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Synthesis of Novel Periodic Mesoporous Organosilicas Containing 1,4,5,8-Naphthalenediimides Within the Pore Walls and Their Reduction To Generate Wall-Embedded Free Radicals

Synthesis of Novel Periodic Mesoporous Organosilicas Containing 1,4,5,8-Naphthalenediimides Within the Pore Walls and Their Reduction To Generate Wall-Embedded Free Radicals

Bruna Castanheira, Eduardo Resende Triboni, Luana Dos Santos Andrade, Fabiane de Jesus Trindade, Larissa Otubo, Antonio Carlos Silva Costa Teixeira, Mário José Politi, Thiago Branquinho de Queiroz, Sergio Brochsztain

Langmuir. 2018 Jul 17;34(28):8195-8204.

PMID: 29909638

Abstract:

Novel periodic mesoporous organosilicas (PMOs) containing 1,4,5,8-Naphthalenediimide (NDI) chromophores as an integral part of the pore walls were synthesized in acidic conditions, in the presence of inorganic tetraethyl orthosilicate, using triblock copolymer surfactant Pluronic P-123 as a template. The NDI precursor, the bridged silsesquioxane N, N'-bis(3-triethoxysilylpropyl)-1,4,5,8-naphthalenediimide, was synthesized by reaction of 1,4,5,8-naphthalenetetracarboxylic dianhydride with excess 3-aminopropyltriethoxysilane. A series of samples containing up to 19% (weight %) of NDI were prepared (the materials were labeled PMONDIs). 13C and 29Si solid-state nuclear magnetic resonance revealed that the NDI moiety was intact in the PMONDIs and efficiently grafted to the silica network. Samples with up to 16% NDI load presented an ordered two-dimensional-hexagonal mesoscopic structure, according to small-angle X-ray scattering, transmission electron microscopy, and nitrogen adsorption isotherms. Fluorescence spectra of the PMONDIs showed excimer formation upon excitation, suggesting high flexibility of the organic moieties. Reduction of PMONDIs with aqueous sodium dithionite led to the formation of wall-embedded NDI anion radicals, as observed by the appearance of new visible/near-infrared absorption bands. The PMONDIs were also shown to be efficient photocatalysts in the degradation of sulfadiazine, an antibiotic selected here as a model pollutant, which is usually present in water bodies and wastewater.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP81301	1,4,5,8-Naphthalenetetracarboxylic dianhydride		81-30-1	Price

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