We study the influence of the nature and ring positioning of amino, hydroxy, and carboxy substituent groups on the fluorescence and some other physicochemical properties of free (H2TPP) and metalled tetraphenylporphyrins (MTPP). Furthermore, we have studied the feasibility of covalently bonding TPP species on the surface of the pores of a silica matrix prepared by the sol-gel method through the bridging action of either one of the following functionalized alkoxides: 3-isocyanatopropyltriethoxysilane, (IPTES) or 3-aminopropyltriethoxysilane (APTES). Importantly, the red fluorescence observed in free porphyrin solutions is preserved even after the macrocyclic species is covalently bound to the silica matrix. The formation of a chemical union between the porphyrin substituting groups and the organic groups of the IPTES or APTES alkoxides render the H2P-f precursory species has been proved successful by FTIR spectroscopy; likewise, the bond between Si-OH groups on the silica surface and the H2P-f has been made evident. The best results, in terms of fluorescence preservation, are obtained by using a TPP substituted with -NH2groups in the ortho position of the phenyl rings, i.e. H2T(o-NH2)PP. A comparative fluorescence study of xerogels physically grafted or covalently bound with the latter TPP species confirm that, in the first case, the interaction of the molecule with the silanol groups of the silica surface of the gel inhibits fluorescence; while in the second case fluorescence is preserved. © 2008 Elsevier B.V. All rights reserved.
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