1-(2-(2'-thienyl)thien-5-yl)-3,4-dimethylphosphole | 126980-18-5

• 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: 1-(2-(2'-thienyl)thien-5-yl)-3,4-dimethylphosphole
• 英文别名: 1-(2,2'-bithienyl)-3,4-dimethylphosphole；1-(2-bithienylyl)-3,4-dimethyl phosphole；2-(3,4-Dimethylphosphol-1-yl)-5-thiophen-2-ylthiophene
• CAS: 126980-18-5
• 化学式: C₁₄H₁₃PS₂
• 分子量: 276.363
• InChiKey: JTCGXMDARPLNBX-UHFFFAOYSA-N

物化性质

• 熔点：
  69 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  1-(2-(2'-thienyl)thien-5-yl)-3,4-dimethylphosphole 在 四溴化碳 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  An Unconventional Synthesis of Dibromophosphines

  摘要：

  Dibromophosphines, RPBr2, are obtained by reaction of tetrabromomethane with 7-substituted 7-phosphanorbornenes in toluene at ca. 100 degrees C. The phosphanorbornenes are obtained in situ by cycloaddition of N-phenylmaleimide with 1-substituted 3,4-di-methylphospholes. The overall reaction sequence shows a good compatibility with functional groups.

  DOI：

  10.1055/s-0033-1339548
• 作为产物：
  描述：

  2,2'-联二噻吩 、 1H-磷杂唑-1-甲腈,3,4-二甲基- 在 正丁基锂 、 四甲基乙二胺 作用下， 生成 1-(2-(2'-thienyl)thien-5-yl)-3,4-dimethylphosphole
  参考文献：
  名称：

  Bevierre, Marc-Olivier; Mercier, Francois; Ricard, Louis, Angewandte Chemie, 1990, vol. 102, # 6, p. 672 - 675

  摘要：

  DOI：

文献信息

• Phosphole-N-phenylmaleimide [4+2] cycloadducts as synthetic equivalents of nucleophilic phosphinidenes
  作者：Rongqiang Tian、Zheng Duan、Xiaoxu Zhou、Dingjin Geng、Yangjie Wu、François Mathey

  DOI：10.1039/b901154d

  日期：——

  Using 1-R-3,4-dimethylphosphole-N-phenylmaleimide cycloadducts as synthetic equivalents of phosphinidenes [R-P], the following sequence has been developed: [R-P] + R(1)X --> RR(1)PX --> RR(1)P-OR(2).

  使用1-R-3,4-二甲基磷脂-N-苯基马来酰亚胺环加合物作为次膦酸酯[RP]的合成等价物，已开发出以下序列：[RP] + R（1）X-> RR（1）PX- > RR（1）P-OR（2）。
• Investigating the Phospholylcarbene to Phosphinine Conversion
  作者：Hui Chen、Jin Li、Huaiqiu Wang、Hui Liu、Zheng Duan、François Mathey

  DOI：10.1002/ejic.201100098

  日期：2011.4

  study suggests that the conversion of arsolylcarbenes into arsenines as described by Markl proceeds via arsabenzvalenes. A similar conversion does not work with phospholylcarbenes. However, we have found that, in some cases, 1-diazoalkylphosphole sulfides are converted into phosphinine sulfides whose in situ reduction by triphenylphosphite affords the dicoordinate phosphinines.

  DFT 研究表明，如 Markl 所描述的，arsolylcarbenes 向砷的转化是通过 arsabenzvalenes 进行的。类似的转化不适用于磷酸卡宾。然而，我们发现，在某些情况下，1-重氮烷基磷硫化物会转化为硫化膦，其被亚磷酸三苯酯原位还原得到双配位膦。
• 2,2′-Biphospholes: Building Blocks for Tuning the HOMO-LUMO Gap of π-Systems Using Covalent Bonding and Metal Coordination
  作者：Hui Chen、Wylliam Delaunay、Liujian Yu、Damien Joly、Zuoyong Wang、Jin Li、Zisu Wang、Christophe Lescop、Denis Tondelier、Bernard Geffroy、Zheng Duan、Muriel Hissler、François Mathey、Régis Réau

  DOI：10.1002/anie.201105924

  日期：2012.1.2

  A new angle: The insertion of a 2,2′‐biphosphole subunit into π‐conjugated systems offers a new way to control the HOMO–LUMO gap. Tuning of the dihedral angle (θ) between the two phosphorous heterocycles, either by metal coordination or covalent bonding through the P substitution can lead to control of the band gap. These new π‐conjugated systems can be used as emitting materials in white organic light‐emitting

  一个新的角度：将2,2'-联磷亚基插入π-共轭体系提供了控制HOMO-LUMO间隙的新方法。通过金属配位或通过P取代的共价键调节两个磷杂环之间的二面角（θ），可以控制带隙。这些新的π共轭体系可用作白色有机发光器件（WOLED）的发光材料。
• A Novel Family of Phosphole-Thiophene Oligomers for Optoelectronic Applications
  作者：Ngoc Hoa Tran Huy、Bruno Donnadieu、François Mathey、Astrid Muller、Kathryn Colby、Christopher J. Bardeen

  DOI：10.1021/om800644m

  日期：2008.11.10

  A 2-terthienylphospholide can be prepared from a 1-terthienylphosphole by reaction with tBuOK in diglyme at 150 degrees C. This phospholide is then transformed into the corresponding 1-methyl-2-terthienylphosphole-borane. This borane complex fluoresces at 5 10 nm in CH2Cl2 with a quantum yield of 0.17. The excited-state displays a significant charge transfer between the terthienyl substituent and the phosphole ring as shown by the shift of the emission to lower energies upon increasing the polarity of the solvent.
• BEVIERRE, MARC-OLIVIER;MERCIER, FRANOIS;RICARD, LOUIS;MATHEY, FRANOIS, ANGEW. CHEM., 102,(1990) N, C. 672-675
  作者：BEVIERRE, MARC-OLIVIER、MERCIER, FRANOIS、RICARD, LOUIS、MATHEY, FRANOIS

  DOI：——

  日期：——