Issue 23, 2004
From the journal:

Organic & Biomolecular Chemistry

Controlling conformations and physical properties of meso-tetrakis(phenylethynyl)porphyrins by ring fusion: synthesis, properties and structural characterizations

Zhen Shen,†a   Hidemitsu Uno,*b   Yusuke Shimizua  and  Noboru Ono*a  

* Corresponding authors

a Department of Chemistry, Faculty of Science, Ehime University, 2-5 Bunkyo-cho, Matsuyama, Japan
E-mail: ononbr@dpc.ehime-u.ac.jp
Fax: +81 899279590
Tel: +81 899279610

b Division of Synthesis and Analysis, Department of Molecular Science, Integrated Center for Sciences, Ehime University, 2-5 Bunkyo-cho, Matsuyama, Japan
E-mail: uno@dpc.ehime-u.ac.jp
Fax: +81 899279670
Tel: +81 899279660

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.

Graphical abstract: Controlling conformations and physical properties of meso-tetrakis(phenylethynyl)porphyrins by ring fusion: synthesis, properties and structural characterizations

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Article information

DOI
https://doi.org/10.1039/B412688B
Article type
Paper
Submitted
17 Aug 2004
Accepted
30 Sep 2004
First published
05 Nov 2004

Org. Biomol. Chem., 2004,2, 3442-3447

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Controlling conformations and physical properties of meso-tetrakis(phenylethynyl)porphyrins by ring fusion: synthesis, properties and structural characterizations

Z. Shen, H. Uno, Y. Shimizu and N. Ono, Org. Biomol. Chem., 2004, 2, 3442 DOI: 10.1039/B412688B

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