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Construction and Multiple Exterior Surface Functionalization of Giant Molecular Cages
Author(s) -
Naseer Muhammad Moazzam,
Wang DeXian,
Zhao Liang,
Wang MeiXiang
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402963
Subject(s) - chemistry , surface modification , supramolecular chemistry , molecule , nucleophilic substitution , bromide , nuclear magnetic resonance spectroscopy , polymer chemistry , stereochemistry , organic chemistry
By a one‐pot reaction strategy and a stepwise fragment‐coupling approach, three types of giant cage molecules with a triangular prism shape and an approximate cavity volume of 930 Å 3 were synthesized. Through efficient aromatic nucleophilic substitution reactions of chlorotriazine with functionalized amines or aliphatic substitution reactions of the linking imino moieties with allyl bromide, the giant cages were successfully functionalized on the surface with multiple hydroxy, 2‐pyridyl, or allyl groups. As evidenced by variable‐temperature 1 H NMR spectroscopy, the D 3 h ‐ and C 3 v ‐symmetric cage molecules underwent very slow conformational changes or deformation in solution because of their giant size and their flexible building units. Their giant cavities, different electronic interiors, and facile multiple exterior surface functionalization could render the molecular cages powerful three‐dimensional macrocyclic hosts that might find wide applications in supramolecular science.