2,5-bis(octyloxy)-4-(4-[2,2':6',2'']terpyridin-4'-yl-phenylethynyl)-benzaldehyde | 943316-90-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,5-bis(octyloxy)-4-(4-[2,2':6',2'']terpyridin-4'-yl-phenylethynyl)-benzaldehyde
• 英文别名: 2,5-bis(octyloxy)-4-(4-[2,2′:6′,2″]terpyridin-4′-ylphenylethynyl)benzaldehyde；2,5-bis(octyloxy)-4-(4-[2,2':6',2"]terpyridin-4'-yl-phenylethynyl)benzaldehyde；4-[2-[4-(2,6-Dipyridin-2-ylpyridin-4-yl)phenyl]ethynyl]-2,5-dioctoxybenzaldehyde
• CAS: 943316-90-3
• 化学式: C₄₆H₅₁N₃O₃
• 分子量: 693.929
• InChiKey: LECANSNEIABYHH-UHFFFAOYSA-N

物化性质

• 沸点：
  810.4±65.0 °C(predicted)
• 密度：
  1.15±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  52
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  74.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,5-bis(octyloxy)-4-(4-[2,2':6',2'']terpyridin-4'-yl-phenylethynyl)-benzaldehyde 、 (4-[2,2':6',2'']terpyridin-4'-yl-benzyl)-phosphonic acid diethyl ester 在 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以92%的产率得到1,4-bis(octyloxy)-2-(4-[2,2':6',2''-terpyridin-4'-yl]phenyl)-ethynyl-5-((E)-2-(4-[2,2':6',2''-terpyridin-4'-yl]-phenyl)-vinyl)-benzene
  参考文献：
  名称：

  Rigid π-Conjugated Mono-, Bis-, and Tris(2,2‘:6‘,2‘ ‘-terpyridines)

  摘要：

  A set of rigid, pi-conjugated linear mono- and bisterpyridines and star-shaped tristerpyridines have been synthesized using Pd(0)-catalyzed coupling reactions and the Horner-Wadsworth-Emmons reaction. The terpyridyl ligands obtained feature strong emission in the blue range with high quantum yields in dilute solution and thin films.

  DOI：

  10.1021/ol0707261
• 作为产物：
  描述：

  4-乙炔基苯甲醛 在 四(三苯基膦)钯 sodium hydroxide 、 copper(l) iodide 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 2,5-bis(octyloxy)-4-(4-[2,2':6',2'']terpyridin-4'-yl-phenylethynyl)-benzaldehyde
  参考文献：
  名称：

  Rigid π-Conjugated Mono-, Bis-, and Tris(2,2‘:6‘,2‘ ‘-terpyridines)

  摘要：

  A set of rigid, pi-conjugated linear mono- and bisterpyridines and star-shaped tristerpyridines have been synthesized using Pd(0)-catalyzed coupling reactions and the Horner-Wadsworth-Emmons reaction. The terpyridyl ligands obtained feature strong emission in the blue range with high quantum yields in dilute solution and thin films.

  DOI：

  10.1021/ol0707261

文献信息

• Synthesis of Rigid<i>π</i>-Conjugated Mono-, Bis-, Tris-, and Tetrakis(terpyridine)s: Influence of the Degree and Pattern of Substitution on the Photophysical Properties
  作者：Andreas Winter、Christian Friebe、Martin D. Hager、Ulrich S. Schubert

  DOI：10.1002/ejoc.200800857

  日期：2009.2

  series of rigid π-conjugated mono-, bis-, tris-, and tetrakis(terpyridine)s 3–8 was synthesized in high yields by means of Horner–Wadsworth–Emmons (HWE) reactions between benzyl phosphonates 1 and an aldehyde-functionalized terpyridine derivative 2. The photophysical properties of the materials in solution and in the solid state depend strongly both on the numbers of terpyridine moieties attached to the

  通过苄基膦酸酯 1 和醛-的 Horner-Wadsworth-Emmons (HWE) 反应，以高产率合成了一系列刚性 π 共轭单-、双-、三-和四（三联吡啶）3-8。功能化的三联吡啶衍生物 2. 溶液和固态材料的光物理性质在很大程度上取决于连接到中心苯基核的三联吡啶部分的数量和化合物的几何形状。邻位取代化合物 5 和 8 的光物理行为表明几何形状发生了显着变化，同时激发后有效 π 共轭系统的主要扩展。对于四（三联吡啶）衍生物 8，观察到具有高量子产率的亮绿色发射。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Dyads and Triads Based on Phenothiazine, Bis(terpyridine)ruthenium(II) Complexes, and Fullerene
  作者：Kevin Barthelmes、Andreas Winter、Ulrich S. Schubert

  DOI：10.1002/ejic.201600793

  日期：2016.11

  donor–photosensitizer–bridge–acceptor (D–P–B–A) triads and D–P dyads for the formation of photoinduced charge-separated species. The structures are based on a phenothiazine unit (D), a bis(terpyridine) [bis(tpy)] ruthenium(II) complex (P), several phenylene(ethynylene)-type spacer units (B), and a pyrrolidino[60]fullerene entity (A). The donor–acceptor distance is between 18 and 37 A and was varied by four different

  我们报告了供体-光敏剂-桥-受体（D-P-B-A）三元组和 D-P 二元组的模块化合成，用于形成光诱导的电荷分离物种。该结构基于吩噻嗪单元 (D)、双(三联吡啶) [双 (tpy)] 钌 (II) 配合物 (P)、几个亚苯基(乙炔) 型间隔单元 (B) 和一个吡咯烷 [60 ]富勒烯实体(A)。供体-受体距离在 18 到 37 A 之间，并由四个不同的桥接单元改变。光物理和电化学表征揭示了地面中的活性部分与激发态之间的某些相互作用。特别是，三元组中减少的基于钌的发射表明发生了由富勒烯实体介导的猝灭过程。
• New Ruthenium Bis(terpyridine) Methanofullerene and Pyrrolidinofullerene Complexes: Synthesis and Electrochemical and Photophysical Properties
  作者：Kevin Barthelmes、Joachim Kübel、Andreas Winter、Maria Wächtler、Christian Friebe、Benjamin Dietzek、Ulrich S. Schubert

  DOI：10.1021/ic502431x

  日期：2015.4.6

  A series of terpyridine (tpy) methanofullerene and pyrrolidinofullerene dyads linked via p-phenylene or p-phenyleneethynylenephenylene (PEP) units is presented. The coordination to ruthenium(II) yields donor-bridge-acceptor assemblies with different lengths. Cyclic voltammetry and UV-vis and luminescence spectroscopy are applied to study the electronic interactions between the active moieties. It is shown that, upon light excitation of the ruthenium(II)-based (MLCT)-M-1 transition, the formed (MLCT)-M-3 state is readily quenched in the presence of C-60. The photoinduced dynamics have been studied by transient absorption spectroscopy, which reveals fast depopulation of the (MLCT)-M-3 (73-406 ps). As a consequence, energy transfer occurs, populating a long-lived triplet state, which could be assigned to the C-3(60)* state.