title: Controlling conformations and physical properties of meso-tetrakis(phenylethynyl)porphyrins by ring fusion: synthesis, properties and structural characterizations.
abstract: 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.
authors.affiliation: Department of Chemistry, Faculty of Science, Ehime University, Matsuyama, Japan.
authors.forename: Zhen
authors.initials: Z
authors.lastname: Shen
authors.forename: Hidemitsu
authors.initials: H
authors.lastname: Uno
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Shimizu
authors.forename: Noboru
authors.initials: N
authors.lastname: Ono