2,9-bis(4-hydroxyphenyl)-1,10-phenanthroline | 88498-43-5

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物 - 酚及其卤化、磺化、硝化或亚硝化衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2,9-bis(4-hydroxyphenyl)-1,10-phenanthroline
• 英文别名: 2,9-di(p-hydroxyphenyl)-1,10-phenanthroline；2,9-bis(p-hydroxyphenyl)-1,10-phenanthroline；2,9-di(p-phenol)-1,10-phenanthroline；2,9-di(4-hydroxyphenyl)-1,10-phenanthroline；Phenol, 4,4'-(1,10-phenanthroline-2,9-diyl)bis-；4-[9-(4-hydroxyphenyl)-1,10-phenanthrolin-2-yl]phenol
• CAS: 88498-43-5
• 化学式: C₂₄H₁₆N₂O₂
• 分子量: 364.403
• InChiKey: GTOXEYAZDAJKFU-UHFFFAOYSA-N

物化性质

• 熔点：
  >260 °C
• 沸点：
  632.9±50.0 °C(Predicted)
• 密度：
  1.341±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.2
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319
• 储存条件：
  存放条件：室温、密封、干燥

反应信息

• 作为反应物：
  描述：

  2,9-bis(4-hydroxyphenyl)-1,10-phenanthroline 在 potassium carbonate 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 63.0h， 生成 2,9-bis[p-(2-iodoethoxy)phenyl]-1,10-phenanthroline
  参考文献：
  名称：

  Multiporphyrinic Rotaxanes: Control of Intramolecular Electron Transfer Rate by Steering the Mutual Arrangement of the Chromophores

  摘要：

  A [2]-rotaxane Zn-2-Au+ made from a dumbbell component ended by Zn(II) porphyrin stoppers and a ring component incorporating a Au(III) porphyrin has been assembled in 13% yield using the transition metal templating route. H-1 NMR studies show that its:conformation in solution is very different from those of its complexes with Cu+, Ag+, and Li+. In particular, removal of the templating metal resulted in a changeover of the molecule, the threaded macrocycle undergoing a pirouetting motion placing the Au(III) porphyrin in the deft formed by the two Zn(II) porphyrin stoppers. At room temperature, the changeover could be either complete or partial, depending on the solvent used. Photoinduced electron transfer from one of the Zn(II) porphyrins to the Au(III) porphyrin of the macrocycle was evidenced in the case of the free rotaxane and its Cu(I) complex, Zn2Cu+Au+. In the former case, the photoinduced electron transfer process could be clearly resolved for an extended conformation that is characterized by the Zn(II) porphyrins pointing far from the Au(III) porphyrin electron acceptor, and accounting for 30% of the total in acetonitrile at room temperature. In both Zn2Cu+Au+ and Zn-2-Au+ rotaxanes, the charge-separated state, in which the Zn(II) porphyrin is a cation radical and the Au(III) porphyrin a neutral radical, was generated at a rate of 5 x 10(9) s(-1) and disappeared at a rate of 2 x 10(8) s(-1). In the case of Zn2Cu+Au+, the primary step is very Likely energy transfer from the Zn(II) porphyrin singlet excited state to the MLCT state of the central Cu(I) complex, followed by an electron transfer from the excited Cu(I) unit to the Au(III) porphyrin and a successive charge shift from the Zn(ll) porphyrin to the oxidized Cu(Ll) complex. [2]-rotaxane Zn-2-Au+, in which no bond pathway can be identified between the donor and the, acceptor, is a typical case of electron transfer involving molecular fragments connected by mechanical bonds.

  DOI：

  10.1021/ja002018f
• 作为产物：
  描述：

  在 吡啶 、 盐酸 、 manganese(IV) oxide 、 水 作用下， 以 二氯甲烷 为溶剂， 生成 2,9-bis(4-hydroxyphenyl)-1,10-phenanthroline
  参考文献：
  名称：

  Tetrathiafulvalene–phenanthroline macrocycles as redox responsive sensors for metal ions

  摘要：

  含有氧化还原活性四硫富瓦烯单元和菲咯啉配体的环状大分子在作为前卡那替络合物的一部分时，能够识别不同的金属离子（Cu+、Ag+和Li+）。

  DOI：

  10.1039/a909320f

文献信息

• Use of Cleavable Coordinating Rings as Protective Groups in the Synthesis of a Rotaxane with an Axis that Incorporates More Chelating Groups Than Threaded Macrocycles
  作者：Antoine Joosten、Yann Trolez、Valérie Heitz、Jean-Pierre Sauvage

  DOI：10.1002/chem.201301717

  日期：2013.9.16

  methodology allowing preparation of a linear “unsaturated” [3]rotaxane consisting of an axis incorporating more coordination sites than threaded rings was developed. It was based on the preliminary synthesis of a “saturated” [5]rotaxane consisting of a four‐chelating site axis threaded through four macrocyclic components, two of them being cleavable rings incorporating a lactone function and the two

  开发了一种允许制备线性“不饱和” [3]轮烷的新方法，该轴由比螺纹环包含更多配位点的轴组成。它基于“饱和” [5]轮烷的初步合成，该轮烷由穿过四个大环组分的四个螯合位点轴组成，其中两个是带有内酯功能的可裂解环，另外两个是“安全的”非-可裂环。终止反应基于点击化学。随后，在碱性培养基中从[5]轮烷中裂解并除去两个含内酯的大环化合物，可定量获得所需的“不饱和” [3]轮烷。
• A supramolecularly templated catenane initiator and a controlled ring expansion strategy
  作者：Peng-Fei Cao、Ajaykumar Bunha、Joey Mangadlao、Mary Jane Felipe、Katrina Irene Mongcopa、Rigoberto Advincula

  DOI：10.1039/c2cc35588d

  日期：——

  We report the first synthesis of a catenated polymer via a ring-expansion strategy, which is based on a supramolecularly templated initiator. The high yielding synthesis and simple isolation method will enable the investigation and development of this unique polymer system for further applications.

  我们报道了通过环扩展策略实现的首例联环聚合物的合成，该策略基于超分子模板引发剂。高产率的合成和简单的分离方法将促进这种独特聚合物体系的研究与发展，为其进一步应用提供可能。
• Characterization and photocatalytic behavior of 2,9-di(aryl)-1,10-phenanthroline copper(<scp>i</scp>) complexes
  作者：M. Mustafa Cetin、Roman T. Hodson、C. Robin Hart、David B. Cordes、Michael Findlater、Dominick J. Casadonte Jr.、Anthony F. Cozzolino、Michael F. Mayer

  DOI：10.1039/c7dt00400a

  日期：——

  The synthesis, characterization, photophysical properties, theoretical calculations, and catalytic applications of 2,9-di(aryl)-1,10-phenanthroline copper(I) complexes are described. Specifically, this study made use of di(aryl)-1,10-phenanthroline ligands including 2,9-di(4-methoxyphenyl)-1,10-phenanthroline (1), 2,9-di(4-hydroxyphenyl)-1,10-phenanthroline (2), 2,9-di(4-methoxy-3-methylphenyl)-1,10-phenanthroline

  描述了2,9-二（芳基）-1,10-菲咯啉铜（I）配合物的合成，表征，光物理性质，理论计算和催化应用。具体地，该研究利用了包括2，9-二（4-甲氧基苯基）-1，10-菲咯啉（1），2，9-二（4-羟苯基）-的二（芳基）-1，10-菲咯啉配体。 1,10-菲咯啉（2），2,9-二（4-甲氧基-3-甲基苯基）-1、10-菲咯啉（3）和2,9-二（4-羟基-3-甲基苯基）-1 ，10-菲咯啉（4）。在2 ：1配体-金属配合物，如PF 6 -的盐，即，（[铜·（1）2 ] PF 6，[Cu·（2）2 ] PF 6，[Cu·（3）2 ] PF 6和[Cu·（4）2 ] PF 6）已经被分离和表征。已经通过单晶X射线分析确定了配体1和2以及配合物[Cu·（1）2 ] PF 6和[Cu·（3）2 ] PF 6的结构。这些铜的photoredox催化活性（我）在原子转移自由基加成（ATRA）反应中研究了复
• Porphyrin–Polyyne [3]- and [5]Rotaxanes
  作者：Daniel R. Kohn、Levon D. Movsisyan、Amber L. Thompson、Harry L. Anderson

  DOI：10.1021/acs.orglett.6b03528

  日期：2017.1.20

  Porphyrin–polyyne [3]- and [5]rotaxanes have been synthesized by condensing aldehyde–rotaxanes with pyrrole or dipyrromethane. The crystal structure of a [3]rotaxane shows that the macrocycles adopt compact conformations, holding the hexaynes near the porphyrin core, and that the phenanthroline units form intermolecular π-stacked dimers in the solid. Fluorescence spectra reveal singlet excited-state

  卟啉-聚炔[3]-和[5]轮烷是通过将醛-轮烷与吡咯或二吡咯甲烷缩合而合成的。[3]轮烷的晶体结构表明，大环具有紧密的构象，将己炔保持在卟啉核附近，并且菲咯啉单元在固体中形成了分子间π堆积的二聚体。荧光光谱揭示了单态激发态能量从带线的己炔到卟啉，从菲咯啉到卟啉以及从菲咯啉到己炔的转移。
• Syntheses, Structural Studies, and Copper Iodide Complexes of Macrocycles Derived from Williamson Ether Syntheses Involving 2,9-Bis(4-hydroxyphenyl)-1,10-phenanthroline, α,ω-Dibromides, and Resorcinol or 2,7-Dihydroxynaphthalene
  作者：Zuzana Baranová、Hashem Amini、Madhav Neupane、Sydney C. Garrett、Andreas Ehnbom、Nattamai Bhuvanesh、Joseph H. Reibenspies、John A. Gladysz

  DOI：10.1071/ch16587

  日期：——

  9-bis(4-hydroxyphenyl)-1,10-phenanthroline in the presence of K2CO3 to give the corresponding 31- to 35-membered macrocycles (3a–d, 22–63 % yield). When 3a–d were treated with CuI, mononuclear 1 : 1 complexes formed, in which the CuI chelates to the nitrogen donor atoms of the phenanthroline moiety (4a–d, 40–80 % yield). The crystal structures of 3a–c and 4a–c were determined and analyzed using density

  制备了1,3-双（6-溴己氧基）苯，2,7-双（6-溴己氧基）萘，1,3-双（4-溴甲基苄氧基）苯和1,3-双（3-溴甲基苄氧基）苯通过间苯二酚或2,7-二羟基萘和1,6-二溴己烷，1,4-双（溴甲基）苯或1,3-双（溴甲基）苯进行的Williamson醚合成（产率21-47％）。在K 2 CO 3存在下，将这些二溴化物与2,9-双（4-羟苯基）-1,10-菲咯啉缩合，得到相应的31至35元大环化合物（3a – d，22–63％收率）。当3a - d用CuI处理时，形成单核1：1的配合物，其中CuI螯合到菲咯啉部分的氮供体原子上（4a – d，40–80％的产量）。使用密度泛函理论计算并在轮烷烷的情况下确定并分析了3a – c和4a – c的晶体结构，轮烷可以通过用末端炔烃处理4a – d来形成（例如大环尺寸，空隙体积）。4a - c中的铜和碘原子显着从菲咯啉部分的最小二乘平面突出（0.46-0