1,1':4',1''-Terphenyl-4-methanethiol | 78540-82-6

• 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: 1,1':4',1''-Terphenyl-4-methanethiol
• 英文别名: 4-Mercaptomethyl(p-terphenyl)；terphenyl-4-methanethiol；[1,1':4',1''-Terphenyl]-4-ylmethanethiol；[4-(4-phenylphenyl)phenyl]methanethiol
• CAS: 78540-82-6
• 化学式: C₁₉H₁₆S
• 分子量: 276.402
• InChiKey: YVJYBBQPXSVPNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,1':4',1''-Terphenyl-4-methanethiol 、 4-Brommethyl-4'-methyl-2,2'-(p-phenylen)bis<5-phenyloxazol> 在 氢氧化钾 作用下， 生成 <2-<4-(4-methyl-5-phenyloxazol-2-yl)phenyl>-5-phenyloxazol-4-ylmethyl>sulfid
  参考文献：
  名称：

  Liphardt, Bodo; Luettke, Wolfgang, Liebigs Annalen der Chemie, 1981, # 6, p. 1118 - 1138

  摘要：

  DOI：
• 作为产物：
  描述：

  4-bromomethyl-p-terphenyl 在 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1,1':4',1''-Terphenyl-4-methanethiol
  参考文献：
  名称：

  Fabrication of a Carboxyl-Terminated Organic Surface with Self-Assembly of Functionalized Terphenylthiols:  The Importance of Hydrogen Bond Formation

  摘要：

  Self-assembled monolayers (SAMs) were prepared from different oligophenylthiol molecules (terphenylthiol, (C6H5C6H4C6H4SH, TPT), terphenylmethanethiol (C6H5C6H4C6H4CH2SH, TPMT), and carboxy terphenylmethanethiol (HOOCC6H4C6H4C6H4CH2SH, CTPMT)) on Au substrates. Compared to the more commonly used alkanethiols this class of organothiols has a much more rigid backbone. It is demonstrated that for organothiols with a strongly interacting function at the omega-position the larger mechanical rigidity significantly affects the molecular structure of the self-assembled films. Whereas the unsubstituted terphenylthiols, TPT and TPMT, form well-ordered monolayers with an average tilt angle of 27 degrees +/- 5 degrees, immersion into ethanolic solutions of the COOH-functionalized terphenylmethanethiol CTPMT yields highly oriented bilayers. The second layer is linked to the first layer by hydrogen bonds. This double-layer formation has not been observed for the corresponding alkanethiols. Single layers of CTPMT on gold could, however, be prepared by adsorption from a mixture with trifluoroacetic acid (TFA) or by immersion of the bilayers into TFA. The immersion of the bilayers into potassium hydroxide solutions leads to the intercalation of potassium ions into the bilayers without removal of the second layer.

  DOI：

  10.1021/ja981872s

文献信息

• Liphardt, Bodo; Luettke, Wolfgang, Liebigs Annalen der Chemie, 1981, # 6, p. 1118 - 1138
  作者：Liphardt, Bodo、Luettke, Wolfgang

  DOI：——

  日期：——
• Fabrication of a Carboxyl-Terminated Organic Surface with Self-Assembly of Functionalized Terphenylthiols:  The Importance of Hydrogen Bond Formation
  作者：Hans-Jörg Himmel、Andreas Terfort、Christof Wöll

  DOI：10.1021/ja981872s

  日期：1998.11.1

  Self-assembled monolayers (SAMs) were prepared from different oligophenylthiol molecules (terphenylthiol, (C6H5C6H4C6H4SH, TPT), terphenylmethanethiol (C6H5C6H4C6H4CH2SH, TPMT), and carboxy terphenylmethanethiol (HOOCC6H4C6H4C6H4CH2SH, CTPMT)) on Au substrates. Compared to the more commonly used alkanethiols this class of organothiols has a much more rigid backbone. It is demonstrated that for organothiols with a strongly interacting function at the omega-position the larger mechanical rigidity significantly affects the molecular structure of the self-assembled films. Whereas the unsubstituted terphenylthiols, TPT and TPMT, form well-ordered monolayers with an average tilt angle of 27 degrees +/- 5 degrees, immersion into ethanolic solutions of the COOH-functionalized terphenylmethanethiol CTPMT yields highly oriented bilayers. The second layer is linked to the first layer by hydrogen bonds. This double-layer formation has not been observed for the corresponding alkanethiols. Single layers of CTPMT on gold could, however, be prepared by adsorption from a mixture with trifluoroacetic acid (TFA) or by immersion of the bilayers into TFA. The immersion of the bilayers into potassium hydroxide solutions leads to the intercalation of potassium ions into the bilayers without removal of the second layer.