2,5-dibromothiophene-3,4-dicarbonyl dichloride | 197370-01-7

• 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: 2,5-dibromothiophene-3,4-dicarbonyl dichloride
• 英文别名: 2,5-dibromothiophene-3,4-dicarboxylic acid chloride；2,5-dibromothiophene-3,4-dicarbonyl chloride
• CAS: 197370-01-7
• 化学式: C₆Br₂Cl₂O₂S
• 分子量: 366.845
• InChiKey: PGJDPMCXBWJJDG-UHFFFAOYSA-N

物化性质

• 沸点：
  375.6±42.0 °C(Predicted)
• 密度：
  2.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-dibromothiophene-3,4-dicarbonyl dichloride 在 三氯化铝 、 tris(dibenzylideneacetone)dipalladium (0) 、 三苯胂 、 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.67h， 生成
  参考文献：
  名称：

  Imine-Bridged Planar Poly(phenylenethiophene)s and Polythiophenes

  摘要：

  Synthetic routes to soluble planar poly(phenylenethiophene)s and polythiophenes are described. The main polymer backbones are synthesized via Pd(0)-catalyzed couplings of the electron-rich N,N'-(bis-tert-butoxycarbonyl)-3,4-diamino-2,5-bis(tri-n-butylstannyl)thiophene with electron-deficient aryldibromodiones. The prebridged polymers have bathochromically shifted absorptions due to donor/acceptor interactions between the consecutive repeat units. Upon exposure of the polymers to trifluoroacetic acid or titanium tetrachloride, imine bridges are formed that force the consecutive units into planarity. The bridging units are sp(2)-hybridized, thus allowing for greater electron delocalization between the consecutive aryl units. The syntheses of model trimeric systems were conducted to provide further data for assessing the optical properties of the polymers. Protonation of the imine moieties causes bathochromic shifts of >100 nm in several cases. The effect is explained by an intramolecular charge transfer. Thus these arrangements of planar structures with imine bridges serve as optically based proton sensors with spectral shift differences far-exceeding those of nonplanar imine-containing polymers.

  DOI：

  10.1021/ja964223u
• 作为产物：
  描述：

  2,5-二溴-噻吩-3,4-二羧酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 2,5-dibromothiophene-3,4-dicarbonyl dichloride
  参考文献：
  名称：

  A D–A copolymer of dithienosilole and a new acceptor unit of naphtho[2,3-c]thiophene-4,9-dione for efficient polymer solar cells

  摘要：

  一种强吸电子单元萘并[2,3-c]噻吩-4,9-二酮与二噻吩硅氧烷共聚，得到一种具有窄带隙和较低HOMO能级的D-A共聚物PDTSNTDO。基于PDTSNTDO的器件的PCE达到5.21%，开路电压高达0.88V。

  DOI：

  10.1039/c1cc14132e

文献信息

• Benzodithiophene and Imide-Based Copolymers for Photovoltaic Applications
  作者：Wade A. Braunecker、Zbyslaw R. Owczarczyk、Andres Garcia、Nikos Kopidakis、Ross E. Larsen、Scott R. Hammond、David S. Ginley、Dana C. Olson

  DOI：10.1021/cm2038427

  日期：2012.4.10

  Conjugated alternating copolymers were designed with low optical band gaps for organic photovoltaic (OPV) applications by considering quinoid resonance stabilization. Copolymers of thienoisoindoledione (TID) and benzodithiophene (BDT) had appreciably lower band gaps (by ∼0.4 eV) than copolymers of thienopyrroledione (TPD) and BDT. In addition to intramolecular charge transfer stabilization (i.e., the

  考虑到醌型共振稳定性，共轭交替共聚物的光学带隙低，设计用于有机光伏（OPV）应用。噻吩异吲哚二酮（TID）和苯并二噻吩（BDT）的共聚物的带隙（约0.4eV）比噻吩并吡咯二酮（TPD）和BDT的共聚物低得多。除了分子内电荷转移稳定化（即“推挽”效应）外，前者共聚物的醌型共振结构还通过增加异吲哚单元中的芳香族共振能而得以稳定。另外，可以通过对BDT单体进行化学修饰来调节共聚物的HOMO含量，从而在光伏器件中产生大于1 V的开路电压。尽管优化了带隙，但含TID的聚合物仍显示出较低的光电导性，由时间分辨的微波电导率确定，与TPD类似物相比，器件效率降低（2.1％对4.8％）。这些结果部分归因于形态，因为计算模型表明TID共聚物具有扭曲的主链，并且X射线衍射数据表明聚合物膜未形成有序域，而TPD共聚物的平面性明显更高，并显示出形成了部分有序域。 。
• Synthesis, properties, and photovoltaic characteristics of p-type donor copolymers having fluorine-substituted benzodioxocyclohexene-annelated thiophene
  作者：Yutaka Ie、Koki Morikawa、Makoto Karakawa、Naresh B. Kotadiya、Gert-Jan A. H. Wetzelaer、Paul W. M. Blom、Yoshio Aso

  DOI：10.1039/c7ta05822e

  日期：——

  increased by increasing the number of introduced fluorine atoms and the HOMO and LUMO energy levels of copolymers are fine-tuned depending on the acceptor units. Organic photovoltaics based on blend films of these D–A copolymers and [6,6]-phenyl-C71-butyric acid methyl ester show photovoltaic responses with a power conversion efficiency of up to 7.30%. Investigation of the device physics shows that

  将受体单元掺入π-共轭体系中是调节有机半导体材料的最高占据分子轨道（HOMO）和最低未占据分子轨道（LUMO）能级的有效方法。我们报告了一系列氟取代的苯并二氧代环己烯基化的噻吩受体单元的设计，并报告了基于这些受体单元和二噻吩甲硅油作为供体单元的供体-受体（DA）型共聚物的合成。共聚物的物理测量表明，通过增加引入的氟原子数可以提高D–A特性，并根据受体单元对共聚物的HOMO和LUMO能级进行微调。基于这些D–A共聚物和[6，6]-苯基-C71-丁酸甲酯显示出光伏响应，功率转换效率高达7.30％。对器件物理特性的研究表明，性能主要受空穴传输的限制，这为材料设计方向向OPV性能的提高提供了见识。这些结果证明了氟取代的苯并二氧代环己烯退火的噻吩作为有机半导体材料中的受体单元的潜力。
• Thieno[3,4-<i>c</i> ]phosphole-4,6-dione: A Versatile Building Block for Phosphorus-Containing Functional π-Conjugated Systems
  作者：Youhei Takeda、Kota Hatanaka、Takuya Nishida、Satoshi Minakata

  DOI：10.1002/chem.201602392

  日期：2016.7.18

  A versatile phosphorus‐containing π‐conjugated building block, thieno[3,4‐c]phosphole‐4,6‐dione (TPHODO), has been developed. The utility of this simple but hitherto unknown building block has been demonstrated by preparing novel functional organophosphorus compounds and bandgap‐tunable conjugated polymers.

  已经开发了一种通用的含磷π共轭结构单元，thieno [3,4- c ]磷-4,6-二酮（TPHODO）。通过制备新型功能性有机磷化合物和能带隙可调的共轭聚合物，已证明了这种简单但迄今未知的结构单元的实用性。
• Effects of a heteroatomic benzothienothiophenedione acceptor on the properties of a series of wide-bandgap photovoltaic polymers
  作者：Xinxin Huang、Kangkang Weng、Lijun Huo、Bingbing Fan、Chunhe Yang、Xiaobo Sun、Yanming Sun

  DOI：10.1039/c6tc02915a

  日期：——

  The effect of heteroatoms (O, S and Se) on the optical, electronic and photovoltaic performance of a series of wide-bandgap copolymers has been studied.

  杂原子（O、S和Se）对一系列宽带隙共聚物的光学、电子和光伏性能的影响已被研究。
• Alkylthio-substitution on wide bandgap conjugated polymers for non-fullerene acceptor-based organic solar cells
  作者：Kiyoung Park、Cheng Sun、Soo-Young Jang、Canjie Wang、Jiaqiang Li、Quinghua Zhao、Hongkyu Kang、Kwanghee Lee、Soon-Ki Kwon、Yun-Hi Kim

  DOI：10.1016/j.dyepig.2020.108601

  日期：2020.11

  showed a wide bandgap of 1.76–1.81 eV with broad absorption range from 300–700 nm and were used as donor polymers in organic photovoltaic (OPV) devices with the non-fullerene acceptor, IT-M. By increasing the number of alkythio groups in their chemical structures, the HOMO levels of the polymers down-shifted as −5.46 eV, −5.51 eV and −5.56 eV, and consequently, the VOC of the OPV cells gradually increased

  我们研究了三种共轭聚合物PSBDB-T，P1SBDB-TS和PSBDB-TS，它们具有不同数量的烷硫基。该聚合物显示出1.76–1.81 eV的宽带隙，吸收范围在300–700 nm之间，并用作带有非富勒烯受体IT-M的有机光伏（OPV）装置的给体聚合物。通过增加其化学结构中烷硫基的数量，聚合物的HOMO能级下移为-5.46 eV，-5.51 eV和-5.56 eV，因此，OPV细胞的V OC逐渐增加至0.91 V， PSBDB-T，P1SBDB-TS和PSBDB-TS分别为0.92 V和0.94V。具有三个烷硫基的P1SBDB-TS（两个用于苯并[1,2- b：4,5- b ']二噻吩，一个用于苯并[1,2- c：4,5- c '] dithiophene-4,8-​​dione unit）由于其高结晶度和在本体异质结体系中的低双分子重组，在三种聚合物中显示出最佳的功率转换效率，为6.88％。