2,7-Diiodobenzo<1,2-b:4,3-b'>dithiophene | 70218-29-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2,7-Diiodobenzo<1,2-b:4,3-b'>dithiophene
• 英文别名: 2,2'-diiodobenzodithiophene；2,7-diiodobenzo[1,2-b:4,3-b′]dithiophene；2,7-diiodo-benzo[1,2-b:4,3-b']dithiophene；2,7-Diiodothieno[3,2-e][1]benzothiole
• CAS: 70218-29-0
• 化学式: C₁₀H₄I₂S₂
• 分子量: 442.083
• InChiKey: IMRJRYXBIIBJRM-UHFFFAOYSA-N

物化性质

• 熔点：
  176-177 °C(Solv: chloroform (67-66-3))
• 沸点：
  488.4±40.0 °C(Predicted)
• 密度：
  2.445±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  2,7-Diiodobenzo<1,2-b:4,3-b'>dithiophene 在 四(三苯基膦)钯 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.0h， 生成 2,7-Bis(dicyanomethylene)-2,7-dihydrobenzo<1,2-b:4,3-b'>dithiophene
  参考文献：
  名称：

  Novel Electron Acceptors Bearing a Heteroquinonoid System. 4. Syntheses, Properties, and Charge-Transfer Complexes of 2,7-Bis(dicyanomethylene)-2,7-dihydrobenzo[2,1-b:3,4-b']dithiophene, 2,7-Bis(dicyanomethylene)-2,7-dihydrobenzo[1,2-b:4,3-b']dithiophene, and 2,6-Bis(dicyanomethylene)-2,6-dihydrobenzo[1,2-b:4,5-b']dithiophene

  摘要：

  The three title compounds were prepared as novel hetero-TCNQ electron accepters comprising the quinonoid skeletons of different benzodithiophene types between two dicyanomethylene groups. On the basis of cyclic voltammetry, they have electron affinities comparable to or stronger than that of TCNQ. In addition, the extensive building blocks serve to induce the effective reduction of on-site coulombic repulsion. They thus behaved as superior electron accepters for forming electrically conductive charge-transfer complexes. In particular, 2,7-bis(dicyanomethylene)-2,7-dihydrobenzo-[2,1-b:3,4-b']dithiophene was the most tractable in terms of stability and solubility, giving a variety of conductive complexes with typical electron donors of TTT, TTF,and TPBP types. Most of these complexes showed a characteristic broad electronic transition in the infrared region of 2.9-4.0 kcm(-1), supporting the idea that their crystal structures assume a stacking form of segregated donor and acceptor columns with mixed valence states.

  DOI：

  10.1021/jo00090a027
• 作为产物：
  描述：

  benzo[1,2-b;4,3-b']dithiophene 在 正丁基锂 、 四甲基乙二胺 、 碘 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以83%的产率得到2,7-Diiodobenzo<1,2-b:4,3-b'>dithiophene
  参考文献：
  名称：

  Novel Electron Acceptors Bearing a Heteroquinonoid System. 4. Syntheses, Properties, and Charge-Transfer Complexes of 2,7-Bis(dicyanomethylene)-2,7-dihydrobenzo[2,1-b:3,4-b']dithiophene, 2,7-Bis(dicyanomethylene)-2,7-dihydrobenzo[1,2-b:4,3-b']dithiophene, and 2,6-Bis(dicyanomethylene)-2,6-dihydrobenzo[1,2-b:4,5-b']dithiophene

  摘要：

  The three title compounds were prepared as novel hetero-TCNQ electron accepters comprising the quinonoid skeletons of different benzodithiophene types between two dicyanomethylene groups. On the basis of cyclic voltammetry, they have electron affinities comparable to or stronger than that of TCNQ. In addition, the extensive building blocks serve to induce the effective reduction of on-site coulombic repulsion. They thus behaved as superior electron accepters for forming electrically conductive charge-transfer complexes. In particular, 2,7-bis(dicyanomethylene)-2,7-dihydrobenzo-[2,1-b:3,4-b']dithiophene was the most tractable in terms of stability and solubility, giving a variety of conductive complexes with typical electron donors of TTT, TTF,and TPBP types. Most of these complexes showed a characteristic broad electronic transition in the infrared region of 2.9-4.0 kcm(-1), supporting the idea that their crystal structures assume a stacking form of segregated donor and acceptor columns with mixed valence states.

  DOI：

  10.1021/jo00090a027

文献信息

• Synthesis and Functionalization of Novel Tetrathia[7]helicenes as New Push-Pull Systems
  作者：Stefano Maiorana、Emanuela Licandro、Clara Rigamonti、Maria Ticozzelli、Marco Monteforte、Clara Baldoli、Clelia Giannini

  DOI：10.1055/s-2006-950222

  日期：2006.11

  The synthesis of new functionalized 1,2-bis(benzodithienyl)ethenes as well as the preparation of the new tetrathia[7]helicenes are described. The helicenes reported are new chiral push-pull molecules, with potential application in optoelectronics.

  描述了新型功能化1,2-双(苯并二噻吩基)乙烯的合成以及新型四硫杂[7]螺烯的制备。报道的螺旋烯是新的手性推挽分子，在光电子学中具有潜在应用。
• Ligand‐Free Suzuki–Miyaura Cross‐Coupling Reactions in Deep Eutectic Solvents: Synthesis of Benzodithiophene Derivatives and Study of their Optical and Electrochemical Performance
  作者：Valentina Pelliccioli、Giuseppe Dilauro、Sara Grecchi、Serena Arnaboldi、Claudia Graiff、Filippo M. Perna、Paola Vitale、Emanuela Licandro、Alessandro Aliprandi、Silvia Cauteruccio、Vito Capriati

  DOI：10.1002/ejoc.202000889

  日期：2020.12.7

  Valuable π‐conjugated benzodithiophene derivatives have been prepared through a ligand‐free Suzuki–Miyaura cross‐coupling reaction, under mild aerobic conditions, in deep eutectic solvents (DESs) as environmentally responsible reaction media, and their optical and electrochemical properties were investigated.

  在温和的需氧条件下，通过无配体的Suzuki-Miyaura交叉偶联反应，在对环境负责的深共溶剂（DES）中制备了宝贵的π共轭苯并二噻吩衍生物，并对其光学和电化学性质进行了研究。
• Enantioselective Synthesis of Dithia[5]helicenes and their Postsynthetic Functionalization to Access Dithia[9]helicenes
  作者：Valentina Pelliccioli、Thierry Hartung、Martin Simon、Christopher Golz、Emanuela Licandro、Silvia Cauteruccio、Manuel Alcarazo

  DOI：10.1002/anie.202114577

  日期：2022.2

  and two successive alkyne hydroarylation events allows the assembly of dithia[5]helicenes with excellent enantioselectivity. Moreover, regioselective postsynthetic bromination of the dithia[5]helicene products generates starting materials for the efficient preparation of even more π-expanded systems, such as dithia[9]helicenes.

  使用带有 α-阳离子亚膦酸酯作为辅助配体的手性 Au 催化剂和两个连续的炔烃加氢芳基化事件，可以组装具有优异对映选择性的二硫杂[5]螺旋烯。此外，二硫杂[5]螺烯产物的区域选择性合成后溴化产生了用于有效制备甚至更多π-展开的系统的起始材料，例如二硫杂[9]螺烯。
• V-shaped nematogens with the “magic bent angle”
  作者：Jens Seltmann、Kathrin Müller、Susanne Klein、Matthias Lehmann

  DOI：10.1039/c1cc10577a

  日期：——

  V-shaped nematogens 1a–c and 2a–b with benzodithiophene bending units have been synthesised. The derivatives 1a–c comprise a flat core with a bending angle of 109°, which is almost the tetrahedral angle proposed to be optimal in the realization of mesogens forming a biaxial nematic thermotropic mesophase.

  我们合成了具有苯并二噻吩弯曲单元的 V 形介子 1aâc 和 2aâb。衍生物 1aâc 包含一个弯曲角度为 109° 的扁平内核，这几乎是在实现形成双轴向列热相中间体的中间体时所建议的最佳四面体角度。
• Ether-based polymers as photo-crosslinkable dielectrics
  申请人：BASF SE

  公开号：US10020456B2

  公开（公告）日：2018-07-10

  Polymers comprising at least one unit of formula (1) wherein n is 0 or 1, m and p are independently from each other 0, 1, 2, 3, 4, 5 or 6, provided that the sum of n, m and p is at least 2, and n and p are not 0 at the same time, Ar1 and Ar2 are independently from each other C6-14-arylene or C6-14-aryl, which may be substituted with 1 to 4 substituents independently selected from the group consisting of C1-30-alkyl, C2-30-alkenyl, C2-30-alkynyl, C5-8-cycloalkyl, C6-14-aryl and 5 to 14 membered heteroaryl, and X1, X2 and X3 are independently from each other and at each occurrence O or S, compositions comprising these polymers, and electronic devices comprising a layer formed from the compositions. Preferably, the electronic device is an organic field effect transistor and the layer is the dielectric layer.

  至少包含一个式 (1) 单元的聚合物 其中 n 为 0 或 1，m 和 p 互不独立地为 0、1、2、3、4、5 或 6，条件是 n、m 和 p 之和至少为 2，且 n 和 p 不同时为 0，Ar1 和 Ar2 互不独立地为 C6-14- 芳基或 C6-14- 芳基、C1-30-烷基、C2-30-烯基、C2-30-炔基、C5-8-环烷基、C6-14-芳基和 5-14 位杂芳基组成的组中，可被 1 至 4 个取代基取代；X1、X2 和 X3 相互独立，且每次出现时均为 O 或 S。电子器件最好是有机场效应晶体管，层最好是介电层。