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Issue 39, 2010
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Synthesis and properties of 5,10,15,20-tetrakis[4-(alkoxysilyl)phenyl]porphyrins: an application of selective deprotection of benzaldehyde diethyl acetals in the presence of alkoxysilyl groups

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Abstract

Selective deprotection of 4-(alkoxysilyl)benzaldehyde diethyl acetals 1a1c in the two-solvent system of hydrochloric acid and chloroform gave 4-(alkoxysilyl)benzaldehydes 2a–2c in good yields. Under these conditions, undesired hydrolysis of the alkoxysilyl group was minimized. The reaction of benzaldehydes 2a and 2b with pyrrole in the presence of boron trifluoride diethyl etherate led to 5,10,15,20-tetrakis[4-(alkoxysilyl)phenyl]porphyrins 3a and 3b. The X-ray structural analysis showed that 3b has a planar porphyrin ring and shows typical structural features of porphyrin rings. Hydrolysis–condensation of 3a in the presence of a surfactant afforded a porphyrinsilica hybrid (PSH) as insoluble brown powder. The PSH was found to be amorphous and to consist of aggregated nonspherical micrometre-sized particles with rough surfaces. The PSH has mesopores, and the specific surface area is 330 m2 g−1 which increases to 810 m2 g−1 upon calcination.

Graphical abstract: Synthesis and properties of 5,10,15,20-tetrakis[4-(alkoxysilyl)phenyl]porphyrins: an application of selective deprotection of benzaldehyde diethyl acetals in the presence of alkoxysilyl groups

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Publication details

The article was received on 05 May 2010, accepted on 08 Jul 2010 and first published on 03 Sep 2010


Article type: Paper
DOI: 10.1039/C0DT00427H
Citation: Dalton Trans., 2010,39, 9421-9426
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    Synthesis and properties of 5,10,15,20-tetrakis[4-(alkoxysilyl)phenyl]porphyrins: an application of selective deprotection of benzaldehyde diethyl acetals in the presence of alkoxysilyl groups

    S. Ishida, M. Ito, H. Horiuchi, H. Hiratsuka, S. Shiraishi and S. Kyushin, Dalton Trans., 2010, 39, 9421
    DOI: 10.1039/C0DT00427H

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