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Authors
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Hofmann, K. ; Kahle, I. ; Simon, F. ; Spange, St.
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Title
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Chromo- and fluorophoric water-soluble polymers and silica particles by nucleophilic substitution reaction using poly(vinyl amine)
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Date
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10.08.2010
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Number
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23742
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Abstract
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Novel chromophoric and fluorescent carbonitrile-functionalized poly(vinyl amine) (PVAm) and PVAm/silica particles were synthesized by means of nucleophilic aromatic substitution of 8-oxo-8H-acenaphtho[1,2-b]pyrrol-9-carbonitrile (1) with PVAm in water. The water solubility of 1 has been mediated by 2,6-O-ß-dimethylcyclodextrin or by pre-adsorption onto silica particles. Furthermore, 1 was converted with isopropylamine into the model compound 1-M. All new compounds were characterized by NMR, FTIR, UVvis and fluorescence spectroscopy. The solvent-dependent UVvis absorption and fluorescence emission band positions of the model compound and the carbonitrile-functionalized PVAm were studied and interpreted using the empirical KamletTaft solvent parameters p* (dipolarity/polarizability), a (hydrogen-bond donating capacity) and ß (hydrogen-accepting ability) in terms of the linear solvation energy relationship (LSER). The solvent-independent regression coefficients a, b and s were determined using multiple linear correlation analysis. It is shown, that the chains of the polymer have a significant influence on the solvatochromic behavior of 1-P. The structure of the carbonitrile 1-Si bound to polymer-modified silica particles was studied by means of X-ray photoelectron spectroscopy (XPS) and BrunauerEmmettTeller (BET) measurements. Fluorescent silica particles were obtained as shown by fluorescence spectroscopy with a diffuse reflectance technique.
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Publisher
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Beilstein Journal of Organic Chemistry
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Wikidata
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Citation
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Beilstein Journal of Organic Chemistry 6 (2010)
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DOI
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https://doi.org/10.3762/bjoc.6.79
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