[5-Bromo-4-(diethoxy-phosphorylmethyl)-2-hexyloxy-benzyl]-phosphonic acid diethyl ester | 610322-34-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: [5-Bromo-4-(diethoxy-phosphorylmethyl)-2-hexyloxy-benzyl]-phosphonic acid diethyl ester
• CAS: 610322-34-4
• 化学式: C₂₂H₃₉BrO₇P₂
• 分子量: 557.399
• InChiKey: LQHNFYGYTKKIBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.94
• 重原子数：
  32.0
• 可旋转键数：
  18.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-Bromo-2-hexyloxy-4-methyl-benzaldehyde 、 [5-Bromo-4-(diethoxy-phosphorylmethyl)-2-hexyloxy-benzyl]-phosphonic acid diethyl ester 在 sodium hydride 作用下， 以 乙二醇二甲醚 为溶剂， 生成 1-bromo-2,5-bis[(E)-2-(5-bromo-2-hexoxy-4-methylphenyl)ethenyl]-4-hexoxybenzene
  参考文献：
  名称：

  Excited States of Bromine-Substituted Distyrylbenzenes:  Models for Conjugated Polymer Emission

  摘要：

  Model 1,4-bis(styryl)benzene derivatives la,b related to poly(2-bromo-5-methoxy-1,4-phenylenevinylene) were synthesized to probe the effect of bromination on excited-state behavior of conjugated phenylenevinylene analogues. They showed solution absorption maxima at about 385 nm, without evidence of excimer formation up to 100 muM. Their fluorescence spectra showed overlapping bands at 435 and 460 run, with quantum yields in tetrahydrofuran of 0.16 and 0.21 for la and 1b, respectively. Excited-state transients were monitored by time-resolved laser flash spectroscopy at room temperature. The triplet states were characterized by absorption maxima at about 520-530 nm with lifetimes of about 0.6 mus, much longer than would be observed for prompt fluorescence states. The quantum yields of singlet to triplet-state intersystem crossing were determined to be 0.45 and 0.28 for la and 1b, respectively. The acceleration of triplet transient decay rates under increased oxygen pressure according to the Stern-Volmer law further supports the triplet-state assignments. The relatively high yields of intersystem crossing and low yields of fluorescence are attributed to a bromine-modulated heavy atom effect that enhances intersystem crossing between excited singlet and triplet states.

  DOI：

  10.1021/jp030041s
• 作为产物：
  描述：

  1-Bromo-2,5-dimethyl-4-hexyloxy-benzene 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 生成 [5-Bromo-4-(diethoxy-phosphorylmethyl)-2-hexyloxy-benzyl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  Excited States of Bromine-Substituted Distyrylbenzenes:  Models for Conjugated Polymer Emission

  摘要：

  Model 1,4-bis(styryl)benzene derivatives la,b related to poly(2-bromo-5-methoxy-1,4-phenylenevinylene) were synthesized to probe the effect of bromination on excited-state behavior of conjugated phenylenevinylene analogues. They showed solution absorption maxima at about 385 nm, without evidence of excimer formation up to 100 muM. Their fluorescence spectra showed overlapping bands at 435 and 460 run, with quantum yields in tetrahydrofuran of 0.16 and 0.21 for la and 1b, respectively. Excited-state transients were monitored by time-resolved laser flash spectroscopy at room temperature. The triplet states were characterized by absorption maxima at about 520-530 nm with lifetimes of about 0.6 mus, much longer than would be observed for prompt fluorescence states. The quantum yields of singlet to triplet-state intersystem crossing were determined to be 0.45 and 0.28 for la and 1b, respectively. The acceleration of triplet transient decay rates under increased oxygen pressure according to the Stern-Volmer law further supports the triplet-state assignments. The relatively high yields of intersystem crossing and low yields of fluorescence are attributed to a bromine-modulated heavy atom effect that enhances intersystem crossing between excited singlet and triplet states.

  DOI：

  10.1021/jp030041s