Preparation and characterization of porphyrin chromophores immobilized on micro-silica gel beads

Matsumoto, Jin; Matsumoto, Tomoko; Senda, Yoshiya; Shiragami, Tsutomu; Yasuda, Masahide

doi:10.1016/j.jphotochem.2007.12.010

Cited by 29 publications

(9 citation statements)

References 28 publications

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“…Moreover, when Sb(tpp) was tightly fixed on SiO 2 through covalent bonds, no photoinactivation occurred [19].…”

Section: Mechanism For Photoinactivation Using M(tpp)/siomentioning

confidence: 99%

Silica Gel–Supported P-, Ge-, and Sb-Porphyrins for Visible Light Inactivation of Bacteria

Yasuda¹,

Matsumoto²

2018

Visible-Light Photocatalysis of Carbon-Based Materials

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This chapter describes the photocatalysis action of (dihydroxo)tetraphenyl¬porphyrinato complexes of high valent P (V), Ge (IV), and Sb (V) (P(tpp), Ge(tpp), and Sb(tpp)). These chromophores were fixed onto silica gel (SiO2) through Coulombic forces and hydrogen bonding between axial hydroxo ligands and silanol groups to produce M(tpp)/SiO2 (M = P, Ge, and Sb) composites. M(tpp)/SiO2 were applied to the photo-inactivation of Escherichia coli and Legionella pneumophila. Moreover, M(tpp)/SiO2 was subjected to practical experiments for the photoinactivation of L. pneumophila naturally occurring in a cooling tower and a public fountain. It is noteworthy that 80 g of Sb(tpp)/SiO2 catalyst, containing 40 mg of Sb(tpp) maintained a concentration of Legionella species below 100 CFU/100 mL for 120 days in 13 m3 of water in a fountain under sunlight exposure. The photoinactivation proceeded through the liberation of M(tpp) from SiO2, adsorption of M(tpp) inside bacteria, and generation of reactive oxygen species, such as singlet oxygen, under visible light irradiation, thus resulting in bacteria apoptosis. Based on these results, we developed water-soluble porphyrins by modification of P and Sb porphyrin axial ligands to alkyloxo, alkylethylenedioxy, and alkylpyridinium groups. These water-soluble porphyrins were applied to the photodynamic inactivation of E. coli and Saccharomyces cerevisiae.

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“…Moreover, when Sb(tpp) was tightly fixed on SiO 2 through covalent bonds, no photoinactivation occurred [19].…”

Section: Mechanism For Photoinactivation Using M(tpp)/siomentioning

confidence: 99%

Silica Gel–Supported P-, Ge-, and Sb-Porphyrins for Visible Light Inactivation of Bacteria

Yasuda¹,

Matsumoto²

2018

Visible-Light Photocatalysis of Carbon-Based Materials

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“…As pH-indicator, meso-tetra(p-cyanophenyl)porphyrin (H 2 tcp) was prepared according to the reported method as follows [23]. BF 3 ·OEt 2 (0.1 mL) were added to CHCl 3 solution (500 mL) of p-cyanobenzaldehyde (1048 mg; 8.0 mmol).…”

Section: Preparation Of Meso-tetra(p-cyanophenyl)porphyrinmentioning

confidence: 99%

Solid-Phase Aromatic Nitration with Mg(NO<sub>3</sub>)<sub>2</sub> on Silica Gel

Matsumoto¹,

Yamauchi²,

Ishikawa³

et al. 2017

IJOC

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Nitroaromatics are usually prepared using a mixed acid of nitric acid with strong acids. However, the use of strong acids caused dangerous work-up and the disposal of large amounts of acid-waste. Therefore, much effort has been made on the improvement of nitration process without strong acids. We examined solid-phase aromatic nitration with Mg(NO 3 ) 2 on silica gel in order to establish the nitration process without strong acids. The nitration of 1,2-and 1,3-, 1,4-dimethoxybenzenes and 4-methylanisole with Mg(NO 3 ) 2 proceeded by heating on silica gel at 150˚C for 4 -5 h to produce the nitroaromatics. The nitration of 1,3,5-trimethoxybenzene produced the nitrated dimer, 2,4,6,2', 4',6'-hexamethoxy-3-nitrobiphenyl, which was not isolated in other solid-phase nitration. In the cases of naphthalene derivatives, the α-nitrated compounds were obtained. In the cases of p-cresol and 2-naphthol, the esterification occurred at the hydroxyl group to give 4-tolyl nitrate and 2-naphthyl nitrate, respectively. It is synthetic interest to note that nitrate esters were isolated in solid phase. Thus Mg(NO 3 ) 2 -SiO 2 composite was mild reagent for solid-phase nitration. Acidity of Mg(NO 3 ) 2 -SiO 2 composite was determined to be pH 0.96 by the measurement of absorption spectra on a micro spectrophotometer using meso-tetra(p-cyanophenyl)porphyrin as a pH-indicator. Mg(NO 3 ) 2 -SiO 2 composite made acidic conditions. Therefore, it was suggested that Mg(NO 3 ) 2 reacted with proton on silica gel to form the 2 NO + . Thus, electron-rich aromatic hydrocarbons led the efficient nitration through electrophilic attack of 2 NO + . After the nitration, acidic Mg(NO 3 ) 2 -SiO 2 composite could be turned into neutrality by exposing wet conditions and disposed safely since the composite did not involve harmful elements. Thus the solid-phase nitration using Mg(NO 3 ) 2 -SiO 2 composite will provide safety and environmentally conscious chemical process.

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“…13 The distribution of the fluorescence intensity of 2a on the lines from the center to the surface at the cross section at a given depth from the uppermost P 1a was analyzed by CLSM. In the case of 1a (Method A), the intense peak with ca.…”

Section: Distribution Of 2a In 1amentioning

confidence: 99%

Quantitative Analysis for a Color-Change of Humidity Indicator by Microscopic Absorption Spectrometry

et al. 2011

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Preparation and characterization of porphyrin chromophores immobilized on micro-silica gel beads

Cited by 29 publications

References 28 publications

Silica Gel–Supported P-, Ge-, and Sb-Porphyrins for Visible Light Inactivation of Bacteria

Silica Gel–Supported P-, Ge-, and Sb-Porphyrins for Visible Light Inactivation of Bacteria

Solid-Phase Aromatic Nitration with Mg(NO<sub>3</sub>)<sub>2</sub> on Silica Gel

Quantitative Analysis for a Color-Change of Humidity Indicator by Microscopic Absorption Spectrometry

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Preparation and characterization of porphyrin chromophores immobilized on micro-silica gel beads

Cited by 29 publications

References 28 publications

Silica Gel–Supported P-, Ge-, and Sb-Porphyrins for Visible Light Inactivation of Bacteria

Silica Gel–Supported P-, Ge-, and Sb-Porphyrins for Visible Light Inactivation of Bacteria

Solid-Phase Aromatic Nitration with Mg(NO&lt;sub&gt;3&lt;/sub&gt;)&lt;sub&gt;2&lt;/sub&gt; on Silica Gel

Quantitative Analysis for a Color-Change of Humidity Indicator by Microscopic Absorption Spectrometry

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Solid-Phase Aromatic Nitration with Mg(NO<sub>3</sub>)<sub>2</sub> on Silica Gel