2,9-di-n-butyl-1,10-phenanthroline-5,6-dione | 379711-32-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 2,9-di-n-butyl-1,10-phenanthroline-5,6-dione
• 英文别名: 2,9-dibutyl-1,10-phenanthroline-5,6-dione；1,10-Phenanthroline-5,6-dione, 2,9-dibutyl-
• CAS: 379711-32-7
• 化学式: C₂₀H₂₂N₂O₂
• 分子量: 322.407
• InChiKey: XTDQDEUTCYPCOA-UHFFFAOYSA-N

物化性质

• 熔点：
  86 °C
• 沸点：
  509.3±50.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  59.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,9-di-n-butyl-1,10-phenanthroline-5,6-dione 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 5.0h， 生成 [Cu(3,6-di-n-butyl-naphto[2,3-f][4,5]phenanthroline-9,14-dicarbonitrile)₂]⁺(PF₆^-)
  参考文献：
  名称：

  New luminescent copper(I) complexes with extended π-conjugation

  摘要：

  While copper(I)-bis(diimine) complexes [Cu-I(L)(2)](+) are considered as potent substitutes for [Ru-II(bpy)(3)](2+), they exhibit low molar extinction coefficients with respect to ruthenium parent analogues. One interesting possibility to improve the light collection ability of [Cu-I(L)(2)](+) consists in increasing the length of the Cu-L dipole. In order to achieve this goal, we propose in this contribution to fuse aromatic rings onto the 2,9-di-nbutyl-1,10-phenanthroline core and examine how the properties of the corresponding copper(I) complexes are impacted. Electrochemical, absorption and emission properties are assessed; rewardingly, the envisioned approach was successful since extinction coefficients above 10,000 M-1.cm(-1) were measured. All copper(I) complexes remain photoluminescent, with emission maxima greatly varying from 725 to 815 nm, strongly affected by the molecular structures. A rationale to explain the variations of the emission quantum yields is proposed. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2017.11.026
• 作为产物：
  描述：

  2,9-二丁基-1,10-邻二氮杂菲 在 硫酸 、 硝酸 、 potassium bromide 作用下， 以82%的产率得到2,9-di-n-butyl-1,10-phenanthroline-5,6-dione
  参考文献：
  名称：

  Synthesis and Structures of 1,10-Phenanthroline-Based Extended Triptycene Derivatives

  摘要：

  通过¹H NMR、¹³C NMR、MALDI-TOF MS 光谱和元素分析确定了它们的结构。

  DOI：

  10.1055/s-0029-1219957

文献信息

• New Heteroleptic Bis-Phenanthroline Copper(I) Complexes with Dipyridophenazine or Imidazole Fused Phenanthroline Ligands: Spectral, Electrochemical, and Quantum Chemical Studies
  作者：Yann Pellegrin、Martina Sandroni、Errol Blart、Aurélien Planchat、Michel Evain、Narayan C. Bera、Megumi Kayanuma、Michel Sliwa、Mateusz Rebarz、Olivier Poizat、Chantal Daniel、Fabrice Odobel

  DOI：10.1021/ic2006343

  日期：2011.11.21

  behavior, corresponding to a copper(I) to copper(II) transition. The half wave potentials increase with the steric bulk at the level of the copper(I) ion, reaching a value as high as 1 V vs SCE, with the assistance of ligand induced electronic effects. L1 and L2 are further end-capped by a bromo functionality. A Suzuki cross-coupling reaction was directly performed on the complexes, in spite of the handicapping

  两个新的空间位挑战二亚胺配体大号1（2,9-二基的2-（4'-溴苯基）咪唑并[4,5- ˚F ] [1,10]菲咯啉）和大号2（3,6-二- ñ -遵循Schmittel和同事开发的HETPHEN概念，合成了丁基-11-bromodipyrido [3,2- a：2'，3'- c ]吩嗪），目的是构建原始的杂铜（I）配合物。L 1的结构基于一个苯并咪唑分子核心，该苯并咪唑分子在菲咯啉腔的2和9位上被两个高度庞大的异氰酸酯基衍生而来，从而阻止了均纯物质的形成，而L 2dppz是dppz衍生物，在螯合氮原子的α位带有正丁基链。基于L 1，L 2和互补匹配配体（2,9-R 2 -1,10-菲咯啉，R = H，甲基，正丁基或异丁基）的六个新型杂铜（I）配合物的明确形成）已被证明，并且所形成的化合物已得到充分表征。所有配合物的电子吸收光谱与DFT计算非常吻合，可以指定主要的跃迁。使用时间分辨单光子计
• Allylation of Orthoquinones Towards Annulated Polycyclic Aromatic Systems
  作者：Mariusz Kędziorek、Liliana Dobrzańska

  DOI：10.3390/molecules23082043

  日期：——

  Promising results of an efficient and convenient strategy for the annulation of polycyclic aromatic compounds (PACs), employing orthoquinones as starting material and comprising allylation, pinacol rearrangement, ring-closing metathesis (RCM), and one-pot reduction followed by Wagner-Meerwein rearrangement, are presented. The strategy involves introducing triallylborane prepared in situ in the allylation

  多环芳族化合物 (PAC) 环化的高效便捷策略的有希望的结果，采用邻醌作为起始材料，包括烯丙基化、频哪醇重排、闭环复分解 (RCM) 和一锅还原，然后是 Wagner-Meerwein 重排, 呈现。该策略涉及在烯丙基化步骤中引入原位制备的三烯丙基硼烷。此外，还介绍了一种制备 9,10-二烯丙基菲的新方法。
• Substituted 1,10-Phenanthroline-5,6-diamines and their Extension to Soluble, Acetylenic Pyrazinophenanthrolines
  作者：Sascha Ott、Rüdiger Faust

  DOI：10.1055/s-2005-916010

  日期：——

  2,9-Disubstituted and 3,8-disubstituted 1,10-phenanthrolines have been converted to the respective 5,6-diamines in three steps. The new heterocycles have been employed in condensation reactions with a protected 1,2-dialkynyl-1,2-dione to afford solubility-improved, acetylenic pyrazinophenanthrolines (pyzphen). In an initial study, the synthetic scope of these novel acetylenic ligands is evaluated.

  通过三个步骤，2,9-二取代和 3,8- 二取代的 1,10-菲罗啉被转化为相应的 5,6- 二胺。新杂环在与受保护的 1,2-二炔基-1,2-二酮的缩合反应中得到了溶解度改进的乙炔基吡嗪菲罗啉（pyzphen）。在一项初步研究中，对这些新型乙炔配体的合成范围进行了评估。
• Self-Assembling of n-Type Semiconductor Tri(phenanthrolino)hexaazatriphenylenes with a Large Aromatic Core
  作者：Tsutomu Ishi-i、Kentaro Yaguma、Rempei Kuwahara、Yoshiki Taguri、Shuntaro Mataka

  DOI：10.1021/ol052779t

  日期：2006.2.1

  Large disk-shaped aromatic tri(phenanthrolino)hexaazatriphenylenes 5a, 5b, and 5c with six butyl, dodecyl, and 4-octylphenyl groups, respectively, were self-assembled both in solution and film state to form one-dimensional aggregates. Their n-type semiconducting nature was indicated from CV measurement, in which the first reduction potentials were evaluated at around -1.7 V (vs Fc/Fc(+)) in dichloromethane.