2-(5'-dodecylthiophen-2'-yl)-9-[(pinacolato)boryl]tetracene | 1179987-72-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: 2-(5'-dodecylthiophen-2'-yl)-9-[(pinacolato)boryl]tetracene
• 英文别名: 2-[9-(5-Dodecylthiophen-2-yl)tetracen-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；2-[9-(5-dodecylthiophen-2-yl)tetracen-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 1179987-72-4
• 化学式: C₄₀H₄₉BO₂S
• 分子量: 604.705
• InChiKey: GFUOXCUHOPZKNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.64
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-dibromo-9,10-bis(triisopropylsilylethynyl)anthracene 、 2-(5'-dodecylthiophen-2'-yl)-9-[(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 30.0h， 以90%的产率得到2,6-bis[9'-(5''-dodecylthiophen-2''-yl)tetracen-2'-yl]-9,10-bis(triisopropysilyllethynyl)anthracene
  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：

  2,9-bis[(pinacolato)boryl]tetracene 、 2-溴-5-十二烷基噻吩 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 2.0h， 以37%的产率得到2-(5'-dodecylthiophen-2'-yl)-9-[(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.