3,10-bis(5-(naphthalen-2-yl)thiophen-2-yl)-1-(2-octyldodecyl)-1H-phenanthro[1,10,9,8-cdefg]carbazole | 1559069-63-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 3,10-bis(5-(naphthalen-2-yl)thiophen-2-yl)-1-(2-octyldodecyl)-1H-phenanthro[1,10,9,8-cdefg]carbazole
• 英文别名: 9,15-Bis(5-naphthalen-2-ylthiophen-2-yl)-12-(2-octyldodecyl)-12-azahexacyclo[11.8.0.02,11.03,8.04,20.016,21]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaene；9,15-bis(5-naphthalen-2-ylthiophen-2-yl)-12-(2-octyldodecyl)-12-azahexacyclo[11.8.0.02,11.03,8.04,20.016,21]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaene
• CAS: 1559069-63-4
• 化学式: C₆₈H₆₇NS₂
• 分子量: 962.419
• InChiKey: MFUJUEBQORVCBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23.9
• 重原子数：
  71
• 可旋转键数：
  22
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  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

文献信息

• A new class of organic semiconductors for solution processed OTFTs: Synthesis and characterization of pyrrolo–perylene derivatives with different end groups
  作者：Kwang Hun Park、Hui-Jun Yun、Wanxiang Lu、Dae Sung Chung、Soon-Ki Kwon、Yun-Hi Kim

  DOI：10.1016/j.dyepig.2013.12.001

  日期：2014.4

  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.