Controlling conformations and physical properties of meso-tetrakis(phenylethynyl)porphyrins by ring fusion: synthesis, properties and structural characterizations.
Controlling conformations and physical properties of meso-tetrakis(phenylethynyl)porphyrins by ring fusion: synthesis, properties and structural characterizations.
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DOI：
10.1039/b412688b
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发表时间：
2004-11
影响因子：
3.2
通讯作者：
Zhen Shen;H. Uno;Y. Shimizu;N. Ono
中科院分区：
文献类型：
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作者：
Zhen Shen;H. Uno;Y. Shimizu;N. Ono
苯炔醛与4，7-二氢-4，7-乙醇基-2H-异吲哚或3，4-二乙基吡咯在二氯甲烷中低温下发生Rothemund缩合反应，得到分别带有双环[2.2.2]辛烯基和八乙基取代基的5，10，15，20-四（苯乙炔基）卟啉。前者经逆Diels-Alder反应定量得到5，10，15，20-四（苯乙炔基）苯并卟啉。用X射线衍射法测定了卟啉周边的不同构象，并研究了它们的氧化还原性质和光谱性质。
The boron trifluoride-catalyzed Rothemund condensations of phenylpropargylaldehyde with 4,7-dihydro-4,7-ethano-2H-isoindole or 3,4-diethylpyrrole in dichloromethane at low temperature give 5,10,15,20-tetrakis(phenylethynyl)porphyrins bearing bicyclo[2.2.2]octadiene and octaethyl substituents, respectively. The former undergoes a retro Diels-Alder reaction to afford 5,10,15,20-tetrakis(phenylethynyl)benzoporphyrin quantitatively. The different conformations of the porphyrin periphery were determined by X-ray diffraction and their redox and spectroscopic properties have been investigated.