5,5'-bis[(3,4-dibutylthienyl)ethynyl]-2,2'-bipyridine | 522599-21-9

• 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: 5,5'-bis[(3,4-dibutylthienyl)ethynyl]-2,2'-bipyridine
• 英文别名: 5,5'-bis[(3,4-dibutylthien-2-yl)ethynyl]-2,2'-bipyridine；5,5'-Bis[(3,4-dibutylthiophen-2-yl)ethynyl]-2,2'-bipyridine；5-[2-(3,4-dibutylthiophen-2-yl)ethynyl]-2-[5-[2-(3,4-dibutylthiophen-2-yl)ethynyl]pyridin-2-yl]pyridine
• CAS: 522599-21-9
• 化学式: C₃₈H₄₄N₂S₂
• 分子量: 592.913
• InChiKey: QKBVUQVOCJJNOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.5
• 重原子数：
  42
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  82.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,5'-bis[(3,4-dibutylthienyl)ethynyl]-2,2'-bipyridine 在 四(三苯基膦)钯 正丙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 20.5h， 生成 5,5'-bis[(3,4-dibutyl-5-{[5'-(3,4-dibutylthien-2-ylethynyl)-2,2'-bipyridin-5-yl]ethynyl}thien-2-yl)ethynyl]-2,2'-bipyridine
  参考文献：
  名称：

  从噻吩和炔烃键逐步合成共轭桥联联吡啶配体

  摘要：

  5,5'-二溴-2,2'-联吡啶与 TMS 和 CMe 2 OH 保护的乙炔的双重 Sonogashira 偶联反应允许合成从 TMS 或 2-羟基-丙二醇选择性脱保护的双对称官能化结构单元-2-基位点。各种组合允许末端炔烃与 3,4-二丁基-2-碘噻吩或 3,4-二丁基-2,5-二碘噻吩互连，从而形成带有两个乙炔基噻吩单元或一个噻吩/一个乙炔官能团的联吡啶骨架。可以构建双位或三位联吡啶配体，其中螯合亚基由 3,4-二丁基-2,5-二乙炔基噻吩间隔物桥接，并由 3,4-二丁基-2-乙炔基噻吩终止剂封端。

  DOI：

  10.1055/s-2005-861847
• 作为产物：
  描述：

  5,5'-二溴-2,2'-联吡啶 在 bis-triphenylphosphine-palladium(II) chloride 、 四(三苯基膦)钯 potassium fluoride 、 copper(l) iodide 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 生成 5,5'-bis[(3,4-dibutylthienyl)ethynyl]-2,2'-bipyridine
  参考文献：
  名称：

  A convenient method of producing thiophene linked bipyridine oligomers

  摘要：

  A series of soluble polybipyridine ligands comprising one to five bipyridine modules sandwiched between rigid carboncarbon triple bonds substituted by 3,4-dibutylthiophene repeating units was synthesized. Two different protocols have been explored with the idea to use a divergent/convergent approach starting from bisymmetrically and symmetrically substituted bipyridine modules. At each stage of the iteration two bipy/thiophene modules are connected. The use of triethylsilylacetylene and 2-methylbut-3-yn-2-ol insures an easy entry to pivotal building blocks, which could be selectively deprotected from the TES or 2-hydroxyprop-2-yl sites. All cross-coupling reactions are promoted with palladium(0) tetrakistriphenylphosphine under mild conditions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.08.062

文献信息

• One-pot synthesis of 2,5-diethynyl-3,4-dibutylthiophene substituted multitopic bipyridine ligands: redox and photophysical properties of their ruthenium(ii) complexes
  作者：Antoinette De Nicola、Yao Liu、Kirk S. Schanze、Raymond Ziessel

  DOI：10.1039/b210279j

  日期：2003.1.7

  A facile and original synthesis of four 2,2'-bipyridine (bipy) ligands grafted with thiophene subunits is described using phase transfer experimental conditions: related Ru(II) complexes exhibit well-defined redox and photophysical properties which were probed by cyclic voltammetry, UV-vis, steady-state emission and transient absorption spectroscopy.

  使用相转移实验条件描述了四种简单的，噻吩亚基接枝的2,2'-联吡啶（bipy）配体的合成方法：相关的Ru（II）配合物表现出良好的氧化还原和光物理性质，可通过循环伏安法进行探测，紫外可见光谱，稳态发射光谱和瞬态吸收光谱。
• Photophysics and Photoinduced Electron-Transfer Reactivity of Ruthenium(II) Complexes with Oligo(thiophene-bipyridine) Ligands^,1
  作者：Yao Liu、Antoinette De Nicola、Olivier Reiff、Raymond Ziessel、Kirk S. Schanze

  DOI：10.1021/jp026971d

  日期：2003.5.1

  A novel series of mono-, di-, and trimeric ruthenium(II) complexes has been synthesized in which the quasi-linear polytopic ligand is constituted by 2,2‘-bipyridine (bpy) subunits linked in the 5,5...

  合成了一系列新的单、二和三聚钌 (II) 配合物，其中准线性多位体配体由 2,2'-联吡啶 (bpy) 亚基连接在 5,5...
• Oligomeric Ligands Incorporating Multiple 5,5‘-Diethynyl-2,2‘-bipyridine Moieties Bridged and End-Capped by 3,4-Dibutylthiophene Units
  作者：Sébastien Goeb、Antoinette De Nicola、Raymond Ziessel

  DOI：10.1021/jo048435i

  日期：2005.3.1

  In this work, we detail the synthesis and photophysical properties of a series of soluble polybipyridine ligands comprising one to five bipyridine units sandwiched between rigid carbon-carbon triple bonds substituted by 3,4-dibutylthiophene repeating units. The dual Sonogashira coupling reaction of 5,5'-dibromo-2,2'-bipyridine with TMS- and (CH3)(2)C(OH)-protected acetylene allows the synthesis of a dissymmetrically functionalized building block which was selectively deprotected at either the TMS or 2-hydroxyprop-2-yl site. Various combinations allow the interconnection of the terminal alkyne to 3,4-dibutyl-2,5-diiodothiophene or 3,4-dibutyl-2-iodothiophene leading to hipyridine frameworks bearing two acetylene-protected groups or one acetylenethiophene/one acetylene-protected function. It is possible therefore to construct dimeric to pentameric bipyridine ligands where the chelating subunit is bridged by a 3,4-dibutyl-2,5-diethynylthiophene spacer and endcapped by a 3,4-dibutyl-2-ethynylthiophene stopper. All cross-coupling reactions are promoted with palladium(0) tetrakistriphenylphosphine under mild conditions. Spectroscopic data for the new oligomers are discussed in terms of the extent of pi-electron conjugation. Upon increasing the number of pi-electrons from 24 to 104, there is a progressive lowering in the energy of absorption and fluorescence transitions, while the emission quantum yields remain essentially constant. The LUMO levels of these large molecules, estimated by cyclic voltammetry, lie in the range -3.06 to -3.18 eV.
• A convenient method of producing thiophene linked bipyridine oligomers
  作者：Antoinette De Nicola、Sébastien Goeb、Raymond Ziessel

  DOI：10.1016/j.tetlet.2004.08.062

  日期：2004.10

  A series of soluble polybipyridine ligands comprising one to five bipyridine modules sandwiched between rigid carboncarbon triple bonds substituted by 3,4-dibutylthiophene repeating units was synthesized. Two different protocols have been explored with the idea to use a divergent/convergent approach starting from bisymmetrically and symmetrically substituted bipyridine modules. At each stage of the iteration two bipy/thiophene modules are connected. The use of triethylsilylacetylene and 2-methylbut-3-yn-2-ol insures an easy entry to pivotal building blocks, which could be selectively deprotected from the TES or 2-hydroxyprop-2-yl sites. All cross-coupling reactions are promoted with palladium(0) tetrakistriphenylphosphine under mild conditions. (C) 2004 Elsevier Ltd. All rights reserved.
• Stepwise Synthesis of Conjugatively Bridged Bipyridine Ligands from Thiophene and Alkyne Linkages
  作者：Raymond Ziessel、Sébastien Goeb、Antoinette De Nicola

  DOI：10.1055/s-2005-861847

  日期：——

  coupling reaction of 5,5'-dibromo-2,2'-bipyridine with TMS and CMe 2 OH protected acetylene allows the synthesis of a disymmetrically functionalized building block which was selectively deprotected from the TMS or the 2-hydroxy-prop-2-yl site. Various combinations allow the interconnection of the terminal alkyne to 3,4-dibutyl-2-iodothiophene or 3,4-dibutyl-2,5-diiodothiophene leading to bipyridine frameworks

  5,5'-二溴-2,2'-联吡啶与 TMS 和 CMe 2 OH 保护的乙炔的双重 Sonogashira 偶联反应允许合成从 TMS 或 2-羟基-丙二醇选择性脱保护的双对称官能化结构单元-2-基位点。各种组合允许末端炔烃与 3,4-二丁基-2-碘噻吩或 3,4-二丁基-2,5-二碘噻吩互连，从而形成带有两个乙炔基噻吩单元或一个噻吩/一个乙炔官能团的联吡啶骨架。可以构建双位或三位联吡啶配体，其中螯合亚基由 3,4-二丁基-2,5-二乙炔基噻吩间隔物桥接，并由 3,4-二丁基-2-乙炔基噻吩终止剂封端。