A Water-Soluble Cycloparaphenylene: Supramolecular Receptor with Visible Fluorescence

Ryo Morito, Takayuki Kataoka, Kunio Saito, Prof. Dr. Kohtaro Osakada, Dr. Tomohito Ide, Dr. Yoshitaka Tsuchido, Prof. Dr. Hidetoshi Kawai
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Abstract

We report the first synthesis of a water-soluble [9]cycloparaphenylene derivative containing three hydrindacene (1,2,3,5,6,7-hexahydro-s-indacene) units with four carboxylates at the 2,6-positions via a macrocyclic gold complex. This crown-shaped macrocyclic compound exhibits remarkable water solubility, of up to 16 mmol L−1 (2.6 g/100 mL), as well as strong visible fluorescence in water (λem=447 nm, ϕF=0.64, brightness (ϵ×ϕF)=5.1×104). This molecule effectively encapsulates cationic guest compounds, such as methyl viologen dichloride, as indicated by a change in visible fluorescence.

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水溶性环联苯:具有可见荧光的超分子受体
我们首次通过大环金配合物合成了一种水溶性[9]环联苯衍生物,该衍生物含有三个氢茚(1,2,3,5,6,7-六氢-s-茚)单元,在 2,6 位有四个羧基。这种冠状大环化合物具有出色的水溶性,高达 16 mmol L-1 (2.6 g/100 mL),在水中还能发出强烈的可见荧光(λem=447 nm,jF=0.64,亮度(ϵ×jF)=5.1×104)。可见荧光的变化表明,这种分子能有效地包裹阳离子客体化合物,如二氯甲基紫精。
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Front Cover: Luminescence and Single-Molecule Magnet Properties in Ideal Symmetry Compounds: Example of a Near-Planar Tricoordinate Ytterbium(III) Amide (ChemistryEurope 6/2024) Cover Feature: Water Chemistry at the Nanoscale: Clues for Resolving the “Water Paradox” Underlying the Emergence of Life (ChemistryEurope 6/2024) Luminescence and Single-Molecule Magnet Properties in Ideal Symmetry Compounds: Example of a Near-Planar Tricoordinate Ytterbium(III) Amide Steering Photoinduced Electron Transfer in Intramolecular Photocatalysts by Peripheral Ligand Control Water Chemistry at the Nanoscale: Clues for Resolving the “Water Paradox” Underlying the Emergence of Life
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