Tetraphenylethylene-embedded pillar[5]arene-based orthogonal self-assembly for efficient photocatalysis in water

Abstract

Herein, we have designed and fabricated a simple and efficient supramolecular self-assembled nanosystem based on host–guest interactions between water-soluble tetraphenylethylene-embedded pillar[5]arene (m-TPEWP5) and ammonium benzoyl-ʟ-alaninate (G) in an aqueous medium. The obtained assembly of m-TPEWP5 and G showed aggregation-induced emission (AIE) via the blocking of intramolecular phenyl-ring rotations and functioned as an ideal donor. After the loading of eosin Y (EsY) as acceptor on the surface of the assembly of m-TPEWP5 and G, the worm-like nanostructures changed into nanorods, which facilitates a Förster resonance energy transfer (FRET) from the m-TPEWP5 and G assembled donor to the EsY acceptor present in the nanorod assembly. The system comprising m-TPEWP5, G and EsY displayed moderate FRET efficiency (31%) at a 2:1 molar ratio of donor-to-acceptor. Moreover, the obtained supramolecular nanorod assembly could act as a nanoreactor mimicking natural photosynthesis and exhibited a high catalytic efficiency for the photocatalytic dehalogenation reaction of various bromoketone derivatives with good yields in short reaction time in water.

Construction of an Artificial Light-Harvesting System with Photocatalytic Activity Based on Nor-seco-cucurbit[10]uril in Aqueous Solution

“…A relative method was used to determine the yield from the 1 H NMR spectra (Figures S19−S26). 35 As shown in Table S1, using a 0.5 mol % catalytic system, the reaction yields reached 78 and 68%, respectively, indicating that the TPEs@ns-Q[10]-RB-NiR and TPEs@ns-Q[10]-ESY systems have a good catalytic effect on the dehalogenation of α-bromoacetophenone in aqueous solution. In contrast, the reaction yield promoted by TPEs alone was only 57% (Table S1), indicating that TPEs@ns-Q [10] has a much poorer catalytic effect than the TPEs@ns-Q[10]-RB-NiR and TPEs@ns-Q[10]-ESY systems without the participation of the dyes.…”

Dimeric Pillar[5]arene as a Novel Fluorescent Host for Controllable Fabrication of Supramolecular Assemblies and Their Photocatalytic Applications

“…The yield was obtained from 1 H NMR spectra (Figure S20, Supporting Information) by relative method. [ 22 ] To understand the role of the donor and acceptor, these catalytic reactions were carried out under different controlled conditions ( Table 1 ). In the absence of EsY (Figure S21, Supporting Information) or m ‐TPE Di‐EtP5 ⊃ G3 (Figure S22, Supporting Information), the obtained product yield was very low under light irradiation.…”

Stereoselective Single Step Cyclization to Give Belt-Functionalized Pillar[6]arenes

“…Alternatively, reacting P5 with benzophenone in the presence of n -BuLi followed by dehydration gives a macrocycle with an alkene functionality at one belt position . While the number of compounds prepared through these approaches is very limited (Figure ), they have found use for photophysical applications ,,– and in the synthesis of functional materials. ,,– …”