5-bromo-3,4-dibutyl-2-hydroxymethyl-thiophene | 247088-08-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 5-bromo-3,4-dibutyl-2-hydroxymethyl-thiophene
• 英文别名: (5-Bromo-3,4-dibutylthiophen-2-yl)methanol
• CAS: 247088-08-0
• 化学式: C₁₃H₂₁BrOS
• 分子量: 305.279
• InChiKey: WSXYEHOCXCQCHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-3,4-dibutyl-2-hydroxymethyl-thiophene 在 potassium tert-butylate 、 三溴化磷 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 74.0h， 生成 2,5-bis[2'-(5''(2'''-(5''''-bromo-3'''',4''''-dibutyl-thienyl)-1'''-ethenyl)-3'',4''-dibutyl-thienyl)-1'-ethenyl]-3,4-dibutyl-thiophene
  参考文献：
  名称：

  Elastic and Inelastic Electron Tunneling Spectroscopy of a New Rectifying Monolayer

  摘要：

  Rectification of electrical current was observed in a Langmuir-Schaefer monolayer of fullerene-bis[ethylthio-tetrakis(3,4-dibutyl-2-thiophene-5-ethenyl)-5-bromo-3,4-dibutyl-2-thiophene] malonate, Au electrodes at room temperature (there are two regimes of asymmetry, at lower bias, i.e., between 0 and +/- 2 V, and at higher bias), and also between Pb and Al electrodes at 4.2 K. The latter experiment was coupled with second harmonic detection of the second derivative of the current with respect to voltage (d(2)I/dV(2)). The d(2)I/dV(2) spectrum shows intramolecular vibrations, and also two antisymmetric broad bands, centered at +/- 0.65 V, due to resonant electron tunneling between the Fermi level(s) of the electrodes and the lowest unoccupied molecular orbital of the molecule.

  DOI：

  10.1021/ja068729g
• 作为产物：
  描述：

  3,4-二丁基噻吩 在 sodium hydroxide 、 sodium tetrahydroborate 、 溴 、 叔丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 正戊烷 为溶剂， 反应 14.0h， 生成 5-bromo-3,4-dibutyl-2-hydroxymethyl-thiophene
  参考文献：
  名称：

  Elastic and Inelastic Electron Tunneling Spectroscopy of a New Rectifying Monolayer

  摘要：

  Rectification of electrical current was observed in a Langmuir-Schaefer monolayer of fullerene-bis[ethylthio-tetrakis(3,4-dibutyl-2-thiophene-5-ethenyl)-5-bromo-3,4-dibutyl-2-thiophene] malonate, Au electrodes at room temperature (there are two regimes of asymmetry, at lower bias, i.e., between 0 and +/- 2 V, and at higher bias), and also between Pb and Al electrodes at 4.2 K. The latter experiment was coupled with second harmonic detection of the second derivative of the current with respect to voltage (d(2)I/dV(2)). The d(2)I/dV(2) spectrum shows intramolecular vibrations, and also two antisymmetric broad bands, centered at +/- 0.65 V, due to resonant electron tunneling between the Fermi level(s) of the electrodes and the lowest unoccupied molecular orbital of the molecule.

  DOI：

  10.1021/ja068729g

文献信息

• US6067186A
  申请人：——

  公开号：US6067186A

  公开（公告）日：2000-05-23
• [EN] NEW CLASS OF HIGH HYPERPOLARIZABILITY ORGANIC CHROMOPHORES AND PROCESS FOR SYNTHESIZING THE SAME<br/>[FR] NOUVELLE CLASSE DE CHROMOPHORES ORGANIQUES HAUTEMENT HYPERPOLARISABLES ET LEUR PROCEDE DE SYNTHESE
  申请人：PACIFIC WAVE IND INC

  公开号：WO2000009613A2

  公开（公告）日：2000-02-24

  A new class of high hyperpolarizability organic chromophores and a process for synthesizing the same. The chromophores incorporate at least one organic substituent and are formed in consideration of molecular shapes and a spatial anisotropy of intermolecular interactions. The chromophores are processed into hardened material lattices to lock-in poling induced electric-optic activity. Preferred organic substituents are alkyl, aryl, and isophorone groups. A composite including the organic chromophore, in a preferred embodiment, includes a polymer such as a poly(methylmethacrylate), polyimide, polyamic acid, polystyrene, polycarbonate or polyurethane. The optimized chromophores result in hardened electro-optic polymers suitable for electro-optic modulators and other devices such as optical switches. These modulators can be configured to work at high frequencies and in arrays for applications in communications and network connections. In addition, they can be implemented in series and parallel combinations in phased array radar, signal processing and sensor technology applications.
• Elastic and Inelastic Electron Tunneling Spectroscopy of a New Rectifying Monolayer
  作者：Andrei Honciuc、Robert M. Metzger、Aijun Gong、Charles W. Spangler

  DOI：10.1021/ja068729g

  日期：2007.7.1

  Rectification of electrical current was observed in a Langmuir-Schaefer monolayer of fullerene-bis[ethylthio-tetrakis(3,4-dibutyl-2-thiophene-5-ethenyl)-5-bromo-3,4-dibutyl-2-thiophene] malonate, Au electrodes at room temperature (there are two regimes of asymmetry, at lower bias, i.e., between 0 and +/- 2 V, and at higher bias), and also between Pb and Al electrodes at 4.2 K. The latter experiment was coupled with second harmonic detection of the second derivative of the current with respect to voltage (d(2)I/dV(2)). The d(2)I/dV(2) spectrum shows intramolecular vibrations, and also two antisymmetric broad bands, centered at +/- 0.65 V, due to resonant electron tunneling between the Fermi level(s) of the electrodes and the lowest unoccupied molecular orbital of the molecule.