7,7'-(benzo[c][1,2,5]thiadiazole-4,7-diyl)bis(9,9-bis((S)-3,7-dimethyloctyl)-9H-fluoren-2-amine) | 1146967-20-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 7,7'-(benzo[c][1,2,5]thiadiazole-4,7-diyl)bis(9,9-bis((S)-3,7-dimethyloctyl)-9H-fluoren-2-amine)
• CAS: 1146967-20-5
• 化学式: C₇₂H₁₀₂N₄S
• 分子量: 1055.69
• InChiKey: CSJYGKSLAAIRPQ-GQYFIECQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.69
• 重原子数：
  77.0
• 可旋转键数：
  30.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  77.82
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  7,7'-(benzo[c][1,2,5]thiadiazole-4,7-diyl)bis(9,9-bis((S)-3,7-dimethyloctyl)-9H-fluoren-2-amine) 、 3,4,5-tris(dodecanyloxy)benzoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以83%的产率得到C₁₅₈H₂₅₄N₄O₈S
  参考文献：
  名称：

  自组装的多色芴共聚体：从分子到通过白光有机有机体的固态

  摘要：

  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。

  DOI：

  10.1002/chem.200900620
• 作为产物：
  描述：

  4,7-二溴-2,1,3-苯并噻二唑 、 BPin-OF1-NH2 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 72.0h， 以53%的产率得到7,7'-(benzo[c][1,2,5]thiadiazole-4,7-diyl)bis(9,9-bis((S)-3,7-dimethyloctyl)-9H-fluoren-2-amine)
  参考文献：
  名称：

  自组装的多色芴共聚体：从分子到通过白光有机有机体的固态

  摘要：

  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。

  DOI：

  10.1002/chem.200900620

文献信息

• Multicolour self-assembled particles of fluorene-based bolaamphiphiles
  作者：Robert Abbel、Rob van der Weegen、E. W. Meijer、Albertus P. H. J. Schenning

  DOI：10.1039/b822943k

  日期：——

  Bolaamphiphilic fluorene-based oligomers self-assemble in water to form fluorescent nanoparticles with tuneable emission colours covering the entire visible range, even including white.

  基于芴的亲水型球状聚集体在水中的自组装形成荧光纳米颗粒，其发射颜色可调，覆盖整个可见光范围，甚至包括白色。
• 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.