3-ethoxycarbonyl-4-(3-iodophenyl)pyrrole | 295800-87-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-ethoxycarbonyl-4-(3-iodophenyl)pyrrole
• CAS: 295800-87-2
• 化学式: C₁₃H₁₂INO₂
• 分子量: 341.148
• InChiKey: HOMLYDFFKODWIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  42.09
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-ethoxycarbonyl-4-(3-iodophenyl)pyrrole 在 盐酸 、 sodium hydroxide 、 三氟化硼乙醚 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 氯仿 、 乙二醇 为溶剂， 反应 22.0h， 生成 5,10,15-trimesityl-2-(4-iodophenyl)porphyrin
  参考文献：
  名称：

  Structural Control of Photoinduced Energy Transfer between Adjacent and Distant Sites in Multiporphyrin Arrays

  摘要：

  A family of diphenylethyne-linked porphyrin dimers and trimers has been prepared via a building block approach for studies of energy-transfer processes. The dimers contain Mg and Zn porphyrins (MgZnU); the trimers contain an additional free base porphyrin (MgZnFbU). In both the dimers and trimers, sites of attachment to the Mg porphyrin (at the meso- or beta-position) and diphenylethyne linker (at the para- or meta-positions) were varied, producing four Mg porphyrin-Zn porphyrin arrangements with the following linker configurations: meso-p/p-meso, meso-m/p-meso, beta-p/p-meso, and beta-m/p-meso. All four trimers employ a meso-p/p-meso Zn porphyrin-Fb porphyrin connection. The ground- and excited-state properties of the porphyrin dimers and trimers have been examined using static and time-resolved optical techniques. The rate of energy transfer from the photoexcited Zn porphyrin to the Mg porphyrin decreases according to the following trend: meso-p/p-meso (9 ps)(-1) > beta-p/p-meso (14 ps)(-1) > meso-m/p-meso (19 ps)(-1) > beta-m/p-meso (27 ps)(-1) In each compound, energy transfer between adjacent porphyrins occurs through a linker-mediated through-bond process. The rate of energy transfer between Zn and Fb porphyrins is constant in each trimer ((24 ps)(-1)). Energy transfer from the photoexcited Zn porphyrin branches to the adjacent Fb and Mg porphyrins, with nearly one-half to three-fourths proceeding to the Mg porphyrin (depending on the linker). Energy transfer from the excited Mg porphyrin to the nonadjacent Fb porphyrin occurs more slowly, with a rate that follows the same trend in linker architecture and porphyrin connection site: meso-p/p-meso (173 ps)(-1) > beta-p/p-meso (225 ps)(-1) > meso-m/p-meso (320 ps)(-1) > beta-m/p-meso (385 ps)(-1). The rate of transfer between nonadjacent Mg and Fb porphyrins does not change significantly with temperature, indicating a superexchange mechanism utilizing orbitals/states on the intervening Zn porphyrin. Energy transfer between nonadjacent sites may prove useful in directing energy flow in multiporphyrin arrays and related molecular photonic devices.

  DOI：

  10.1021/ja001031x
• 作为产物：
  描述：

  3-碘苯甲醛 在 哌啶 、 吡啶 、 sodium hydride 、 二甲基亚砜 作用下， 以 乙醚 为溶剂， 反应 7.5h， 生成 3-ethoxycarbonyl-4-(3-iodophenyl)pyrrole
  参考文献：
  名称：

  Structural Control of Photoinduced Energy Transfer between Adjacent and Distant Sites in Multiporphyrin Arrays

  摘要：

  A family of diphenylethyne-linked porphyrin dimers and trimers has been prepared via a building block approach for studies of energy-transfer processes. The dimers contain Mg and Zn porphyrins (MgZnU); the trimers contain an additional free base porphyrin (MgZnFbU). In both the dimers and trimers, sites of attachment to the Mg porphyrin (at the meso- or beta-position) and diphenylethyne linker (at the para- or meta-positions) were varied, producing four Mg porphyrin-Zn porphyrin arrangements with the following linker configurations: meso-p/p-meso, meso-m/p-meso, beta-p/p-meso, and beta-m/p-meso. All four trimers employ a meso-p/p-meso Zn porphyrin-Fb porphyrin connection. The ground- and excited-state properties of the porphyrin dimers and trimers have been examined using static and time-resolved optical techniques. The rate of energy transfer from the photoexcited Zn porphyrin to the Mg porphyrin decreases according to the following trend: meso-p/p-meso (9 ps)(-1) > beta-p/p-meso (14 ps)(-1) > meso-m/p-meso (19 ps)(-1) > beta-m/p-meso (27 ps)(-1) In each compound, energy transfer between adjacent porphyrins occurs through a linker-mediated through-bond process. The rate of energy transfer between Zn and Fb porphyrins is constant in each trimer ((24 ps)(-1)). Energy transfer from the photoexcited Zn porphyrin branches to the adjacent Fb and Mg porphyrins, with nearly one-half to three-fourths proceeding to the Mg porphyrin (depending on the linker). Energy transfer from the excited Mg porphyrin to the nonadjacent Fb porphyrin occurs more slowly, with a rate that follows the same trend in linker architecture and porphyrin connection site: meso-p/p-meso (173 ps)(-1) > beta-p/p-meso (225 ps)(-1) > meso-m/p-meso (320 ps)(-1) > beta-m/p-meso (385 ps)(-1). The rate of transfer between nonadjacent Mg and Fb porphyrins does not change significantly with temperature, indicating a superexchange mechanism utilizing orbitals/states on the intervening Zn porphyrin. Energy transfer between nonadjacent sites may prove useful in directing energy flow in multiporphyrin arrays and related molecular photonic devices.

  DOI：

  10.1021/ja001031x