3,4-dibutyl-2,5-bis{5'-[(3,4-dibutylthien-2-yl)ethynyl-2,2'-bipyridin-5-yl]ethynyl}thiophene | 794529-31-0

• 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: 3,4-dibutyl-2,5-bis{5'-[(3,4-dibutylthien-2-yl)ethynyl-2,2'-bipyridin-5-yl]ethynyl}thiophene
• 英文别名: 2-[5-[2-[3,4-Dibutyl-5-[2-[6-[5-[2-(3,4-dibutylthiophen-2-yl)ethynyl]pyridin-2-yl]pyridin-3-yl]ethynyl]thiophen-2-yl]ethynyl]pyridin-2-yl]-5-[2-(3,4-dibutylthiophen-2-yl)ethynyl]pyridine；2-[5-[2-[3,4-dibutyl-5-[2-[6-[5-[2-(3,4-dibutylthiophen-2-yl)ethynyl]pyridin-2-yl]pyridin-3-yl]ethynyl]thiophen-2-yl]ethynyl]pyridin-2-yl]-5-[2-(3,4-dibutylthiophen-2-yl)ethynyl]pyridine
• CAS: 794529-31-0
• 化学式: C₆₄H₆₈N₄S₃
• 分子量: 989.469
• InChiKey: ZHYZZGLFDOZUAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.6
• 重原子数：
  71
• 可旋转键数：
  28
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  136
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  六氟磷酸钾 、 锇二(2,2'-联吡啶)氯化物 、 3,4-dibutyl-2,5-bis{5'-[(3,4-dibutylthien-2-yl)ethynyl-2,2'-bipyridin-5-yl]ethynyl}thiophene 以 乙醇 为溶剂， 以50%的产率得到
  参考文献：
  名称：

  基于以Re（I），Ru（II）和Os（II）单元修饰的噻吩取代的乙炔基联吡啶二聚体的杂化物中的能量转移。

  摘要：

  报告了一系列基于刚性双位配体的弯曲共轭骨架，二聚体部分3,4-的含噻吩杂化物的制备，结构特征，电化学行为和光学性质（在室温和77 K下）。二丁基-2,5-双{5'-[（3,4-二丁基噻吩-2-基乙炔基）-2,2'-联吡啶-5-基]乙炔噻吩（TBTBT）。在二聚体中，二乙炔基-2,2'-联吡啶单元（bpy，配位点）与三个3,4-二丁硫基噻吩单元交替排列，并与[Re（CO）3Cl]，[Ru（bpy）2] 2配位+和[Os（bpy）2] 2+中心生成单核种RuTBTBT和OsTBTBT以及双核种RuTBTBTRu，OsTBTBTO，RuTBTBTO和ReTBTBTO。在室温下，通过光激发获得的发射态具有3MLCT性质，发射光谱的振动和电子分析表明，它们在TBTBT配体上很大程度上离域。在双核物种中，金属间的分离约为。在图17A中，对于RuTBTBTO，发生有效的Ru-> Os激发转移，仅导致基于

  DOI：

  10.1021/ic051717w
• 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 正丙胺 、 potassium fluoride 、 sodium hydroxide 、 copper(l) iodide 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 19.5h， 生成 3,4-dibutyl-2,5-bis{5'-[(3,4-dibutylthien-2-yl)ethynyl-2,2'-bipyridin-5-yl]ethynyl}thiophene
  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

文献信息

• 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.
• 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.
• Energy Transfer in Hybrids Based on a Thiophene-Substituted Ethynylbipyridine Dimer Decorated with Re(I), Ru(II), and Os(II) Units
  作者：Sébastien Goeb、Antoinette De Nicola、Raymond Ziessel、Cristiana Sabatini、Andrea Barbieri、Francesco Barigelletti

  DOI：10.1021/ic051717w

  日期：2006.2.1

  of thiophene-containing hybrids based on the bent conjugated backbone of a rigid ditopic ligand, the dimeric moiety 3,4-dibutyl-2,5-bis5'-[(3,4-dibutylthien-2-ylethynyl)-2,2'-bipyridin-5-yl]ethyny l}thiophene (TBTBT). Within the dimer, the diethynyl-2,2'-bipyridine units (bpy, the coordination sites) alternate with three 3,4-dibuthylthiophene units and coordination of the [Re(CO)3Cl], [Ru(bpy)2]2+

  报告了一系列基于刚性双位配体的弯曲共轭骨架，二聚体部分3,4-的含噻吩杂化物的制备，结构特征，电化学行为和光学性质（在室温和77 K下）。二丁基-2,5-双5'-[（3,4-二丁基噻吩-2-基乙炔基）-2,2'-联吡啶-5-基]乙炔噻吩（TBTBT）。在二聚体中，二乙炔基-2,2'-联吡啶单元（bpy，配位点）与三个3,4-二丁硫基噻吩单元交替排列，并与[Re（CO）3Cl]，[Ru（bpy）2] 2配位+和[Os（bpy）2] 2+中心生成单核种RuTBTBT和OsTBTBT以及双核种RuTBTBTRu，OsTBTBTO，RuTBTBTO和ReTBTBTO。在室温下，通过光激发获得的发射态具有3MLCT性质，发射光谱的振动和电子分析表明，它们在TBTBT配体上很大程度上离域。在双核物种中，金属间的分离约为。在图17A中，对于RuTBTBTO，发生有效的Ru-> Os激发转移，仅导致基于
• 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。