1,2,8,9-tetraethyl-4,4,11,11-tetrafluoro-3,5,10,12-tetramethyl-4,11-dibora-3a,4a,10a,11a-tetraazabenzo[1,2-a:4,5-a']di-s-indacene | 1394292-58-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 1,2,8,9-tetraethyl-4,4,11,11-tetrafluoro-3,5,10,12-tetramethyl-4,11-dibora-3a,4a,10a,11a-tetraazabenzo[1,2-a:4,5-a']di-s-indacene
• 英文别名: 1,2,10,11-tetraethyl-4,4,8,8-tetrafluoro-3,5,7,9-tetramethyl-4,8-dibora-3a,4a,7a,8a-tetraazabenzo[1,2-a:5,4-a′]-s-indacene；7,8,20,21-Tetraethyl-11,11,24,24-tetrafluoro-9,13,22,26-tetramethyl-10,23-diaza-12,25-diazonia-11,24-diboranuidaheptacyclo[14.10.0.03,14.04,12.06,10.017,25.019,23]hexacosa-1,3(14),4,6,8,12,15,17,19,21,25-undecaene
• CAS: 1394292-58-0
• 化学式: C₃₂H₃₆B₂F₄N₄
• 分子量: 574.28
• InChiKey: IGVNLIGHMNTPBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  42
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  15.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,2,8,9-tetraethyl-4,4,11,11-tetrafluoro-3,5,10,12-tetramethyl-4,11-dibora-3a,4a,10a,11a-tetraaza-6,11-dihydrobenzo[1,2-a:4,5-a']di-s-indacene 在 四氯苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以100%的产率得到1,2,8,9-tetraethyl-4,4,11,11-tetrafluoro-3,5,10,12-tetramethyl-4,11-dibora-3a,4a,10a,11a-tetraazabenzo[1,2-a:4,5-a']di-s-indacene
  参考文献：
  名称：

  4,8-Dihydropyrrol[3,4-f]isoindole as a Useful Building Block for Near-Infrared Dyes

  摘要：

  4,8-Dihydropyrrol[3,4-f]isoindole was prepared from 4,7-dihydroisoindole based on the modified Barton-Zard reaction. Addition of phenylsulfenyl chloride followed by oxidation and dehydrochlorination gave phenylsulfonyldihydroisoindole, which underwent the smooth reaction with an isocyanoacetate under basic conditions to give 4,8-dihydropyrrol[3,4-f]isoindole-1,5- and 1,7-dicarboxylates in good yields. The pyrrolisoindole was successfully converted to the benzene-fused bisBODIPY, absorption maximum of which was 758 nm.

  DOI：

  10.3987/com-14-s(k)91

文献信息

• π-Fused bis-BODIPY as a candidate for NIR dyes
  作者：Mitsunori Nakamura、Hiroyuki Tahara、Kohtaro Takahashi、Toshi Nagata、Hiroki Uoyama、Daiki Kuzuhara、Shigeki Mori、Tetsuo Okujima、Hiroko Yamada、Hidemitsu Uno

  DOI：10.1039/c2ob25930c

  日期：——

  Benzene-fused bis-(borondipyrromethene)s (bis-BODIPYs) were synthesized by retro-Diels–Alder reaction of the corresponding bicyclo[2.2.2]octadiene-fused (BCOD-fused) bis-BODIPYs, which were, in turn, prepared from 4,8-ethano-4,8-dihydropyrrolo[3,4-f]isoindole derivatives. The π-fused bis-BODIPY chromophores were designed to show intensive absorption and strong fluorescence in the near-infrared region and not to have any strong absorption in the visible region. A 6,10-dibora-5a,6a,9a,10a-tetraaza-s-indaceno[2,3-b:6,5-b′]difluorene derivative (syn-bis-benzoBODIPY) obtained by a thermal retro-Diels–Alder reaction of the corresponding BCOD-fused BODIPY dimer has strong absorption and emission bands at 775 and 781 nm, respectively. The absolute quantum yield is 0.36. The absorption is more than 5.0 times stronger than other absorptions observed in the visible region. In the case of 6,15-dibora-5a,6a,14a,15a-tetraaza-s-indaceno[2,3-b:6,7-b′]difluorene derivatives (anti-bis-benzoBODIPY), the absorption and emission maxima exceed 840 nm.

  通过对相应的双环[2.2.2]辛二烯融合（BCOD-fused）双 BODIPYs 进行逆-DielsâAlder 反应，合成了苯融合双（硼二吡咯并二酮）（bis-BODIPYs），而这些双 BODIPYs 又是由 4,8-ethano-4,8-dihydropyrrolo[3,4-f]isoindole 衍生物制备的。融合的双 BODIPY 发色团在近红外区域表现出强吸收和强荧光，而在可见光区域没有任何强吸收。由相应的 BCOD 融合 BODIPY 二聚体通过热逆-DielsâAlder 反应得到的 6,10-二硼-5a,6a,9a,10a-四氮杂-s-茚并[2,3-b:6,5-bâ²]二芴衍生物（syn-biszoBODIPY）在 775 和 781 nm 处分别有强吸收带和发射带。绝对量子产率为 0.36。该吸收比在可见光区域观察到的其他吸收强 5.0 倍以上。至于 6,15-二硼-5a,6a,14a,15a-四氮杂-s-茚并[2,3-b:6,7-bâ²]二芴衍生物（抗-双苯并-BODIPY），其吸收和发射最大值超过了 840 纳米。
• 4,8-Dihydropyrrol[3,4-f]isoindole as a Useful Building Block for Near-Infrared Dyes
  作者：Hidemitsu Uno、Mitsunori Nakamura、Kazuki Jodai、Shigeki Mori、Tetsuo Okujima

  DOI：10.3987/com-14-s(k)91

  日期：——

  4,8-Dihydropyrrol[3,4-f]isoindole was prepared from 4,7-dihydroisoindole based on the modified Barton-Zard reaction. Addition of phenylsulfenyl chloride followed by oxidation and dehydrochlorination gave phenylsulfonyldihydroisoindole, which underwent the smooth reaction with an isocyanoacetate under basic conditions to give 4,8-dihydropyrrol[3,4-f]isoindole-1,5- and 1,7-dicarboxylates in good yields. The pyrrolisoindole was successfully converted to the benzene-fused bisBODIPY, absorption maximum of which was 758 nm.