2-chloro-4,6-di(thiophen-2-yl)-1,3,5-triazine | 39242-14-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 2-chloro-4,6-di(thiophen-2-yl)-1,3,5-triazine
• 英文别名: 2,4-bis(thiophen-2-yl)-6-chloro-1,3,5-triazine；2-chloro-4,6-dithiophen-2-yl-1,3,5-triazine
• CAS: 39242-14-3
• 化学式: C₁₁H₆ClN₃S₂
• 分子量: 279.774
• InChiKey: UHAJVALTYQAFPE-UHFFFAOYSA-N

物化性质

• 沸点：
  516.6±48.0 °C(Predicted)
• 密度：
  1.467±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-chloro-4,6-di(thiophen-2-yl)-1,3,5-triazine 、 间苯二酚 在 aluminum (III) chloride 作用下， 以 氯苯 为溶剂， 反应 5.5h， 以71%的产率得到4-(4,6-di(thiophen-2-yl)-1,3,5-triazin-2-yl)benzene-1,3-diol
  参考文献：
  名称：

  基于时变密度泛函计算和三维定量结构-性质关系的1,3,5-三嗪类化合物作为紫外线吸收剂的合成，光谱和理论研究。

  摘要：

  合成了一系列1,3,5-三嗪，并测试了它们的紫外线吸收性能。利用计算化学方法构建了定量的结构-性质关系（QSPR），并将其用于新型1,3,5-三嗪紫外线吸收剂化合物的计算机辅助设计。实验性紫外线吸收数据与使用时变密度泛函理论（TD-DFT）[B3LYP / 6–311 + G（d，p）]的预测数据非常吻合。合适的预测模型（R  > 0.8，P <0.0001）。利用Sybyl程序的多重拟合分子比对规则，建立了可预测的三维定量结构-性质关系（3D-QSPR）模型，该结论与TD-DFT计算吻合。对这种紫外线吸收剂化合物的异常光稳定性机理进行了研究，并证实其主要归因于它们通过超快激发态质子转移（ESIPT）进行激发态失活的能力。1,3,5-三嗪化合物的分子内氢键（IMHB）是激发态质子转移的基础，已通过红外光谱，紫外光谱，不同构象异构体的结构和能量方面以及前沿分子轨道分析进行了探索。

  DOI：

  10.1007/s10895-018-2235-2
• 作为产物：
  描述：

  2-噻吩基锂 、 2,4-dichloro-6-(thiophen-2-yl)-1,3,5-triazine 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 生成 2-chloro-4,6-di(thiophen-2-yl)-1,3,5-triazine
  参考文献：
  名称：

  Kauffmann,T. et al., Angewandte Chemie, 1972, vol. 84, p. 830 - 831

  摘要：

  DOI：

文献信息

• A New Route to Light Emitting Organic Materials Based on Triazine Derivatives
  作者：Krzysztof Idzik、Jadwiga Sołoducho、Mieczysław Łapkowski、Przemysław Data

  DOI：10.1007/s10895-010-0659-4

  日期：2010.9

  Novel light-emitting organic materials comprising conjugated oligomers chemically attached via a flexible spacer to an electron–or hole-conducting core were synthesized by Stille cross-coupling methodology and designed for tunable charge injection and optical properties. The hyperbranched structures have been characterized by 1H NMR, 13C NMR, and UV-VIS spectroscopy. The obtained structures show good stability in common organic solvents such as CHCl3, toluene, and CH2Cl2 and exhibit excellent thermal stability. A preliminary electroluminescence properties were also investigated. This class of materials will help to balance charge injection and transport and to spread out the charge recombination zone, thereby significantly improving the device efficiency and lifetime of unpolarized and polarized OLEDs.

  通过 Stille 交叉偶联方法合成了新型发光有机材料，这些材料由通过柔性间隔物化学连接到电子或空穴传导内核的共轭低聚物组成，并设计了可调电荷注入和光学特性。超支化结构通过 1H NMR、13C NMR 和 UV-VIS 光谱进行了表征。所获得的结构在 CHCl3、甲苯和 CH2Cl2 等常见有机溶剂中表现出良好的稳定性，并具有出色的热稳定性。此外，还对电致发光特性进行了初步研究。这一类材料将有助于平衡电荷注入和传输，分散电荷重组区，从而显著提高非极化和极化有机发光二极管的器件效率和使用寿命。
• Star-shaped triazine–thiophene conjugated systems
  作者：Philippe Leriche、Flavia Piron、Emilie Ripaud、Pierre Frère、Magali Allain、Jean Roncali

  DOI：10.1016/j.tetlet.2009.07.126

  日期：2009.10

  Star-shaped molecules consisting of short-chain oligothiophenes attached onto an electron acceptor triazine core have been synthesized. Results of the analysis of the electronic properties of these compounds by UV-vis spectroscopy and cyclic voltammetry are used to discuss the impact of the electron-withdrawing node on the properties of the compounds. The electrochemical oxidation of some of these systems into the corresponding electroactive polymers is briefly discussed. (C) 2009 Published by Elsevier Ltd.
• Conjugated Asymmetric Donor-Substituted 1,3,5-Triazines: New Host Materials for Blue Phosphorescent Organic Light-Emitting Diodes
  作者：Zhong-Fu An、Run-Feng Chen、Jun Yin、Guo-Hua Xie、Hui-Fang Shi、Taiju Tsuboi、Wei Huang

  DOI：10.1002/chem.201101118

  日期：2011.9.19

  AbstractConjugated asymmetric donor‐substituted 1,3,5‐triazines (ADTs) have been synthesized by nucleophilic substitution of organolithium catalyzed by [Pd(PPh3)4]. Theoretical and experimental investigations show that ADTs possess high solubility and thermostability, high fluorescent quantum yield (35 %), low HOMO (−6.0 eV) and LUMO (−2.8 eV), and high triplet energy (ET, 3.0 eV) according to the different substitution pattern of triazine. The application as host materials for blue PHOLEDs yielded a maximum current efficiency of 20.9 cd A−1, a maximum external quantum efficiency of 9.8 %, and a brightness of 9671 cd m−2 at 5.4 V, making ADTs good candidates for optoelectronic devices.
• Efficient blue emitters based on 1,3,5-triazine for nondoped organic light emitting diode applications
  作者：Jian Liu、Ming-Yu Teng、Xiao-Peng Zhang、Kai Wang、Cheng-Hui Li、You-Xuan Zheng、Xiao-Zeng You

  DOI：10.1016/j.orgel.2012.06.013

  日期：2012.10

  Two novel efficient blue emitters (TTT-1, TTT-2) containing 1,3,5-triazine, thiophene and triphenylamine have been designed and synthesized. Organic light emitting diodes (OLEDs) using these new triazine derivatives as emissive layers, ITO/TAPC (60 nm)/TTT-1 (Device A) or TTT-2 (Device B) (40 nm)/TPBi (60 nm)/LiF (1 nm)/Al (100 nm), were fabricated and tested. The OLEDs exhibited good performances with low turn-on voltage of 3 V, maximum luminance of ca. 8990 cd/m(2) for TTT-1 and 15,980 cd/m(2) for TTT-2, and maximum luminance efficiency of 4.7 cd/A for TTT-1 and 4.0 cd/A for TTT-2, respectively. (C) 2012 Elsevier B.V. All rights reserved.
• Synthesis and Electrochemical Study of 4,4’,5-tris(methylthio)-5’-{2-[4,6-di(thiophen-2-yl)-1,3,5-triazin-2-yloxy]ethylthio}tetrathiafulvalene
  作者：Evgenii A. Ignatenko、Pavel A. Slepukhin、Elena V. Shklyaeva、Georgii G. Abashev

  DOI：10.1016/j.mencom.2012.05.011

  日期：2012.5

  New unsymmetrical 4,4',5-tris(methylthio)5'-2-[4,6-di(thiophen-2-yl)-1,3,5-triazin-2-yloxy]ethylthio}tetrathiafulvalene bearing a polymerizable moiety has been designed and successfully synthesized; its electrochemical properties, susceptibility towards polymerization and crystal structure have been determined.