7,7-dimethyl-2,5-bis-trimethylsilanyl-7H-3,4-dithia-7-sila-cyclopenta[a]pentalene | 1187970-50-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 7,7-dimethyl-2,5-bis-trimethylsilanyl-7H-3,4-dithia-7-sila-cyclopenta[a]pentalene
• 英文别名: (7,7-Dimethyl-10-trimethylsilyl-3,11-dithia-7-silatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraen-4-yl)-trimethylsilane
• CAS: 1187970-50-8
• 化学式: C₁₆H₂₆S₂Si₃
• 分子量: 366.771
• InChiKey: XHMZDCBUDWHPRC-UHFFFAOYSA-N

物化性质

• 沸点：
  394.2±42.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  7,7-dimethyl-2,5-bis-trimethylsilanyl-7H-3,4-dithia-7-sila-cyclopenta[a]pentalene 在 一氯化碘 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 6.0h， 以65%的产率得到4,10-Diiodo-7,7-dimethyl-3,11-dithia-7-silatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene
  参考文献：
  名称：

  Palladium-Catalyzed Cross-Coupling Reactions of Dithienosilole with Indium Reagents: Synthesis and Characterization of Dithienosilole Derivatives and Their Application to Organic Light-Emitting Diodes

  摘要：

  Three dithienosilole (DTS) derivatives bearing naphthyl segments, 5,5'-dinaphthyl-1,1-dimethyldithienosilol (1), 5,5'-dinaphthyl-l-methyl-l-phenyldithienosilole (2), and 5,5'-dinaphthyl-1,1-diphenyldithienosilol (3), are prepared through Pd(II)-catalyzed cross-coupling using an organoindium reagent as a nucleophile. The molecular structure of 3 is confirmed by single-crystal X-ray analysis. In addition, thermal, photophysical, and electrochemical properties for all three compounds are systematically investigated. The introduction of naphthyl segments into the DTS framework leads to an excellent enhancement of thermal stability with relatively high glass transition (T(g): 87 degrees C) and decomposition temperatures (T(d): 320-380 degrees C). A red shift in both absorption and emission is observed in the DTS series as the 1,1-substituents on the ring silicon atom become more electronegative. On the basis of absorption spectra and DFT/TDDFT calculations, intense green photoluminescence observed for all compounds can be attributed to the effective pi-pi* transition of the DTS and naphthyl group with a small contribution of the sigma* orbital of the exocyclic Si-C bond. The electron-transporting properties of 1, 2, and 3 were evaluated by the performance of organic light-emitting diodes (OLEDs), comprising 4,4',4 ''-tris(N-(2-naphthyl)-N-phenylamino)triphenylamine (2-TNA-TA) as hole-injection layer, 4,4'-bis(N-phenyl-1-naphthylamino)biphenyl (NPB) as hole-transport layer, 10-(2-benzothiazolyl)-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-benzo[l]pyrano[678-ij]quinolizin]-11-one(C545T)/tris(8-quinolinato)aluminum (Alq(3)) as emitting layer, and the DTS series as electron-transporting layer, respectively. The device shows intense green emission with a high efficiency of 8.0 cd/A at 1000 cd/m(2).

  DOI：

  10.1021/om100222b
• 作为产物：
  描述：

  3,3'-二溴-2,2'-联噻吩 在 正丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 为溶剂， 反应 3.0h， 生成 7,7-dimethyl-2,5-bis-trimethylsilanyl-7H-3,4-dithia-7-sila-cyclopenta[a]pentalene
  参考文献：
  名称：

  Substituted oligo- or polythiophenes

  摘要：

  描述了一种制备取代2,2'-二硫代苯的方法，该方法包括步骤(a)、(c)和可选步骤(b)和(d)：a)将具有以下结构式的化合物与适当的有机锂化合物发生反应，优选为Li-烷基或Li-烷基胺；b)可选地将锂与从Mg1、Zn和Cu中选择的另一金属进行交换；c)将在步骤(a)或(b)中获得的金属化中间体与适当的亲电试剂发生反应，该亲电试剂为CO2或醛（加成反应），或化合物Y'-R17或Y'-R18-Z（取代反应），其中R17和R18如权利要求1所定义；并可选地d)修改在步骤(c)中获得的产物，例如通过引入一个或多个共轭基团Y环闭合在适当的一价残基R17之间，交换或延伸功能基团或取代基团，例如在R17或R18中的羰基加成或羰基取代。所得产物，包括或对应的聚合物，是优秀的导电材料

  公开号：

  US08436208B2

文献信息

• Substituted oligo- or polythiophenes
  申请人：Kirner Hans Jürg

  公开号：US08436208B2

  公开（公告）日：2013-05-07

  A process for the preparation of a substituted 2,2′-dithiophene is described, which process comprises the steps (a), (c) and optional steps (b) and (d): a reaction of a compound of the formula: with a suitable lithium organic compound, preferably Li-alkyl or Li-alkylamide; b) optional exchange of lithium against another metal selected from Mg1 Zn and Cu; c) reaction of the metallated intermediate obtained in step (a) or (b) with a suitable electrophil, which is CO2 or an aldehyde (addition reaction), or a compound Y′—R17 or Y′—R18-Z (substitution reaction), where R17 and R18 are as defined in claim 1; and optionally d) modification of the product obtained in step (c), e.g. by introducing one or more conjugating moieties Y ring closure between suitable monovalent residues R17, exchange or extension of functional groups or substituents such as addition to carbonyl or substitution of carbonyl in R17 or R18. The products, including or corresponding polymers, are excellent conducting materials

  描述了一种制备取代2,2'-二硫代苯的方法，该方法包括步骤(a)、(c)和可选步骤(b)和(d)：a)将具有以下结构式的化合物与适当的有机锂化合物发生反应，优选为Li-烷基或Li-烷基胺；b)可选地将锂与从Mg1、Zn和Cu中选择的另一金属进行交换；c)将在步骤(a)或(b)中获得的金属化中间体与适当的亲电试剂发生反应，该亲电试剂为CO2或醛（加成反应），或化合物Y'-R17或Y'-R18-Z（取代反应），其中R17和R18如权利要求1所定义；并可选地d)修改在步骤(c)中获得的产物，例如通过引入一个或多个共轭基团Y环闭合在适当的一价残基R17之间，交换或延伸功能基团或取代基团，例如在R17或R18中的羰基加成或羰基取代。所得产物，包括或对应的聚合物，是优秀的导电材料
• Palladium-Catalyzed Cross-Coupling Reactions of Dithienosilole with Indium Reagents: Synthesis and Characterization of Dithienosilole Derivatives and Their Application to Organic Light-Emitting Diodes
  作者：Hwasoon Jung、Hyonseok Hwang、Ki-Min Park、Jinho Kim、Dong-Ha Kim、Youngjin Kang

  DOI：10.1021/om100222b

  日期：2010.6.28

  Three dithienosilole (DTS) derivatives bearing naphthyl segments, 5,5'-dinaphthyl-1,1-dimethyldithienosilol (1), 5,5'-dinaphthyl-l-methyl-l-phenyldithienosilole (2), and 5,5'-dinaphthyl-1,1-diphenyldithienosilol (3), are prepared through Pd(II)-catalyzed cross-coupling using an organoindium reagent as a nucleophile. The molecular structure of 3 is confirmed by single-crystal X-ray analysis. In addition, thermal, photophysical, and electrochemical properties for all three compounds are systematically investigated. The introduction of naphthyl segments into the DTS framework leads to an excellent enhancement of thermal stability with relatively high glass transition (T(g): 87 degrees C) and decomposition temperatures (T(d): 320-380 degrees C). A red shift in both absorption and emission is observed in the DTS series as the 1,1-substituents on the ring silicon atom become more electronegative. On the basis of absorption spectra and DFT/TDDFT calculations, intense green photoluminescence observed for all compounds can be attributed to the effective pi-pi* transition of the DTS and naphthyl group with a small contribution of the sigma* orbital of the exocyclic Si-C bond. The electron-transporting properties of 1, 2, and 3 were evaluated by the performance of organic light-emitting diodes (OLEDs), comprising 4,4',4 ''-tris(N-(2-naphthyl)-N-phenylamino)triphenylamine (2-TNA-TA) as hole-injection layer, 4,4'-bis(N-phenyl-1-naphthylamino)biphenyl (NPB) as hole-transport layer, 10-(2-benzothiazolyl)-1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-benzo[l]pyrano[678-ij]quinolizin]-11-one(C545T)/tris(8-quinolinato)aluminum (Alq(3)) as emitting layer, and the DTS series as electron-transporting layer, respectively. The device shows intense green emission with a high efficiency of 8.0 cd/A at 1000 cd/m(2).