5,5'-dibromo-3,3'-dipentoxy-2,2'-bithiophene | 1404166-45-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5,5'-dibromo-3,3'-dipentoxy-2,2'-bithiophene
• 英文别名: 5,5'-dibromo-3,3'-bis(pentyloxy)-2,2'-bithiophene；5,5'-Dibromo-3,3'-bis(pentyloxy)-2,2'-bithiophene；5-bromo-2-(5-bromo-3-pentoxythiophen-2-yl)-3-pentoxythiophene
• CAS: 1404166-45-5
• 化学式: C₁₈H₂₄Br₂O₂S₂
• 分子量: 496.327
• InChiKey: IGYISVZWDNIFMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  74.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,5'-dibromo-3,3'-dipentoxy-2,2'-bithiophene 在 potassium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 生成 5,5'-bis-(3,5-di-tert-butyl-4-oxo-2,5-cyclohexadiene-1-ylidene)-3,3'-dipentoxy-2,2'-bithiophenylidene
  参考文献：
  名称：

  Outside rules inside: the role of electron-active substituents in thiophene-based heterophenoquinones

  摘要：

  硫代噻吩基杂苯醌的基态特性取决于分子骨架上取代基的性质和位置。

  DOI：

  10.1039/c4cp05748a
• 作为产物：
  描述：

  噻吩,3-(戊氧基)- 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 5,5'-dibromo-3,3'-dipentoxy-2,2'-bithiophene
  参考文献：
  名称：

  用于高性能倒置钙钛矿太阳能电池的分子内非共价相互作用启用无掺杂空穴传输材料

  摘要：

  通过将分子内小号⋅⋅⋅ ö非共价相互作用（核），用于升压的固有空穴迁移率，两个简单的结构自由掺杂物的空穴输送材料（HTMS）设计并与反转体面器件稳定性递送的21.10％的显着的效率钙钛矿太阳能电池，展示了 INI 策略在获取高性能无掺杂 HTM 方面的巨大前景。

  DOI：

  10.1002/anie.202113749

文献信息

• Tuning the Quinoid versus Biradicaloid Character of Thiophene-Based Heteroquaterphenoquinones by Means of Functional Groups
  作者：Eleonora V. Canesi、Daniele Fazzi、Letizia Colella、Chiara Bertarelli、Chiara Castiglioni

  DOI：10.1021/ja3072385

  日期：2012.11.21

  A series of quinoidal bithiophenes (QBTs) with controlled variations in steric hindrance and electron activity of the substituents has been synthesized. Evidence of their quinoidal versus biradicaloid ground state electronic character has been experimentally detected and coherently identified as fingerprints by spectroscopic methods such as NMR, UV-vis, multiwavelength Raman. From this analysis, alkoxy groups have been shown to strongly affect the electronic structure and the ground-state energy and stability of QBTs. Quantum-chemical calculations correctly predict the experimental spectroscopic response, even while changing the alkyl on phenone from a tertiary carbon atom to secondary to primary toward an unsubstituted phenone, further confirming the validity of the approach proposed. A control of the electronic structure accompanied by negligible variations of the optical gap of the molecules has thus been demonstrated, extending the potential use of quinoidal species in fields ranging from photon harvesting to magnetic applications.