2-[4-[2-(4-Iodophenyl)ethynyl]phenyl]ethynyl-tri(propan-2-yl)silane | 1173821-50-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[4-[2-(4-Iodophenyl)ethynyl]phenyl]ethynyl-tri(propan-2-yl)silane
• CAS: 1173821-50-5
• 化学式: C₂₅H₂₉ISi
• 分子量: 484.495
• InChiKey: HAJWYFMENLBDRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.26
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (4-溴苯基)乙炔 、 2-[4-[2-(4-Iodophenyl)ethynyl]phenyl]ethynyl-tri(propan-2-yl)silane 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以73%的产率得到
  参考文献：
  名称：

  Outstanding Multi‐Photon Absorption at π‐Delocalizable Metallodendrimers

  摘要：

  AbstractMulti‐photon absorption (MPA) has attracted interest for applications exploiting the tight spatial control of interaction volume and long wavelength excitation. However, a deficiency of molecules exhibiting higher‐order nPA (n‐photon absorption, n>2) and a lack of structure–property studies to define the key structural characteristics needed to optimize higher‐order MPA performance have hindered practical development. We herein report the syntheses of second‐ and third‐generation metallodendrimers and assessment of their nonlinear absorption, together with those of zero‐ and first‐generation analogues. We report the first 5PA and 6PA data for an organometallic. The largest dendrimer exhibits exceptional three‐, four‐, five‐ and six‐photon absorption to femtosecond‐pulsed light. The systematically varied compounds highlight the crucial role of metal‐to‐oligo(phenyleneethynylene) charge transfer in promoting outstanding MPA activity.

  DOI：

  10.1002/anie.202116181
• 作为产物：
  描述：

  [4-(4-bromophenylethynyl)phenylethynyl]triisopropylsilane 在 正丁基锂 、 碘 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.17h， 以94%的产率得到2-[4-[2-(4-Iodophenyl)ethynyl]phenyl]ethynyl-tri(propan-2-yl)silane
  参考文献：
  名称：

  Electronic, Redox, and Photophysical Consequences of Metal-for-Carbon Substitution in Oligo-Phenylene-Ethynylenes

  摘要：

  The electronic structures, redox chemistry, and excited-state properties of tungsten-containing oligo-phenylene-ethynylenes (OPEs) of the form W[C(p-C6H4CC)(n-1)Ph](dppe)(2)Cl (n = 1-5; dppe =1,2-bis-(diphenylphosphino)ethane) are reported and compared with those of organic analogues in order to elucidate the effects of metal-for-carbon substitution on OPE bonding and electronic properties. Key similarities between the metallo- and organic OPEs that bear on materials-related functions include their nearly identical effective conjugation lengths, reduction potentials, and;14 orbital energies and delocalization. In addition to these conserved properties, the tungsten centers endow OPEs with reversible one-electron oxidation chemistry and long-lived emissive triplet excited states that are not accessible to organic OPEs. The electronic similarities and differences between metallo- and organic OPEs can be understood largely on the basis of pi/pi* orbital energy matching between tungsten and organic PE fragments and the introduction of an orthogonal mid-pi/pi*-gap d orbital in metallo-OPEs. These orbital energies can be tuned by varying the supporting ligands; this provides a means to rationally implement and control the emergent properties of metallo-OPE materials.

  DOI：

  10.1021/ja411354d

文献信息

• Length-Dependent Convergence and Saturation Behavior of Electrochemical, Linear Optical, Quadratic Nonlinear Optical, and Cubic Nonlinear Optical Properties of Dipolar Alkynylruthenium Complexes with Oligo(phenyleneethynylene) Bridges
  作者：Bandar Babgi、Luca Rigamonti、Marie P. Cifuentes、T. Christopher Corkery、Michael D. Randles、Torsten Schwich、Simon Petrie、Robert Stranger、Ayele Teshome、Inge Asselberghs、Koen Clays、Marek Samoc、Mark G. Humphrey

  DOI：10.1021/ja902793z

  日期：2009.7.29

  r formulation that affords efficient quadratic and cubic NLO compounds; the identity of 19 was confirmed by a structural study. The electrochemical properties of 19-24 and related complexes with shorter pi-bridge ligands were assessed by cyclic voltammetry, and the linear optical, quadratic nonlinear optical, and cubic nonlinear optical properties were assayed by UV-vis-NIR spectroscopy, hyper-Rayleigh

  4''',4''''-C[三键]CC(6)H(4)C[三键]CC(6)H(4)C[三键]CC(6)H(2) [2,5-(OEt)(2)]C[三键]CC(6)H(2)[2,5-(OEt)(2)]C[三键]CC(6)H(4)报道了 NO(2)}Cl(dppm)(2)] (24) 以及前体炔烃与供体-π-桥-受体配方的配合物，可提供有效的二次和三次 NLO 化合物；结构研究证实了 19 的身份。通过循环伏安法评估 19-24 和具有较短 pi 桥配体的相关配合物的电化学性质，并通过紫外-可见-近红外光谱、超瑞利散射测定线性光学、二次非线性光学和三次非线性光学性质1064 和 1300 nm 的研究，以及宽光谱范围的飞秒 Z 扫描研究。Ru(II/III) 氧化电位和光吸收最大值的波长随着 pi 桥延长而减小，直到达到三（亚苯基乙炔）配合物，进一步链延长使这些参数保持不变；采用时间相关密度泛函理论
• Synthesis of Optically Active π-Stacked Molecules: Effect of π-Stacking Position on the Chiroptical Properties
  作者：Risa Sawada、Masayuki Gon、Yoshiki Chujo、Ryo Inoue、Yasuhiro Morisaki

  DOI：10.1246/bcsj.20220153

  日期：2022.9.15

  Optically active V-shaped and X-shaped molecules consisting of stacked five-ringed para-phenylene-ethynylenes (PPEs) were prepared using planar chiral [2.2]paracyclophanes as chiral building blocks. Despite having the same absolute configurations, the V- and X-shaped molecules exhibited opposite circular dichroism (CD) and circularly polarized luminescence (CPL) signals. For example, (Sp)-isomer of

  使用平面手性 [2.2] 对环芳烃作为手性结构单元，制备了由堆叠的五环对苯乙炔 (PPE)组成的光学活性 V 形和 X 形分子。尽管具有相同的绝对构型，V 形和 X 形分子表现出相反的圆二色性 (CD) 和圆偏振发光 (CPL) 信号。例如，V 形分子的 ( S p )-异构体和 X 形分子的 ( S p )-异构体分别表现出负 CPL 发射和正 CPL发射。使用时间相关的密度泛函理论计算的模拟表明，S 1中 V 形分子的最低未占分子轨道 (LUMO)状态定位在其中一个堆叠的 PPE 中，而 S 1状态的两个 X 形分子的 LUMO通过 [2.2] 对环芳基部分在两个 PPE 中离域。理论结果被复制并很好地解释了 CD 和 CPL 行为。