2-quinolin-2-yl-3H-naphtho[3,2-e]benzimidazole-6,11-dione | 1254332-23-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-quinolin-2-yl-3H-naphtho[3,2-e]benzimidazole-6,11-dione
• CAS: 1254332-23-4
• 化学式: C₂₄H₁₃N₃O₂
• 分子量: 375.386
• InChiKey: NSSAPGYZHFMNGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 [iridium(III)(μ-chloro)(2-phenylpyridine)2]2 、 2-quinolin-2-yl-3H-naphtho[3,2-e]benzimidazole-6,11-dione 在 Na₂CO₃ 作用下， 以 乙二醇甲醚 为溶剂， 以77%的产率得到[Ir(2-phenylpyridine(-H))2(C15H6N2O2(C9H6N))]*methanol
  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：

  喹啉-2-甲醛 、 1,2-二氨基蒽醌 以 硝基苯 为溶剂， 反应 16.0h， 以92%的产率得到2-quinolin-2-yl-3H-naphtho[3,2-e]benzimidazole-6,11-dione
  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