5''-ethynyl-[2,2';5',2'']terthiophene-5-carbaldehyde | 791111-24-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5''-ethynyl-[2,2';5',2'']terthiophene-5-carbaldehyde
• 英文别名: 5-[5-(5-Ethynylthiophen-2-yl)thiophen-2-yl]thiophene-2-carbaldehyde；5-[5-(5-ethynylthiophen-2-yl)thiophen-2-yl]thiophene-2-carbaldehyde
• CAS: 791111-24-5
• 化学式: C₁₅H₈OS₃
• 分子量: 300.426
• InChiKey: WZZUPEKSAJIIOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5''-ethynyl-[2,2';5',2'']terthiophene-5-carbaldehyde 、 [RuCl(dppe)2]OTf 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  钌-噻吩基乙炔基钌配合物的设计与合成。声致非线性光学的新材料

  摘要：

  已经开发了一系列围绕不同长度的基于噻吩的π共轭间隔基构建的新的供体-π-受体钌钌系统。这些供体-π-受体生色团的线性和三阶非线性光学性质的比较表明，基于低聚噻吩的间隔基的延伸或进一步引入双键导致二噻吩基乙烯间隔基产生最大吸收的显着红移以及分子立方超极化性的显着增强。此外，对于掺入PMMA基质中的这些复合物的薄膜复合材料，还观察到了声诱发的第二谐波产生（AISHG），其值达到了迄今为​​止报道的最高值。

  DOI：

  10.1021/om049236s
• 作为产物：
  描述：

  5-溴-5'-甲酰基-2,2':5'2'-三噻吩 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 5''-ethynyl-[2,2';5',2'']terthiophene-5-carbaldehyde
  参考文献：
  名称：

  χ⁽²⁾ Grating in Ru Derivative Chromophores Incorporated within the PMMA Polymer Matrices

  摘要：

  We have found that Ru derivative chromophores incorporated into the PMMA polymer matrices might be considered as promising materials for optical poling. The maximally achieved effective second-order optical susceptibility for the wavelength 1.89 mum is about 1.94 pm/V. The investigated composites possess metastable trapping levels originating both from the d states of Ru and due to effective charge transfer due to the presence of pi-conjugated states. Because of incorporation of the chromophore into polymer matrices, we have revealed that the maximal susceptibility is observed at 5-6% of the chromophore in weighting units. The further increase of the second-order susceptibility is limited by the appearance of chromophore agglomerates substantially restraining second-order susceptibilities. The investigated composites possess long-lived chi((2)) grating, which decreases less than 76% after 600 min of laser treatment. The electrostatic field causes additional reanimation of the second harmonic generation during the decay regime. The electron microscopy pictures clearly confirm appearance of the chi((2)) grating.

  DOI：

  10.1021/jp048794h

文献信息

• Synthesis, photovoltaic performances and TD-DFT modeling of push–pull diacetylide platinum complexes in TiO₂ based dye-sensitized solar cells
  作者：Sébastien Gauthier、Bertrand Caro、Françoise Robin-Le Guen、Nattamai Bhuvanesh、John A. Gladysz、Laurianne Wojcik、Nicolas Le Poul、Aurélien Planchat、Yann Pellegrin、Errol Blart、Denis Jacquemin、Fabrice Odobel

  DOI：10.1039/c4dt00301b

  日期：——

  Five new Pt-containing dyes have been synthesised and characterised in the framework of DSSC applications.

  在DSSC应用的框架内，已合成并表征了五种新的含铂染料。
• Second-order optical effects in organometallic nanocomposites induced by an acoustic field
  作者：A. Migalska-Zalas、B. Sahraoui、I. V. Kityk、S. Tkaczyk、V. Yuvshenko、J.-L. Fillaut、J. Perruchon、T. J. J. Muller

  DOI：10.1103/physrevb.71.035119

  日期：——

  Acoustically stimulated second-order optical effects in Ru-derivative nanocomposites were discovered. The alkynyl ruthenium derivatives were embedded in a polymethyl methacrylate (PMMA) polymer matrix. As second-order optical effects we studied second-harmonic generation (SHG) and linear electro-optics (LEO) phenomena. The physical insight of the effect observed consists in a coexistence of nanocofined chromophore levels and localized d states of ruthenium. A transverse acoustic field favors the occurrence of charge density noncentrosymmetry required for observation of the second-order optical effects, particularly SHG. We have found that acoustically induced SHG and LEO for fundamental YAB-Gd3+ laser light (lambda=1.76 mum) increases and achieves a maximum value at acoustic power density of about 1.45 W/cm(2). The values of the SHG for several Ru chromophores were higher than those for well-known inorganic crystals. With decreasing temperature, the SHG signal strongly increases below 55 K and correlates well with occurrence of "softlike" low-frequency anharmonic quasiphonon modes responsible for the phase transitions. The SHG maxima were observed at acoustic frequencies of about 13 kHz. Increasing of acoustical frequencies up to the megahertz range suppresses the observed phenomena. Comparing the obtained results with the acoustically induced Raman spectra at different temperatures one can conclude that the observed effects are due to acoustically induced electron-vibration anharmonicity, and are observed at temperatures below 55 K. Varying the chromophore content within the embedded matrices we were able to use effective nanoparticle sizes within the range 5-60 nm. It is clearly shown that the enhancement of the effective nanosize effectively suppresses the observed second-order optical effects.
• χ⁽²⁾ Grating in Ru Derivative Chromophores Incorporated within the PMMA Polymer Matrices
  作者：A. Migalska-Zalas、Z. Sofiani、B. Sahraoui、I. V. Kityk、S. Tkaczyk、V. Yuvshenko、J.-L. Fillaut、J. Perruchon、T. J. J. Muller

  DOI：10.1021/jp048794h

  日期：2004.9.1

  We have found that Ru derivative chromophores incorporated into the PMMA polymer matrices might be considered as promising materials for optical poling. The maximally achieved effective second-order optical susceptibility for the wavelength 1.89 mum is about 1.94 pm/V. The investigated composites possess metastable trapping levels originating both from the d states of Ru and due to effective charge transfer due to the presence of pi-conjugated states. Because of incorporation of the chromophore into polymer matrices, we have revealed that the maximal susceptibility is observed at 5-6% of the chromophore in weighting units. The further increase of the second-order susceptibility is limited by the appearance of chromophore agglomerates substantially restraining second-order susceptibilities. The investigated composites possess long-lived chi((2)) grating, which decreases less than 76% after 600 min of laser treatment. The electrostatic field causes additional reanimation of the second harmonic generation during the decay regime. The electron microscopy pictures clearly confirm appearance of the chi((2)) grating.
• Design and Synthesis of Ruthenium Oligothienylacetylide Complexes. New Materials for Acoustically Induced Nonlinear Optics
  作者：Jean-Luc Fillaut、Johann Perruchon、Philippe Blanchard、Jean Roncali、Stéphane Golhen、Magali Allain、Anna Migalsaka-Zalas、Ivan V. Kityk、Bouchta Sahraoui

  DOI：10.1021/om049236s

  日期：2005.2.1

  A series of new donor−π-acceptor ruthenium acetylide systems built around thiophene-based π-conjugating spacers of different lengths have been developed. Comparison of the linear and third-order nonlinear optical properties of these donor−π-acceptor chromophores shows that the elongation of the oligothiophene-based spacer or further introduction of a double bond leading to a dithienylethylene spacer

  已经开发了一系列围绕不同长度的基于噻吩的π共轭间隔基构建的新的供体-π-受体钌钌系统。这些供体-π-受体生色团的线性和三阶非线性光学性质的比较表明，基于低聚噻吩的间隔基的延伸或进一步引入双键导致二噻吩基乙烯间隔基产生最大吸收的显着红移以及分子立方超极化性的显着增强。此外，对于掺入PMMA基质中的这些复合物的薄膜复合材料，还观察到了声诱发的第二谐波产生（AISHG），其值达到了迄今为​​止报道的最高值。