2,7-bis(7-bromobenzo[c][1,2,5]thiadiazol-4-yl)-9,9'-spirobi[fluorene] | 1174926-52-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2,7-bis(7-bromobenzo[c][1,2,5]thiadiazol-4-yl)-9,9'-spirobi[fluorene]
• CAS: 1174926-52-3
• 化学式: C₃₇H₁₈Br₂N₄S₂
• 分子量: 742.517
• InChiKey: KLFBTRZBOBGFHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  45.0
• 可旋转键数：
  2.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  51.56
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-(二苯基氨基)苯硼酸频那醇酯 、 2,7-bis(7-bromobenzo[c][1,2,5]thiadiazol-4-yl)-9,9'-spirobi[fluorene] 在 四(三苯基膦)钯 、 三叔丁基膦 、 potassium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 72.0h， 以82%的产率得到2,7-di(4-(diphenylamino)phenyl-2,1,3-benzothiadiazol-7-yl)-9,9'-spirobiuorene
  参考文献：
  名称：

  Electrochemistry and Electrogenerated Chemiluminescence of a Spirobifluorene-Based Donor (Triphenylamine)−Acceptor (2,1,3-Benzothiadiazole) Molecule and Its Organic Nanoparticles

  摘要：

  A new D-A-pi-A-D molecule (Spiro-BTA) containing two 2,1,3-benzothiadiazole (BTA) as the acceptor (A) and triphenylamine as the donor (D) bridged by a spirobifluorene moiety has been synthesized. The novel D-A molecule shows intense red emission (612 nm) with a high PL quantum yield (Phi(PL) = 0.51) in a solid film. A cyclic voltammogram of Spiro-BTA in 1:2 MeCN:benzene/0.1 M Bu4NPF6 shows two reversible oxidation waves and one reversible reduction wave. The first oxidation wave and reduction wave were assigned as two successive electron transfer peaks separated by similar to 50 mV related to the oxidation of the two noninteracting donors and the reduction of the two noninteracting acceptors, respectively. Electrogenerated chemiluminescence (ECL) of Spiro-BTA upon cyclic oxidation and reduction in MeCN:benzene 1:2 shows a very bright and stable red emission that could be seen in a well-lit room. Using a reprecipitation method, well-dispersed organic nanoparticles (NPs) of the Spiro-BTA were prepared in aqueous solution. The nanoparticles were analyzed by dynamic light scattering (DLS) and scanning electron microscopy (SEM), yielding a NP size (without surfactant) of 130 +/- 20 nm, while with surfactant, 100 +/- 20 nm. Bathochromic shifts of absorption spectra (similar to 16 +/- 2 nm), as compared to that of the dissolved Spiro-BTA in THF, were observed for both NPs in water and as a thin film. While blue shifts (14 +/- 2 nm) were observed for the photoluminescence (PL). The PL intensity of the Spiro-BTA nanoparticles was slightly enhanced (Phi(PL) of nanoparticles in water = 48%) over that of the dissolved Spiro-BTA in THF. The ECL of the organic Spiro-BTA nanoparticles in aqueous solution could be observed upon oxidation with tri-n-propylamine as a coreactant.

  DOI：

  10.1021/ja2000825
• 作为产物：
  描述：

  4,7-二溴-2,1,3-苯并噻二唑 、 2，7-二硼酸酯-9，9'-螺二芴 在 四(三苯基膦)钯 、 三叔丁基膦 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 60.0h， 以30%的产率得到2,7-bis(7-bromobenzo[c][1,2,5]thiadiazol-4-yl)-9,9'-spirobi[fluorene]
  参考文献：
  名称：

  高荧光苯并噻二唑和芴衍生物的绿色电生化学发光

  摘要：

  合成并表征了一组高荧光2,1,3-苯并噻二唑衍生物（BH0-BH3），包括两种芴衍生物（AB2和CO1）。测定了化合物的电化学、光谱和电致化学发光 (ECL) 特性。苯并噻二唑衍生物 BH1、BH2 和 BH3 显示出可逆的氧化和还原波，并在非水溶液中产生强烈的绿色 ECL。即使在光线充足的房间里，也可以用肉眼看到这种 ECL。芴衍生物 CO1 和 AB2 也产生明亮、易于观察的 ECL。由于 ECL 光谱与光致发光 (PL) 光谱的波长基本相同，并且电子转移反应的能量大于单线态能量，我们建议在离子湮灭过程中直接形成激发单线态。BH0 显示准可逆氧化波，仅通过直接湮灭产生弱 ECL，但以过氧化苯甲酰 (BPO) 作为共反应物产生强 ECL。与 9,10-二苯蒽相比，该系列的 ECL 量子效率估计在 0.05% 到 7% 之间。该系列显示罕见的绿色光致发光（λ(PL) = 490-556 nm），在溶液中具有高

  DOI：

  10.1021/ja904135y