2,6-二碘苯并[1,2-b:4,5-b']二噻吩 | 155904-20-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 2,6-二碘苯并[1,2-b:4,5-b']二噻吩
• 英文名称: 2,6-diiodobenzo[1,2-b:4,5-b']dithiophene
• 英文别名: 2,6-diiodothieno[2,3-f][1]benzothiole
• CAS: 155904-20-4
• 化学式: C₁₀H₄I₂S₂
• 分子量: 442.083
• InChiKey: AWBYFGZHMVWYNF-UHFFFAOYSA-N

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：

  2,6-二碘苯并[1,2-b:4,5-b']二噻吩 在 四(三苯基膦)钯 lead(IV) acetate 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 2,6-Bis(dicyanomethylene)-2,6-dihydrobenzo<1,2-b:4,5-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：

  2,6-bis(trimethylsilyl)benzo[1,2-b:4,5-b']dithiophene 在 一氯化碘 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以82%的产率得到2,6-二碘苯并[1,2-b:4,5-b']二噻吩
  参考文献：
  名称：

  Molecular Modification of 2,6-Diphenylbenzo[1,2-b:4,5-b′]dichalcogenophenes by Introduction of Strong Electron-withdrawing Groups: Conversion from p- to n-Channel OFET Materials

  摘要：

  2,6-Diphenylbenzo[1,2-b:4,5-b′]dithiophene (DPh-BDT) 和 -diselenophene (DPh-BDS) 作为 p 沟道半导体材料，通过在所附苯基中引入氟基、氰基或三氟甲基进行了改性。在对使用这些改性化合物制造的有机场效应晶体管进行检查时发现，三氟甲基取代的 DPh-BDT 和 BDS 衍生物可用作 n 沟道半导体，电子迁移率分别高达 0.044 和 0.10 cm2 V-1 s-1。

  DOI：

  10.1246/cl.2006.1200

文献信息

• [EN] ANTIVIRAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIVIRAUX
  申请人：GILEAD SCIENCES INC

  公开号：WO2010132601A1

  公开（公告）日：2010-11-18

  The invention is related to anti-viral compounds, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.

  这项发明涉及抗病毒化合物，含有这种化合物的组合物，包括给予这种化合物的治疗方法，以及用于制备这种化合物的过程和中间体。
• Development of organic field-effect properties by introducing aryl-acetylene into benzodithiophene
  作者：Qing Meng、Lang Jiang、Zhongming Wei、Chengliang Wang、Huaping Zhao、Hongxiang Li、Wei Xu、Wenping Hu

  DOI：10.1039/c0jm02895a

  日期：——

  Ethynylene-containing benzo[1,2-b:4,5-b′]dithiophene derivatives 1a–c (BPEBDT, BTEBDT and BHPEBDT) were designed and synthesized. Their physicochemical properties were studied by absorption spectra and electrochemistry. 1a–c displayed high field-effect transistors performance, a mobility up to 1.17 cm2 V−1 s−1 with on/off current ratio of 107 was achieved.

  含乙炔基的苯并[1,2-b:4,5-b′]二硫烯衍生物1a–c（BPEBDT、BTEBDT和BHPEBDT）被设计和合成。通过吸收光谱和电化学研究了它们的物理化学性质。1a–c展现出高场效应晶体管性能，达到了高达1.17 cm² V⁻¹ s⁻¹的迁移率，以及107的开/关电流比。
• Discovery of Ledipasvir (GS-5885): A Potent, Once-Daily Oral NS5A Inhibitor for the Treatment of Hepatitis C Virus Infection
  作者：John O. Link、James G. Taylor、Lianhong Xu、Michael Mitchell、Hongyan Guo、Hongtao Liu、Darryl Kato、Thorsten Kirschberg、Jianyu Sun、Neil Squires、Jay Parrish、Terry Keller、Zheng-Yu Yang、Chris Yang、Mike Matles、Yujin Wang、Kelly Wang、Guofeng Cheng、Yang Tian、Erik Mogalian、Elsa Mondou、Melanie Cornpropst、Jason Perry、Manoj C. Desai

  DOI：10.1021/jm401499g

  日期：2014.3.13

  A new class of highly potent NS5A inhibitors with an unsymmetric benzimidazole-difluorofluorene-imidazole core and distal [2.2.1]azabicyclic ring system was discovered. Optimization of antiviral potency and pharmacokinetics led to the identification of 39 (ledipasvir, GS-5885). Compound 39 (GT1a replicon EC50 = 31 pM) has an extended plasma half-life of 37–45 h in healthy volunteers and produces a

  发现了一类具有不对称苯并咪唑-二氟芴-咪唑核心和远端[2.2.1]氮杂双环系统的新型高效NS5A抑制剂。抗病毒效力和药代动力学的优化导致鉴定出39 种（ledipasvir，GS-5885）。化合物39 (GT1a 复制子 EC 50 = 31 pM) 在健康志愿者中具有延长的血浆半衰期 37-45 小时，并且在口服剂量为 3 mg 或更大且每天一次的单一疗法中产生快速 > 3 log 病毒载量降低在基因型 1a HCV 感染患者中给药。39已被证明是安全有效的，当与具有互补机制的直接作用抗病毒药物联合使用时，SVR12 率高达 100%。
• 2,6-Dialkylbenzo[1,2-<i>b</i>:4,5-<i>b</i>′]dithiophenes (C<i>_n</i>-BDTs) as Soluble Organic Semiconductors for Solution-processed Organic Field-effect Transistors
  作者：Tomoya Kashiki、Eigo Miyazaki、Kazuo Takimiya

  DOI：10.1246/cl.2008.284

  日期：2008.3.5

  2,6-Dialkyl[1,2-b:4,5-b′]dithiophenes were synthesized as novel solution-processible organic semiconductors. Thin films of the organic semiconductors deposited on Si/SiO2 substrates by spin coating have well-ordered structures as confirmed by XRD analysis. Evaluations of the devices under ambient conditions showed typical p-channel FET responses with the field-effect mobility of ca. 10−2 cm2 V−1 s−1 and Ion⁄Ioff of ca. 105.

  研究人员合成了 2,6-二烷基[1,2-b:4,5-b′]二噻吩，作为新型溶液可加工有机半导体。经 XRD 分析证实，通过旋涂法沉积在硅/二氧化硅基底上的有机半导体薄膜具有良好的有序结构。在环境条件下对器件进行的评估显示了典型的 p 沟道场效应晶体管响应，其场效应迁移率约为 10-2 cm2 V-1 s-1，离子⁄Ioff 约为 105。
• Alkylated 2,6-Bis(dicyanomethylene)-2,6-dihydrobenzo[1,2-<i>b</i>:4,5-<i>b</i>′]dithiophenes: New Soluble n-Channel Organic Semiconductors for Air-stable OFETs
  作者：Tomoya Kashiki、Eigo Miyazaki、Kazuo Takimiya

  DOI：10.1246/cl.2009.568

  日期：2009.6.5

  New solution-prosessable n-channel organic semiconductors were developed based on a 2,6-bis(dicyanomethylene)-2,6-dihydrobenzo[1,2-b:4,5-b′]dithiophene core. The OFETs showed n-channel transistor characteristics under ambient conditions with electron field-effect mobility up to 6.3×10−3 cm2 V−1 s−1.

  基于2,6-双(二氰基亚甲基)-2,6-二氢苯并[1,2-b:4,5-b′]二噻吩核，开发了新的可加工n沟道有机半导体。在环境条件下，OFET表现出n沟道晶体管特性，电子场效应迁移率高达6.3×10−3 cm2 V−1 s−1。