Clickable Periodic Mesoporous Organosilicas: Synthesis, Click Reactions, and Adsorption of Antibiotics

Abstract

Pharmaceutical antibiotics are not easily removed from water by conventional water-treatment technologies and have been recognized as new emerging pollutants. Herein, we report the synthesis of clickable azido periodic mesoporous organosilicas (PMOs) and their use as adsorbents for the adsorption of antibiotics. Ethane-bridged PMOs, functionalized with azido groups at different densities, were synthesized by the co-condensation of 1,2-bis(trimethoxysilyl)ethane (BTME) and 3-azidopropyltrimethoxysilane (AzPTMS), in the presence of nonionic-surfactant triblock-copolymer P123, in an acidic medium. Four different alkynes were conjugated to azide-terminated PMOs by means of an efficient click reaction. The clicked PMOs showed improved adsorption capacity (241 μg g(-1)) for antibiotics (ciprofloxacin hydrochloride) compared with azido-functionalized PMOs because of the enhanced π-π stacking interactions. These results indicate that click reactions can introduce multifunctional groups onto PMOs, thus demonstrating the great potential of PMOs for environmental applications.

Elucidating the electrostatic interaction of sulfonic acid functionalized SBA-15 for ciprofloxain adsorption

“…4). The increase of adsorption capacity of SH-SBA-15 compared with SBA-15 could be ascribed to the increase of the hydrophobicity of SH-SBA-15, where increasing the hydrophobicity of mesoporous silicas adsorbents would improve the adsorption property as it has been reported by different researchers [9,10,23]. However, it is irregular for SO 3 H-SBA-15, where the most hydrophilic adsorbent exhibits the best adsorption property.…”

“…Accordingly, organofunctionalized mesoporous silicas, which is pore size fit for antibiotics molecules and easy functionalization, have been very promising in adsorptive removal of water contaminants [17][18][19], such as heavy metal pollutants [20], toxic anions [21] and a variety of organic pollutants [22][23][24], via electrostatic interaction [20,21], hydrogen bonding [25], -interaction [9,10,26], hydrophilic/hydrophobic interactions [27], covalent bond formation [28] interaction and adverse hydrophilic interaction for antibiotics adsorption. Thus, it is desirable to systematically and comparably investigate the interaction between mesoporous adsorbents and antibiotics adsorbates, which would be benefit for developing effective adsorbents.…”

“…Due to the inefficiency of conventional biological wastewater treatments for pharmaceutical antibiotics pollutants [1][2][3], deemed to be emerging pollutants, which have been detected in surface water, groundwater, and even drinking water and might cause potential risks of environmental toxicity and impact the structure and activity of environmental microorganism, extensive research interests have been focused on developing other antibiotics pollutant treating technologies, such as photocatalysis [4,5], ozonation [6], chemical oxidation [7], electrochemical advanced oxidation [8] and adsorption [9,10], for the removal of antibiotics pollutants recently. Among them, the first four treating technologies are effective for pharmaceutical waste water polluted with high antibiotics concentration, but challenged by surface water, ground water and drinking water polluted with low concentration of antibiotics.…”

Synthesis of novel triazoles bearing 1,2,4-oxadiazole and phenylsulfonyl groups by 1,3-dipolar cycloaddition of some organic azides and their biological activities

“…A simple and practical method for the preparation of 11 novel phenylsulfonyl substituted triazoles carrying a 3-p-substituted phenyl-1,2,4-oxadiazole unit and 10 novel bis dihydropyrrolo [3,4-d] [1,2,3]triazole-4,6(3aH,5H )-diones carrying a 3-para-substituted phenyl-1,2,4-oxadiazole unit is introduced. The target compounds were assayed against MCF-7 breast cancer cells, but IC 50 values were not low.…”

“…The exact structures of the novel cycloadducts 4a-k were identified by IR, NMR ( 1 H, 13 C, COSY, NOESY, HMBC, and HSQC), mass spectra (low and high resolution), mp, and R f characteristics. In the IR spectra, the disappearance of the N=N=N absorption of the corresponding starting azides 3a-k at around 2100-2200 cm −1 and the appearance of the symmetric (1160-1120 cm −1 ) and asymmetric (1300-1350 cm −1 ) stretching absorptions of the sulfone group are evidence for 4-(phenylsulfonyl)-4,5-dihydro- [1,2,3]triazoles 4a-k.…”