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5,10,15,20-tetrakis(4-carboxyphenyl)porphyrin Covalently Bound to Nano-silica Surface: Preparation, Characterization and Chemosensor Application to Detect TNT

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Abstract

Mesoporous silica is a very suitable carrier for preparation of sensors for detection of explosive compounds with high selectivity and rapid responsiveness by incorporating chemical sensing units into silica films. Three types of porphyrin-doped silica with mesoporous and amorphous structures were prepared. 5,10,15,20-tetrakis(4-carboxyphenyl)porphyrin was synthesized in two steps starting from p-methoxycarbonylbenzaldehyde. 5,10,15,20-tetrakis(4-(methoxycarbonyl) phenyl) porphyrin (1a) was hydrolyzed with trifluoroacetic acid (TFA) to produce 5,10,15,20-tetrakis(4-carboxyphenyl) porphyrin (1b) in 100 % yield. Different kinds of silica such as Hexagonal SBA-15 (SBA-15(Hex)), Spherical SBA-15 (SBA-15(Sp)) and commercial SiO2(SiO2(Ald)) were functionalized using 3-aminopropyltriethoxysilane (3-APS). Porphyrin with carboxylic substituent was reacted with N-hydroxysuccinimide (NHS) and N, N'-dicyclohexylcarbodiimide (DCC) to produce 5-[4-(succinimidyloxycarbonyl)phenyl]-10,15,20-tri(4-carboxyphenyl)porphyrin (H 2 SPTCPP) and grafted to the surface of modified silica to obtain porphyrin-doped silica materials. Results suggest that the synthetic route achieves a high content of porphyrin incorporated to the support. The percentage of porphyrin incorporated to the support, which is higher in the case of SBA-15(Sp) with higher surface area and containing a larger number of silanol groups available for grafting, is directly related to the catalytic activity. Time-dependent fluorescence quenching of porphyrin-doped silica films was studied for three different mesostructures and it showed a rapid quenching upon exposure to a trace amount of TNT vapor due to the high surface area and highly ordered structure of silica.

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Authors and Affiliations

  1. Department of Chemistry, University of Zanjan, P. O. Box 45195-313, Zanjan, Iran

    Ebrahim Ahmadi, Ali Ramazani, Zahra Hamdi & Asemeh Mashhadi-Malekzadeh

  2. Department of Chemistry, Institute for Advanced Studies in Basic Sciences(IASBS), Gava zang, P. O. Box 45195-1159, Zanjan, Iran

    Zahra Mohamadnia

Authors
  1. Ebrahim Ahmadi
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  2. Ali Ramazani
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  3. Zahra Hamdi
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  4. Asemeh Mashhadi-Malekzadeh
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  5. Zahra Mohamadnia
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Correspondence to Ebrahim Ahmadi.

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Ahmadi, E., Ramazani, A., Hamdi, Z. et al. 5,10,15,20-tetrakis(4-carboxyphenyl)porphyrin Covalently Bound to Nano-silica Surface: Preparation, Characterization and Chemosensor Application to Detect TNT. Silicon 7, 323–332 (2015). https://doi.org/10.1007/s12633-015-9304-9

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  • DOI: https://doi.org/10.1007/s12633-015-9304-9

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