2-iodo-(5-trimethylsilylethynyl)thiophene | 182323-28-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-iodo-(5-trimethylsilylethynyl)thiophene
• 英文别名: ((5-iodothiophen-2-yl)ethynyl) trimethylsilane；2-(5-Iodothiophen-2-yl)ethynyl-trimethylsilane
• CAS: 182323-28-0
• 化学式: C₉H₁₁ISSi
• 分子量: 306.242
• InChiKey: FBUDUAILUOLQBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-iodo-(5-trimethylsilylethynyl)thiophene 在 copper(l) iodide bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 5-(5-{5-[5-(5-Methoxy-thiophen-2-ylethynyl)-thiophen-2-ylethynyl]-thiophen-2-ylethynyl}-thiophen-2-ylethynyl)-thiophene-2-carbaldehyde
  参考文献：
  名称：

  具有末端供体-受体取代的低聚（2,5-噻吩亚乙炔）

  摘要：

  五个低聚（2,5-噻吩亚乙炔）系列（OTE，n = 1-5），即推挽取代化合物 1b-5b 和 1c-5c，纯供体取代化合物 1a-5a 和两个带有保护和通过收敛合成策略分别获得脱保护的乙炔基端基。供体-受体 OTE (DAOTE) 系列中共轭发色团的延伸由分子内电荷转移 (ICT) 叠加，该转移随着重复单元数量 n 的增加而减少。通过紫外/可见光吸收最大值 λmax (n) → λ∞ for n → ∞ 的收敛来研究整体效果。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2006 年）

  DOI：

  10.1002/ejoc.200500449
• 作为产物：
  描述：

  2-三甲基硅乙炔基噻吩 在 lithium diisopropyl amide 、 碘 作用下， 以 乙醚 为溶剂， 反应 0.25h， 以4.3 g的产率得到2-iodo-(5-trimethylsilylethynyl)thiophene
  参考文献：
  名称：

  Novel planar and star-shaped molecules: Synthesis, electrochemical and photophysical properties

  摘要：

  Three novel planar and star-shaped molecules containing thiophene-functionalized group and acetylenic spacers, 4((5 ''-iodo-[2,2':5',2 ''-terthiophen]-5-yl)ethynyl)aniline (I3TEA), 4,4'-([2,2':5',2 ''-terthiophene]-5,5 ''-diylbis(ethyne-2,1-diyl))dianiline (3TDDA), 1,3,5-tris((5-((trimethylsilyl)ethynyl)thiophen-2-yl)-ethynyl)benzene (TETEB) were synthesized through Sonogashira coupling reaction. Their photophysical and electrochemical properties were explored by UV-vis, photoluminescence (PL) emission and DFT calculation. Three compounds possess unusual phenomena of PL, with the concentration of gradually decreased, the intensity of PL firstly increased and then decreased, this may be due to the aggregate-enhanced emission (AEE) effect and aggregation-caused quenching (ACQ) effect. Their spectroscopic data demonstrate that D-pi-A-pi-D structured organic dye 3TDDA based on NH2 as donor units and 3T as acceptor units with acetylenic spacers it-conjugated chain between them exhibits good luminescent properties. Dye I3TEA with donor(D) acceptor(A) structure shows good charge transfer because of amino functional group and iodine atom. Octupolar organic pi-conjugated star-shaped molecule TETEB possesses excellent luminescent properties because of its unique structure applied in the optoelectronic field. The redox curves and results of DFT calculations suggest that three compounds have low ionization potential and low E-oxd. All the good properties demonstrate three compounds could be promising candidates for photovoltaic materials. (c) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2013.01.047

文献信息

• Site-selective aromatic C–H λ³-iodanation with a cyclic iodine(<scp>iii</scp>) electrophile in solution and solid phases
  作者：Wei Ding、Chen Wang、Jie Ren Tan、Chang Chin Ho、Felix León、Felipe García、Naohiko Yoshikai

  DOI：10.1039/d0sc02737e

  日期：——

  (BXT) as an electrophile under room temperature conditions. The reaction tolerates a variety of electron-rich arenes and heteroarenes to afford the corresponding arylbenziodoxoles in moderate to good yields. The reaction can also be performed mechanochemically by grinding a mixture of solid arenes and BXT under solvent-free conditions. The arylbenziodoxoles can be used for various C–C and C–heteroatom

  在室温条件下，使用苯并三唑三氟甲磺酸酯（BXT）作为亲电试剂，可实现高效且选择性的芳族CH 3碘化反应。该反应可耐受多种富电子芳烃和杂芳烃，以中等至良好的产率提供相应的芳基苯并恶唑。该反应还可以通过在无溶剂条件下研磨固体芳烃和BXT的混合物以机械化学方式进行。芳基苯并恶唑可用于各种C–C和C–杂原子键的形成，也可通过亲电子卤化进一步改性。DFT计算表明，本反应的进行通过协调一致的λ 3-碘化-去质子化过渡态，其中三氟甲磺酸根阴离子充当内部碱。
• Iron(II) and iron(III) complexes containing ethynyl thiophene fragments
  作者：Séverine Roué、Claude Lapinte

  DOI：10.1016/j.jorganchem.2004.10.006

  日期：2005.1

  The synthesis of the new complexes Cp*(dppe)FeCC2,5-C4H2SR (Cp* = 1,2,3,4,5-pentamethylcyclopentadienyl; dppe = 1,2-bis(diphenylphosphino)ethane; 2a, R = CCH; 2b, R = CCSi(CH3)3; 2c, R = CCSi(CH(CH3)2)3; 3a, R = CC2,5-C4H2SCCH; 3c, R = CC2,5-C4H2SCCSi(CH(CH3)2)3) is described. The 13C NMR and FTIR spectroscopic data indicate that the π-back donation from the metal to the carbon rich ligand increases

  新配合物Cp *（dppe）FeCC2,5-C 4 H 2 SR（Cp * = 1,2,3,4,5-五甲基环戊二烯基; dppe = 1,2-双（二苯基膦基）乙烷; 2a， R = CCH; 2b，R = CCSi（CH 3）3 ; 2c，R = CCSi（CH（CH 3）2）3 ; 3a，R = CC2,5-C 4 H 2 SCCH; 3c，R = CC2，描述了5-C 4 H 2 SCCSi（CH（CH 3）2）3）。在1313 C NMR和FTIR光谱数据表明，从金属到富碳配体的π返给随着有机π电子体系的大小而增加。还通过CV分析了新的配合物，并使用1当量的[Cp 2 Fe] [PF 6 ]进行了2a和3c的化学氧化。相应的配合物2a [PF 6 ]和3c [PF 6 ]是热稳定的，而2a [PF 6太活泼而不能分离为纯化合物。光谱数据表明，对于这些新的有机铁（III）衍生物，大型有
• Molecular Wires Built from Binuclear Cyclometalated Complexes
  作者：Sandrine Fraysse、Christophe Coudret、Jean-Pierre Launay

  DOI：10.1021/ja0299506

  日期：2003.5.1

  the calculation of the electronic coupling element V(ab). This series of complexes exhibit relatively large couplings when comparing with complexes of similar metal-metal distances, with a special mention for the anthracene-containing spacer, which appears particularly efficient for mediating the metal-metal interaction. The results can be rationalized by theoretical calculations at the extended Hückel

  已经制备了具有 [Ru(bpy)(2)(ppH)](+) 型（bpy = 2,2'-联吡啶，ppH = 2-苯基吡啶）的环金属化末端的双核配合物，由各种间隔基连接。这些间隔基由一个或两个三键或双乙炔基芳基组成，芳基 = 苯、噻吩或蒽。从 [Ru(bpy)(2)(ppBr)](+) 合成子开始，通过 Sonogashira 与合适的双炔烃偶联获得具有双乙炔基芳基间隔基的复合物。从真正的炔烃 [Ru(bpy)(2)(pp-CCH)](+) 环金属化前体中获得具有一个或两个三键的配合物，分别使用 Sonogashira 偶联与碘衍生物 [Ru(bpy)(2) (ppI)](+) 或氧化同源偶联。还获得了一些带有叔丁基取代的联吡啶辅助配体的配合物。双核复合物的氧化发生在 0.5 V 附近，即。例如，比基于 [Ru(bpy)(3)](2+) 的配合物更容易。观察到单个阳极波，几乎没有可检测到的分裂，
• Thiophene-based dyes for probing membranes
  作者：Ismael López-Duarte、Phoom Chairatana、Yilei Wu、Javier Pérez-Moreno、Philip M. Bennett、James E. Reeve、Igor Boczarow、Wojciech Kaluza、Neveen A. Hosny、Samuel D. Stranks、Robin J. Nicholas、Koen Clays、Marina K. Kuimova、Harry L. Anderson

  DOI：10.1039/c4ob02507e

  日期：——

  We report the synthesis of four new cationic dipolar push–pull dyes, together with an evaluation of their photophysical and photobiological characteristics pertinent to imaging membranes by fluorescence and second harmonic generation (SHG). All four dyes consist of an N,N-diethylaniline electron-donor conjugated to a pyridinium electron-acceptor via a thiophene bridge, with either vinylene (–CHCH–)

  我们报告了四种新型阳离子偶极推挽式染料的合成，并通过荧光和二次谐波生成（SHG）对它们与成像膜有关的光物理和光生物学特性进行了评估。四种染料均由一个通过噻吩桥与吡啶鎓电子受体共轭的N，N-二乙基苯胺电子给体组成，带有一个亚乙烯基（–CH CH–）或亚乙炔基（–CC C–）连接基团，或两个充电或双充电的吡啶鎓端子。将这些染料的吸收和荧光行为与市售的荧光膜染色剂，苯乙烯基染料FM4-64进行了比较。。使用800 nm的超瑞利散射比较了所有染料的超极化性。使用组织细胞培养物（HeLa，SK-OV-3和MDA-231）评估细胞的摄取，定位，毒性和光毒性。用噻吩取代FM4-64的中心烯烃桥基并不会实质上改变吸收，荧光或超极化性，而将亚乙烯基键更改为乙炔基会使吸收和荧光移至较短的波长，并使超极化性降低大约两倍。在活细胞中进行的SHG和荧光成像实验表明，与FM4-64相比，双电荷噻吩染料位于质膜中，并且
• Push-Pull-Substituted Oligo(2,5-thienyleneethynylene)s
  作者：Herbert Meier、Bastian Mühling、Sonja Theisinger

  DOI：10.1055/s-2006-926348

  日期：——

  Oligo(2,5-thienyleneethynylene)s (OTE) with terminal donor-acceptor substitution were synthesized by applying Sono-gashira-Hagihara reactions and a protection group technique. The combination of the alkylthio and nitro substituents provides a DAOTE series, whose long-wavelength absorption shows a monotonous bathochromic effect for increasing numbers n of repeat units. The convergence limit is already

  应用 Sono-gashira-Hagihara 反应和保护基技术合成了具有末端供体-受体取代的 Oligo(2,5-thienyleneethynylene)s (OTE)。烷硫基和硝基取代基的组合提供了 DAOTE 系列，其长波长吸收对于增加 n 的重复单元数显示出单调的红变色效应。n = 3 时已经达到收敛极限。