2,7-[bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-bis(3-(tert-butyl propanoate))]fluorene | 1030632-68-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2,7-[bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-bis(3-(tert-butyl propanoate))]fluorene
• 英文别名: Tert-butyl 3-[9-[3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)fluoren-9-yl]propanoate
• CAS: 1030632-68-8
• 化学式: C₃₉H₅₆B₂O₈
• 分子量: 674.491
• InChiKey: CMIQVMHEZFSBPJ-UHFFFAOYSA-N

物化性质

• 沸点：
  708.5±50.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  49
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,7-[bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-bis(3-(tert-butyl propanoate))]fluorene 、 9,9-bis(2'-(N,N-dimethylamino)ethyl)-2-bromofluorene 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 24.0h， 以30%的产率得到
  参考文献：
  名称：

  Neutral amine based alcohol-soluble interface materials for inverted polymer solar cells: realizing high performance and overcoming solvent erosion

  摘要：

  我们使用中性电子传输材料来制造倒置型聚合物太阳能电池，实现了高性能并同时解决了溶剂侵蚀问题。

  DOI：

  10.1039/c5cc02630j
• 作为产物：
  描述：

  2,7-二溴-9,9-双(3-(叔丁基丙酸酯))芴 、 联硼酸频那醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以95%的产率得到2,7-[bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-bis(3-(tert-butyl propanoate))]fluorene
  参考文献：
  名称：

  悬垂二硫键连接到PEG链的水溶性共轭聚合物：一种高效的比率式探针，具有溶解性诱导的荧光转化，用于硫醇检测。

  摘要：

  我们研究了具有与聚（乙二醇）（PEG）链相连的二硫键侧链的水溶性共轭聚合物（WSCP），这是一种高效的比率式探针，具有用于硫醇检测的溶解度诱导的荧光转换。该WSCP掺杂有低带隙荧光团1,4-二噻吩基苯并噻二唑（DBT），并通过二硫键被PEG修饰，以增加其水溶性。游离探针在水溶液（28 mg / mL）中表现出良好的溶解性，并且由于DBT的掺杂率低，因此显示出紫色荧光。由二硫键断裂引起的水溶性PEG链与共轭骨架的分离将导致探针的水溶性大大降低。结合使用扫描电子显微镜，动态光散射，荧光分光光度计进一步证实，溶解度的降低会导致疏水性共轭主链的聚集，进而提高了从共轭主链到DBT的荧光共振能量转移效率，表现为荧光从紫色到红色的转换。荧光比率法（探针的I 628 / I 420）从最小值0.095到1.15（最大增强12倍）变化。检出限为2.56μg/ mL（0.021 mM）。通过检查各种生物分子，

  DOI：

  10.1021/ma5021775

文献信息

• Synthesis and chemosensory application of water-soluble polyfluorenes containing carboxylated groups
  作者：Chia-Shing Wu、Hsiao-Chu Su、Yun Chen

  DOI：10.1039/c4ob00944d

  日期：——

  Detection of metal ions in aqueous solutions is a major issue for environmental protection. Conjugated polyelectrolytes showing high sensitivity and selectivity towards the detection of metal ions are highly desirable. We report a water-soluble polyfluorene containing carboxylated groups (P1), poly[9,9′-bis(3′′-propanoate)fluoren-2,7-yl] sodium salt, which shows high recognition capability toward Cu+ and Cu2+. P1 was prepared via the hydrolysis of poly[9,9′-bis(tert-butyl-3′′-propanoate)fluoren-2,7-yl] (P0) which was synthesized by Suzuki coupling polymerization. The photoluminescence (PL) spectra of P1 in aqueous solution are significantly quenched in the presence of Cu+ and Cu2+. P1 shows high selectivity and sensitivity toward Cu+ and Cu2+, with the Stern–Volmer constants (Ksv) being 3.5 × 106 and 5.78 × 106 M−1, respectively. Moreover, the stoichiometric ratio of the P1 repeat unit to Cu+ or Cu2+ is 2 : 1 obtained from Job's plot. P1 maintains high selectivity towards Cu+ or Cu2+ in the presence of various metal cations. Our results demonstrate that P1 shows very high sensitivity and selectivity in recognizing Cu+ and Cu2+, indicating that it is a promising functional material for chemical sensors.

  检测水溶液中的金属离子是环境保护的一个重要问题。对金属离子检测具有高灵敏度和高选择性的共轭聚电解质非常受欢迎。我们报告了一种含有羧基的水溶性聚芴（P1）--聚[9,9′-双（3′′-丙酸）芴-2,7-基]钠盐，它对 Cu+ 和 Cu2+ 具有很高的识别能力。P1 是通过水解聚[9,9′-双(叔丁基-3′′-丙酸)芴-2,7-基]（P0）制备的，P0 是通过铃木偶联聚合反应合成的。P1 在水溶液中的光致发光（PL）光谱在 Cu+ 和 Cu2+ 的存在下被明显淬灭。P1 对 Cu+ 和 Cu2+ 具有很高的选择性和敏感性，其 Stern-Volmer 常数（Ksv）分别为 3.5 × 106 和 5.78 × 106 M-1。此外，P1 重复单元与 Cu+ 或 Cu2+ 的化学计量比为 2 ：1。在各种金属阳离子存在的情况下，P1 对 Cu+ 或 Cu2+ 保持较高的选择性。我们的研究结果表明，P1 在识别 Cu+ 和 Cu2+ 时具有极高的灵敏度和选择性，这表明它是一种很有前途的化学传感器功能材料。
• Electronic Structure and Optical Properties of an Alternated Fluorene–Benzothiadiazole Copolymer: Interplay between Experimental and Theoretical Data
  作者：Paula C. Rodrigues、Leonardo S. Berlim、Diego Azevedo、Nestor C. Saavedra、Paras N. Prasad、Wido H. Schreiner、Teresa D. Z. Atvars、Leni Akcelrud

  DOI：10.1021/jp211042v

  日期：2012.4.12

  The donor-acceptor copolymer containing benzothiadiazole (electron acceptor), linked to functionalized fluorene (electron donor), [poly[9,9-bis(3'-(tert-butyl propanoate))fluorene-co-4,7-(2,1,3-benzothiadiazole)] (LaPPS40), was synthesized through the Suzuki route. The polymer was characterized by scanning electron microscopy, gel permeation chromatography, NMR, thermal analysis, cyclic voltammetry, X-ray photoelectron spectroscopy, UV-vis spectrometry, and photophysical measurements. Theoretical calculations (density functional theory and semiempirical methodologies) used to simulate the geometry of some oligomers and the dipole moments of molecular orbitals involved were in excellent agreement with experimental results. Using such data, the higher energy absorption band was attributed to the pi-pi* (S-0 -> S-4) transition of the fluorene units and the lower lying band was attributed to the intramolecular (ICT) (S-0 -> S-1) charge transfer between acceptor (benzothiadiazole) and donor groups (fluorene) (D-A structure). The ICT character of this band was confirmed by its solvatochromic properties using solvents with different dielectric properties, and this behavior could be well described by the Lippert-Mataga equation. To explain the solvatochromic behavior, both the magnitude and orientation of the dipole moments in the electronic ground state and in the excited state were analyzed using the theoretical data. According to these data, the change in magnitude of the dipole moments was very small for both transitions but the spatial orientation changed remarkably for the lower energy band ascribed to the ICT band.