N-hexyldibenzothieno[3,2-b:2′,3′-d]pyrrole | 1101752-36-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: N-hexyldibenzothieno[3,2-b:2′,3′-d]pyrrole
• 英文别名: N-hexyldibenzothieno[3,2-b:2',3'-d]pyrrole；11-Hexyl-3,19-dithia-11-azapentacyclo[10.7.0.02,10.04,9.013,18]nonadeca-1(12),2(10),4,6,8,13,15,17-octaene；11-hexyl-3,19-dithia-11-azapentacyclo[10.7.0.02,10.04,9.013,18]nonadeca-1(12),2(10),4,6,8,13,15,17-octaene
• CAS: 1101752-36-6
• 化学式: C₂₂H₂₁NS₂
• 分子量: 363.547
• InChiKey: SZODQLQMQZZQHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  2,2'-bibenzo[b]thiophene 在 硝酸 、 溶剂黄146 、 三苯基膦 、 potassium hydroxide 作用下， 以 邻二氯苯 、 丙酮 为溶剂， 生成 N-hexyldibenzothieno[3,2-b:2′,3′-d]pyrrole
  参考文献：
  名称：

  Advantage of arch-shaped structure on transistor performances over linear-shaped structure in dibenzothienopyrrole semiconductors

  摘要：

  To understand the influence of molecular shape on the optoelectronic properties of heteroacenes, we report here the syntheses and characterizations of two linear- and two arch-shaped dibenzothienopyrrole (DBTP) derivatives, namely, N-hexyldibenzothieno[3,2-b:2',3'-d]pyrrole (l-HDBTP), N-phenyldibenzothieno[3,2-b:2',3'-d] pyrrole (l-PDBTP), N-hexyldibenzothieno[2,3-b:3',2'-d]pyrrole (a-HDBTP) and N-phenyldibenzothieno[2,3-b:3',2'-d]pyrrole (a-PDBTP). Their structure-property relationships have been systematically studied by optical absorption, cyclic voltammetry, single-crystal X-ray diffraction analyses and the single-crystal-based and thin-film-based field-effect transistors (FETs). The results demonstrate that the arch-shaped DBTP derivatives can modify their electronic structures and molecular arrangements by tuning of substituents, to obtain a better charge-transporting ability relative to the linear-shaped ones. The arch-shaped N-phenyl substituted a-PDBTP exhibits optimum molecular pi-stacking arrangement and charge transport properties, with the hole mobility of 0.75 cm(2)V(-1)s(-1) and 0.058 cm(2)V(-1)s(-1) for the single-crystal and the thin-film OFETs, respectively. These results indicate that the arch-shaped DBTP core is a promising building block in the area of organic semiconducting materials.

  DOI：

  10.1016/j.orgel.2018.06.044

文献信息

• Synthesis and properties of the anti and syn isomers of dibenzothieno[b,d]pyrrole
  作者：Ting Qi、Yunlong Guo、Yunqi Liu、Hongxia Xi、Hengjun Zhang、Xike Gao、Ying Liu、Kun Lu、Chunyan Du、Giu Yu、Daoben Zhu

  DOI：10.1039/b813683a

  日期：——

  A novel type of anti and syn isomers of a pentacyclic compound consisting of two thiophene rings and one pyrrole ring were efficiently synthesized from benzo[b]thiophene, and the anti isomer exhibits better charge transport and OFET properties compared with the syn isomer and its N-hexyl substitution.

  由苯并[b]噻吩有效地合成了由两个噻吩环和一个吡咯环组成的五环化合物的新型反式和顺式异构体，与同式异构体及其氮原子相比，该反式异构体具有更好的电荷传输和OFET性质-己基取代。