6-phenyl-6H-pyrrolo[3,2-b:4,5-b']bis[1,4]benzothiazine | 54392-74-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-phenyl-6H-pyrrolo[3,2-b:4,5-b']bis[1,4]benzothiazine
• 英文别名: 6-phenyl-6H-dibenzo[e,e']pyrrolo[3,2-b;4,5-b']bis[1,4]thiazine；12-Phenyl-3,21-dithia-10,12,14-triazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1,4,6,8,10,13,15,17,19-nonaene
• CAS: 54392-74-4
• 化学式: C₂₂H₁₃N₃S₂
• 分子量: 383.497
• InChiKey: DFIQWYCFMKNQAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  zinc 2-aminobenzenethiolate 以 溶剂黄146 为溶剂， 生成 6-phenyl-6H-pyrrolo[3,2-b:4,5-b']bis[1,4]benzothiazine
  参考文献：
  名称：

  研究杂环色素第II部分：Δ 2,2' -Bi（2 ħ -1,4-苯并噻嗪）†

  摘要：

  一种新的单步的Δ的“逆靛蓝合成” 2,2' -bi（3,4-二氢-3-氧代-2- ħ -1,4-苯并噻嗪）发色团进行说明。已经针对已知的硫靛蓝研究了该系统的结构，取代反应，形成机理，颜色和其他相关特性。据报道，一种“ Trichosiderins”的基本骨架是人类红头发的着色物质的合成。

  DOI：

  10.1002/hlca.19740570846

文献信息

• 6H-Pyrrolo[3,2-b:4,5-b′]bis[1,4]benzothiazines: facilely synthesized semiconductors for organic field-effect transistors
  作者：Wei Hong、Zhongming Wei、Hongxia Xi、Wei Xu、Wenping Hu、Quanrui Wang、Daoben Zhu

  DOI：10.1039/b809486a

  日期：——

  6H-Pyrrolo[3,2-b:4,5-b′]bis[1,4]benzothiazine (PBBTZ, 1) and its two 6-substituted derivatives (2 and 3) were conveniently synthesized. Their optical properties were studied by UV-vis and fluorescence spectroscopy, and electrochemical properties were investigated by cyclic voltammetry (CV). Good thermal stability was observed by thermogravimetric analysis. X-Ray analysis revealed a coplanar structure and a column stacking in the single crystal of compound 1. OFET measurements showed that 1–3 were p-type semiconductors. The performance of these devices displayed good reproducibility at ambient conditions. When devices containing 1 were fabricated on OTS-treated SiO2/Si substrates at 60 °C, the best performance was achieved with the average hole mobility as high as 0.34 cm2V−1 s−1 and the on/off ratio about 106–107. This performance resulted from the well-ordered molecular packing as revealed by XRD and AFM analysis.

  6H-Pyrrolo[3,2-b:4,5-bâ²]bis[1,4]benzothiazine (PBBTZ, 1) 及其两种 6 取代衍生物（2 和 3）被方便地合成出来。它们的光学性质通过紫外-可见光谱和荧光光谱进行了研究，电化学性质通过循环伏安法（CV）进行了研究。热重分析表明它们具有良好的热稳定性。X 射线分析表明，化合物 1 的单晶体具有共面结构和柱状堆叠。在环境条件下，这些器件的性能具有良好的再现性。在 60 °C 的温度下，在经过 OTS 处理的二氧化硅/硅衬底上制造含有化合物 1 的器件时，性能达到最佳，平均空穴迁移率高达 0.34 cm2Vâ1 sâ1 ，导通/截止比约为 106â107。XRD 和原子力显微镜分析表明，这种性能得益于有序的分子堆积。
• Dimroth,P.; Reicheneder,F., Angewandte Chemie, 1969, vol. 81, p. 742 - 743
  作者：Dimroth,P.、Reicheneder,F.

  DOI：——

  日期：——
• KAUL B. L., HELVETICA CHIM. ACTA <HCAC-AV>, 1974, 57, NO 8, 2664-2678
  作者：KAUL B. L.

  DOI：——

  日期：——
• HETEROAROMATIC COMPOUNDS FOR ORGANIC ELECTRONICS
  申请人：BASF SE

  公开号：US20170365791A1

  公开（公告）日：2017-12-21

  The present invention provides compounds of formula (I) wherein X is O, S or NR 10 , wherein R 10 is H, C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 2-30 -alkynyl, substituted C 2-30 -alkynyl or C(0)-OR, R 1 and R 11 are independently from each other selected from the group consisting of C 1-30 -alkyl, substituted C 1-30 -alkyl, C 2-30 -alkenyl, substituted C 2-30 -alkenyl, C 2-30 -alkynyl, substituted C 2-30 -alkynyl, C 5-8 -cycloalkyl, substituted C 5-8 -cycloalkyl, C 5-8 -cycloalkenyl, and substituted C 5-8 -cycloalkenyl, and an electronic device comprising the compounds as semiconducting material.