2,6-dibromo-4,4-dimethyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene | 1314116-06-7

• 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: 2,6-dibromo-4,4-dimethyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene
• 英文别名: 2,6-dibromo-4,4-dimethylcyclopenta[2,1-b:3,4-b']dithiophene；4,10-Dibromo-7,7-dimethyl-3,11-dithiatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene；4,10-dibromo-7,7-dimethyl-3,11-dithiatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene
• CAS: 1314116-06-7
• 化学式: C₁₁H₈Br₂S₂
• 分子量: 364.125
• InChiKey: NZRNSJJUKMPEOO-UHFFFAOYSA-N

物化性质

• 沸点：
  397.0±42.0 °C(Predicted)
• 密度：
  1.838±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  2,6-dibromo-4,4-dimethyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene 在 正丁基锂 、 四甲基乙二胺 、 5%-palladium/activated carbon 、 水 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 39.5h， 生成 2,6-bis(diphenylhydroxysilyl)-4,4-dimethylcyclopenta[2,1-b:3,4-b']dithiophene
  参考文献：
  名称：

  Synthesis and properties of cyclopentadithiophene-based poly(silarylenesiloxane) derivatives

  摘要：

  Poly(silarylenesiloxane) derivatives with 4,4-dimethylcyclopenta[2,1-b:3,4-b']dithiophene moiety, bearing dimethyl- (P1), methylphenyl- (P2) and diphenyl- (P3) substituents on silyl moieties, were prepared via polycondensation of the corresponding disilanol monomers, that is, 2,6-bis(dimethylhydroxysilyl)-4,4-dimethylcyclopenta[2,1 -b:3,4-b']dithiophene (M1), 2,6-bis(methylphenylhydroxysilyl)-4,4-dimethylcyclopenta[2,1-b:3,4-b']dithiophene (M2), and 2,6-bis(diphenylhydroxysilyl)-4,4-dimethylcyclopenta[2,1-b:3,4-b']dithiophene (M3), respectively. P1 P3 exhibited the good solubility in common organic solvents, such as benzene, toluene, chloroform, dichloromethane, THF, and so on. The glass transition temperatures (T(g)s) of P1, P2 and P3 were determined by differential scanning calorimetry to be 56, 97 and 137 degrees C, respectively, depending on the substituent on the silyl moieties. No melting temperatures (T(m)s) of P1, P2 and P3 were observed, suggesting the obtained P1 P3 are amorphous polymers. The temperatures at 5% weight loss (T(d5)s) of P1, P2 and P3 were 460, 459 and 479 degrees C, respectively, indicating that the larger number of phenyl group on the silyl moieties resulted in the better thermostability. Bathochromic and hyperchromic effects were observed in the absorption and fluorescence spectra by introducing silyl substituents onto 4,4-dimethylcyclopenta[2,1-b:3,4-b']dithiophene moiety. In addition, the bathochromic shift of the maximum absorption (lambda(abs)) and the increase in the fluorescence quantum yield (phi(F)) were observed by the introduction of phenyl group onto the silyl moieties. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2011.09.031
• 作为产物：
  描述：

  环戊联噻吩 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 、 potassium iodide 、 potassium hydroxide 作用下， 以 氯仿 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 2,6-dibromo-4,4-dimethyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene
  参考文献：
  名称：

  一种有机发光材料及其有机发光器件

  摘要：

  本发明公开了一种有机发光材料及其有机发光器件，属于有机光电材料技术领域。本发明有机发光材料以2,6‑二氨基‑4H‑环戊二烯并二噻吩1,1,7,7‑四氧化物为主体结构，主体结构通过连接不同的配体基团，从而得到一种有机发光材料，同时具有电子和空穴双极性传输能力。采用本发明有机发光材料制备的有机发光器件，具有更高的发光效率、更低的驱动电压、更优良的膜稳定性及热稳定性、且光色均匀。

  公开号：

  CN107216341A

文献信息

• Hemilabile Ligands as Mechanosensitive Electrode Contacts for Molecular Electronics
  作者：Nicolò Ferri、Norah Algethami、Andrea Vezzoli、Sara Sangtarash、Maeve McLaughlin、Hatef Sadeghi、Colin J. Lambert、Richard J. Nichols、Simon J. Higgins

  DOI：10.1002/anie.201906400

  日期：2019.11.11

  allow reversible monodentate⇄bidentate contact transitions as the junction is modulated in size. We observed an up to ≈100-fold sensitivity boost of the (methylthio)thiophene-terminated molecular wire compared with its non-hemilabile (methylthio)benzene counterpart and demonstrate a previously unexplored application of hemilabile ligands to molecular electronics.

  对压缩或伸长敏感的单分子结是一类新兴的纳米机电系统（NEMS）。尽管可以设计分子-电极界面来赋予这种功能，但迄今为止，大多数研究都依赖于定义不明确的相互作用。我们通过合成分子线专注于这个问题，该分子线设计为具有基于（甲硫基）噻吩基团的化学定义的半不稳定接触。我们测量了它们的电导随结尺寸的变化，并观察到随着结被压缩和拉伸，电导变化最多两个数量级。弱配位的噻吩硫基与电极之间的局部相互作用是所观察到的效应的原因，并且由于结的尺寸受到调节，因此可逆的单齿-双齿接触转变。
• 噻吩类化合物、其制备方法与应用、钙钛矿太 阳电池
  申请人：中国科学院长春应用化学研究所

  公开号：CN106432265B

  公开（公告）日：2018-06-01

  本发明提供了一种噻吩类化合物、其制备方法与应用、钙钛矿太阳电池，该噻吩类化合物如式(I)所示，R1与R1′各自独立地为H、C1～C12烃基或C1～C12烷氧基；R2、R3与R4各自独立地为H、C1～C12烃基、C1～C12烷氧基或C1～C12烷氧基取代的苯基。与现有技术相比，本发明提供的噻吩类化合物为并三噻吩、噻吩并吡咯或双噻吩并环戊二烯与两个三芳胺共轭偶联的结构，使其空穴迁移率较高，进而提高使具有该噻吩类化合物制备而成的空穴输运层的钙钛矿太阳电池具有较高的能量转换效率。
• PI-ELECTRON CONJUGATED BLOCK COPOLYMER AND PHOTOELECTRIC CONVERSION ELEMENT
  申请人：Inagaki Takuya

  公开号：US20140084220A1

  公开（公告）日：2014-03-27

  Provided is a conjugated block copolymer that is capable of morphology control and that can achieve superior conversion efficiency. A π-electron conjugated block copolymer contiguously or non-contiguously bonding polymer block (A) involving a monomer unit having in a portion of a chemical structure at least one heteroaryl skeleton selected from a thiophene, a fluorine, a carbazole, a dibenzosilole and a dibenzogermole; and a polymer block (B) involving a monomer unit similarly having at least one heteroaryl skeleton; wherein the polymer block (A) comprises a homopolymer block of a monomer unit having a substituent R nA that is an alkoxy group or an alkyl group having 1-18 carbon atoms, and the polymer block (B) comprises a copolymer block of at least two different each other types of monomer units having substituent R nB selected from an alkoxy group or an alkyl group having 1-18 carbon atoms, which may be substituted with an alkoxy group, a halogen atom, a hydroxyl group, an amino group, a thiole group, a silyl group, an ester group, an aryl group, hetero aryl group.

  提供的是一种共轭嵌段共聚物，能够控制形态并实现更高的转化效率。该共轭嵌段共聚物由连续或非连续键合的聚合物块（A）和聚合物块（B）组成，聚合物块（A）包括至少在化学结构的一部分中具有来自噻吩、氟、咔唑、二苯基硅烷和二苯基锗烷中至少一个杂环骨架的单体单元，其中聚合物块（A）包括单体单元的同源聚合物块，该单体单元具有取代基RnA，该取代基为具有1-18个碳原子的烷氧基或烷基，并且聚合物块（B）包括至少两种不同类型的单体单元的共聚物块，该单体单元具有取代基RnB，该取代基为具有1-18个碳原子的烷氧基或烷基，可以用烷氧基、卤素原子、羟基、氨基、硫醇基、硅基、酯基、芳基、杂芳基进行取代。
• From Peripheral Stereogenic Center to Axial Chirality: Synthesis of 3‐Arylthiophene Atropisomers
  作者：Lin Li、Junwei Xi、Biqiong Hong、Zhenhua Gu

  DOI：10.1002/adsc.202200957

  日期：2023.2.21

  A practical synthesis of axially chiral biaryls via chirality transfer from peripheral stereogenic carbon centers is reported. In contrast to the traditional aromatization process of a non-aromatic structure with ipso stereogenic centers, this method is based on a Pd-catalyzed carbon-carbon bond cleavage/ring-opening reaction of optically active 8H-indenothiophen-8-ols with an achiral ligand, enabling

  报道了通过从外围立体异构碳中心进行的手性转移来实际合成轴向手性联芳基化合物。与具有ipso手性中心的非芳香结构的传统芳构化过程相比，该方法基于 Pd 催化的具有光学活性的 8 H -茚并噻吩 -8-醇的碳 - 碳键裂解/开环反应非手性配体，能够以高对映选择性合成高度功能化的 3-芳基噻吩阻转异构体。
• Fluorescent cyclopentadithiophene derivatives having phenyl-substituted silyl moieties
  作者：Hitoshi Hanamura、Ryoko Haneishi、Nobukatsu Nemoto

  DOI：10.1016/j.tetlet.2011.05.128

  日期：2011.8

  4,4-Dimethylcyclopenta[2,1-b:3,4-b']dithiophene derivatives bearing trimethyl-, dimethylphenyl-, diphenylmethyl-, or triphenyl-silyl moieties were synthesized. The introduction of the silyl moieties onto cyclopenta[2,1-b:3,4-b']dithiophene induced fluorescent emission as well as the bathochromic shift of wavelength at the maximum absorption and fluorescence. It was found that the larger number of phenyl group on silyl moiety resulted in the higher fluorescence quantum yield. (C) 2011 Elsevier Ltd. All rights reserved.