2,6-二溴-4,4-二辛基环戊并[2,1-b:3,4-b’]二噻吩 | 478404-10-3

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 2,6-二溴-4,4-二辛基环戊并[2,1-b:3,4-b’]二噻吩
• 中文别名: 2,6-二溴-4,4-二辛基-4H-环戊[2,1-b;3,4-b']二噻吩
• 英文名称: 2,6-dibromo-4,4-dioctyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene
• 英文别名: 2,6-Dibromo-4,4-dioctyl-4H-cyclopenta[1,2-b:5,4-b']dithiophene；4,10-dibromo-7,7-dioctyl-3,11-dithiatricyclo[6.3.0.02,6]undeca-1(8),2(6),4,9-tetraene
• CAS: 478404-10-3
• 化学式: C₂₅H₃₆Br₂S₂
• 分子量: 560.501
• InChiKey: IGJLWOFZCHUCMY-UHFFFAOYSA-N

物化性质

• 沸点：
  560.0±50.0 °C(Predicted)
• 密度：
  1.299

计算性质

• 辛醇/水分配系数(LogP)：
  13.5
• 重原子数：
  29
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2,6-二溴-4,4-二辛基环戊并[2,1-b:3,4-b’]二噻吩 在 盐酸 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 反应 16.0h， 生成 1,1'-[(4,4-dioctyl-4H-cyclopenta[2,1-b:3,4-b']dithiophene-2,6-diyl)bis(2,2'-bithiene-5',5-diyl)]diheptan-1-one
  参考文献：
  名称：

  Effects of bridging atom and π-bridge length on physical and photovoltaic properties of A–π-D–π-A oligomers for solution-processed organic solar cells

  摘要：

  Synthesis of novel acceptor-donor-acceptor oligomers with electron-withdrawing alkyldicyanovinyl groups linked through an oligothiophene pi-bridge with either dithienosilole or cyclopentadithiophene electron donor units is described. Changing the bridgehead atom from carbon to silicon in the central donor unit leads to a significant change in optical, thermal and structural properties of the oligomers. In addition, elongation of the oligothiophene pi-bridge in the oligomers increases energies of HOMO and LUMO levels and leads to an unexpected hypsochromic shift of their absorption spectrum, because extension of the conjugation length cannot compensate a decrease of the intramolecular charge transfer between the dithienosilole and dicyanovinyl units. Although these minor changes in the chemical structures have a pronounced impact on the morphologies of their blends with PC70BM, the optimized solution-processed organic solar cells based on these small molecules demonstrate similar power conversion efficiencies. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2015.06.026
• 作为产物：
  描述：

  正辛基镁溴盐 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 硫酸 作用下， 以 正辛烷 、 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 62.25h， 生成 2,6-二溴-4,4-二辛基环戊并[2,1-b:3,4-b’]二噻吩
  参考文献：
  名称：

  4, 4' disubstituted 4H-cyclopentadithiophene and new methods for synthesising the same

  摘要：

  公开号：

  EP2397475B1

文献信息

• Highly efficient and facile alkylation of 4H-cyclopenta-[2,1-b:3,4-b′]dithiophene in water
  作者：Telugu Bhim Raju、Peddaboodi Gopikrishna、Parameswar Krishnan Iyer

  DOI：10.1039/c4ra08119f

  日期：——

  A facile and highly economical methodology for the dialkylation of 4H-cyclopenta-[2,1-b:3,4-b′]dithiophene is reported.

  报道了一种简便且高度经济的方法，用于对4H-环戊-[2,1-b:3,4-b′]二硫杂苯进行二烷基化。
• <i>In situ</i> monitoring the thermal degradation of PCPDTBT low band gap polymers with varying alkyl side-chain patterns
  作者：Lidia Marin、Huguette Penxten、Sarah Van Mierloo、Robert Carleer、Laurence Lutsen、Dirk Vanderzande、Wouter Maes

  DOI：10.1002/pola.26920

  日期：2013.11.15

  The degradation pattern of a series of low band gap PCPDTBT polymers under thermal stress is investigated by in situ UV–vis and FT‐IR techniques combined with thermal degradation analysis. Thermogravimetric analysis is used to predetermine the decomposition intervals, revealing that thermolysis occurs in two stages. TG‐TD‐GC/MS shows that loss of the alkyl side chains predominantly happens within the

  通过原位研究了一系列低带隙PCPDTBT聚合物在热应力下的降解方式。UV-vis和FT-IR技术与热降解分析相结合。热重分析用于确定分解间隔，表明热分解发生在两个阶段。TG-TD-GC / MS表明，烷基侧链的损失主要发生在第一个温度范围内，随后聚合物主链发生降解。紫外可见光谱法用于监测加热时光学性质的变化，反映出共轭骨架的热稳定性，而傅立叶变换红外光谱法则用于评估热应力下的化学变化，重点是聚合物的外围。侧链的影响和可能的缺陷，取决于所应用的合成方案，讨论了最终聚合物的热稳定性，并涉及所述材料在有机光伏中的应用。©2013 Wiley Periodicals，Inc. J. Polym。科学，A部分：Polym。化学2013，51，4912-4922
• New routes to poly(4,4-dialkylcyclopentadithiophene-2,6-diyls)Electronic supplementary information (ESI) available: partial MALDI-TOF mass spectrum of polymer 5. See http://www.rsc.org/suppdata/jm/b2/b206477d/
  作者：Paolo Coppo、Domenico C. Cupertino、Stephen G. Yeates、Michael L. Turner

  DOI：10.1039/b206477d

  日期：2002.8.30

  Two new polymerisation routes to poly(4,4-dioctylcyclopentadithiophene-2,6-diyl) are reported. The polymer prepared by Kumada type cross-coupling showed significantly reduced molecular weight over that prepared by direct oxidative polymerisation using iron(III) chloride. The higher molecular weight polymer was shown to have extended conjugation by UV-visible spectroscopy.

  报道了两种新的聚合路线用于聚(4,4-二辛基环戊二噁烯-2,6-二基)的合成。通过Kumada类型的交叉偶联法制备的聚合物显示出分子量明显低于通过使用氯化铁(III)进行直接氧化聚合法制备的聚合物。通过紫外-可见光谱法显示，较高分子量的聚合物具有扩展的共轭结构。
• Near‐Infrared Nonfullerene Acceptors Based on 4 <i>H</i> ‐Cyclopenta[1,2‐ <i>b</i> :5,4‐ <i>b</i> ′]dithiophene for Organic Solar Cells and Organic Field‐Effect Transistors
  作者：Likai Yuan、Shijie Liang、Chengyi Xiao、Qiaomei Chen、Weiwei Li

  DOI：10.1002/asia.202101147

  日期：2021.12.13

  non-fullerene acceptors containing a different number of 4H-cyclopenta[1,2-b : 5,4-b′]dithiophene (CPDT) units. With increasing CPDT units from one to three, a change of energy levels can be clearly observed, and hence, the charge transport polarity was switched from electron-only to ambipolar and hole dominating. As a consequence, these molecules showed distinct photovoltaic performance in organic solar cells

  我们合成了三种非富勒烯受体，其中包含不同数量的 4 H -环戊二烯 [1,2- b  : 5,4- b '] 二噻吩 (CPDT) 单元。随着 CPDT 单元从 1 增加到 3，可以清楚地观察到能级的变化，因此，电荷传输极性从仅电子变为双极性和空穴主导。因此，这些分子在有机太阳能电池中表现出独特的光伏性能。
• 4, 4' DISUBSTITUTED 4H-CYCLOPENTADITHIOPHENE AND NEW METHODS FOR SYNTHESISING THE SAME
  申请人：Vanderzande Dirk

  公开号：US20110313175A1

  公开（公告）日：2011-12-22

  The present preferred embodiments relate to a method for the synthesis of a compound having the following general formula: the method comprising the step of reacting, in presence of a diprotic acid having a negative pKa, a compound having the general formula: wherein R 1 and R 2 are organic groups and wherein X and Y are independently selected from the group consisting of hydrogen, chloro, bromo, iodo, boronic acid, boronate esters, borane, pseudohalogen and organotin. It further relates to compounds so obtained and to compounds resulting from the ring closure of compound (II).

  本发明的首选实施例涉及一种合成具有以下一般式的化合物的方法：该方法包括在具有负pKa的二元酸存在下反应具有以下一般式的化合物：其中R1和R2是有机基团，而X和Y独立地选自氢、氯、溴、碘、硼酸、硼酸酯、硼烷、伪卤素和有机锡的群。它还涉及由化合物（II）环合而成的化合物和由此获得的化合物。