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Terphen[ n ]arenes and Quaterphen[ n ]arenes ( n =3–6): One‐Pot Synthesis, Self‐Assembly into Supramolecular Gels, and Iodine Capture
Author(s) -
Li Bin,
Wang Bin,
Huang Xiayang,
Dai Lu,
Cui Lei,
Li Jian,
Jia Xueshun,
Li Chunju
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201813972
Subject(s) - monomer , terphenyl , supramolecular chemistry , stacking , chemistry , condensation , methylene , polymer chemistry , aqueous medium , iodine , aqueous solution , crystallography , organic chemistry , crystal structure , polymer , physics , thermodynamics
Herein, two new classes of macrocyclic compounds, terphen[ n ]arenes (TP n s) ( n =3–6) and quaterphen[ n ]arenes (QP n s) ( n =3–6), were designed and synthesized by a one‐step condensation reaction in relatively high yields. They comprise 2,2′′‐dimethoxy terphenyl and 2,2′′′‐dimethoxy quaterphenyl monomers, respectively, linked by methylene bridges. Given their long and rigid monomers, TP n s and QP n s have much larger cavities and better self‐assembly properties than classic macrocycles. More interestingly, the cyclic pentamers and hexamers TP5, TP6, QP5, and QP6 formed supramolecular organogels, which were composed of interwoven fibers, nanosheets, or entangled macropore networks formed by multiple face‐to‐face and edge‐to‐face π⋅⋅⋅π stacking interactions. The xerogel materials effectively captured volatile iodine, not only in aqueous media but also in the gaseous state, and could be recycled multiple times without obvious loss in performance.