A new triazine functionalized luminescent covalent organic framework for nitroaromatic sensing and CO2 storage

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Abstract

A hexagonal COF has been designed via Schiff-base condensation reaction between 1,3,5-tris-(4-aminophenyl)triazine and 1,3,5-triformylphloroglucinol. It showed excellent sensing behavior towards nitroaromatic compounds through fluorescence quenching and excellent CO ₂ uptake.

Abstract

A new hexagonally ordered covalent organic framework (COF), TRIPTA has been synthesized using Schiff base condensation reaction between 1,3,5-tris-(4-aminophenyl)triazine (TAPT) and 1,3,5-triformylphloroglucinol (TFP). TRIPTA exhibits high crystallinity, a large BET surface area (609 m ² g ⁻¹) and pore volume (0.351 cm ³ g ⁻¹) and possesses high nitrogen content (14.97%). TRIPTA was found to be highly luminescent when suspended in polar solvents upon irradiation of UV light and can detect various nitroaromatic compounds with good sensitivity by fluorescence quenching at concentrations as low as in the range of 10 ⁻⁸ M. The maximum fluorescence quenching was observed for trinitrophenol (61.7% at 5.46 × 10 ⁻⁷ M) with a Stern–Volmer constant of 2.7 × 10 ⁶ M ⁻¹. The COF also showed excellent CO ₂ uptake capacity of 57.07 wt% at 273 K and 16.02 wt% at 298 K up to 5 bar pressure, with an initial heat of adsorption ( Q _st) value 56.77 kJ mol ⁻¹.

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Conjugated microporous polymers as molecular sensing devices: microporous architecture enables rapid response and enhances sensitivity in fluorescence-on and fluorescence-off sensing.

Xiaoming Liu, Yanhong Xu, Donglin Jiang (2012)

Conjugated polymers are attractive materials for the detection of chemicals because of their remarkable π-conjugation and photoluminescence properties. In this article, we report a new strategy for the construction of molecular detection systems with conjugated microporous polymers (CMPs). The condensation of a carbazole derivative, TCB, leads to the synthesis of a conjugated microporous polymer (TCB-CMP) that exhibits blue luminescence and possesses a large surface area. Compared with a linear polymer analogue, TCB-CMP showed enhanced detection sensitivity and allowed for the rapid detection of arenes upon exposure to their vapors. TCB-CMP displayed prominent fluorescence enhancement in the presence of electron-rich arene vapors and drastic fluorescence quenching in the presence of electron-deficient arene vapors, and it could be reused without a loss of sensitivity and responsiveness. These characteristics are attributed to the microporous conjugated network of the material. Specifically, the micropores absorb arene molecules into the confined space of the polymer, the skeleton possesses a large surface area and provides a broad interface for arenes, and the network architecture facilitates exciton migration over the framework. These structural features function cooperatively, enhancing the signaling activity of TCB-CMP in fluorescence-on and fluorescence-off detection.

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Room Temperature Synthesis of Covalent–Organic Framework Films through Vapor-Assisted Conversion

Dana Medina, Julian M. Rotter, Yinghong Hu … (2014)

We describe the facile synthesis of several two-dimensional covalent–organic frameworks (2D COFs) as films by vapor-assisted conversion at room temperature. High-quality films of benzodithiophene-containing BDT-COF and COF-5 with tunable thickness were synthesized under different conditions on various substrates. BDT-COF films of several micrometer thickness exhibit mesoporosity as well as textural porosity, whereas thinner BDT-COF films materialize as a cohesive dense layer. In addition, we studied the formation of COF-5 films with different solvent mixture compositions serving as vapor source. Room temperature vapor-assisted conversion is an excellent method to form COF films of fragile precursors and on sensitive substrates.