1,8-bis(2-pyridyl)octa-1,7-diyne | 222042-10-6

• 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: 1,8-bis(2-pyridyl)octa-1,7-diyne
• 英文别名: 1,8-bis(pyridin-2-yl)octa-1,7-diyne；2-(8-Pyridin-2-ylocta-1,7-diynyl)pyridine
• CAS: 222042-10-6
• 化学式: C₁₈H₁₆N₂
• 分子量: 260.338
• InChiKey: WPWQJHXWHHHMBV-UHFFFAOYSA-N

物化性质

• 沸点：
  452.7±30.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,8-bis(2-pyridyl)octa-1,7-diyne 在 正丁基锂 、 二氯二茂锆 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 17.0h， 生成 N,N-di(propan-2-yl)-1,3-dipyridin-2-yl-4,5,6,7-tetrahydroisophosphindol-2-amine
  参考文献：
  名称：

  Phosphole-Containing π-Conjugated Systems: From Model Molecules to Polymer Films on Electrodes

  摘要：

  Two series of 2.5-dipyridyl and 2.5-dithienylphosphole derivatives containing sigma (3)- or sigma (4)-P atoms were prepared. and their optical (UV/Vis absorption, fluorescence spectra) and electrochemical properties were systematically evaluated. These physical properties depend mainly on the natures of the 2.5-substituents and of the phosphorus moiety, and they revealed that these compounds contain extended pi- conjugated systems. Structure -property relationships were established on the basis of these experimental data and ab initio calculations on the parent molecules. The limited aromatic character and low-lying LUMO of the phosphole ring appear to be crucial for achieving a highly delocalised pi system. Electrooxidation of 2,5-dithienylphosphole derivatives affords electroactive films with low optical band gaps. As observed for the corresponding monomers, the optical and electrochemical properties of the polymers can be varied over a wide range by modifying the nature of the phosphorus moiety.

  DOI：

  10.1002/1521-3765(20011001)7:19<4222::aid-chem4222>3.0.co;2-3
• 作为产物：
  描述：

  2-溴吡啶 、 1,7-辛二炔 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 反应 12.0h， 以94%的产率得到1,8-bis(2-pyridyl)octa-1,7-diyne
  参考文献：
  名称：

  Phosphole-Containing π-Conjugated Systems: From Model Molecules to Polymer Films on Electrodes

  摘要：

  Two series of 2.5-dipyridyl and 2.5-dithienylphosphole derivatives containing sigma (3)- or sigma (4)-P atoms were prepared. and their optical (UV/Vis absorption, fluorescence spectra) and electrochemical properties were systematically evaluated. These physical properties depend mainly on the natures of the 2.5-substituents and of the phosphorus moiety, and they revealed that these compounds contain extended pi- conjugated systems. Structure -property relationships were established on the basis of these experimental data and ab initio calculations on the parent molecules. The limited aromatic character and low-lying LUMO of the phosphole ring appear to be crucial for achieving a highly delocalised pi system. Electrooxidation of 2,5-dithienylphosphole derivatives affords electroactive films with low optical band gaps. As observed for the corresponding monomers, the optical and electrochemical properties of the polymers can be varied over a wide range by modifying the nature of the phosphorus moiety.

  DOI：

  10.1002/1521-3765(20011001)7:19<4222::aid-chem4222>3.0.co;2-3

文献信息

• Cobalt-mediated regio- and stereoselective assembly of dienamides by hydroaminative alkyne coupling of α,ω-diynes
  作者：Vincent Gandon、Corinne Aubert、Max Malacria、K. Peter C. Vollhardt

  DOI：10.1039/b716841a

  日期：——

  In the presence of CpCo(C(2)H(4))(2), alpha,omega-diynes undergo hydroaminative coupling with amides to furnish new dienamides with control of regio- and stereochemistry.

  在存在CpCo（C（2）H（4））（2）的情况下，α，ω-二炔与酰胺进行水合胺化反应，以控制区域和立体化学的方式提供新的二烯酰胺。
• 2,5-Di(2-pyridyl)phospholes: model compounds for the engineering of π-conjugated donor–acceptor co-oligomers with a chemically tunable HOMO–LUMO gap
  作者：Caroline Hay、Delphine Le Vilain、Valérie Deborde、Régis Réau、Loïc Toupet

  DOI：10.1039/a808408d

  日期：——

  2,5-Di(2-pyridyl)phospholes possess an extended π-conjugated system with a charge transfer structure; high yielding chemical modifications involving the phosphorus atom allow fine tuning of the HOMO–LUMO gap.

  2,5-二(2-吡啶基)磷烯具有扩展的π-共轭系统和电荷转移结构；涉及磷原子的高产率化学修饰允许对HOMO-LUMO能隙进行精细调节。
• Coordination Behaviour of a Hexadentate 1,1′‐Ferrocenylene‐Bridged Bisphosphole towards Coinage Metal Centres
  作者：Andreas Orthaber、Stefan Borucki、Wenting Shen、Regis Réau、Christophe Lescop、Rudolf Pietschnig

  DOI：10.1002/ejic.201301281

  日期：2014.4

  freedom relative to its previously described p-phenylene-bridged congener. The coordination behaviour of this ferrocenylene-based bis-N,P,N pincer towards coinage metal centres MI with M = Cu and Au was explored, revealing different coordination modes with and without involvement of N donation. Upon coordination of AuI metal centres, different isomers of a bimetallic AuI complex were isolated in the crystalline

  我们描述了二茂铁桥连的双 [2,5-双 (2-吡啶基)] 磷配体的合成，该配体显示出相对于其先前描述的对亚苯基桥连的同类物的额外旋转自由度。探索了这种基于二茂铁的双 N,P,N 钳对 M = Cu 和 Au 的铸币金属中心 MI 的配位行为，揭示了有和没有 N 捐赠的不同配位模式。在 AuI 金属中心配位后，双金属 AuI 配合物的不同异构体以结晶固态分离，显示（或不显示）分子内亲热相互作用。已经通过从头计算的方式研究了亲嗜性以及 Au-N 相互作用。
• Synthesis of rhenacyclopentadienes and η2:η2-diyne complexes from a labile dirhenium carbonyl and π-conjugated 1,7-octadiynes: Structural and photophysical characterization
  作者：Claudia Cardozo、Axel Mendoza、Gabriela Farías、André Luiz Barboza Formiga、Deisy Peña、Franmerly Fuentes、Alejandro Arce、Yomaira Otero

  DOI：10.1016/j.jorganchem.2018.12.003

  日期：2019.2

  calculations were used to evaluate the proposed geometries for the two η2:η2-diyne complexes [Re2(CO)6(CH3CN)2(μ-η2:η2-C18H16N2)] (3b), [Re2(CO)6(CH3CN)2(η2:η2-C26H20N2)] (4c), and the rhenacyclopentadiene [Re2(CO)6(CH3CN)(μ-η1:η1:η2:η2-C36H26)] (2d). The photophysical properties of all complexes were assessed, in that they exhibited fluorescence between 408 and 599 nm with quantum yields of Φf = 0.02–0.09. An

  通过[Re 2（CO）8（CH 3 CN）2 ]与1,8-bis（芳基）-1,7-辛二炔衍生物[芳基= 2-噻吩基（a），2-吡啶基（b），2-喹啉基（c）和9-菲基（d）]。我们发现二炔配体在桥联或螯合模式下与不稳定的di双核发生配位，但是，金属环戊二烯配合物的形成受到了有利的观察。所有产品均通过IR，NMR，ESI-MS，UV-Vis和荧光光谱进行了充分表征。三个新的2,5-二（芳基）rhenacyclopentadienes单晶结构[回复2（CO）7（μ-η 1：η 1：η 2：η 2 -C 16 ħ 14 š 2）]（1A）， [重2（CO）6（CH 3 CN）（μ-η 1：η 1：η 2：η 2 -C 16 ħ 14 š 2）]（2A）和[重2（CO）6（CH 3 CN）（μ-η 1：η 1：η 2：η 2 -C 26 ħ 20 Ñ 2）说明（2c）。DFT计算用于评价针对两个η所提出的几何结构2：η
• Synthesis, structure and physical properties of the manganese(ii) selenide/selenolate cluster complexes [Mn32Se14(SePh)36(PnPr3)4] and [Na(benzene-15-crown-5)(C4H8O)2]2[Mn8Se(SePh)16]
  作者：Andreas Eichhöfer、Paul T. Wood、Raghavan N. Viswanath、Richard A. Mole

  DOI：10.1039/b714582a

  日期：——

  The synthesis, molecular structures, and magnetic and optical properties of [Mn(32)Se(14)(SePh)(36)(PnPr(3))(4)] and [Na(benzene-15-crown-5)(C(4)H(8)O)(2)](2)[Mn(8)Se(SePh)(16)] have been investigated which are the first examples of manganese chalcogenide cluster complexes, despite known manganese oxo compounds, which comprise more than four manganese atoms.

  [Mn（32）Se（14）（SePh）（36）（PnPr（3））（4）]和[Na（苯-15-冠-5）（ C（4）H（8）O）（2）] [2] [Mn（8）Se（SePh）（16）]已被研究，这是锰硫族化物簇复合物的第一个实例，尽管已知锰氧基化合物，其中包含四个以上的锰原子。