2,9-bis[(pinacolato)boryl]tetracene | 1179987-62-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: 2,9-bis[(pinacolato)boryl]tetracene
• 英文别名: 4,4,5,5-Tetramethyl-2-[9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)tetracen-2-yl]-1,3,2-dioxaborolane；4,4,5,5-tetramethyl-2-[9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)tetracen-2-yl]-1,3,2-dioxaborolane
• CAS: 1179987-62-2
• 化学式: C₃₀H₃₄B₂O₄
• 分子量: 480.22
• InChiKey: VBTBCSMOTVTIQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-溴-5-正辛基噻吩 、 2,9-bis[(pinacolato)boryl]tetracene 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate 、 palladium diacetate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 以63%的产率得到2,9-bis(5'-octylthiophen-2'-yl)tetracene
  参考文献：
  名称：

  2,8- and 2,9-Diboryltetracenes as Useful Building Blocks for Extended π-Conjugated Tetracenes

  摘要：

  Ir-catalyzed direct diborylation of tetracene gave a 1:1 mixture of 2,8- and 2,9-bis[(pinacolato)boryl]tetracenes, which were separated by recrystallization. These diboryltetracenes are useful building blocks for the regiospecific synthesis of extended pi-conjugated tetracenes directed to semiconductors for organic field-effect transistors (OFETs). Syntheses of thiophene-tetracene-thiophene, thiophene-tetracene-bithiophene-tetracene-thiophene, and thiophene-tetracene-anthracene-tetracene-thiophene pi-systems have been achieved on the basis of the 2,8- and 2,9-diboryltetracenes.

  DOI：

  10.1021/ol901420p
• 作为产物：
  描述：

  并四苯 、 联硼酸频那醇酯 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 环己烷 为溶剂， 反应 20.0h， 生成 2,8-bis[(pinacolato)boryl]tetracene 、 2,9-bis[(pinacolato)boryl]tetracene
  参考文献：
  名称：

  2,8- and 2,9-Diboryltetracenes as Useful Building Blocks for Extended π-Conjugated Tetracenes

  摘要：

  Ir-catalyzed direct diborylation of tetracene gave a 1:1 mixture of 2,8- and 2,9-bis[(pinacolato)boryl]tetracenes, which were separated by recrystallization. These diboryltetracenes are useful building blocks for the regiospecific synthesis of extended pi-conjugated tetracenes directed to semiconductors for organic field-effect transistors (OFETs). Syntheses of thiophene-tetracene-thiophene, thiophene-tetracene-bithiophene-tetracene-thiophene, and thiophene-tetracene-anthracene-tetracene-thiophene pi-systems have been achieved on the basis of the 2,8- and 2,9-diboryltetracenes.

  DOI：

  10.1021/ol901420p

文献信息

• 2,8- and 2,9-Diboryltetracenes as Useful Building Blocks for Extended π-Conjugated Tetracenes
  作者：Takakazu Kimoto、Kenro Tanaka、Yoshimasa Sakai、Akira Ohno、Kenji Yoza、Kenji Kobayashi

  DOI：10.1021/ol901420p

  日期：2009.8.20

  Ir-catalyzed direct diborylation of tetracene gave a 1:1 mixture of 2,8- and 2,9-bis[(pinacolato)boryl]tetracenes, which were separated by recrystallization. These diboryltetracenes are useful building blocks for the regiospecific synthesis of extended pi-conjugated tetracenes directed to semiconductors for organic field-effect transistors (OFETs). Syntheses of thiophene-tetracene-thiophene, thiophene-tetracene-bithiophene-tetracene-thiophene, and thiophene-tetracene-anthracene-tetracene-thiophene pi-systems have been achieved on the basis of the 2,8- and 2,9-diboryltetracenes.