO）5（Ph 2 P（C 4 H 2 S）2 PPh 2）Mo（CO）5和边角顺式-Mo（ CO）4（Ph 2 P（C 4 H 2 S）2 H）2和顺-Mo（CO）4（PH 2 PC 4 ħ 2
• Field, John S.; Haines, Raymond J.; Lakoba, Elena I., Journal of the Chemical Society. Perkin Transactions 1 (2001), 2001, # 24, p. 3352 - 3360
  作者：Field, John S.、Haines, Raymond J.、Lakoba, Elena I.、Sosabowski, M. Hal

  DOI：——

  日期：——
• Structural and Electronic Properties of Phosphino(oligothiophene) Gold(I) Complexes
  作者：Tracey L. Stott、Michael O. Wolf、Brian O. Patrick

  DOI：10.1021/ic0493200

  日期：2005.2.1

  A series of gold(I) complexes containing phosphino(oligothiophene) ligands of varying conjugation length has been prepared. Solid state crystal structures of (PT3)AuCl (PT3 = 5-diphenylphosphino-2,2':5',2"-terthiophene) and AuCl-(PTP)AuCl (PTP = 2,5-diphenylphosphinothiophene) have been obtained. The complex AuCl(PTP)AuCl crystallizes as a dimer with two intermolecular Au-Au contacts. Variable temperature NMR spectroscopy is used to demonstrate the presence of aurophilic interactions in solution for Aul(PTP)Aul. Dual emission is observed for AuCl(PTP)AuCl in solution and is attributed to emission from both monomer and dimer. In the solid state, dimer emission is dominant. The iodo analogue, Aul(PTP)Aul, shows only low energy dimer emission in both solution and the solid state. Compounds in which the ligands contain longer bridges (either bithienyl or terthienyl) show absorption and emission bands due to the pi-pi* transition only, both in solution and the solid state.