A novel fluorescent macroloop with solid-state fluorescent chromic and selective gas adsorption properties

On June 20, 2023, Professor Yang Yingwei’s research team from the School of Chemistry of Jilin University published a research paper entitled “Emissive fluoren-triangles for solid-state fluorochromism and selective gas sorption” in the journal Chem.

The study reported a novel fluoren-triangle fluorene-based fluorophore. By skillfully combining fluorene units with traditional rannophenol skeletons, a novel supramolecular macroloop with triangular configuration was efficiently synthesized. Fluorescence experiments have proved that it has significant aggregation-induced luminescence enhancement properties and excitation wavelength dependence. In addition, its amorphous powder exhibits good CO2 and CH4 selective adsorption properties. This research will provide new perspectives for the development of functional photoresponsive materials, as well as new inspiration for the design of molecular adsorbents.

The corresponding author of the paper is Professor Yang Yingwei, and the first author is Wu Gengxin.

The birth and development of supramolecular chemistry has always accompanied and relied on the innovation and development of new supramolecular macrocycles, and the rapid development of macromolecular chemistry is a key link to promote the vigorous development of the field of supramolecular chemistry and materials and make them go to application. Therefore, the design and synthesis of new macrocyclic molecules with unique geometry and excellent properties has always been one of the most challenging research hotspots in the field of organic supramolecular chemistry and materials.

In recent years, Professor Yang Yingwei’s research team has made a series of research progress in the design and synthesis of new supramolecular macrocyclic aromatic hydrocarbons and the construction and performance development of supramolecular materials (Chem. Commun. 2016, 52, 5804; Angew. Chem. Int. Ed. 2018, 57, 9853; J. Am. Chem. Soc. 2019, 141, 12280; J. Am. Chem. Soc. 2021, 143, 20395)。 Based on this, in this work, the authors developed a new class of macrocyclic aromatic hydrocarbons Fluoren-triangle(FT) with large-sized cavities and fluorescent properties by combining fluorene fluorene with a rigid backbone of ranlockol (Figure 1). The single crystal structure indicates that the large ring exhibits a triangular conformation, and the monomer connection presents a cup-like[4]1,3-alternating conformations of aromatic hydrocarbons and conical conformations (Figure 2).

Figure 1: Schematic diagram of molecular design and characterization: tunable fluorescence emission and selective gas adsorption.

Figure 2: Crystal structure of a macrocyclic molecule.

Subsequently, the authors studied the fluorescence properties of the solid-liquid state of the macrocyclic molecule and found that the macrocyclic had a significant aggregation-induced luminescence enhancement. In addition, at different excitation wavelengths (280 nm, 450 nm, 550 nm), the large ring exhibits significant excitation wavelength dependence, showing blue, green, and orange-red fluorescence emission (Figure 3).

Figure 3: Excitation wavelength dependence in solid-state.

In addition, the authors constructed two non-porous amorphous adsorption materials and explored their capabilities in selective adsorption of CO2 and CH4 (Figure 4). The results show that the two materials show good adsorption selectivity, which provides new inspiration for the construction of amorphous adsorption separation materials.

Figure 4: Gas selective adsorption experiment.

This work is supported by the National Natural Science Foundation of China (52173200, 22201096), the Natural Science Foundation of Jilin Province (20230101052JC), the China Postdoctoral Science Foundation (BX2021112) and the special fund of the basic scientific research business fund of the central universities. (Source: Science Network)

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