Issue 39, 2010

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 alkoxysilylgroups

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

Supplementary files

Article information

Article type
Paper
Submitted
05 May 2010
Accepted
08 Jul 2010
First published
03 Sep 2010

Dalton Trans., 2010,39, 9421-9426

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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