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Internal Polarity of Class I and Class II Type Sol–Gel Hybrid Materials Using Aromatic Aminoketones as Solvatochromic Probes for Adsorbed Solvents and the Silicatic Cage

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Abstract

2-Hydroxyethylamino functionalized aromatic amino ketones bearing furyl and thienyl as well as 4-N, N-dimethylaminophenyl moieties have been used as solvatochromic probes when entrapped physically (Class I) and chemically bonded (Class II), respectively, to silicatic sol–gel hybrid materials. Class I hybrid materials have been obtained by encapsulation the dissolved probe during the acidically induced sol–gel procedure using various amounts of methyltrimethoxysilane and tetramethoxysilane as components. Class II xerogels have been synthesized by functionalization of the 2-hydroxyethylamino substituted aryl ketones with 3-isocyanatopropyltriethoxysilane and subsequent sol–gel process with TEOS (tetraethoxysilane). Molecular structures of the hybrid materials have been confirmed by solid-state MAS CP -29Si and -13C NMR spectroscopy.

Significant influences of the polarity of adsorbed solvents and of composition of the sol–gel material on the UV/Vis absorption spectrum of the encapsulated solvatochromic moiety are observed.

Mobility of the entrapped probe and the associated influence of the adsorbed solvent upon the probe in the pores are significantly different for the two different classes of sol–gel materials studied.

Solvatochromism of Class I xerogels shows that opposite effects of primary alcohols as function of alkyl chain length on the interfacial polarity are observed. They are caused by the influence of the internal surface modified with the solvent and origin solvent polarity on the UV/Vis spectrum of the encapsulated probe. Class II xerogels show related effects as observed for the probes studied in well behaved regular solvents.

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  1. Department of Polymer Chemistry, Institute of Chemistry, Chemnitz University of Technology, Strasse der Nationen 62, D-09111, Chemnitz, Germany

    Mohamed El-Sayed, Andreas Seifert & Stefan Spange

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  1. Mohamed El-Sayed
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  2. Andreas Seifert
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  3. Stefan Spange
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Correspondence to Stefan Spange.

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El-Sayed, M., Seifert, A. & Spange, S. Internal Polarity of Class I and Class II Type Sol–Gel Hybrid Materials Using Aromatic Aminoketones as Solvatochromic Probes for Adsorbed Solvents and the Silicatic Cage. J Sol-Gel Sci Technol 34, 77–94 (2005). https://doi.org/10.1007/s10971-005-1265-9

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