A Water‐Soluble Cycloparaphenylene: Supramolecular Receptor with Visible Fluorescence

• Published in: ChemistryEurope Vol. 2; no. 6
• Main Authors: Morito, Ryo, Kataoka, Takayuki, Saito, Kunio, Osakada, Kohtaro, Ide, Tomohito, Tsuchido, Yoshitaka, Kawai, Hidetoshi
• Format: Journal Article
• Language: English
• Published: Wiley-VCH 01-11-2024
• Subjects: Au(I) Complex; Cycloparaphenylene; Host-Guest Chemistry; Water-soluble
• ISSN: 2751-4765; 2751-4765
• DOI: 10.1002/ceur.202400025

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.
We have synthesized a water‐soluble [9]cycloparaphenylene derivative consisting of three hydrindacene units with four carboxylates though a macrocyclic gold complex. This crown‐shaped compound exhibits high water solubility and strong visible fluorescence. Furthermore, it encapsulates cationic guest molecules such as methyl viologen dichloride in aqueous solution, demonstrating visible fluorescence changes.