5,10,15,20-tetrahydrotriindolo[2’,3’:3,4:2’,3’:5,6:2’,3’:7,8]cycloocta[1,2-b]indole | 479501-23-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5,10,15,20-tetrahydrotriindolo[2’,3’:3,4:2’,3’:5,6:2’,3’:7,8]cycloocta[1,2-b]indole
• 英文别名: 5,10,15,20-tetrahydrotriindole[2',3':3,4:2',3':5,6:2',3':7,8]cycloocta[1,2-b]indole；5,10,15,20-tetrahydrotriindolo[2',3':3,4:2',3':5,6:2',3':7,8]cycloocta[1,2-b]indole；5,10,15,20-tetrahydrocycloocta[1,2-b:3,4-b':5,6-b'':7,8-b''']tetraindole
• CAS: 479501-23-0
• 化学式: C₃₂H₂₀N₄
• 分子量: 460.538
• InChiKey: PIOSNRLYBDCSGL-HEAOOCDTSA-N

物化性质

• 熔点：
  >350 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 密度：
  1.507±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.59
• 重原子数：
  36.0
• 可旋转键数：
  0.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.16
• 氢给体数：
  4.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  5,10,15,20-tetrahydrotriindolo[2’,3’:3,4:2’,3’:5,6:2’,3’:7,8]cycloocta[1,2-b]indole 在 N-溴代丁二酰亚胺(NBS) 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 C₆₄H₈₃BrN₄
  参考文献：
  名称：

  Tetraindole-based saddle-shaped organic dyes for efficient dye-sensitized solar cells

  摘要：

  Two new metal-free organic dyes which consist of a saddle-shaped tetraindole donor, a cyanoacrylic acid acceptor/anchoring group and a thiophene or bithiophene it-bridge have been successfully designed and synthesized for dye-sensitized solar cells. The two dyes showed good photoelectric properties, and the saddle-shaped structure of the tetraindole unit was found to be favorable for preventing intermolecular aggregation and enhancing the photovoltage. The two tetraindole-based dyes exhibited good photovoltaic performances in solar cells. An efficiency up to 6.46% with a high open-circuit photovoltage of 762 mV was achieved for the dye JY15 with a 2,2`-bithiophene moiety as the pi-bridge using an iodine electrolyte under standard conditions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2015.05.015
• 作为产物：
  描述：

  C₃₂H₂₆N₆ 在 zinc(II) chloride 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以144 mg的产率得到5,10,15,20-tetrahydrotriindolo[2’,3’:3,4:2’,3’:5,6:2’,3’:7,8]cycloocta[1,2-b]indole
  参考文献：
  名称：

  双吲哚生物碱卡勒平结构类似物的合成研究：环状吲哚-四聚体的逐步合成

  摘要：

  研究了双吲哚生物碱考勒平的结构异构体的合成。Caulerpin骨架的构建基于适当的环辛烷二酮或环辛酮的Fisher吲哚化反应。另外，首先描述了由可能的四种环状吲哚-四聚物逐步合成一种异构体的方法。

  DOI：

  10.1016/j.tet.2010.01.005

文献信息

• Tetra-indole core as a dual agent: a hole selective layer that passivates defects in perovskite solar cells
  作者：Meenakshi Pegu、Samrana Kazim、Peng Huang、Luis Lezama、Shahzada Ahmad

  DOI：10.1039/d1tc01258d

  日期：——

  An organic small molecule composed of a tetra-indole core was introduced as a hole selective layer that can also act a passivating agent to supress the surface defects in perovskite solar cells (PSCs).

  一种由四吲哚核心组成的有机小分子被引入作为孔选择层，同时也可以作为一种钝化剂，用于抑制钙钛矿太阳能电池（PSCs）中的表面缺陷。
• 一种四聚吲哚的制备方法
  申请人：南京邮电大学

  公开号：CN103936746B

  公开（公告）日：2016-04-13

  本发明公开一种四聚吲哚（5,10,15,20-tetrahydrotriindolo[2’,3’:3,4:2’,3’:5,6:2’,3’:7,8]cycloocta[1,2-b]indole）的制备方法。该方法简洁快速，通过在2-吲哚酮原料中加入一定量的三氯氧磷，加热到80-100℃反应6-10h，纯化后可得四聚吲哚产物。该发明是首次通过“一步法”制备得到四聚吲哚化合物的方法，解决了四聚吲哚合成困难的问题，为拓展其在生物、化学及材料等领域的应用提供了技术基础。其反应通式如下式I所示：
• Synthesis and Characterization of Symmetric Cyclooctatetraindoles: Exploring the Potential as Electron-Rich Skeletons with Extended π-Systems
  作者：Fang Wang、Xiang-Chun Li、Wen-Yong Lai、Yao Chen、Wei Huang、Fred Wudl

  DOI：10.1021/ol501083d

  日期：2014.6.6

  A facile one-pot tetramerization of indolin-2-one with phosphoryl chloride was applied for the first convenient direct synthesis of C2v-symmetric cyclooctatetraindole with an 8π annulene as the center. Tetra- and octa-arylated cyclooctatetraindole derivatives functionalized with fluorescent fluorene and pyrene units were thus facilely synthesized and characterized.

  吲哚啉-2-一与磷酰氯的简单的一锅四聚反应被用于第一个方便的直接合成，以8π环戊烯为中心的C 2 v-对称环辛酸酯基。因此，容易地合成和表征了用荧光芴和pyr单元官能化的四芳基和八芳基化的环辛二烯衍生物。
• Configuration‐Induced Multichromism of Phenanthridine Derivatives: A Type of Versatile Fluorescent Probe for Microenvironmental Monitoring
  作者：Wei Huang、Shiyu Feng、Jie Liu、Baoshuai Liang、Ya Zhou、Mengya Yu、Jiayuan Liang、Jiaguo Huang、Xujie Lü、Weiguo Huang

  DOI：10.1002/anie.202219337

  日期：2023.2.20

  In sharp contrast to conventional fluorophores that can only detect one or few stimuli in microenvironments, a group of phenanthridine-based fluorophores, namely B1, F1, and T1 with 1D, 2D, and 3D molecular configurations, respectively, have been developed. They show excellent capability in tracking a variety of stimuli through distinct fluorescence evolutions, thus offering promising applications

  与只能检测微环境中的一个或几个刺激的传统荧光团形成鲜明对比的是，已经开发了一组基于菲啶的荧光团，即分别具有 1D、2D 和 3D 分子构型的 B1、F1 和 T1。它们在通过不同的荧光演变跟踪各种刺激方面表现出出色的能力，从而在生物成像、光学传感和许多其他方面提供了有前途的应用。
• Octupolar (<i>C</i>₃ and <i>S</i>₄) Symmetric Cyclized Indole Derivatives: Syntheses, Structures, and NLO Properties
  作者：Lei Wang、Qi Fang、Qing Lu、Shao-jun Zhang、Ying-ying Jin、Zhi-qiang Liu

  DOI：10.1021/acs.orglett.5b01912

  日期：2015.9.4

  Several cyclized indole derivatives have been synthesized, and their structures been determined. The C-3-symmetric single-chiral N-phenyltriindole (Tr-Ph3) crystallized in the P1 space group, and the S-4-symmetric saddle-like tetraindole (TTr) crystallized in the 14 space group. The Tr-Ph3 and TTr crystals exhibit remarkable powder SHG intensities 5 and 11 times that of KH2PO4 (KDP), respectively. TTr is a useful octupolar core to build S-4-symmetric molecules and crystals for second-NLO materials.