4,4’-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(benzo[c][1,2,5]thiadiazole) | 1088119-02-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 4,4’-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(benzo[c][1,2,5]thiadiazole)
• 英文别名: 4,7-bis(benzo[2,1,3]thiadiazol-4-yl)-9,9-dioctyl-9H-fluorene；2,7-di(2,1,3-benzothiadiazol-4-yl)-9,9-dioctylfluorene；4-[7-(2,1,3-Benzothiadiazol-4-yl)-9,9-dioctylfluoren-2-yl]-2,1,3-benzothiadiazole；4-[7-(2,1,3-benzothiadiazol-4-yl)-9,9-dioctylfluoren-2-yl]-2,1,3-benzothiadiazole
• CAS: 1088119-02-1
• 化学式: C₄₁H₄₆N₄S₂
• 分子量: 658.975
• InChiKey: ZVYLHYQYIYVVLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15
• 重原子数：
  47
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4’-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(benzo[c][1,2,5]thiadiazole) 在 2,4,6-tributylpyridine 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 97.0h， 生成
  参考文献：
  名称：

  Facile Arylation of Four-Coordinate Boron Halides by Borenium Cation Mediated Boro-desilylation and -destannylation

  摘要：

  The addition of AlCl3 to four-coordinate boranes of the general formula (C-N-chelate)BCl2 results in halide abstraction and formation of three-coordinate borenium cations of the general formula [(C-N-chelate)BCl](+) The latter react with both arylstannanes and arylsilanes by boro-destannylation and -desilylation, respectively, to form arylated boranes. Catalytic quantities of AlCl3 were sufficient to effect high-yielding arylation of (C-N-chelate)BCl2. Boro-destannylation is more rapid than boro-desilylation and leads to double arylation at the boron center, whereas in reactions with arylsilanes either single or double arylation occurs dependent on the nudeophilicity of the arylsilane and on the electrophilicity of the borenium cation. The electrophilicity of the borenium cation derived from 2-phenylpyridine was greater than that of the benzothiadiazole analogues, enabling the boro-desilyation of less nucleophilic silanes and the direct electrophilic borylation of 2-methylthiophene.

  DOI：

  10.1021/acs.organomet.5b00857
• 作为产物：
  描述：

  在 三乙胺 作用下， 生成 4,4’-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(benzo[c][1,2,5]thiadiazole)
  参考文献：
  名称：

  Enhancing electron affinity and tuning band gap in donor–acceptor organic semiconductors by benzothiadiazole directed C–H borylation

  摘要：

  使用BCl3和苯并噻二唑进行亲电硼化，以引导相邻芳香基团的C-H官能化反应，可以产生融合的硼杂环材料，其HOMO能量基本不变，但LUMO能量显著降低。

  DOI：

  10.1039/c5sc01800e

文献信息

• Polyarylene Synthesis by Cross-Coupling with HOMSi Reagents
  作者：Kenta Shimizu、Yasunori Minami、Yoshiaki Nakao、Ken-ichiro Ohya、Hideyuki Ikehira、Tamejiro Hiyama

  DOI：10.1246/cl.2013.45

  日期：2013.1.5

  Cross-coupling reaction of dibromoarenes with HOMSi reagents (organo[2-(hydroxymethyl)phenyl]dimethylsilanes), or alternatively bromoarenes with arylene-bisHOMSi reagents, proceeded smoothly in the presence of a Pd catalyst and a weak base, and ter- or quaterarenes are produced in excellent yields. The present reaction was successfully applied to polyarylene synthesis using 4,7-dibromobenzothiadiazole or a 2,7-dibromofluorene derivative along with a 2,7-fluorenylene-bisHOMSi reagent.

  在钯催化剂和弱碱存在下，二溴烯烃与 HOMSi 试剂（有机[2-（羟甲基）苯基]二甲基硅烷）或溴烯烃与芳基-双 HOMSi 试剂的交叉偶联反应顺利进行，并以极好的产率生成三元烯烃或四元烯烃。本反应成功地应用于使用 4,7-二溴苯并噻二唑或 2,7-二溴芴衍生物和 2,7-芴-双 HOMSi 试剂合成聚芳醚。
• [EN] BORYLATED COMPOUNDS<br/>[FR] COMPOSÉS BORYLÉS
  申请人：UNIV MANCHESTER

  公开号：WO2015189627A1

  公开（公告）日：2015-12-17

  Borylated compounds are disclosed, as well as their methods of preparation and their applications. The disclosed borylated compounds are highly stable, and have reduced band gap properties, thereby making them attractive candidates for incorporation into semiconducting materials for use in a variety of electronic, optical or electro-optical devices or components.

  本文披露了硼化合物，以及它们的制备方法和应用。披露的硼化合物具有高度稳定性，并具有降低的带隙特性，因此它们是吸引人的候选材料，可以用于制造各种电子、光学或电光器件或组件中。
• A Simple Route toward the Synthesis of Bisbenzothiadiazole Derivatives
  作者：Piyush Anant、Nigel T. Lucas、Josemon Jacob

  DOI：10.1021/ol8022837

  日期：2008.12.18

  A simple and efficient route toward the synthesis of 4,4'-bis(2,1,3-benzothiadiazole) and 7,7'-dibromo-4,4'-bis(2,1,3-benzothiadiazole) has been developed. Oligomers were synthesized with bisbenzothiadiazole units either at the periphery or core, and each oligomer was characterized by X-ray crystallography. Both crystal structures display supramolecular interactions between the conjugated backbones, although the former, bearing two bisbenzothiadiazole units, has extended interactions within layers that engage all of the thiadiazole rings.
• Facile Arylation of Four-Coordinate Boron Halides by Borenium Cation Mediated Boro-desilylation and -destannylation
  作者：Daniel L. Crossley、Jessica Cid、Liam D. Curless、Michael L. Turner、Michael J. Ingleson

  DOI：10.1021/acs.organomet.5b00857

  日期：2015.12.28

  The addition of AlCl3 to four-coordinate boranes of the general formula (C-N-chelate)BCl2 results in halide abstraction and formation of three-coordinate borenium cations of the general formula [(C-N-chelate)BCl](+) The latter react with both arylstannanes and arylsilanes by boro-destannylation and -desilylation, respectively, to form arylated boranes. Catalytic quantities of AlCl3 were sufficient to effect high-yielding arylation of (C-N-chelate)BCl2. Boro-destannylation is more rapid than boro-desilylation and leads to double arylation at the boron center, whereas in reactions with arylsilanes either single or double arylation occurs dependent on the nudeophilicity of the arylsilane and on the electrophilicity of the borenium cation. The electrophilicity of the borenium cation derived from 2-phenylpyridine was greater than that of the benzothiadiazole analogues, enabling the boro-desilyation of less nucleophilic silanes and the direct electrophilic borylation of 2-methylthiophene.
• Enhancing electron affinity and tuning band gap in donor–acceptor organic semiconductors by benzothiadiazole directed C–H borylation
  作者：D. L. Crossley、I. A. Cade、E. R. Clark、A. Escande、M. J. Humphries、S. M. King、I. Vitorica-Yrezabal、M. J. Ingleson、M. L. Turner

  DOI：10.1039/c5sc01800e

  日期：——

  Electrophilic borylation using BCl₃and benzothiadiazole to direct the C–H functionalisation of an adjacent aromatic unit produces fused boracyclic materials with minimally changed HOMO energies but significantly reduced LUMO energies.

  使用BCl3和苯并噻二唑进行亲电硼化，以引导相邻芳香基团的C-H官能化反应，可以产生融合的硼杂环材料，其HOMO能量基本不变，但LUMO能量显著降低。