1,4-Bis(4-formylphenyl)buta-1(E),3(E)-diene | 170707-94-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,4-Bis(4-formylphenyl)buta-1(E),3(E)-diene
• 英文别名: 4-[(1E,3E)-4-(4-formylphenyl)buta-1,3-dienyl]benzaldehyde
• CAS: 170707-94-5
• 化学式: C₁₈H₁₄O₂
• 分子量: 262.308
• InChiKey: IZLXYXOQHDOTNC-ZPUQHVIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-双(叔丁基)苯甲醛 、 bis(3-hexyl-4-methyl-2-pyrrolyl)methane 、 1,4-Bis(4-formylphenyl)buta-1(E),3(E)-diene 在 四氯苯醌 、 三氯乙酸 作用下， 生成
  参考文献：
  名称：

  Synthesis and Intramolecular Electron- and Energy-Transfer Reactions of Polyyne- or Polyene-Bridged Diporphyrins

  摘要：

  A series of geometrically restricted polyyne- or polyene-bridged diporphyrins 1-7 has been prepared by a convenient, one-pot, double porphyrin cyclization reaction in acceptable yields from the corresponding dialdehydes 1-7CHO. Polyene-bridged diporphyrins 8 and 9 were prepared by a double Horner-Emmons-Wadsworth reaction of formyl-substituted zinc-porphyrin monomer 12 with bis-phosphonate esters 13 and 14, respectively. The diporphyrins 1-9 were transformed into zinc-free-base and zinc-ferric hybrid diporphyrins. Photoinduced intramolecular electron transfer in the zinc-ferric hybrid diporphyrins as well as intramolecular excitation energy transfer in the zinc-free-base hybrid diporphyrins have been studied by picosecond time-resolved fluorescence spectroscopy. Rate constants through the polyene-bridges are larger than those through the polyyne-bridges in both reactions. The distance dependence of the electron-transfer rate was found to be quite small: the attenuation factors were determined to be 0.08 and 0.1 Angstrom(-1) for the polyene- and polyyne-bridged diporphyrins, respectively. The distance dependence of the energy-transfer rate was quite similar to that of the electron transfer and was explained better by the Dexter mechanism rather than by the Forster mechanism. These results clearly demonstrate that the linear pi-conjugated polyyne and polyene spacers enhance through-bond electronic coupling between the donor and acceptor.

  DOI：

  10.1021/jo00127a024
• 作为产物：
  描述：

  4-(5,5-dimethyl-1,3-dioxan-2-yl)benzaldehyde 在 正丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 1,4-Bis(4-formylphenyl)buta-1(E),3(E)-diene
  参考文献：
  名称：

  Synthesis and Intramolecular Electron- and Energy-Transfer Reactions of Polyyne- or Polyene-Bridged Diporphyrins

  摘要：

  A series of geometrically restricted polyyne- or polyene-bridged diporphyrins 1-7 has been prepared by a convenient, one-pot, double porphyrin cyclization reaction in acceptable yields from the corresponding dialdehydes 1-7CHO. Polyene-bridged diporphyrins 8 and 9 were prepared by a double Horner-Emmons-Wadsworth reaction of formyl-substituted zinc-porphyrin monomer 12 with bis-phosphonate esters 13 and 14, respectively. The diporphyrins 1-9 were transformed into zinc-free-base and zinc-ferric hybrid diporphyrins. Photoinduced intramolecular electron transfer in the zinc-ferric hybrid diporphyrins as well as intramolecular excitation energy transfer in the zinc-free-base hybrid diporphyrins have been studied by picosecond time-resolved fluorescence spectroscopy. Rate constants through the polyene-bridges are larger than those through the polyyne-bridges in both reactions. The distance dependence of the electron-transfer rate was found to be quite small: the attenuation factors were determined to be 0.08 and 0.1 Angstrom(-1) for the polyene- and polyyne-bridged diporphyrins, respectively. The distance dependence of the energy-transfer rate was quite similar to that of the electron transfer and was explained better by the Dexter mechanism rather than by the Forster mechanism. These results clearly demonstrate that the linear pi-conjugated polyyne and polyene spacers enhance through-bond electronic coupling between the donor and acceptor.

  DOI：

  10.1021/jo00127a024

文献信息

• Synthesis and Intramolecular Electron- and Energy-Transfer Reactions of Polyyne- or Polyene-Bridged Diporphyrins
  作者：Atsuhiro Osuka、Nobuhiro Tanabe、Shigeki Kawabata、Iwao Yamazaki、Yoshinobu Nishimura

  DOI：10.1021/jo00127a024

  日期：1995.11

  A series of geometrically restricted polyyne- or polyene-bridged diporphyrins 1-7 has been prepared by a convenient, one-pot, double porphyrin cyclization reaction in acceptable yields from the corresponding dialdehydes 1-7CHO. Polyene-bridged diporphyrins 8 and 9 were prepared by a double Horner-Emmons-Wadsworth reaction of formyl-substituted zinc-porphyrin monomer 12 with bis-phosphonate esters 13 and 14, respectively. The diporphyrins 1-9 were transformed into zinc-free-base and zinc-ferric hybrid diporphyrins. Photoinduced intramolecular electron transfer in the zinc-ferric hybrid diporphyrins as well as intramolecular excitation energy transfer in the zinc-free-base hybrid diporphyrins have been studied by picosecond time-resolved fluorescence spectroscopy. Rate constants through the polyene-bridges are larger than those through the polyyne-bridges in both reactions. The distance dependence of the electron-transfer rate was found to be quite small: the attenuation factors were determined to be 0.08 and 0.1 Angstrom(-1) for the polyene- and polyyne-bridged diporphyrins, respectively. The distance dependence of the energy-transfer rate was quite similar to that of the electron transfer and was explained better by the Dexter mechanism rather than by the Forster mechanism. These results clearly demonstrate that the linear pi-conjugated polyyne and polyene spacers enhance through-bond electronic coupling between the donor and acceptor.