thioacetic acid S-[4-(4-ethynylphenylethynyl)benzyl] ester | 562823-76-1

• 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: thioacetic acid S-[4-(4-ethynylphenylethynyl)benzyl] ester
• 英文别名: 1-acetylthiomethyl-(4-(4'-ethynyl)phenylethynyl)benzene；S-[[4-[2-(4-ethynylphenyl)ethynyl]phenyl]methyl] ethanethioate
• CAS: 562823-76-1
• 化学式: C₁₉H₁₄OS
• 分子量: 290.386
• InChiKey: HWVHLSKYWHZKTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  thioacetic acid S-[4-(4-ethynylphenylethynyl)benzyl] ester 、 4-[4-[3,5,7-tris(4-iodophenyl)adamantan-1-yl]phenylethynyl]benzoic acid methyl ester 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以10%的产率得到4-[[4-[3,5,7-tris[4-(4-acetylsulfanylmethylphenylethynyl)phenylethynyl]phenyl]adamantan-1-yl]phenylethynyl]benzoic acid methyl ester
  参考文献：
  名称：

  Nanoscale Tripodal 1,3,5,7-Tetrasubstituted Adamantanes for AFM Applications

  摘要：

  The synthesis of four novel nanoseale 1,3,5,7-tetrasubstituted adamantanes 22 and 25-27 designed for atomic force microscopy (AFM) applications is described. Each tetrahedrally shaped molecule incorporates a broad tripodal base made up of three identical legs that terminate with a sulfurcontaining moiety, which is either a 4-acetylsulfanylmethylphenyl unit or else a (1,2,5-dithiazepan1-yl)phenyl unit. The sulfur atoms are intended for eventual binding of the molecule multivalently to the apex of a gold-coated commercial AFM tip through formation of multiple S-Au bonds. In each molecule, the fourth terminus is a para-substituted benzoic acid methyl ester that is designed to scan the sample. We demonstrate that 27 is sufficiently large and rigid to be imaged by a conventional AFM tip. Adamantanes 22 and 25-27 may also find application as chemically well-defined nanoscale objects for calibration of AFM tips.

  DOI：

  10.1021/jo026923p
• 作为产物：
  描述：

  (4-碘苯基乙炔)三甲基硅烷 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 21.5h， 生成 thioacetic acid S-[4-(4-ethynylphenylethynyl)benzyl] ester
  参考文献：
  名称：

  Nanoscale Tripodal 1,3,5,7-Tetrasubstituted Adamantanes for AFM Applications

  摘要：

  The synthesis of four novel nanoseale 1,3,5,7-tetrasubstituted adamantanes 22 and 25-27 designed for atomic force microscopy (AFM) applications is described. Each tetrahedrally shaped molecule incorporates a broad tripodal base made up of three identical legs that terminate with a sulfurcontaining moiety, which is either a 4-acetylsulfanylmethylphenyl unit or else a (1,2,5-dithiazepan1-yl)phenyl unit. The sulfur atoms are intended for eventual binding of the molecule multivalently to the apex of a gold-coated commercial AFM tip through formation of multiple S-Au bonds. In each molecule, the fourth terminus is a para-substituted benzoic acid methyl ester that is designed to scan the sample. We demonstrate that 27 is sufficiently large and rigid to be imaged by a conventional AFM tip. Adamantanes 22 and 25-27 may also find application as chemically well-defined nanoscale objects for calibration of AFM tips.

  DOI：

  10.1021/jo026923p

文献信息

• A spectroscopic study of self-assembled monolayer of porphyrin-functionalized oligo(phenyleneethynylene)s on gold: the influence of the anchor moiety
  作者：Somsakul Watcharinyanon、Daniel Nilsson、Ellen Moons、Andrey Shaporenko、Michael Zharnikov、Bo Albinsson、Jerker Mårtensson、Lars S. O. Johansson

  DOI：10.1039/b802914h

  日期：——

  Porphyrin-functionalized oligo(phenyleneethynylene)s (OPE) are promising molecules for molecular electronics applications. Three such molecules (1–3) with the common structure P–OPE–AG (P and AG are a porphyrin and anchor group, respectively) and different anchor groups, viz. an acetyl protected thiol, –S–COCH3 (1), an acetyl protected thiol with methylene linker, –CH2–S–COCH3 (2), and a trimethylsilylethynyl group, –CC–Si(CH3)3 (3) have been synthesized and the corresponding self-assembled monolayers (SAMs) on Au(111) substrates have been prepared. The integrity and structural properties of these films were studied by X-ray photoelectron spectroscopy and near-edge X-ray absorption fine structure spectroscopy. The results suggest that the films formed from 1 have a high orientational order with an almost upright orientation and dense packing of the molecular constituents, i.e. represent a high quality SAM. In contrast, molecule 2 formed disordered molecular layers on Au, even though the molecule–surface bonding (thiolate) is the same as in the case of molecule 1. This suggests that the methylene linker in molecule 2 has a strong impact on the quality of the resulting film, so that a well-ordered SAM cannot be formed. The silane system, 3, is also able to bind to the gold surface but the resulting SAM has a poor quality, being significantly disordered and/or comprised of strongly inclined molecules. The above results suggest that the nature of the anchor group along with a possible linker is an important parameter which, to a high extent, predetermines the entire quality of OPE-based molecular layers.

  卟啉功能化低聚亚苯基乙炔基 (OPE) 是分子电子学应用中很有前景的分子。三个这样的分子（1-3）具有共同结构P-OPE-AG（P和AG分别是卟啉和锚定基团）和不同的锚定基团，即。已合成乙酰基保护的硫醇 –S–COCH3 (1)、带亚甲基连接基的乙酰基保护的硫醇 –CH2–S–COCH3 (2) 和三甲基甲硅烷基乙炔基 –CC–Si(CH3)3 (3)并在Au(111)基底上制备了相应的自组装单层(SAM)。通过X射线光电子能谱和近边X射线吸收精细结构光谱研究了这些薄膜的完整性和结构特性。结果表明，由 1 形成的薄膜具有高取向顺序，几乎垂直取向且分子成分紧密堆积，即代表了高质量的 SAM。相比之下，分子 2 在 Au 上形成无序分子层，尽管分子-表面键合（硫醇盐）与分子 1 的情况相同。这表明分子 2 中的亚甲基连接体对金的质量有很大影响。所得薄膜，从而无法形成良好有序的SAM。硅烷系统 3 也能够结合到金表面，但所得 SAM 质量较差，明显无序和/或由强烈倾斜的分子组成。上述结果表明，锚定基团的性质以及可能的连接体是一个重要参数，它在很大程度上预先确定了基于 OPE 的分子层的整体质量。
• Nanoscale Tripodal 1,3,5,7-Tetrasubstituted Adamantanes for AFM Applications
  作者：Quan Li、Aleksey V. Rukavishnikov、Pavel A. Petukhov、Tatiana O. Zaikova、Changshu Jin、John F. W. Keana

  DOI：10.1021/jo026923p

  日期：2003.6.1

  The synthesis of four novel nanoseale 1,3,5,7-tetrasubstituted adamantanes 22 and 25-27 designed for atomic force microscopy (AFM) applications is described. Each tetrahedrally shaped molecule incorporates a broad tripodal base made up of three identical legs that terminate with a sulfurcontaining moiety, which is either a 4-acetylsulfanylmethylphenyl unit or else a (1,2,5-dithiazepan1-yl)phenyl unit. The sulfur atoms are intended for eventual binding of the molecule multivalently to the apex of a gold-coated commercial AFM tip through formation of multiple S-Au bonds. In each molecule, the fourth terminus is a para-substituted benzoic acid methyl ester that is designed to scan the sample. We demonstrate that 27 is sufficiently large and rigid to be imaged by a conventional AFM tip. Adamantanes 22 and 25-27 may also find application as chemically well-defined nanoscale objects for calibration of AFM tips.