Anthra(1.9-bc:4,10-b'c')-bis[1]benzothiopyran | 132080-04-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻喃类
• 英文名称: Anthra(1.9-bc:4,10-b'c')-bis[1]benzothiopyran
• CAS: 132080-04-7
• 化学式: C₂₆H₁₄O₂S₂
• 分子量: 422.528
• InChiKey: WQHFRJIJYJWUMC-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  Anthra(1.9-bc:4,10-b'c')-bis[1]benzothiopyran 以 二氯甲烷 为溶剂， 生成 15,20-dithiaheptacyclo[14.10.2.02,7.08,28.09,14.019,27.021,26]octacosa-1(27),2,4,6,8(28),9,11,13,16,18,21,23,25-tridecaene
  参考文献：
  名称：

  Rate parameters for the two-step photofragmentation of aromatic endoperoxides in solution

  摘要：

  The formation of dimethylhomoocoerdianthrone (HOCD) following subpicosecond laser photolysis of its endoperoxide (PO) was studied by laser-induced fluorescence (LIF) in the solvents dichloromethane and toluene. The measured rise time of the LIf signal refers to a time constant of tau-2 = 1.7 +/- 0.5 ps at 22-degrees-C. The study of the characteristic rate constant at different temperatures gives an activation energy of E(a) = 5.5 +/-0.5 kcal/mol and a preexponential factor of A = 10(15.7 +/- 0.3) s-1 in toluene. These parameters are consistent with our earlier model for the two-step photofragmentation of aromatic endoperoxides, which assumes a short-lived 1.6-biradical intermediate crossing an activation barrier. The photolysis study of the newly synthesized endoperoxide of anthrabisbenzothiopyran (ABTPO) reveals that photocycloreversion starting from S3(pi-pi*) proceeds with a time constant of tau-2 = 46 +/- 6 ps in dichloromethane (at 22-degrees-C). In this case the activation parameters amount to E(a) = 5.0 +/- 0.6 kcal/mol and A = 10(14.8 +/- 0.3) s-1. The observed activation barrier on the potential energy surface can be a result from resonance effects in the chromophores of the peroxy biradical. The large A factors reflect the importance of internal degrees of freedom in the transition state.

  DOI：

  10.1021/j100156a051
• 作为产物：
  描述：

  15,20-dithiaheptacyclo[14.10.2.02,7.08,28.09,14.019,27.021,26]octacosa-1(27),2,4,6,8(28),9,11,13,16,18,21,23,25-tridecaene 在 氧气 作用下， 以 甲苯 为溶剂， 生成 Anthra(1.9-bc:4,10-b'c')-bis[1]benzothiopyran
  参考文献：
  名称：

  Photochromism Based on the Reversible Reaction of Singlet Oxygen With Aromatic Compounds

  摘要：

  The photolysis of the endoperoxides anthrabisbenzothiopyran (ABTPO) and of benzobisthioxanthene (BTXPO) has been studied in the wavelength range from 333 to 248 nm. At lambda = 248 nm maximum quantum yields ac of 0.09 (ABTPO) and 0.10 (BTXPO) are found for the photocycloreversion reaction. Besides photocycloyeversion a rearrangement reaction takes place with quantum yields Q(R)(248) of 0.013 for ABTPO and 0.018 for BTXPO. Furthermore the selfsensitized photooxygenation of ABT and BTX has been investigated in the concentration range from 10(-5) to 10(-4) M. The mean values of the quantum yield ($) over bar Q(P) were found to be 0.02 (ABT) and 0.05 (BTX). The results indicate that ABT and BTX and their corresponding endoperoxides are components of highly reversible photochromic systems.

  DOI：

  10.1080/10587259408037798