anthra[2,3-c][1,2,5]thiadiazole-4,11-dionetriisobutylsilylacetylene

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: anthra[2,3-c][1,2,5]thiadiazole-4,11-dionetriisobutylsilylacetylene
• 英文别名: anthra[2,3-c][1,2,5]thiadiazole-4,11-dione；naphtho[2,3-f][2,1,3]benzothiadiazole-4,11-dione
• 化学式: C₁₄H₆N₂O₂S
• 分子量: 266.28
• InChiKey: NNEUHVCWLVWEIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三乙基矽乙炔 、 anthra[2,3-c][1,2,5]thiadiazole-4,11-dionetriisobutylsilylacetylene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Alkynylated Aceno[2,1,3]thiadiazoles

  摘要：

  Enlarged acenothiadiazoles, which are easily prepared, display attractive optical and electrochemical properties. The annulation of thiadiazole to anthracene gives a stable material with optical properties similar to those of substituted pentacenes.

  DOI：

  10.1021/ol902156x
• 作为产物：
  描述：

  1,4-蒽醌 在 吡啶 、 氯化亚砜 、 氨基甲酸甲酯 作用下， 以 苯 为溶剂， 反应 9.0h， 以75%的产率得到anthra[2,3-c][1,2,5]thiadiazole-4,11-dionetriisobutylsilylacetylene
  参考文献：
  名称：

  Use of Thiazyl Chlorides, Alkyl Carbamates, and Thionyl Chloride To Fuse 1,2,5-Thiadiazoles to Quinones and To Oxidize, Chlorinate, and Aminate Them

  摘要：

  Thiazyl chlorides in a simple one-step procedure fuse 1,2,5-thiadiazole rings to quinones. So do alkyl carbamates mixed with excess thionyl chloride and pyridine. Evidence is put forward to support the hypothesis that NSCl or a related thiazyl derivative is the reactive species that brings about the transformations. Selenoyl chloride mixed with an alkyl carbamate, pyridine, and quinones similarly gives 1,2,5-selenodiazoloquinones. Thionyl chloride in pyridine chlorinates quinones and oxidizes hydroquinones. 2,3-Dichloro-1,4-quinones with S4N4 or. with alkyl N-sulfinylcarbamates give 1,2,5-thiadiazoloquinones. Quinones and their 2 3-dichloro derivatives with TsNSO in pyridine give betaine derivatives of 2,3-diaminoquinones, which pyrrolidine converts into 2-amino-3(tosylamino)quinones. A unified set of mechanisms is presented that accounts for these transformations.

  DOI：

  10.1021/jo00110a036

文献信息

• (Aza)Pentacenes Clipped into a Ring: Stabilization of Large (Aza)Acenes
  作者：Lukas Ahrens、Olena Tverskoy、Svenja Weigold、Michael Ganschow、Frank Rominger、Jan Freudenberg、Uwe H. F. Bunz

  DOI：10.1002/anie.202015348

  日期：2021.4.19

  bridged azapentacenes display superior photochemical, oxidative and thermal stabilities compared to azapentacenes protected by bis(TIPS‐ethynyl)‐substituents—clipping an azaacene into a large ring is a viable complement in stabilization.

  制备了双亚烷基桥接的6,13-​​二苯并五苯和类似的桥接氮杂并戊烯；他们是持久的。与双（TIPS-乙炔基）取代基保护的氮杂戊二烯相比，双桥氮杂戊二烯显示出优异的光化学，氧化和热稳定性-将氮杂并烯切割成大环是稳定稳定的可行补充。
• Coronene-Containing N-Heteroarenes: 13 Rings in a Row
  作者：Alexander H. Endres、Manuel Schaffroth、Fabian Paulus、Hilmar Reiss、Hubert Wadepohl、Frank Rominger、Roland Krämer、Uwe H. F. Bunz

  DOI：10.1021/jacs.5b12642

  日期：2016.2.17

  We describe the modular synthesis of three novel large N-heteroarenes, containing 9, 11, and 13 annulated rings. This modular system features fused azaacene units to a coronene nucleus. We evaluate the optical and electronic properties and the solid-state packing of the targets. The electronic properties of the 13-ring N-heteroarene allow the fabrication of a proof-of-concept thin-film transistor.

  我们描述了三种新型大 N-杂芳烃的模块化合成，其中包含 9、11 和 13 个环。这种模块化系统的特点是将氮杂并苯单元融合到冠烯核上。我们评估了目标的光学和电子特性以及固态包装。13 环 N-杂芳烃的电子特性允许制造概念验证薄膜晶体管。多晶薄膜的电子迁移率高达 8 × 10(-4) cm/(V s)。
• Use of Thiazyl Chlorides, Alkyl Carbamates, and Thionyl Chloride To Fuse 1,2,5-Thiadiazoles to Quinones and To Oxidize, Chlorinate, and Aminate Them
  作者：Shuhao Shi、Thomas J. Katz、Bingwei V. Yang、Longbin Liu

  DOI：10.1021/jo00110a036

  日期：1995.3

  Thiazyl chlorides in a simple one-step procedure fuse 1,2,5-thiadiazole rings to quinones. So do alkyl carbamates mixed with excess thionyl chloride and pyridine. Evidence is put forward to support the hypothesis that NSCl or a related thiazyl derivative is the reactive species that brings about the transformations. Selenoyl chloride mixed with an alkyl carbamate, pyridine, and quinones similarly gives 1,2,5-selenodiazoloquinones. Thionyl chloride in pyridine chlorinates quinones and oxidizes hydroquinones. 2,3-Dichloro-1,4-quinones with S4N4 or. with alkyl N-sulfinylcarbamates give 1,2,5-thiadiazoloquinones. Quinones and their 2 3-dichloro derivatives with TsNSO in pyridine give betaine derivatives of 2,3-diaminoquinones, which pyrrolidine converts into 2-amino-3(tosylamino)quinones. A unified set of mechanisms is presented that accounts for these transformations.
• Alkynylated Aceno[2,1,3]thiadiazoles
  作者：Anthony Lucas Appleton、Shaobin Miao、Scott M. Brombosz、Nancy J. Berger、Stephen Barlow、Seth R. Marder、Brian M. Lawrence、Kenneth I. Hardcastle、Uwe H. F. Bunz

  DOI：10.1021/ol902156x

  日期：2009.11.19

  Enlarged acenothiadiazoles, which are easily prepared, display attractive optical and electrochemical properties. The annulation of thiadiazole to anthracene gives a stable material with optical properties similar to those of substituted pentacenes.