2-[4-[4-[10-(6,8-Dimethyl-1-azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-7-yl)anthracen-9-yl]phenyl]phenyl]-6-octylpyrrolo[3,4-f]isoindole-1,3,5,7-tetrone | 1262757-95-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 2-[4-[4-[10-(6,8-Dimethyl-1-azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-7-yl)anthracen-9-yl]phenyl]phenyl]-6-octylpyrrolo[3,4-f]isoindole-1,3,5,7-tetrone
• 英文别名: 2-[4-[4-[10-(6,8-dimethyl-1-azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-7-yl)anthracen-9-yl]phenyl]phenyl]-6-octylpyrrolo[3,4-f]isoindole-1,3,5,7-tetrone
• CAS: 1262757-95-8
• 化学式: C₅₈H₅₃N₃O₄
• 分子量: 856.077
• InChiKey: CWDWRCGIALJRQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.9
• 重原子数：
  65
• 可旋转键数：
  11
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,5-dimethyl-4-(10-(4'-aminobiphenyl)anthracenyl)julolidine 、 N-octylbenzene-1,2-dicarboxyanhydride-4,5-dicarboximide 在 吡啶 作用下， 反应 14.0h， 以65%的产率得到2-[4-[4-[10-(6,8-Dimethyl-1-azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-7-yl)anthracen-9-yl]phenyl]phenyl]-6-octylpyrrolo[3,4-f]isoindole-1,3,5,7-tetrone
  参考文献：
  名称：

  Magnetic Field-Induced Switching of the Radical-Pair Intersystem Crossing Mechanism in a Donor−Bridge−Acceptor Molecule for Artificial Photosynthesis

  摘要：

  A covalent, fixed-distance donor-bridge- acceptor (D-B-A) molecule was synthesized that upon photoexcitation undergoes ultrafast charge separation to yield a radical ion pair (RP) in which the spin-spin exchange interaction (2J) between the two radicals is sufficiently large to result in preferential RP intersystem crossing to the highest-energy RP eigenstate (T+1) at the 350 mT magnetic field characteristic of X-band (9.5 GHz) EPR spectroscopy. This behavior is unprecedented in covalent D-B-A molecules, and is evidenced by the time-resolved EPR (TREPR) spectrum at X-band of (3*) D-B-A derived from RP recombination, which shows all six canonical EPR transitions polarized in emission (e,e,e,e,e,e). In contrast, when the RP is photogenerated in a 3400 mT magnetic field, the TREPR triplet spectrum at W-band (94 GHz) of (3*) D-B-A displays the (a,e,e,a,a,e) polarization pattern characteristic of a weakly coupled RP precursor, similar to that observed in photosynthetic reaction center proteins, and indicates a switch to selective population of the lower-energy T-0 eigenstate.

  DOI：

  10.1021/ja1094815

文献信息

• Magnetic Field-Induced Switching of the Radical-Pair Intersystem Crossing Mechanism in a Donor−Bridge−Acceptor Molecule for Artificial Photosynthesis
  作者：Michael T. Colvin、Annie Butler Ricks、Amy M. Scott、Amanda L. Smeigh、Raanan Carmieli、Tomoaki Miura、Michael R. Wasielewski

  DOI：10.1021/ja1094815

  日期：2011.2.9

  A covalent, fixed-distance donor-bridge- acceptor (D-B-A) molecule was synthesized that upon photoexcitation undergoes ultrafast charge separation to yield a radical ion pair (RP) in which the spin-spin exchange interaction (2J) between the two radicals is sufficiently large to result in preferential RP intersystem crossing to the highest-energy RP eigenstate (T+1) at the 350 mT magnetic field characteristic of X-band (9.5 GHz) EPR spectroscopy. This behavior is unprecedented in covalent D-B-A molecules, and is evidenced by the time-resolved EPR (TREPR) spectrum at X-band of (3*) D-B-A derived from RP recombination, which shows all six canonical EPR transitions polarized in emission (e,e,e,e,e,e). In contrast, when the RP is photogenerated in a 3400 mT magnetic field, the TREPR triplet spectrum at W-band (94 GHz) of (3*) D-B-A displays the (a,e,e,a,a,e) polarization pattern characteristic of a weakly coupled RP precursor, similar to that observed in photosynthetic reaction center proteins, and indicates a switch to selective population of the lower-energy T-0 eigenstate.