5,5'-bis(3,5-di-iso-propyl-4-hydroxy)phenyl-3,3'-dipentoxy-2,2'-bithiophene | 1404166-48-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5,5'-bis(3,5-di-iso-propyl-4-hydroxy)phenyl-3,3'-dipentoxy-2,2'-bithiophene
• CAS: 1404166-48-8
• 化学式: C₄₂H₅₈O₄S₂
• 分子量: 691.052
• InChiKey: RJXLSRNLSHOWJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.85
• 重原子数：
  48.0
• 可旋转键数：
  17.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5,5'-bis(3,5-di-iso-propyl-4-hydroxy)phenyl-3,3'-dipentoxy-2,2'-bithiophene 在 potassium hexacyanoferrate(III) 、 potassium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 5,5'-bis(3,5-di-iso-propyl-4-oxo-2,5-cycloesadiene-1-ylidene)-3,3'-dipentoxy-2,2'-dihydroxy bithiophene
  参考文献：
  名称：

  Tuning the Quinoid versus Biradicaloid Character of Thiophene-Based Heteroquaterphenoquinones by Means of Functional Groups

  摘要：

  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.

  DOI：

  10.1021/ja3072385
• 作为产物：
  描述：

  3,3'-dipentoxy-2,2'-bithiophene 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 碳酸氢钠 作用下， 以 乙二醇二甲醚 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 5,5'-bis(3,5-di-iso-propyl-4-hydroxy)phenyl-3,3'-dipentoxy-2,2'-bithiophene
  参考文献：
  名称：

  Tuning the Quinoid versus Biradicaloid Character of Thiophene-Based Heteroquaterphenoquinones by Means of Functional Groups

  摘要：

  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.

  DOI：

  10.1021/ja3072385