2-(thiophen-2-yl)-1H-anthra[1,2-d]imidazole-6,11-dione | 1254332-24-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(thiophen-2-yl)-1H-anthra[1,2-d]imidazole-6,11-dione
• 英文别名: 2-(2-Thenyl)-6,2-d]imidazole-6,11-dione；2-thiophen-2-yl-3H-naphtho[3,2-e]benzimidazole-6,11-dione
• CAS: 1254332-24-5
• 化学式: C₁₉H₁₀N₂O₂S
• 分子量: 330.367
• InChiKey: JQAINGASXHGYRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [iridium(III)(μ-chloro)(2-phenylpyridine)2]2 、 2-(thiophen-2-yl)-1H-anthra[1,2-d]imidazole-6,11-dione 在 Na₂CO₃ 作用下， 以 乙二醇甲醚 为溶剂， 以68%的产率得到[Ir(2-phenylpyridine(-H))2(C15H6N2O2(C4H3S))]
  参考文献：
  名称：

  Neutral and cationic cyclometallated Ir(III) complexes of anthra[1,2-d]imidazole-6,11-dione-derived ligands: Syntheses, structures and spectroscopic characterisation

  摘要：

  The syntheses of two new ligands and five new heteroleptic cyclometallated Ir(III) complexes are reported. The ligands are based upon a functionalised anthra[1,2-d]imidazole-6,11-dione core giving LH1 (3) incorporating a pendant pyridine, quinoline or thiophene unit respectively. Neutrally charged, octahedral complexes [Ir(ppy)(2)(L1-3)] are chelated by two cyclometallated phenylpyridine (ppy) ligands and a third, ancillary deprotonated ligand L1-3, whilst cationic analogues could only be isolated for [Ir(ppy)(2)(LH1-2)] [PF6]. X-ray crystal structures for [Ir(ppy)(2)(L-1)], [Ir(ppy)(2)(LH1)][PF6] and [Ir(ppy)(2)(L-2)] showed the complexes adopt a distorted octahedral coordination geometry, with the anthra[1,2-d]imidazole-6,11dione ligands coordinating in a bidentate fashion. Preliminary DFT calculations revealed that for the complexes of LH1 and LH2 the LUMO is exclusively localized on the ancillary ligand, whereas the nature of the HOMO depends on the protonation state of the ancillary ligand, often being composed of both Ir(III) and phenylpyridine character. UV-vis. and luminescence data showed that the ligands absorb into the visible region ca. 400 nm and emit ca. 560 nm, both of which are attributed to an intra-ligand CT transition within the anthra[1,2-d]imidazole-6,11-dione core. The complexes display absorption bands attributed to overlapping ligand-centred and (MLCT)-M-1-type electronic transitions, whilst only [Ir(ppy)(2)(L-2)] appeared to possess typical (MLCT)-M-3 behaviour (lambda(em) 616 nm; tau = 96 ns in aerated MeCN). The remaining complexes were generally visibly emissive (lambda(em) approximate to 560-570 nm; tau < 10 ns in aerated MeCN) with very oxygen-sensitive lifetimes more indicative of ligand-centred processes. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.07.017
• 作为产物：
  描述：

  2-噻吩甲醛 、 1,2-二氨基蒽醌 在 phosphotungstic acid 作用下， 反应 2.0h， 以94%的产率得到2-(thiophen-2-yl)-1H-anthra[1,2-d]imidazole-6,11-dione
  参考文献：
  名称：

  基于蒽咪唑二酮的可逆和可重复使用的氟离子选择性化学传感器：裸眼，比色法和荧光“ ON-OFF”

  摘要：

  新型基于蒽咪唑二酮的化合物（1-3）被合成为氟离子的选择性比色和荧光传感器。在乙腈溶剂中，用不同的阴离子研究了探针（1-3）的结合特性。当氟化物添加到1-3中时，观察到吸收光谱中的光谱红移和“关闭”发射。击打绿色到在所述环境光的橙色的颜色变化被认为是由于由基本F上的探针的咪唑部分的N-H质子去质子化-离子。有趣的是，在这三种情况下非荧光探针-F -溶液经高氯酸铜处理后，显示出从橙色到金黄色的明显颜色变化，并恢复了荧光强度。此外，传感器（1-3）用于检测的F的可逆性-离子与四个周期指示“ON-OFF-ON”机制是可操作的测试。基于传感器2的测试条作为可重复使用的成本中生效F -传感器。

  DOI：

  10.1007/s10895-017-2038-x

文献信息

• One-pot protocol for J-aggregated anthraimidazolediones catalyzed by phosphotungstic acid in PEG-400 under aerobic condition
  作者：Bhaswati Bhattacharyya、Arijit Kundu、Aniruddha Das、Kaliprasanna Dhara、Nikhil Guchhait

  DOI：10.1039/c5ra19190d

  日期：——

  A precise and productive one pot green protocol has been developed for the chemoselective synthesis of anthra[1,2-d]imidazole-6,11-diones using phosphotungstic acid (PTA) as a reusable catalyst on polyethylene glycol-400 (PEG-400) support under aerobic condition. It involves a simple synthetic procedure for a wide range of anthraimidazolediones from 1,2-diaminoanthraquinone and various aldehydes possessing

  已经开发出一种精确且高效的一锅绿色方案，用于蒽的化学选择性合成[1,2- d在有氧条件下，使用磷钨酸（PTA）作为可重复使用的催化剂在聚乙二醇-400（PEG-400）载体上使用]咪唑-6,11-二酮。它涉及一种简单的合成方法，可用于从1,2-二氨基蒽醌和具有π富集的芳族/杂芳族环和亲脂性烷基链的各种醛类中制备各种蒽咪唑二酮。在惰性气氛中，反应遵循不同的途径，从而产生独特的萘喹喔啉衍生物。合成的蒽咪唑二酮衍生物显示出受取代模式影响的不同自聚集形态。还观察到晶体堆积图案和具有J-聚集形态的光物理性质之间的良好协议。