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Supramolecular Construction of a [16]‐Imidazolium Cage via a Quadruple [2+2] Photocycloaddition and Its Selective Fluorescent Recognition of Pyranine (HPTS)
Author(s) -
Hua Kai,
An YuanYuan,
Wang YaoYu,
Han YingFeng
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202001138
Subject(s) - supramolecular chemistry , carbene , fluorescence , chemistry , pyrene , salt (chemistry) , combinatorial chemistry , cycloaddition , cage , photochemistry , molecule , template , materials science , nanotechnology , organic chemistry , catalysis , physics , mathematics , quantum mechanics , combinatorics
Polyimidazolium‐based cages are considered promising materials based on their fascinating properties and potential applications. These three‐dimensional functional structures are highly desirable for the recognition of particular guest molecules, however, their synthesis remains challenging. In this work, we have designed and synthesizes a pure [ n ]‐imidazolium ( n =16) cage, the hexadecakisimidazolium salt H 16 ‐ 2 (PF 6 ) 16 , from tetragonal octakisimidazolium salt H 8 ‐ 1 (PF 6 ) 8 . The synthetic method involves formation of metal‐carbene templates, a quadruple photochemical [2+2] cycloaddition reaction and subsequent removal of metal ions. Specifically, the synthesized cage, featuring sixteen imidazolium moieties, demonstrated high efficiency for the selective fluorescent recognition of 8‐hydroxy‐1,3,6‐pyrene trisulfonate (HPTS). The present work not only further develops the metal‐carbene template strategy by exploiting a new type of polyimidazolium cage, but also provides encouraging prospects for the design of versatile imidazolium‐based functional acceptors.