7-methylacenaphtho[1,2-c]pyrrole | 665019-61-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-methylacenaphtho[1,2-c]pyrrole
• 英文别名: 7-methyl-8H-acenaphtho[1,2-c]pyrrole；9-methyl-8H-acenaphthyleno[1,2-c]pyrrole
• CAS: 665019-61-4
• 化学式: C₁₅H₁₁N
• 分子量: 205.259
• InChiKey: SFHCHMBKMWDDMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(4-乙基-3,5-二甲基-1H-吡咯-2-基)-乙酮 、 7-methylacenaphtho[1,2-c]pyrrole 在 三氯氧磷 、 三氟化硼乙醚 、 N,N-二异丙基乙胺 作用下， 以 氯仿 为溶剂， 反应 21.0h， 以36%的产率得到7-Ethyl-10,10-difluoro-4,6,8,12-tetramethyl-9-aza-11-azonia-10-boranuidahexacyclo[12.7.1.02,13.03,11.05,9.018,22]docosa-1(21),2(13),3,5,7,11,14,16,18(22),19-decaene
  参考文献：
  名称：

  A New Synthesis of Functional Dyes from 2-Acenaphtho[1,2-c]pyrrole

  摘要：

  Incorporation of acenaphtho[1,2-c]pyrrole units into the pi-conjugated systems is very effective to get the narrow HOMO-LUMO gap materials, and the absorption spectra of pi-conjugated polymers, porphyrins, and boron dipyrromethene dyes fused with acenaphthene rings are extensively red-shifted.

  DOI：

  10.3987/com-03-s58
• 作为产物：
  描述：

  Ethyl acenaphtho<1,2-c>pyrrole-7-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以64%的产率得到7-methylacenaphtho[1,2-c]pyrrole
  参考文献：
  名称：

  A New Synthesis of Functional Dyes from 2-Acenaphtho[1,2-c]pyrrole

  摘要：

  Incorporation of acenaphtho[1,2-c]pyrrole units into the pi-conjugated systems is very effective to get the narrow HOMO-LUMO gap materials, and the absorption spectra of pi-conjugated polymers, porphyrins, and boron dipyrromethene dyes fused with acenaphthene rings are extensively red-shifted.

  DOI：

  10.3987/com-03-s58

文献信息

• A series of π-expanded coplanar BODIPY dyes with deep-red emission: Synthesis, optical properties, and application in amplified spontaneous emission
  作者：Yang Wang、Lei Xie、Qinning Sun、Liang Liu

  DOI：10.1039/d3nj01667f

  日期：——

  dipyrromethene (BODIPY)-derived dyes are a class of superior emitters, and a classic BODIPY structure has absorption and emission at ∼500 nm. To meet the practical application requirements, this work was dedicated to the design and synthesis of BODIPY emitters covering the deep-red region with a high emission quantum yield. Aromatic rings and a well-known electron-withdrawing group, –CF3, were introduced

  硼二吡咯亚甲基 (BODIPY) 衍生染料是一类优异的发射体，经典的 BODIPY 结构在~500 nm 处具有吸收和发射。为了满足实际应用需求，本工作致力于设计和合成覆盖深红色区域、具有高发射量子产率的BODIPY发射体。芳香环和著名的吸电子基团 –CF 3，被引入π展开的BODIPY结构中。详细讨论了这些 BODIPY 发射器，包括它们的热稳定性和光学参数，以及它们的光动力治疗性能。讨论了BODIPY光物理性能与其取代基之间的相关性。研究发现，π扩展共面共轭链的形成成功地将BODIPY发射转移到深红色区域（626 nm），并具有高量子产率（0.99）。然而，BODIPY内消旋-C 上的-CF 3修饰猝灭了其发射。ASE（放大自发发射）效应的阈值能量为 980 μJ，效率为 5.5%。使用这些 BODIPY 染料作为光敏剂，细胞活力降低至 9.0 ± 4.6%。
• 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.