1-(10-acetylsulfanyldecyl)-4-methylquinolinium iodide | 448897-05-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-(10-acetylsulfanyldecyl)-4-methylquinolinium iodide
• 英文别名: N-(10-acetylthiodecyl)-4-methylquinolinium iodide；1-[10-(Acetylsulfanyl)decyl]-4-methylquinolin-1-ium iodide；S-[10-(4-methylquinolin-1-ium-1-yl)decyl] ethanethioate;iodide
• CAS: 448897-05-0
• 化学式: C₂₂H₃₂NOS*I
• 分子量: 485.473
• InChiKey: OSEGHDMTQTZTJY-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7,7,8,8-四氰基对苯二醌二甲烷 、 1-(10-acetylsulfanyldecyl)-4-methylquinolinium iodide 在 N-甲基哌啶 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Au-S-CnH2n-Q3CNQ: self-assembled monolayers for molecular rectification

  摘要：

  在金涂层高取向热解石墨上形成的、由Z-β-[N-(ω-乙酰硫代烷基)-4-喹啉季]-α-氰基-4-苯乙烯基二氰亚甲基（1）组成之自组装单层膜，展现出了与连接基团长度无关的非对称电流-电压特性[Au-S-CnH2n-Q3CNQ，其中3 ≤ n ≤ 12]。相比于由非平面给体-(π桥)-受体部分诱导的电性不对称，发色团非对称地位于电极间所产生的电性不对称贡献可以忽略不计。典型情况下，在±1 V的电压下，电流整流比为30（对比C16H33-Q3CNQ朗缪尔-布洛杰特膜的8），但在±1 V下也落在10到80的范围内。膜内分子尺寸与D-π-A发色团直立且紧密排列的情况一致：厚度随着连接CnH2n基团的长度增加而增加，而每分子0.33 ± 0.03 nm²的面积接近于发色团的范德华横截面。

  DOI：

  10.1039/b403942d
• 作为产物：
  描述：

  1,10-二碘癸烷 以 四氢呋喃 、 异丙醇 为溶剂， 反应 264.0h， 生成 1-(10-acetylsulfanyldecyl)-4-methylquinolinium iodide
  参考文献：
  名称：

  Merocyanine dyes: self-assembled monolayers

  摘要：

  4-{2-[N-(10-硫代癸基)喹啉鎓-4-基]乙烯基}苯酚自组装在金上，接触面积为 0.35 ± 0.03 nm2 molecule-1，单层厚度为 1.64 ± 0.07 nm，在 632.8 nm 波长处介电常数分量为 εr ≈ 2.8 和 εi ≈ 0.6。薄膜从紫色（美拉菁形式）变为黄色（质子化形式），通过监测反射率的变化，可用作传感器，对载气中 NH3 的检测限小于 1 ppm。N-octadecyl 类似物的 Langmuir-Blodgett (LB) 薄膜表现出类似的特性，但在传感应用中，由于苯酚基与基底相邻，因此处于劣势。它们的接触面积和单层厚度分别为 0.46 ± 0.03 nm2 molecule-1 和 1.75 ± 0.10 nm。

  DOI：

  10.1039/b110676g

文献信息

• Molecular diodes and ultra-thin organic rectifying junctions: Au–S–C_nH_2n–Q3CNQ and TCNQ derivatives
  作者：Geoffrey J. Ashwell、Katarzyna Moczko、Marta Sujka、Anna Chwialkowska、L. R. Hermann High、Daniel J. Sandman

  DOI：10.1039/b616607e

  日期：——

  Attempts to obtain derivatives of the molecular diode, 2-4-[1-cyano-2-(1-(ω-acetylsulfanylalkyl)-1H-quinolin-4-ylidene)-ethylidene]-cyclohexa-2,5-dienylidene}-malonitrile [1, CH3CO–S–CnH2n–Q3CNQ], from either 2,3,5,6-tetrafluoro-7,7,8,8-tetracyano-p-quinodimethane (TCNQF4) or 2,3,5,6-tetramethyl-7,7,8,8-tetracyano-p-quinodimethane (TMTCNQ) result in ring closure via the cyano group of the π-bridge and yield di-substituted analogues: 2-2,3,5,6-tetrafluoro-4-[6-(10-acetylsulfanyldecyl)-3-(1-(10-acetylsulfanyldecyl)-1H-quinolin-4-ylidenemethyl)-6H-benzo[f][1,7]naphthyridin-2-ylidene]-cyclohexa-2,5-dienylidene}-malonitrile (2a) and the 2,3,5,6-tetramethyl derivative (2b). Self-assembled monolayers (SAMs) of these donor–(π-bridge)–acceptor molecular diodes exhibit asymmetric current–voltage characteristics with electron flow at forward bias from the top contact to surface C(CN)2 groups. Comparison is made with I–V curves from ultra-thin films of an organic rectifying junction in which TCNQ− is electron-donating and a donor–(σ-bridge)–acceptor diode in which TCNQ° is electron-accepting.

  试图从 2,3,5,6-四氟-7,7,8,8-四氰基-对二醌甲烷（TCNQF4）或 2,3,5,6-四甲基-7,7,8,8-四氰基-对二醌甲烷（TCNQF4）中获得分子二极管 2-4-[1-氰基-2-(1-(Ï-乙酰硫烷基)-1H-喹啉-4-亚基)-亚乙基]-环己-2,5-二烯基}-丙二腈[1, CH3COâSâCnH2nâQ3CNQ] 的衍生物、2-2,3,5,6-四氟-7,7,8,8-四氰基对二醌甲烷 (TCNQF4) 或 2,3,5,6-四甲基-7,7,8,8-四氰基对二醌甲烷 (TMTCNQ)，通过 Ï-桥的氰基实现闭环，生成二取代类似物：2-2,3,5,6-tetrafluoro-4-[6-(10-acetylsulfanyldecyl)-3-(1-(10-acetylsulfanyldecyl)-1H-quinolin-4-ylidenemethyl)-6H-benzo[f][1,7]萘啶-2-亚基]-环己-2,5-二烯亚基}-丙二腈（2a）和 2,3,5,6-四甲基衍生物（2b）。这些供体â（Ï-桥）â受体分子二极管的自组装单层（SAM）显示出不对称的电流电压特性，在正向偏压下电子从顶部接触流向表面的 C(CN)2 基团。我们将其与以 TCNQâ 为电子供体的有机整流结和以 TCNQ° 为电子受体的供体â（Ï-桥）â-受体二极管的超薄薄膜的 IâV 曲线进行了比较。
• Do alkyl tunnelling barriers contribute to molecular rectification?
  作者：Geoffrey J. Ashwell、Robert J. Stokes

  DOI：10.1039/b401018c

  日期：——

  A recent model for molecular rectification has focused upon asymmetric alkyl tunnelling barriers that link the electrodes to a conjugated unit but experimental data reported here are contradictory: self-assembled monolayers (SAMs) exhibit symmetrical current–voltage characteristics when squaraine chromophores are located at one electrode and isolated from the other by extended alkanethiolate tails.

  分子整流的最新模型关注的是将电极连接到共轭单元的不对称烷基隧道屏障，但这里报告的实验数据是矛盾的：当喹吖啶酮发色团位于一个电极上，并通过延伸的烷基硫醇尾与另一个电极隔开时，自组装单层（SAM）表现出对称的电流-电压特性。
• Induced rectification from self-assembled monolayers of sterically hindered π-bridged chromophores
  作者：Geoffrey J. Ashwell、Abdul Mohib、James R. Miller

  DOI：10.1039/b417880g

  日期：——

  Self-assembled monolayers (SAMs) obtained via the chemisorption of bis-[1-(10-decyl)-4-2-(4-methoxynaphthalen-1-yl)vinyl}quinolinium]disulfide diiodide (1) on gold-coated highly oriented pyrolytic graphite (HOPG) substrates exhibit asymmetric current–voltage characteristics with rectification ratios of ca. 30 at ±1 V when contacted by PtIr or Au probes. The ratio decreases to ca. 10 at ±1 V for pentanethiolate-coated gold probes, which locate the donor–(π-bridge)–acceptor moiety approximately midway between the electrodes: Au–S–C5H11//D–π–A–C10H20–S–Au. The I–V characteristics are different but the current versus electric field dependence is indistinguishable for both types of electrode, the field being calculated for a monolayer thickness of 2.4 ± 0.1 nm and an assumed bilayer thickness of 3.2 nm (i.e. 0.8 nm for pentanethiolate). SAMs obtained from bis-[1-(10-decyl)-4-2-(4-methoxyphenyl)vinyl}pyridinium]disulfide diiodide (2) exhibit symmetrical I–V characteristics and, unlike the bulkier rectifying analogue above, its D–π–A chromophore is almost planar. This structure–property relationship highlights the significance of steric hindrance for rectification from π-bridged donor–acceptor molecules and consistent I–V characteristics have been obtained from SAMs investigated by scanning tunnelling spectroscopy (STS) as well as electrometer-based techniques with an alkanethiolate-coated mercury droplet electrode.

  通过双[1-(10-癸基)-4-2-(4-甲氧基萘-1-基)乙烯基}喹啉鎓]二硫醚二碘化物（1）在金涂层高取向热解石墨（HOPG）基底上的化学吸附形成的自组装单层（SAM）表现出非对称电流-电压特性，当与PtIr或Au探针接触时，整流比约为30（±1 V）。对于五硫醇盐涂层金探针，该比值在±1 V时降至约10，其将供体（Β-桥）-受体部分定位在电极之间的大约中间位置：Au-S-C5H11//D-Β-A-C10H20-S-Au。I-V特性不同，但两种电极的电流与电场依赖性无法区分，电场是根据单层厚度为2.4±0.1 nm和假设的双层厚度为3.2 nm（即五硫醇盐为0.8 nm）计算的。从双[1-(10-癸基)-4-2-(4-甲氧基苯基)乙烯基}吡啶鎓]二硫醚二碘化物（2）获得的SAM表现出对称的
• Molecular Rectification:  Self-Assembled Monolayers in Which Donor−(π-Bridge)−Acceptor Moieties Are Centrally Located and Symmetrically Coupled to Both Gold Electrodes
  作者：Geoffrey J. Ashwell、Wayne D. Tyrrell、Anne J. Whittam

  DOI：10.1021/ja049633u

  日期：2004.6.1

  Self-assembled monolayers (SAMS) obtained from 1-(10-acetylsulfanyldecyl)-4-[2-(4-dimethylaminophenyl)vinyl]quinolinium iodide exhibit asymmetric current-voltage (I-V) characteristics. The rectification may be reversibly switched: it is suppressed when the film is exposed to HCl vapor, the intramolecular charge-transfer axis being inhibited by protonation, but restored when exposed to NH3. The behavior is intrinsic to the donor- (pi-bridge)-acceptor moiety, and ambiguity in the assignment has been excluded by matching the alkyl tails on the substrate and contacting STM tip to locate the chromophore midway between the electrodes: Au-S-C10H21//D-pi-A-C10H20-S-Au. Films contacted by gold tips exhibit rectification ratios of ca. 18 at +/-1 V, whereas those contacted by pentanethiolate (Au-S-C5H11)- and decanethiolate (Au-S-C10H21)-coated tips have corresponding ratios of ca. 11 and 5, respectively. The I-V curves are different, but when adjusted for thickness the current versus electric field dependence is indistinguishable. Seven dyes are reported: SAMs with sterically hindered D-pi-A moieties, in which the donor and acceptor are twisted out of plane, exhibit rectification, whereas those that are planar or have a weak donor-acceptor combination do not.
• Improved Molecular Rectification from Self-Assembled Monolayers of a Sterically Hindered Dye
  作者：Geoffrey J. Ashwell、Abdul Mohib

  DOI：10.1021/ja054699q

  日期：2005.11.23

  Self-assembled monolayers (SAMS) formed from the reaction of 1-(10-acetylsulfanyldecyl)-4-2-(4-dimethylaminonaphthalen-1-yl)-vinyl}-quinolinium iodide (1a) and gold-coated substrates exhibit asymmetric current-voltage (I-V) characteristics with a rectification ratio of 50-150 at 1 V. It is the highest to date for a molecular diode, and the improved behavior may be assigned in part to the controlled alignment of the donor-(pi-bridge)-acceptor moieties and in part to steric hindrance, which imposes a nonplanar structure and effectively isolates the molecular orbitals of the donor and acceptor end groups. The molecular origin of the rectification is verified by its suppression upon exposure to HCl vapor, which protonates the dimethylamino group and inhibits the electron-donating properties, with restoration upon exposure to NH3. It is also established by a reduced rectification ratio of ca. 2 at 1 V when the cationic D-pi-A(+) moieties adopt an antiparallel arrangement in self-assembled films of the derivative, bis-[1-(10-decyl)-4-2-(4-dimethylaminonaphthalen-1-yl)-vinyl}-quinolinium]-disulfide diiodide (1b), which adsorbs via one of its terminal donors without rupture of the sulfur-sulfur bond: Au vertical bar D-pi-A(+)-C10H20-S-S-C10H20-(+)A-pi-D (l(-))(2).