2,5,9,12-tetrahexylanthra[1,2-b:4,3-b':5,6-b'':8,7-b''']tetrathiophene

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2,5,9,12-tetrahexylanthra[1,2-b:4,3-b':5,6-b'':8,7-b''']tetrathiophene
• 英文别名: 6,11,19,24-Tetrahexyl-5,12,18,25-tetrathiaheptacyclo[14.10.0.03,14.04,8.09,13.017,21.022,26]hexacosa-1(26),2,4(8),6,9(13),10,14,16,19,21,23-undecaene；6,11,19,24-tetrahexyl-5,12,18,25-tetrathiaheptacyclo[14.10.0.03,14.04,8.09,13.017,21.022,26]hexacosa-1(26),2,4(8),6,9(13),10,14,16,19,21,23-undecaene
• 化学式: C₄₆H₅₈S₄
• 分子量: 739.231
• InChiKey: JYFRVCLCNFFKKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.8
• 重原子数：
  50
• 可旋转键数：
  20
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  碳酸亚乙烯酯 、 2,5,9,12-tetrahexylanthra[1,2-b:4,3-b':5,6-b'':8,7-b''']tetrathiophene 以 甲苯 为溶剂， 反应 72.0h， 以76%的产率得到2,5,9,12-tetrahexyl-7,14,15,19-tetrahydro-7,14-[4,5]epidioxoloanthra[1,2-b:4,3-b':5,6-b'':8,7-b''']tetrathio-phen-17-one
  参考文献：
  名称：

  Evaluation of semiconducting molecular thin films solution-processed via the photoprecursor approach: the case of hexyl-substituted thienoanthracenes

  摘要：

  光前体法比直接旋涂在制备高质量有机半导体薄膜方面更为优越。

  DOI：

  10.1039/c5tc00794a
• 作为产物：
  描述：

  2-正己基噻吩 在 正丁基锂 、 三氯化铁 作用下， 以 四氢呋喃 、 硝基甲烷 、 正己烷 、 二氯甲烷 为溶剂， 反应 14.25h， 生成 2,5,9,12-tetrahexylanthra[1,2-b:4,3-b':5,6-b'':8,7-b''']tetrathiophene
  参考文献：
  名称：

  Thin Film Organic Transistors from Air-Stable Heteroarenes:  Anthra[1,2-b:4,3-b‘:5,6-b‘ ‘:8,7-b‘ ‘‘]tetrathiophene Derivatives

  摘要：

  A facile synthesis of air-stable anthra[1,2-b:4,3-b':5,6-b '':8,7-e''']tetrathiophene derivatives la and 1b has been developed for applications in organic thin film transistors. Both molecules tend to self-associate through pi-pi stacking in solution and in different films. The hole mobility of 0.012 cm(2) V-1 S-1 is obtained from la due to morphology changes in films from less ordered to highly ordered structures after thermal annealing. Good performance remained persistent over a period of 14 days, indicating the high stability of such transistors.

  DOI：

  10.1021/ol701690y

文献信息

• Oligothiophene-Functionalized Benzene and Tetrathienoanthracene: Effect of Enhanced π-Conjugation on Optoelectronic Properties, Self-Assembly and Device Performance
  作者：Alicea A. Leitch、Kimberly A. Stobo、Bashir Hussain、Mireille Ghoussoub、Saeedeh Ebrahimi-Takalloo、Peyman Servati、Ilia Korobkov、Jaclyn L. Brusso

  DOI：10.1002/ejoc.201300731

  日期：2013.9

  The versatility of fourfold Stille coupling to afford oligothiophene-functionalized tetrathienoanthracene (TTA) and benzene derivatives is described. The influence of the larger, more rigid TTA core on the electronic and structural properties was investigated. Comparative optical and electrochemical studies demonstrate a diminishing HOMO–LUMO gap as the length of the oligothiophene chain increases

  描述了四重 Stille 耦合的多功能性，以提供低聚噻吩官能化的四噻吩蒽 (TTA) 和苯衍生物。研究了更大、更刚性的 TTA 核对电子和结构特性的影响。比较光学和电化学研究表明，随着低聚噻吩链的长度增加，HOMO-LUMO 间隙减小，刚性 TTA 化合物比更灵活的苯类似物表现出更低的能隙。X 射线晶体学研究表明，噻吩取代的 TTA 结构由滑动的 π 堆栈和几个紧密的堆栈内 π-π 相互作用组成；由于噻吩配体在平面外扭曲，没有观察到苯衍生物的紧密接触。最后，苯类似物中的分子与它们的邻居分离。噻吩和联噻吩官能化的 TTA 化合物被制造成底部接触配置的 OTFT 器件，并表现出大约 10 的迁移率。10–4 cm2 V–1 s–1 和超过四个数量级的开/关比。
• Functionalized Tetrathienoanthracene: Enhancing π–π Interactions Through Expansion of the π-Conjugated Framework
  作者：Alicea A. Leitch、Aya Mansour、Kimberly A. Stobo、Ilia Korobkov、Jaclyn L. Brusso

  DOI：10.1021/cg201521w

  日期：2012.3.7

  The functionalization of tetrathienoanthracene (TTA) with bromine and 2-hexylthiophene moieties is described, and their influence at both the molecular and solid-state level has been investigated. Comparative optical and electrochemical studies indicate an increase in conjugation for the thiophene derivative compared to the parent TTA. In the solid state, these materials form slipped pi-stack structures with a number of close intermolecular contacts. Comparison of the two structures reveals a more steeply inclined slipped pi-stack for the thiophene derivative resulting in a closer interplanar separation. This, coupled with the extended molecular framework, leads to an enhanced number of pi-pi interactions within the stack. The combination of increased conjugation at the molecular level, and pi-stacked structures with strong intermolecular communication at the solid-state level, augurs well for the use of TTA materials in optoelectronic applications.
• US7186355B2
  申请人：——

  公开号：US7186355B2

  公开（公告）日：2007-03-06
• Evaluation of semiconducting molecular thin films solution-processed via the photoprecursor approach: the case of hexyl-substituted thienoanthracenes
  作者：Cassandre Quinton、Mitsuharu Suzuki、Yoshitaka Kaneshige、Yuki Tatenaka、Chiho Katagiri、Yuji Yamaguchi、Daiki Kuzuhara、Naoki Aratani、Ken-ichi Nakayama、Hiroko Yamada

  DOI：10.1039/c5tc00794a

  日期：——

  The photoprecursor approach is superior to direct spin coating in preparing high quality organic semiconducting thin films.

  光前体法比直接旋涂在制备高质量有机半导体薄膜方面更为优越。
• Thin Film Organic Transistors from Air-Stable Heteroarenes:  Anthra[1,2-<i>b</i>:4,3-<i>b</i>‘:5,6-<i>b</i>‘ ‘:8,7-<i>b</i>‘ ‘‘]tetrathiophene Derivatives
  作者：Wen-Jun Liu、Yan Zhou、Yuguo Ma、Yong Cao、Jian Wang、Jian Pei

  DOI：10.1021/ol701690y

  日期：2007.10.1

  A facile synthesis of air-stable anthra[1,2-b:4,3-b':5,6-b '':8,7-e''']tetrathiophene derivatives la and 1b has been developed for applications in organic thin film transistors. Both molecules tend to self-associate through pi-pi stacking in solution and in different films. The hole mobility of 0.012 cm(2) V-1 S-1 is obtained from la due to morphology changes in films from less ordered to highly ordered structures after thermal annealing. Good performance remained persistent over a period of 14 days, indicating the high stability of such transistors.