5-(3-iodophenyl)dipyrromethane | 221247-12-7

• 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: 5-(3-iodophenyl)dipyrromethane
• 英文别名: 2,2 inverted exclamation mark-[(3-Iodophenyl)methylene]bis(1H-pyrrole)；2-[(3-iodophenyl)-(1H-pyrrol-2-yl)methyl]-1H-pyrrole
• CAS: 221247-12-7
• 化学式: C₁₅H₁₃IN₂
• 分子量: 348.186
• InChiKey: SXKCEJLYQXYNHX-UHFFFAOYSA-N

物化性质

• 熔点：
  102-103 °C
• 沸点：
  480.1±45.0 °C(Predicted)
• 密度：
  1.647±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  5-(3-iodophenyl)dipyrromethane 、 3-(S-acetylthiomethyl)benzaldehyde 在 三氟化硼乙醚 、 氯化铵 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙腈 为溶剂， 反应 5.5h， 以3%的产率得到10,20-bis[3-(S-acetylthiomethyl)phenyl]-5,15-bis(3-iodophenyl)porphyrin
  参考文献：
  名称：

  Thiol-Derivatized Porphyrins for Attachment to Electroactive Surfaces

  摘要：

  The attachment of porphyrin monomers and multiporphyrin arrays in controlled architectures on electroactive surfaces opens many opportunities for electrochemical studies. Toward this goal, we have developed routes for the preparation of thiol-derivatized porphyrin monomers and porphyrin building blocks that require minimal or no handling of free thiols. Routes to S-protected p-thiobenzaldehydes and m-(thiomethyl)benzaldehydes have been developed. TRIO sets of mesosubstituted porphyrins with variation in electrochemical potentials have been prepared for vertical or horizontal orientation with respect to the electroactive surface. In one set, each porphyrin bears one S-protected p-thiophenyl unit and substituents at the three remaining meso-positions. In the other set each porphyrin possesses four S-protected m-(thiomethyl)phenyl units. Tuning the electrochemical potential in the former set has been achieved by variation of the meso substituents (mesityl, 2,4,6-trimethoxyphenyl, n-pentyl, pentafluorophenyl) and in the latter set by variation of the central metal (Zn, Cu, Co, Ag). Six thiol protecting groups ES-cyano, S-(N-ethylcarbamoyl), S-acetyl, S-(9-anthrylmethyl), S-(2,4-dinitrophenyl), S-pivaloyl] have been found to be compatible with porphyrin formation and metalation with zinc. The S-cyano, S-(N-ethylcarbamoyl), and S-acetyl groups undergo in situ cleavage and/or binding on a gold surface. Of these three, only the S-acetyl protecting group is compatible with the Pd-mediated iodo-ethyne coupling conditions for the preparation of multiporphyrin arrays. Three trans-substituted porphyrin building blocks have been prepared for the synthesis of multiporphyrin arrays that can be attached to an electroactive surface. One porphyrin has two mesityl, one p-iodophenyl, and one p-(S-acetylthio)phenyl substituent for vertical positioning, and two porphyrins each have two m-iodophenyl and two S-protected m-(thiomethyl)phenyl substituents for horizontal positioning. Altogether, 16 free base and 16 metalloporphyrins have been prepared. This work establishes the foundation for preparing diverse thiol-derivatized porphyrin monomers and building blocks.

  DOI：

  10.1021/jo9911084
• 作为产物：
  描述：

  吡咯 、 3-碘苯甲醛 在 三氟乙酸 作用下， 反应 0.08h， 以40%的产率得到5-(3-iodophenyl)dipyrromethane
  参考文献：
  名称：

  Refined Synthesis of 5-Substituted Dipyrromethanes

  摘要：

  DOI：

  10.1021/jo982015+

文献信息

• A 1,3-Phenylene-Bridged Hexameric Porphyrin Wheel and Efficient Excitation Energy Transfer along the Wheel
  作者：Hua-Wei Jiang、Sujin Ham、Naoki Aratani、Dongho Kim、Atsuhiro Osuka

  DOI：10.1002/chem.201302361

  日期：2013.9.27

  A 1,3‐phenylene‐bridged hexameric ZnII porphyrin wheel was synthesized by a Suzuki–Miyaura coupling reaction through a one‐pot or a stepwise route. The hexameric wheel structure was revealed by using X‐ray diffraction analysis. The porphyrin wheel exhibits a split Soret band due to effective exciton coupling and displays efficient excitation energy transfer along the wheel. Measurements of fluorescence

  Suzuki-Miyaura偶联反应通过一锅法或分步法合成了一个1,3-亚苯基桥联的六价Zn II卟啉轮。通过使用X射线衍射分析揭示了六聚体轮的结构。卟啉轮由于有效的激子耦合而显示出分裂的索雷特带，并沿该轮显示出有效的激发能传递。荧光各向异性衰减和泵浦功率相关衰减的测量结果表明，沿车轮以1.4 ps的速率跳跃的快速激发能。
• Thiol-Derivatized Porphyrins for Attachment to Electroactive Surfaces
  作者：Daniel T. Gryko、Christian Clausen、Jonathan S. Lindsey

  DOI：10.1021/jo9911084

  日期：1999.11.1

  The attachment of porphyrin monomers and multiporphyrin arrays in controlled architectures on electroactive surfaces opens many opportunities for electrochemical studies. Toward this goal, we have developed routes for the preparation of thiol-derivatized porphyrin monomers and porphyrin building blocks that require minimal or no handling of free thiols. Routes to S-protected p-thiobenzaldehydes and m-(thiomethyl)benzaldehydes have been developed. TRIO sets of mesosubstituted porphyrins with variation in electrochemical potentials have been prepared for vertical or horizontal orientation with respect to the electroactive surface. In one set, each porphyrin bears one S-protected p-thiophenyl unit and substituents at the three remaining meso-positions. In the other set each porphyrin possesses four S-protected m-(thiomethyl)phenyl units. Tuning the electrochemical potential in the former set has been achieved by variation of the meso substituents (mesityl, 2,4,6-trimethoxyphenyl, n-pentyl, pentafluorophenyl) and in the latter set by variation of the central metal (Zn, Cu, Co, Ag). Six thiol protecting groups ES-cyano, S-(N-ethylcarbamoyl), S-acetyl, S-(9-anthrylmethyl), S-(2,4-dinitrophenyl), S-pivaloyl] have been found to be compatible with porphyrin formation and metalation with zinc. The S-cyano, S-(N-ethylcarbamoyl), and S-acetyl groups undergo in situ cleavage and/or binding on a gold surface. Of these three, only the S-acetyl protecting group is compatible with the Pd-mediated iodo-ethyne coupling conditions for the preparation of multiporphyrin arrays. Three trans-substituted porphyrin building blocks have been prepared for the synthesis of multiporphyrin arrays that can be attached to an electroactive surface. One porphyrin has two mesityl, one p-iodophenyl, and one p-(S-acetylthio)phenyl substituent for vertical positioning, and two porphyrins each have two m-iodophenyl and two S-protected m-(thiomethyl)phenyl substituents for horizontal positioning. Altogether, 16 free base and 16 metalloporphyrins have been prepared. This work establishes the foundation for preparing diverse thiol-derivatized porphyrin monomers and building blocks.
• Refined Synthesis of 5-Substituted Dipyrromethanes
  作者：Benjamin J. Littler、Mark A. Miller、Chen-Hsiung Hung、Richard W. Wagner、Donal F. O'Shea、Paul D. Boyle、Jonathan S. Lindsey

  DOI：10.1021/jo982015+

  日期：1999.2.1