3,6-bis(trimethylsilylethynyl)carbazole | 1233502-91-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3,6-bis(trimethylsilylethynyl)carbazole
• 英文别名: trimethyl-[2-[6-(2-trimethylsilylethynyl)-9H-carbazol-3-yl]ethynyl]silane
• CAS: 1233502-91-4
• 化学式: C₂₂H₂₅NSi₂
• 分子量: 359.618
• InChiKey: DZFZHIKGKLPBTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.78
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3,6-bis(trimethylsilylethynyl)carbazole 在 甲醇 、 potassium carbonate 、 potassium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.17h， 生成 3,6-diethynyl-9-(prop-2-yn-1-yl)-9H-carbazole
  参考文献：
  名称：

  Selective hydration of electron-rich aryl-alkynes by a Schrock-type molybdenum alkylidene catalyst

  摘要：

  We present herein the regioselective hydration of electron-rich aryl-alkynes in presence of a Schrock-type molybdenum alkylidene catalyst. The structures of the obtained ketones were confirmed by NMR spectroscopy and HRMS as well as by single-crystal X-ray diffraction. We found out that in our conditions the hydration reaction is efficient only for aryl-alkynes and their reactivity is highly dependent on the electronic nature of the substituents on the aryl group.

  DOI：

  10.33224/rrch.2020.65.7-8.07
• 作为产物：
  描述：

  3,6-二碘咔唑 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 反应 12.0h， 生成 3,6-bis(trimethylsilylethynyl)carbazole
  参考文献：
  名称：

  使用G-四链体DNA连接的磁性纳米粒子确定G-四链体配体的特异性的竞争性下拉分析法。

  摘要：

  在本文中，我们开发了一种竞争性筛选方法，其中G-四链体DNA连接的磁性纳米颗粒从一系列小分子中下拉出特定四链体拓扑结构的选择性配体。筛选策略首先使用已知的G-四链体配体进行优化，然后再使用由Cu（I）催化的叠氮化物-炔烃环加成反应合成的一系列新的G-四链体相互作用双-三唑基配体。该测定法能够鉴定特异性靶向癌细胞中启动子G-四链体的c-MYC和BCL2 G-四链体选择性双三唑配体。

  DOI：

  10.1021/acs.analchem.9b00889

文献信息

• Fluorescence and visual sensing of nitroaromatic explosives using electron rich discrete fluorophores
  作者：Sankarasekaran Shanmugaraju、Sachin A. Joshi、Partha Sarathi Mukherjee

  DOI：10.1039/c1jm10406c

  日期：——

  Several π-electron rich fluorescent aromatic compounds containing trimethylsilylethynyl functionality have been synthesized by employing Sonogashira coupling reaction and they were characterized fully by NMR (1H, 13C)/IR spectroscopy. Incorporation of bulky trimethylsilylethynyl groups on the peripheral of the fluorophores prevents self-quenching of the initial intensity through π–π interaction and thereby maintains the spectroscopic stability in solution. These compounds showed fluorescence behavior in chloroform solution and were used as selective fluorescence sensors for the detection of electron deficient nitroaromatics. All these fluorophores showed the largest quenching response with high selectivity for nitroaromatics among the various electron deficient aromatic compounds tested. Quantitative analysis of the fluorescence titration profile of 9,10-bis(trimethylsilylethynyl)anthracene with picric acid provided evidence that this particular fluorophore detects picric acid even at ppb level. A sharp visual detection of 2,4,6-trinitrotoluene was observed upon subjecting 1,3,6,8-tetrakis(trimethylsilylethynyl)pyrene fluorophore to increasing quantities of 2,4,6-trinitrotoluene in chloroform. Furthermore, thin film of the fluorophores was made by spin coating of a solution of 1.0 × 10−3 M in chloroform or dichloromethane on a quartz plate and was used for the detection of vapors of nitroaromatics at room temperature. The vapor-phase sensing experiments suggested that the sensing process is reproducible and quite selective for nitroaromatic compounds. Selective fluorescence quenching response including a sharp visual color change for nitroaromatics makes these fluorophores as promising fluorescence sensory materials for nitroaromatic compounds (NAC) with a detection limit of even ppb level as judged with picric acid.

  利用 Sonogashira 偶联反应合成了几种富含 π 电子的荧光芳香族化合物，并通过核磁共振（1H、13C）/红外光谱对其进行了全面鉴定。在荧光团外围加入笨重的三甲基硅乙炔基团，可防止通过 π-π 相互作用产生的初始强度自淬，从而保持溶液中的光谱稳定性。这些化合物在氯仿溶液中显示出荧光特性，并被用作检测缺电子硝基芳香族化合物的选择性荧光传感器。在测试的各种缺电子芳香族化合物中，所有这些荧光团对硝基芳香族化合物的淬灭反应最大，选择性高。对 9,10-双（三甲基硅乙炔基）蒽与苦味酸的荧光滴定曲线进行的定量分析证明，这种荧光团即使在 ppb 水平也能检测到苦味酸。将 1,3,6,8 四(三甲基硅乙炔基)芘荧光团置于氯仿中不断增加的 2,4,6- 三硝基甲苯中，可观察到 2,4,6- 三硝基甲苯的敏锐视觉检测。此外，还在石英板上旋涂了 1.0 × 10-3 M 的氯仿或二氯甲烷溶液，制成了荧光团薄膜，用于在室温下检测硝基芳烃的蒸气。气相传感实验表明，该传感过程具有可重复性，并且对硝基芳香族化合物具有相当高的选择性。这些荧光团对硝基芳香族化合物具有选择性荧光淬灭反应，包括明显的视觉颜色变化，因此有望成为硝基芳香族化合物（NAC）的荧光传感材料。
• Heteroaryl-linked norbornadiene dimers with redshifted absorptions
  作者：Mads Mansø、Behabitu Ergette Tebikachew、Kasper Moth-Poulsen、Mogens Brøndsted Nielsen

  DOI：10.1039/c8ob01470a

  日期：——

  Development of Molecular Solar Thermal (MOST) systems for harvesting and storing solar energy is based on molecular photoswitches that undergo photoisomerizations to metastable isomers. One challenge is to achieve low-molecular weight molecules that absorb at sufficiently long wavelengths to match the solar spectrum. Here we show that this can be achieved by linking two norbornadiene (NBD) photoswitches

  用于收获和储存太阳能的分子太阳能热（MOST）系统的开发基于分子光开关，该光开关经历了光异构化为亚稳态异构体的过程。一项挑战是要获得在足够长的波长下吸收以匹配太阳光谱的低分子量分子。在这里，我们表明，这可以通过两种降冰片（NBD）光电继电器连接到中央杂环，噻吩或咔唑来实现，通过炔烃附件。在这种方法中，相同的杂芳基用于同时调节两个光开关的特性，从而使分子量保持尽可能低。通过Sonogashira偶联反应制备了一系列NBD二聚体，这些化合物显示出显着的红移吸收，起始吸收高达468 nm，热半衰期为44秒至16小时。
• Experimental and Theoretical Investigation for the Level of Conjugation in Carbazole-Based Precursors and Their Mono-, Di-, and Polynuclear Pt(II) Complexes
  作者：Rayya A. Al-Balushi、Ashanul Haque、Maharaja Jayapal、Mohammed K. Al-Suti、John Husband、Muhammad S. Khan、Olivia F. Koentjoro、Kieran C. Molloy、Jonathan M. Skelton、Paul R. Raithby

  DOI：10.1021/acs.inorgchem.6b00523

  日期：2016.7.5

  the terminal alkynes in iPr2NH/CH2Cl2 affords a series of Pt(II) mono- and diynes, while the dehydrohalogenation polycondensation reactions with trans-[(PnBu3)2PtCl2] under similar reaction conditions yields four Pt(II) poly-ynes of the form trans-[(PnBu3)2Pt–C≡C–R–C≡C−]n. The acetylide-functionalized carbazole ligands and the mono-, di-, and polynuclear Pt(II) σ-acetylide complexes have been characterized

  一系列带有咔唑间隔基的三甲基甲硅烷基保护的单炔烃（Me 3 SiCsilC–R）和双炔烃（Me 3 SiC≡C–R–C≡CSiMe 3）（R =咔唑-2-基，咔唑-3） -基，咔唑-2,7-二基，N-（2-乙基己基）咔唑-2,7-二基，咔唑-3,6-二基，N-（2-乙基己基）咔唑-3,6-二基），连同相应的末端单炔烃（H–C≡C–R）和双炔烃（H–C≡C–R–C≡C–H）一起进行了合成和表征。反式-[（Ph）（Et 3 P）2 PtCl]，反式-[（Et 3 P）2 PtCl 2 ]与CuI之间的CuI催化的脱卤化氢反应反式-[（P n Bu 3）2 PtCl 2 ]和i Pr 2 NH / CH 2 Cl 2中的末端炔烃提供了一系列的Pt（II）单-和二炔，而反式-[（ P n Bu 3）2 PtCl 2 ]在相似的反应条件下会生成四个反式-[（P n Bu 3）2 Pt–C≡C–R–C≡C-]
• Coordination-Driven Self-Assembly of Metallamacrocycles via a New Pt^II₂ Organometallic Building Block with 90° Geometry and Optical Sensing of Anions
  作者：Sankarasekaran Shanmugaraju、Arun Kumar Bar、Ki-Whan Chi、Partha Sarathi Mukherjee

  DOI：10.1021/om100202c

  日期：2010.7.12

  itrate)(ethynyl)]carbazole (5), containing an ethynyl functionality is synthesized in reasonable yield by employing a Sonagashira coupling reaction. Multinuclear NMR and electrospray ionization mass spectrometry (ESI-MS) including a single-crystal X-ray diffraction study characterized this 90° building unit. The self-assembly of 5 with three flexible ditopic donors (La−Lc) afforded [2 + 2] metallamacrocycles

  一种新的具有90°几何形状的Pt II 2有机金属砌块3,6-双[反铂（三乙基膦）2（硝酸盐）（乙炔基）]咔唑（5）含有乙炔基官能团，其合成方法如下： Sonagashira偶联反应。包括单晶X射线衍射研究在内的多核NMR和电喷雾电离质谱（ESI-MS）对该90°构造单元进行了表征。具有三个柔性对位供体（L a - L c）的5的自组装提供[2 + 2]个金属环（6a - c）[其中L a= 1,3-双（4-吡啶基）间苯二甲酰胺; L b＝ 1，3-双（3-吡啶基）间苯二甲酰胺，L c＝ 1，2-二（4-吡啶基）乙烷]。通过各种光谱技术对所有三个[2 + 2]自组装大环进行了表征，并通过单晶X射线衍射法确定了6a的分子结构。方形大环化合物6a是使用基于酰胺的配体L a设计的，使其适合由荧光团-受体组合组成的系统。酰胺官能团是阴离子的受体位点，可以通过氢键相互作用结合，而基于咔唑的90°构造
• A Competitive Pull-Down Assay Using G-quadruplex DNA Linked Magnetic Nanoparticles To Determine Specificity of G-quadruplex Ligands
  作者：Deepanjan Panda、Puja Saha、Ritapa Chaudhuri、Thumpati Prasanth、Velayutham Ravichandiran、Jyotirmayee Dash

  DOI：10.1021/acs.analchem.9b00889

  日期：2019.6.18

  Herein, we develop a competitive screening method in which G-quadruplex DNA linked magnetic nanoparticles pull down selective ligands for a particular quadruplex topology from a series of small molecules. The screening strategy is first optimized with known G-quadruplex ligands and then used with a new series of G-quadruplex interactive bis-triazolyl ligands that are synthesized by Cu(I)-catalyzed

  在本文中，我们开发了一种竞争性筛选方法，其中G-四链体DNA连接的磁性纳米颗粒从一系列小分子中下拉出特定四链体拓扑结构的选择性配体。筛选策略首先使用已知的G-四链体配体进行优化，然后再使用由Cu（I）催化的叠氮化物-炔烃环加成反应合成的一系列新的G-四链体相互作用双-三唑基配体。该测定法能够鉴定特异性靶向癌细胞中启动子G-四链体的c-MYC和BCL2 G-四链体选择性双三唑配体。