BPin-OF1-NH2 | 1101928-64-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: BPin-OF1-NH2
• 英文别名: H2N-OF1-BPin
• CAS: 1101928-64-6
• 化学式: C₃₉H₆₂BNO₂
• 分子量: 587.738
• InChiKey: ZOHQXQRHGDAPAL-KYJUHHDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.32
• 重原子数：
  43.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  44.48
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  BPin-OF1-NH2 、 H-OF2-I 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 以50%的产率得到2-amino-9,9,9',9',9'',9''-hexa((S)-3,7-dimethyloctyl)-7,2':7',2''-terfluorene
  参考文献：
  名称：

  White-Light Emitting Hydrogen-Bonded Supramolecular Copolymers Based on π-Conjugated Oligomers

  摘要：

  Three different pi-conjugated oligomers (a blue-emitting oligofluorene, a green-emitting oligo(phenylene vinylene), and a red-emitting perylene bisimide) have been functionalized with self-complementary quadruple hydrogen bonding ureidopyrimidinone (UPy) units at both ends. The molecules self-assemble in solution and in the bulk, forming supramolecular polymers. When mixed together in solution, random noncovalent copolymers are formed that contain all three types of chromophores, resulting in energy transfer upon excitation of the oligofluorene energy donor. At a certain mixing ratio, a white emissive supramolecular polymer can be created in solution. In contrast to their unfunctionalized counterparts, bis-UPy-chromophores can easily be deposited as smooth thin films on surfaces by spin coating. No phase separation is observed in these films, and energy transfer is much more efficient than in solution, giving rise to white fluorescence at much lower ratios of energy acceptor to donor. Light emitting diodes based on these supramolecular polymers have been prepared from all three types of pure materials, yielding blue, green, and red devices, respectively. At appropriate mixing ratios of these three compounds, white electroluminescence is observed. This approach yields a toolbox of molecules that can be easily used to construct pi-conjugated supramolecular polymers with a variety of compositions, high solution viscosities, and tuneable emission colors.

  DOI：

  10.1021/ja807996y
• 作为产物：
  描述：

  异丙醇频哪醇硼酸酯 、 2-bromo-7-amino-9,9-di((S)-3,7-dimethyloctyl)fluorene 在 正丁基锂 作用下， 以 四氢呋喃 、 hexanes 为溶剂， 反应 1.0h， 以64%的产率得到BPin-OF1-NH2
  参考文献：
  名称：

  White-Light Emitting Hydrogen-Bonded Supramolecular Copolymers Based on π-Conjugated Oligomers

  摘要：

  Three different pi-conjugated oligomers (a blue-emitting oligofluorene, a green-emitting oligo(phenylene vinylene), and a red-emitting perylene bisimide) have been functionalized with self-complementary quadruple hydrogen bonding ureidopyrimidinone (UPy) units at both ends. The molecules self-assemble in solution and in the bulk, forming supramolecular polymers. When mixed together in solution, random noncovalent copolymers are formed that contain all three types of chromophores, resulting in energy transfer upon excitation of the oligofluorene energy donor. At a certain mixing ratio, a white emissive supramolecular polymer can be created in solution. In contrast to their unfunctionalized counterparts, bis-UPy-chromophores can easily be deposited as smooth thin films on surfaces by spin coating. No phase separation is observed in these films, and energy transfer is much more efficient than in solution, giving rise to white fluorescence at much lower ratios of energy acceptor to donor. Light emitting diodes based on these supramolecular polymers have been prepared from all three types of pure materials, yielding blue, green, and red devices, respectively. At appropriate mixing ratios of these three compounds, white electroluminescence is observed. This approach yields a toolbox of molecules that can be easily used to construct pi-conjugated supramolecular polymers with a variety of compositions, high solution viscosities, and tuneable emission colors.

  DOI：

  10.1021/ja807996y

文献信息

• Multicolour Self-Assembled Fluorene Co-Oligomers: From Molecules to the Solid State via White-Light-Emitting Organogels
  作者：Robert Abbel、Rob van der Weegen、Wojciech Pisula、Mathieu Surin、Philippe Leclère、Roberto Lazzaroni、E. W. Meijer、Albertus P. H. J. Schenning

  DOI：10.1002/chem.200900620

  日期：2009.9.28

  Five fluorene‐based co‐oligomers have been prepared to study their self‐assembly in a wide range of concentrations, from dilute solutions to the solid state. Subtle changes to the chemical structures, introduced to tune the emission colours over the entire visible range, induce strong differences in aggregation behaviour. Only two of the fluorescent co‐oligomer derivatives self‐assemble to form soluble

  已经准备了五种芴基共聚体，以研究从稀溶液到固态的各种浓度下的自组装。化学结构的细微变化被引入以在整个可见光范围内调整发射颜色，从而引起聚集行为的强烈差异。荧光共聚低聚物的衍生物中只有两种会自组装形成可溶性原纤维，荧光有机凝胶会从可溶性原纤维中以更高的浓度出现。相反，其他化合物形成沉淀。混合荧光共聚体系统表现出部分能量转移，这允许创建发白光的凝胶。最后，根据实验结果和分子模型计算，提出了此类材料的分层自组装机制。
• Pre- and Postfunctionalized Self-Assembled π-Conjugated Fluorescent Organic Nanoparticles for Dual Targeting
  作者：Katja Petkau、Adrien Kaeser、Irén Fischer、Luc Brunsveld、Albertus P. H. J. Schenning

  DOI：10.1021/ja2075345

  日期：2011.10.26

  There is currently a high demand for novel approaches to engineer fluorescent nanoparticles with precise surface properties suitable for various applications, including imaging and sensing. To this end, we report a facile and highly reproducible one-step method for generating functionalized fluorescent organic nanoparticles via self-assembly of prefunctionalized pi-conjugated oligomers. The engineered design of the nonionic amphiphilic oligomers enables the introduction of different ligands at the extremities of inert ethylene glycol side chains without interfering with the self-assembly process. The intrinsic fluorescence of the nanoparticles permits the measurement of their surface properties and binding to dye-labeled target molecules via Forster resonance energy transfer (FRET). Co-assembly of differently functionalized oligomers is also demonstrated, which enables the tuning of ligand composition and density. Furthermore, nanoparticle prefunctionalization has been combined with subsequent postmodification of azide-bearing oligomers via click chemistry. This allows for expanding ligand diversity at two independent stages in the nanoparticle fabrication process. The practicability of the different methods entails greater control over surface functionality. Through labeling with different ligands, selective binding of proteins, bacteria, and functionalized beads to the nanoparticles has been achieved. This, in combination with the absence of unspecific adsorption, clearly demonstrates the broad potential of these nanoparticles for selective targeting and sequestration. Therefore, controlled bifunctionalization of fluorescent pi-conjugated oligomer nanoparticles represents a novel approach with high applicability to multitargeted imaging and sensing in biology and medicine.