difluoro(2-[(4-iodophenyl)(3-methyl-4,5-dihydro-2Hbenzo[g]indol-2-ylidene-κN)methyl]-3-methyl-4,5-dihydro-1H-benzo[g]indolato-κN)boron

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: difluoro(2-[(4-iodophenyl)(3-methyl-4,5-dihydro-2Hbenzo[g]indol-2-ylidene-κN)methyl]-3-methyl-4,5-dihydro-1H-benzo[g]indolato-κN)boron
• 英文别名: 2,2-Difluoro-16-(4-iodophenyl)-14,18-dimethyl-3-aza-1-azonia-2-boranuidaheptacyclo[15.11.0.03,15.04,13.05,10.019,28.022,27]octacosa-1(28),4(13),5,7,9,14,16,18,22,24,26-undecaene；2,2-difluoro-16-(4-iodophenyl)-14,18-dimethyl-3-aza-1-azonia-2-boranuidaheptacyclo[15.11.0.03,15.04,13.05,10.019,28.022,27]octacosa-1(28),4(13),5,7,9,14,16,18,22,24,26-undecaene
• 化学式: C₃₃H₂₆BF₂IN₂
• 分子量: 626.295
• InChiKey: HKGSCBSVCIKCHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.94
• 重原子数：
  39
• 可旋转键数：
  1
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  7.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  difluoro(2-[(4-iodophenyl)(3-methyl-4,5-dihydro-2Hbenzo[g]indol-2-ylidene-κN)methyl]-3-methyl-4,5-dihydro-1H-benzo[g]indolato-κN)boron 在 四(三苯基膦)钯 copper(l) iodide 、 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 difluoro(3-methyl-2-[(3-methyl-4,5-dihydro-2H-benzo[g]indol-2-ylidene-κN)(4-ethynylphenyl)methyl]-4,5-dihydro-1H-benzo[g]indolato-κN)boron
  参考文献：
  名称：

  基于间苯二酚[4]芳烃cavitand的分子开关中的几何精确定义的多纳米膨胀/收缩运动。

  摘要：

  DOI：

  10.1002/anie.200500970
• 作为产物：
  描述：

  ethyl 3-methyl-4,5-dihydro-1H-benzo[g]indole-2-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 、 水 、 乙二醇 、 1,2-二氯乙烷 为溶剂， 反应 74.83h， 生成 difluoro(2-[(4-iodophenyl)(3-methyl-4,5-dihydro-2Hbenzo[g]indol-2-ylidene-κN)methyl]-3-methyl-4,5-dihydro-1H-benzo[g]indolato-κN)boron
  参考文献：
  名称：

  4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) Dyes Modified for Extended Conjugation and Restricted Bond Rotations

  摘要：

  Five new, constrained, aryl-substituted 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes (3f,g and 4h-j) were prepared and investigated to see if they have more favorable fluorescence characteristics than the unconstrained systems 2 that were prepared in previous studies. Dye types 3 and 4 have relatively rigid conformations caused by the heteroatom (3f and 3g) or ethylene bridge (4h-j) linkers that preclude free rotation of the substituted-benzene molecular fragments. In the event, the new dye types 3 and 4 have longer lambda(max) (abs) (620-660 nm) and lambda(max) (fluor) (630-680 nm) values than compounds 2, They also exhibit higher extinction coefficients (>100 000 M (1) cm(-1) except for 3g). Their fluorescent quantum yields are high (up to 0.72 for 4j), with the exception of compound 3g, which has a quantum yield of only 0.05. The redox properties of dyes 3 and 4 have also been examined.

  DOI：

  10.1021/jo991927o

文献信息

• Functionalized Calix[4]resorcinarene Cavitands. Versatile Platforms for the Modular Construction of Extended Molecular Switches
  作者：Vladimir A. Azov、Anna Schlegel、François Diederich

  DOI：10.1246/bcsj.79.1926

  日期：2006.12

  vase–kite conformational switching of bridged calix[4]resorcinarene-based cavitands bearing iodo or ethynyl substituents on the upper rim of the cavity. These reactive centers make the cavitands versatile platforms for further modular extension by means of Sonogashira cross-couplings, thereby enabling the construction of diverse functional architectures that are switchable between two highly restricted conformations

  我们报告了在空腔上缘带有碘或乙炔基取代基的桥接杯 [4] 间苯二酚基空腔体的花瓶-风筝构象转换的合成和研究。这些反应中心通过 Sonogashira 交叉耦合使腔体成为进一步模块化扩展的多功能平台，从而能够构建多种功能架构，这些架构可在两个高度受限的构象之间切换，并在多纳米尺度上进行几何定义的膨胀/收缩. 这可以通过将带有末端供体和受体 BODIPY（二吡咯亚甲基硼二氟化物）染料的低聚（苯乙炔基）片段连接到二碘取代的空腔中来说明。展开的风筝和收缩的花瓶状态之间的多纳米大小的切换运动，由温度或 pH 值变化引起，已通过 1 H NMR 光谱和 FRET（荧光共振能量转移）测量证明。腔体系统以其模块化结构方案，有望成为准分子和激基复合物形成、PET（光致电子转移）或其他过程的受控开/关切换以及研究潜在分子间距离依赖性的通用工具。相互作用。
• Geometrically Precisely Defined Multinanometer Expansion/Contraction Motions in a Resorcin[4]arene Cavitand Based Molecular Switch
  作者：Vladimir A. Azov、Anna Schlegel、François Diederich

  DOI：10.1002/anie.200500970

  日期：2005.7.18
• 4,4-Difluoro-4-bora-3a,4a-diaza-<i>s</i>-indacene (BODIPY) Dyes Modified for Extended Conjugation and Restricted Bond Rotations
  作者：Jiong Chen、Armin Burghart、Agnes Derecskei-Kovacs、Kevin Burgess

  DOI：10.1021/jo991927o

  日期：2000.5.1

  Five new, constrained, aryl-substituted 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes (3f,g and 4h-j) were prepared and investigated to see if they have more favorable fluorescence characteristics than the unconstrained systems 2 that were prepared in previous studies. Dye types 3 and 4 have relatively rigid conformations caused by the heteroatom (3f and 3g) or ethylene bridge (4h-j) linkers that preclude free rotation of the substituted-benzene molecular fragments. In the event, the new dye types 3 and 4 have longer lambda(max) (abs) (620-660 nm) and lambda(max) (fluor) (630-680 nm) values than compounds 2, They also exhibit higher extinction coefficients (>100 000 M (1) cm(-1) except for 3g). Their fluorescent quantum yields are high (up to 0.72 for 4j), with the exception of compound 3g, which has a quantum yield of only 0.05. The redox properties of dyes 3 and 4 have also been examined.