1,4-bis{2-(4-ethynylphenyl)ethynyl}benzene | 157875-10-0

• 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: 1,4-bis{2-(4-ethynylphenyl)ethynyl}benzene
• 英文别名: 1,4-bis(4-ethynylphenylethynyl)benzene；1,4-Bis[2-(4-ethynylphenyl)ethynyl]benzene
• CAS: 157875-10-0
• 化学式: C₂₆H₁₄
• 分子量: 326.397
• InChiKey: PYCRSVGNBWTWOW-UHFFFAOYSA-N

物化性质

• 沸点：
  489.7±40.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1,4-bis{2-(4-ethynylphenyl)ethynyl}benzene 、 2,6-diethyl-4,4-difluoro-1,3,5,7-tetramethyl-8-(4-iodophenyl)-4-bora-3a,4a-diaza-s-indacene 在 palladium dichloride copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以76%的产率得到
  参考文献：
  名称：

  Signal Ratio Amplification via Modulation of Resonance Energy Transfer:  Proof of Principle in an Emission Ratiometric Hg(II) Sensor

  摘要：

  Boradiazaindacene dyads designed as energy transfer casettes can be modified to signal cation concentrations ratiometrically. If the energy transfer efficiency is increased via changing spectral overlap on cation binding, an enhancement of emission signal ratios can be obtained. A larger range of ratios results in highly improved sensitivity to analyte concentrations. We demonstrate this approach in a de novo design of a novel and highly selective ratiometric chemosensor for Hg(II) ions.

  DOI：

  10.1021/ja066144g
• 作为产物：
  描述：

  1,4-bis((4-((trimethylsilyl)ethynyl)phenyl)ethynyl)benzene 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 生成 1,4-bis{2-(4-ethynylphenyl)ethynyl}benzene
  参考文献：
  名称：

  Signal Ratio Amplification via Modulation of Resonance Energy Transfer:  Proof of Principle in an Emission Ratiometric Hg(II) Sensor

  摘要：

  Boradiazaindacene dyads designed as energy transfer casettes can be modified to signal cation concentrations ratiometrically. If the energy transfer efficiency is increased via changing spectral overlap on cation binding, an enhancement of emission signal ratios can be obtained. A larger range of ratios results in highly improved sensitivity to analyte concentrations. We demonstrate this approach in a de novo design of a novel and highly selective ratiometric chemosensor for Hg(II) ions.

  DOI：

  10.1021/ja066144g

文献信息

• Syntheses, structures, two-photon absorption cross-sections and computed second hyperpolarisabilities of quadrupolar A–π–A systems containing E-dimesitylborylethenyl acceptors
  作者：Christopher D. Entwistle、Jonathan C. Collings、Andreas Steffen、Lars-Olof Pålsson、Andrew Beeby、David Albesa-Jové、Jacquelyn M. Burke、Andrei S. Batsanov、Judith A. K. Howard、Jackie A. Mosely、Suk-Yue Poon、Wai-Yeung Wong、Fatima Ibersiene、Sofiane Fathallah、Abdou Boucekkine、Jean-François Halet、Todd B. Marder

  DOI：10.1039/b905719f

  日期：——

  A series of bis(E-dimesitylborylethenyl)-substituted arenes, namely arene = 1,4-benzene, 1,4-tetrafluorobenzene, 2,5-thiophene, 1,4-naphthalene, 9,10-anthracene, 4,4′-biphenyl, 2,7-fluorene, 4,4′-E-stilbene, 4,4′-tolan, 5,5′-(2,2′-bithiophene), 1,4-bis(4-phenylethynyl)benzene, 1,4-bis(4-phenylethynyl)tetrafluorobenzene and 5,5″-(2,2′:5′,2″-terthiophene), have been synthesised viahydroboration of the corresponding diethynylarenes with dimesitylborane. Their absorption and emission maxima, fluorescence lifetimes and quantum yields are reported along with the two-photon absorption (TPA) spectra and TPA cross-sections for the 5,5′-bis(E-dimesitylborylethenyl)-2,2′-bithiophene and 5,5′-bis(E-dimesitylborylethenyl)-2,2′:5′,2″-terthiophene derivatives. The TPA cross-section of the latter compound of ca. 1800 GM is the largest yet reported for a 3-coordinate boron compound and is in the range of the largest values measured for quadrupolar compounds with similar conjugation lengths. The X-ray crystal structures of 1,4-benzene, 2,5-thiophene, 4,4′-biphenyl and 5,5″-(2,2′:5′,2″-terthiophene) derivatives indicate π-conjugation along the BCC–arene–CCB chain. Theoretical studies show that the second molecular hyperpolarisabilities, γ, in each series of compounds are generally related to the HOMO energy, which itself increases with increasing donor strength of the spacer. A strong enhancement of γ is predicted as the number of thiophene rings in the spacer increases.

  一系列双(E-二甲基丁烯基苯基)取代的烯烃，即烯 = 1,4-苯、1,4-四氟苯、2,5-噻吩、1,4-萘、9,10-蒽、4,4â²-联苯、2、7-芴、4,4â²-E-二苯乙烯、4,4â²-甲苯、5,5â²-（2,2â²-二噻吩）、1,4-双（4-苯乙炔基）苯、1,4-双（4-苯乙炔基）四氟苯和 5,5â³-（2,2â²：5,5â³-（2,2â²: 5â²,2â³-四噻吩）的合成是通过相应的二乙炔基烯烃与二美辛基硼烷的硼氢化反应实现的。报告了它们的吸收和发射最大值、荧光寿命和量子产率，以及 5,5â²-双（E-二甲酰基丁烯基苯基）-2,2â²-噻吩和 5,5â²-双（E-二甲酰基丁烯基苯基）-2,2â²:5â²,2â³-四噻吩衍生物的双光子吸收（TPA）光谱和 TPA 截面。后一种化合物的 TPA 横截面约为 1800 GM，是迄今为止所报道的三配位硼化合物中最大的，也在具有类似共轭长度的四极化合物所测得的最大值范围内。1,4-苯、2,5-噻吩、4,4â²-联苯和 5,5â³-（2,2â²:5â²,2â³-四噻吩）衍生物的 X 射线晶体结构表明，Ï-共轭沿着 BCCâareneâCCB 链进行。理论研究表明，各系列化合物中的第二分子超极性δ³ 通常与 HOMO 能量有关，而 HOMO 能量本身会随着间隔物供体强度的增加而增加。预计随着间隔物中噻吩环数量的增加，δ³ 也会强烈增强。
• Luminescent Dinuclear Bis-Cyclometalated Gold(III) Alkynyls and Their Solvent-Dependent Morphologies through Supramolecular Self-Assembly
  作者：King-Chin Yim、Vonika Ka-Man Au、Ling-Ling Hung、Keith Man-Chung Wong、Vivian Wing-Wah Yam

  DOI：10.1002/chem.201603186

  日期：2016.11.2

  mixing of 3IL π–π* character of the alkynyl ligands. The electrochemical study of a nonsymmetric dinuclear complex shows two successive reduction processes originating from the reductions of the two different cyclometalating ligands. The complexes are found to undergo supramolecular self‐assembly processes driven by π–π stacking and hydrophobic/hydrophilic interactions to give honeycomb nanostructures

  合成和表征了一系列具有不同性质的桥联炔基配体的发光双环金属化金（III）配合物。配合物的光物理性质已经通过电子吸收光谱法和发射研究进行了研究。发现振动发射带起源于双环金属化配体的三重配位体（IL）π–π *激发态，并且混合3炔基配体的IL π–π *特性。非对称双核配合物的电化学研究表明，两个连续的还原过程源自两个不同的环金属化配体的还原。从SEM图像中可以发现，该复合物在π-π堆积和疏水/亲水相互作用的作用下经历了超分子自组装过程，从而形成了蜂窝状的纳米结构。还观察到了溶剂依赖性的形态转变，这已通过SEM和1 H NMR光谱进行了研究。
• Controlling Self-Assembly Mechanisms through Rational Molecular Design in Oligo(<i>p</i>-phenyleneethynylene)-Containing Alkynylplatinum(II) 2,6-Bis(<i>N</i>-alkylbenzimidazol-2′-yl)pyridine Amphiphiles
  作者：Michael Ho-Yeung Chan、Sammual Yu-Lut Leung、Vivian Wing-Wah Yam

  DOI：10.1021/jacs.8b03628

  日期：2018.6.20

  dinuclear alkynylplatinum(II) bzimpy (bzimpy = 2,6-bis( N-alkylbenzimidazol-2'-yl)pyridine) complexes containing the shape-persistent oligo( p-phenyleneethynylene)s. Multistage morphological transformations from plates to fibers and to spherical nanostructures under different solvent compositions have been demonstrated. The subtle balances between multiple noncovalent interactions including Pt···Pt, hydrophobic

  通过合理设计和合成一系列两亲性双核炔基铂（II）bzimpy（bzimpy = 2,6-bis（N-烷基苯并咪唑-2'-yl）吡啶，证明了对自组装材料缔合机制的系统控制) 包含形状持久性低聚 (对苯乙炔) 的复合物。已经证明了在不同溶剂组成下从板到纤维和球形纳米结构的多阶段形态转变。发现包括Pt…Pt、疏水、亲水和π-π堆积相互作用在内的多种非共价相互作用之间的微妙平衡对系统的超分子组装产生了深远的影响，
• Understanding the role of conjugation length on the self-assembly behaviour of oligophenyleneethynylenes
  作者：Beatriz Matarranz、Goutam Ghosh、Ramesh Kandanelli、Angel Sampedro、Kalathil K. Kartha、Gustavo Fernández

  DOI：10.1039/d1cc01054a

  日期：——

  We unravel the relationship between conjugation length and self-assembly behaviour of oligophenyleneethynylenes (OPEs).

  我们揭示了寡苯乙炔（OPEs）的共轭长度与自组装行为之间的关系。
• Bimetallic Ruthenium Complexes: Synthesis, Characterization, and the Effect of Appending Long Carbon Chains to Their Bridges
  作者：Xiang-Hua Wu、Jin Hua Liang、Jian-Long Xia、Shan Jin、Guang-Ao Yu、Sheng Hua Liu

  DOI：10.1021/om901025q

  日期：2010.3.8

  A series of binuclear ruthenium complexes [RuCl(CO)(PMe3)(3)](2)(mu-CH=CH-Ar-CH=CH) (Ar = C6H2(OR)(2)-2,5; R = CH3 (4a), (C4H9)-C-n (4b), (C6H13)-C-n (4c), (C8H17)-C-n (4d), (C10H21)-C-n (4e), (C12H25)-C-n (4f), (C14H29)-C-n (4g)), [RuCl(CO)(PMe3)(3)](2)(mu-CH=CH-Ar--Ar-CH=CH) (Ar = C6H2(R)(2)-2,5; R = OCH3 (10a), (OC8H17)-C-n (10b), H (10c)), and [RuCl(CO)(PMe3)(3)](2)(mu-CH=CH-Ar--Ar--Ar-CH=CH) (Ar = C6H2(R)(2)-2,5; R = OCH3 (13a), (OC8H17)-C-n (13b), H (13c)) have been synthesized. These complexes have been characterized by elemental analysis, NMR, and UV/vis spectrophotometry. The structures of 4b and 4d have been determined by X-ray crystallography. Electrochemical studies have shown that long carbon chains attached to the bridges of the complexes facilitate the stability of mixed-valence bimetallic ruthenium complexes.