ethyl 4,13-dihydro-5,12-diphenyl-4,13-ethano-2H-fluorantho[8,9-f]isoindole-1-carboxylate | 1226965-82-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 4,13-dihydro-5,12-diphenyl-4,13-ethano-2H-fluorantho[8,9-f]isoindole-1-carboxylate
• CAS: 1226965-82-7
• 化学式: C₃₉H₂₉NO₂
• 分子量: 543.665
• InChiKey: WFISWKQFSUZQDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  42.0
• 可旋转键数：
  4.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  42.09
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  ethyl 4,13-dihydro-5,12-diphenyl-4,13-ethano-2H-fluorantho[8,9-f]isoindole-1-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Synthesis of Tetrabenzoporphyrins Fused with Fluoranthenes

  摘要：

  Tetrabenzoporphyrins fused with fluoranthenes were prepared by the retro Diels-Alder reaction of the precursors composed of a porphyrin and four fluoranthenes connected with bicyclo[2.2.2]octadiene (BCOD). These porphyrins exhibited the Soret (480-494 nm, epsilon = 243,000-277,000) and intense Q bands (739-760 nm, epsilon = 375,000-509,000). Free bases and Zn complexes of them fluoresce at 760 nm and 746 nm with small Storks shifts and high quantum yields of 30 and 10 %, respectively.

  DOI：

  10.3987/com-09-s(s)98
• 作为产物：
  描述：

  7,9-二苯基-8H-环戊并[a]苊烯-8-酮 、 ethyl 4,7-dihydro-4,7-ethano-2H-isoindole-1-carboxylate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 氯仿 为溶剂， 反应 93.0h， 以76%的产率得到ethyl 4,13-dihydro-5,12-diphenyl-4,13-ethano-2H-fluorantho[8,9-f]isoindole-1-carboxylate
  参考文献：
  名称：

  Synthesis of Tetrabenzoporphyrins Fused with Fluoranthenes

  摘要：

  Tetrabenzoporphyrins fused with fluoranthenes were prepared by the retro Diels-Alder reaction of the precursors composed of a porphyrin and four fluoranthenes connected with bicyclo[2.2.2]octadiene (BCOD). These porphyrins exhibited the Soret (480-494 nm, epsilon = 243,000-277,000) and intense Q bands (739-760 nm, epsilon = 375,000-509,000). Free bases and Zn complexes of them fluoresce at 760 nm and 746 nm with small Storks shifts and high quantum yields of 30 and 10 %, respectively.

  DOI：

  10.3987/com-09-s(s)98

文献信息

• Synthesis, Characterization, and Electronic Structures of Porphyrins Fused with Polycyclic Aromatic Ring Systems
  作者：Tetsuo Okujima、John Mack、Jun Nakamura、Gugu Kubheka、Tebello Nyokong、Hua Zhu、Naoki Komobuchi、Noboru Ono、Hiroko Yamada、Hidemitsu Uno、Nagao Kobayashi

  DOI：10.1002/chem.201602213

  日期：2016.10.4

  A series of porphyrins fused with acenaphthylene, phenanthroline, and benzofluoranthene polycyclic aromatic rings were prepared by means of a 3+1 porphyrin synthesis approach and subsequent retro‐Diels–Alder reaction of bicyclo[2.2.2]octadiene‐fused precursors. Analysis of the magnetic circular dichroism spectra and the results of time‐dependent DFT calculations are used to identify the reasons for

  通过3 + 1卟啉合成方法和随后的双环[2.2.2]辛二烯稠合前体的Diels-Alder逆反应，制备了一系列与,、菲咯啉和苯并荧蒽多环芳环稠合的卟啉。通过分析圆二色性光谱和时间依赖DFT计算的结果，可以确定在产品Q波段的波长和相对强度中观察到趋势的原因。Michl的周长模型用作解释边界π分子轨道相对能量变化的概念框架。
• Synthesis of π-expanded BODIPYs and their fluorescent properties in the visible–near–infrared region
  作者：Tetsuo Okujima、Yuya Tomimori、Jun Nakamura、Hiroko Yamada、Hidemitsu Uno、Noboru Ono

  DOI：10.1016/j.tet.2010.06.045

  日期：2010.8

  A series of pi-expanded boron-dipyrromethenes (BODIPYs) fused with aromatic rings at beta,beta-positions, such as benzene, acenaphthylene, and benzofluoranthene were prepared by the reaction of BF(3)center dot OEt(2) with bicyclo[2.2.2]octadiene-fused dipyrromethene and the subsequent retro Diels-Alder reaction. These BODIPYs exhibited the absorptions and the fluorescence emissions over wide range of visible-near infrared region at 500-800 nm. BODIPYs composed of two fluorantho[8,9-f]isoindoles absorbed and emitted at red-region over 750 nm with absolute fluorescence quantum yield (Phi(f)) of ca. 0.3, although they are unstable under air in room light. BODIPY composed fluorantho[8,9-f]isoindole and acenaphtho [1,2-c]pyrrole was stable and showed a bright fluorescence emission at 695 nm with high Phi(f) of 0.70. (C) 2010 Elsevier Ltd. All rights reserved.