2,7-di(4-(diphenylamino)phenyl-2,1,3-benzothiadiazol-7-yl)-9,9'-spirobiuorene | 1269440-84-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,7-di(4-(diphenylamino)phenyl-2,1,3-benzothiadiazol-7-yl)-9,9'-spirobiuorene
• 英文别名: spiro-BTA；N,N-diphenyl-4-[4-[7'-[7-[4-(N-phenylanilino)phenyl]-2,1,3-benzothiadiazol-4-yl]-9,9'-spirobi[fluorene]-2'-yl]-2,1,3-benzothiadiazol-7-yl]aniline
• CAS: 1269440-84-7
• 化学式: C₇₃H₄₆N₆S₂
• 分子量: 1071.34
• InChiKey: XARNJMRBFINCEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.1
• 重原子数：
  81
• 可旋转键数：
  10
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.01
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  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

文献信息

• Electrochemistry and Electrogenerated Chemiluminescence of a Spirobifluorene-Based Donor (Triphenylamine)−Acceptor (2,1,3-Benzothiadiazole) Molecule and Its Organic Nanoparticles
  作者：Khalid M. Omer、Sung-Yu Ku、Jian-Zhang Cheng、Shu-Hua Chou、Ken-Tsung Wong、Allen J. Bard

  DOI：10.1021/ja2000825

  日期：2011.4.13

  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.