THDTAP | 15994-50-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: THDTAP
• 英文别名: 2,3,5,6-Tetrahydro-1,4-thiazino<4,3,2-de>-1,4-benzothiazin；2,3,5,6-Tetrahydro<1,4>thiazino<4,3,2-de><1,4>benzothiazin；2,3,4,5-tetrahydro-1,6-dithia-3a-aza-phenalene；4,10-Dithia-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8-triene
• CAS: 15994-50-0
• 化学式: C₁₀H₁₁NS₂
• 分子量: 209.336
• InChiKey: UBRKMOISJHATPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  53.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  THDTAP 在 盐酸 、 sodium nitrite 作用下， 生成 2,3,4,5,2',3',4',5'-octahydro-[8,8']bi[1,6-dithia-3a-aza-phenalenyl]
  参考文献：
  名称：

  Rich,D.H.; Tarnowski,B.H., Journal of Heterocyclic Chemistry, 1970, vol. 7, p. 245 - 246

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N-双(2-氯乙基)苯胺 在 potassium methanethiosulphonate 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 THDTAP
  参考文献：
  名称：

  Dunbar,J.E.; Tarnowski,B.H., Journal of Heterocyclic Chemistry, 1967, vol. 4, p. 339 - 343

  摘要：

  DOI：

文献信息

• Decorating BODIPY with electron-rich unit THDTAP: An ICT-based fluorometric sensor toward peroxide, acid, and electrochemical stimuli
  作者：Taoshan Xu、Chaoxian Yan、Yuewei Wu、Chengshan Yuan、Xiangfeng Shao

  DOI：10.1016/j.dyepig.2019.04.069

  日期：2019.9

  A new type of BODIPY dye, compound 2 which possesses donor-acceptor (D-A) type structure, is synthesized by decorating electron-rich THDTAP unit onto the meso-position of BODIPY. The THDTAP has two chemically active sites (S and N atoms) that are utilized to manipulate the optoelectronic properties. By stepwise oxidation of two S-atoms on THDTAP moiety with m-CPBA, the 2 was converted to 3, trans-4, syn-4, 5, and 6. This transformation results in large influence on optoelectronic properties. The theoretical calculations reveal that the LUMOs of 2-6 are all located on BODIPY core, whereas their HOMOs show the different distributions. The 2 and 3 show the intramolecular charge-transfer (ICT) transition as proved by TD-DFT calculations, red-shifts of absorption and emission bands, and solvatochromism. The ICT process is inhibited in trans-4, syn-4, 5, and 6 due to the high oxidation states of S-atoms on THDTAP moieties. As a result, these four compounds display characteristic fluorescence of BODIPY. The femtosecond transient absorption (fs-TA) spectroscopic study reveals that 2 shows photoinduced hole-transfer (PHT) process in dichloromethane (DCM) solution. Upon acidification and neutralization of N-atom on THDTAP moiety, the ICT/PHT process of 2 in DCM is reversibly manipulated to result in fluorescence ON/OFF of BODIPY core. Moreover, the fluorescence of BODIPY core on 2 can be switched on through electrochemical oxidation of N-atom on THDTAP moiety. The compound 2 is thus a promising fluorometric sensor toward peroxide, acid, and electrochemical stimuli.
• Dunbar,J.E.; Tarnowski,B.H., Journal of Heterocyclic Chemistry, 1967, vol. 4, p. 339 - 343
  作者：Dunbar,J.E.、Tarnowski,B.H.

  DOI：——

  日期：——
• Rich,D.H.; Tarnowski,B.H., Journal of Heterocyclic Chemistry, 1970, vol. 7, p. 245 - 246
  作者：Rich,D.H.、Tarnowski,B.H.

  DOI：——

  日期：——