4,4,5,5-tetramethyl-2-(5-(naphthalen-2-yl)thiophen-2-yl)-1,3,2-dioxaborolane | 1559069-62-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,4,5,5-tetramethyl-2-(5-(naphthalen-2-yl)thiophen-2-yl)-1,3,2-dioxaborolane
• 英文别名: 4,4,5,5-Tetramethyl-2-(5-naphthalen-2-ylthiophen-2-yl)-1,3,2-dioxaborolane
• CAS: 1559069-62-3
• 化学式: C₂₀H₂₁BO₂S
• 分子量: 336.263
• InChiKey: BZXVLXKYOIYARJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  3,10-dibromo-1-(2-octyldodecyl)-1H-phenanthro[1,10,9,8-cdefg]carbazole 、 4,4,5,5-tetramethyl-2-(5-(naphthalen-2-yl)thiophen-2-yl)-1,3,2-dioxaborolane 在 potassium carbonate 、 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 24.5h， 以64.5%的产率得到3,10-bis(5-(naphthalen-2-yl)thiophen-2-yl)-1-(2-octyldodecyl)-1H-phenanthro[1,10,9,8-cdefg]carbazole
  参考文献：
  名称：

  A new class of organic semiconductors for solution processed OTFTs: Synthesis and characterization of pyrrolo–perylene derivatives with different end groups

  摘要：

  New pyrrolo perylene derivatives, a new class of organic semiconductor, were designed for solution processed organic thin film transistors (OTFTs). Newly designed 2-(naphthalen-2-yl)thiophene end capped pyrrolo perylene, 3,10-bis(5-(naphthalen-2-yl)thiophen-2-yl)-1-(2-octyldodecyl)-1H-phenanthro[1,10,9,8-cdefg]carbazole (NTPP), and bithiophene end capped pyrrolo-perylene, 3,10-bis([2,2'-bithiophen]-5-yl)-1-(2-octyldodecyl)-1H-phenanthro[1,10,9,8-cdefg]carbazole (BTPP), were synthesized by Suzuki coupling and Stille coupling reaction, respectively. NTPP and BTPP showed good solubility in common organic solvents and were characterized by various spectroscopy. Solution processed OTFTs using BTPP exhibited high field-effect mobilities up to 0.11 cm(2) V-1 s(-1) an on/off ratio of 1 x 10(4) and a very small threshold voltage of 0 V. while OTFTs using NTPP exhibited far lower performances. The high mobility of BTPP is attributed to three dimensional multi-layered crystalline structure based on the results of the two dimensional grazing incidence X-ray diffraction pattern analysis and theoretical calculation using Gaussian, together with morphological study. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.12.001
• 作为产物：
  描述：

  2-溴萘 在 正丁基锂 、 magnesium 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 13.0h， 生成 4,4,5,5-tetramethyl-2-(5-(naphthalen-2-yl)thiophen-2-yl)-1,3,2-dioxaborolane
  参考文献：
  名称：

  A new class of organic semiconductors for solution processed OTFTs: Synthesis and characterization of pyrrolo–perylene derivatives with different end groups

  摘要：

  New pyrrolo perylene derivatives, a new class of organic semiconductor, were designed for solution processed organic thin film transistors (OTFTs). Newly designed 2-(naphthalen-2-yl)thiophene end capped pyrrolo perylene, 3,10-bis(5-(naphthalen-2-yl)thiophen-2-yl)-1-(2-octyldodecyl)-1H-phenanthro[1,10,9,8-cdefg]carbazole (NTPP), and bithiophene end capped pyrrolo-perylene, 3,10-bis([2,2'-bithiophen]-5-yl)-1-(2-octyldodecyl)-1H-phenanthro[1,10,9,8-cdefg]carbazole (BTPP), were synthesized by Suzuki coupling and Stille coupling reaction, respectively. NTPP and BTPP showed good solubility in common organic solvents and were characterized by various spectroscopy. Solution processed OTFTs using BTPP exhibited high field-effect mobilities up to 0.11 cm(2) V-1 s(-1) an on/off ratio of 1 x 10(4) and a very small threshold voltage of 0 V. while OTFTs using NTPP exhibited far lower performances. The high mobility of BTPP is attributed to three dimensional multi-layered crystalline structure based on the results of the two dimensional grazing incidence X-ray diffraction pattern analysis and theoretical calculation using Gaussian, together with morphological study. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.12.001

文献信息

• 신규한 화합물 및 이를 이용한 유기태양전지
  申请人：INDUSTRY-ACADEMIC COOPERATION FOUNDATION GYEONGSANG NATIONAL UNIVERSITY 경상국립대학교산학협력단(220040107194) BRN ▼613-82-11653

  公开号：KR20160101676A

  公开（公告）日：2016-08-25

  본 발명은 신규한 화합물 및 이를 이용한 유기태양전지에 관한 것으로, 보다 상세하게 안트라센 또는 벤조다이싸이오펜을 모핵으로 분자내 비대칭으로 치환된 치환기를 포함하는 신규한 유기 반도체 화합물은 산화 안정성이 우수하고, 전기적 특성이 우수하여 이를 광활성층 재료로 채용한 유기태양전지는 우수한 산화안정성, 높은 개방 전압값 및 전류밀도를 가질 수 있다.

  This invention relates to novel compounds and organic solar cells using them. Novel organic semiconductor compounds containing a substituent asymmetrically substituted on the core molecule of anthracene or benzodithiophene exhibit excellent oxidation stability and superior electrical properties. Organic solar cells adopting these compounds as active layer materials can have excellent oxidation stability, high open-circuit voltage, and current density.