N-(4-ethynyl-2,6-dimethylphenyl)-N'-(n-octyl)-naphthalene-1,8:4,5-tetracarboxydiimide | 1176889-24-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-(4-ethynyl-2,6-dimethylphenyl)-N'-(n-octyl)-naphthalene-1,8:4,5-tetracarboxydiimide
• 英文别名: N-(4-ethynyl-2,6-dimethylphenyl)-N'-(n-octyl)naphthalene-1,8:4,5-tetracarboxydiimide；6-(4-Ethynyl-2,6-dimethylphenyl)-13-octyl-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone；6-(4-ethynyl-2,6-dimethylphenyl)-13-octyl-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone
• CAS: 1176889-24-9
• 化学式: C₃₂H₃₀N₂O₄
• 分子量: 506.601
• InChiKey: LOQWAUHORIRQBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dichloro(4,4'-di-tert-butyl-2,2'-bipyridine)platinum(II) 、 N-(4-ethynyl-2,6-dimethylphenyl)-N'-(n-octyl)-naphthalene-1,8:4,5-tetracarboxydiimide 、 10-(4'-ethynyl-2,2',6,6'-tetramethylbiphenyl-4-yl)-10H-phenothiazine 在 copper(l) iodide 、 二异丙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以21%的产率得到
  参考文献：
  名称：

  Photoinduced charge separation of phenothiazine–platinum–naphthalene diimide triads linked by twisted phenylene bridges

  摘要：

  我们制备了两种三元组（即 3PTZ-Pt-MNDI 和 10PTZ-Pt-MNDI ），它们由 3-吩噻嗪（3PTZ）或 10-吩噻嗪（10PTZ）、联吡啶二乙酰铂络合物（Pt）和萘二亚胺（MNDI）发色团组成，并通过高度扭曲的联苯间隔相连。通过选择性激发铂分子，利用皮秒和纳秒激光进行光解，研究了甲苯中电荷分离（CS）态的形成和衰减。经测定，由 PTZ-3Pt*-MNDI 形成 CS 态 PTZ+-Pt-MNDI- 所需的时间为：3PTZ+-Pt-MNDI- τ CS = 280 ps 和 10PTZ+-Pt-MNDI- τ CS = 230 ps。经测定，3PTZ+-Pt-MNDI- 的 CS 状态寿命为 τ CR1 = 75 ns (95 %) 和 τ CR2 = 285 ns (5 %)，10PTZ+-Pt-MNDI- 的 CS 状态寿命为 τ CR = 830 ns 。根据马库斯理论和自旋相关自由基对机制讨论了 CS 状态的形成和衰变。

  DOI：

  10.1007/s11164-012-0642-6
• 作为产物：
  描述：

  N-[2,6-dimethyl-4-(trimethylsilyl)ethynylphenyl]-N'-(n-octyl)-naphthalene-1,8:4,5-tetracarboxydiimide 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 0.83h， 以94%的产率得到N-(4-ethynyl-2,6-dimethylphenyl)-N'-(n-octyl)-naphthalene-1,8:4,5-tetracarboxydiimide
  参考文献：
  名称：

  Highly Efficient Photoproduction of Charge-Separated States in Donor−Acceptor-Linked Bis(acetylide) Platinum Complexes

  摘要：

  We report a highly efficient charge separation system, D-Pt-A, where D (triphenylamine) and A (naphthatenediimide) are bonded to the Pt moiety through highly twisted phenylene ethynylene linkages. The quantum yields for the formation of the charge-separated state were determined to be nearly unity. The lifetimes of D+-Pt-A(-) were similar to 1 mu s at room temperature and much longer at low temperature. The spin-correlated radical ion pair was directly observed by means of time-resolved EPR spectroscopy.

  DOI：

  10.1021/ja904241r

文献信息

• Photoinduced charge separation of phenothiazine–platinum–naphthalene diimide triads linked by twisted phenylene bridges
  作者：Ryoji Sugimura、Shuichi Suzuki、Masatoshi Kozaki、Kazutoshi Keyaki、Koichi Nozaki、Hironori Matsushita、Noriaki Ikeda、Keiji Okada

  DOI：10.1007/s11164-012-0642-6

  日期：2013.1

  Two triads (i.e., 3PTZ–Pt–MNDI and 10PTZ–Pt–MNDI) consisting of 3-phenothiazine (3PTZ) or 10-phenothiazine (10PTZ), bipyridine–diacetylide platinum complex (Pt), and naphthalene diimide (MNDI) chromophores linked by highly twisted biphenylene spacers have been prepared. The formation and decay of the charge-separated (CS) states in toluene were studied by use of picosecond and nanosecond laser photolysis via selective excitation of the Pt moiety. The time required for formation of the CS state, PTZ+–Pt–MNDI−, from PTZ–3Pt*–MNDI was determined to be τ CS = 280 ps for 3PTZ+–Pt–MNDI− and τ CS = 230 ps for 10PTZ+–Pt–MNDI−. The lifetimes of the CS states were determined to be τ CR1 = 75 ns (95 %) and τ CR2 = 285 ns (5 %) for 3PTZ+–Pt–MNDI− and τ CR = 830 ns for 10PTZ+–Pt–MNDI−. Formation and decay of the CS states are discussed in terms the Marcus theory and the spin-correlated radical pair mechanism.

  我们制备了两种三元组（即 3PTZ-Pt-MNDI 和 10PTZ-Pt-MNDI ），它们由 3-吩噻嗪（3PTZ）或 10-吩噻嗪（10PTZ）、联吡啶二乙酰铂络合物（Pt）和萘二亚胺（MNDI）发色团组成，并通过高度扭曲的联苯间隔相连。通过选择性激发铂分子，利用皮秒和纳秒激光进行光解，研究了甲苯中电荷分离（CS）态的形成和衰减。经测定，由 PTZ-3Pt*-MNDI 形成 CS 态 PTZ+-Pt-MNDI- 所需的时间为：3PTZ+-Pt-MNDI- τ CS = 280 ps 和 10PTZ+-Pt-MNDI- τ CS = 230 ps。经测定，3PTZ+-Pt-MNDI- 的 CS 状态寿命为 τ CR1 = 75 ns (95 %) 和 τ CR2 = 285 ns (5 %)，10PTZ+-Pt-MNDI- 的 CS 状态寿命为 τ CR = 830 ns 。根据马库斯理论和自旋相关自由基对机制讨论了 CS 状态的形成和衰变。
• Highly Efficient Photoproduction of Charge-Separated States in Donor−Acceptor-Linked Bis(acetylide) Platinum Complexes
  作者：Shuichi Suzuki、Ryoji Sugimura、Masatoshi Kozaki、Kazutoshi Keyaki、Koichi Nozaki、Noriaki Ikeda、Kimio Akiyama、Keiji Okada

  DOI：10.1021/ja904241r

  日期：2009.8.5

  We report a highly efficient charge separation system, D-Pt-A, where D (triphenylamine) and A (naphthatenediimide) are bonded to the Pt moiety through highly twisted phenylene ethynylene linkages. The quantum yields for the formation of the charge-separated state were determined to be nearly unity. The lifetimes of D+-Pt-A(-) were similar to 1 mu s at room temperature and much longer at low temperature. The spin-correlated radical ion pair was directly observed by means of time-resolved EPR spectroscopy.