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Rationally Designed Supramolecular Organic Hosts for Benzo[ a ]pyrene Binding and Detection
Author(s) -
Radaram Bhasker,
Levine Mindy
Publication year - 2015
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.201500684
Subject(s) - chemistry , pyrene , fluorophore , supramolecular chemistry , ring (chemistry) , benzo(a)pyrene , acceptor , covalent bond , stereochemistry , fluorescence , combinatorial chemistry , computational chemistry , molecule , organic chemistry , physics , quantum mechanics , condensed matter physics
Abstract A series of electronically dissymmetric all‐organic macrocycles were synthesized using straightforward synthetic procedures. These macrocycles vary in the nature of the substituents, the geometry of the linkage that connects the electron‐deficient aromatic ring, the type of linkage, and the presence or absence of a heteroaromatic ring. These small structural variations impart significant differences in the performance of these macrocycles in binding benzo[ a ]pyrene, with binding constants up to 2.5 × 10 4 M –1 obtained. They also lead to significant differences in their ability to promote non‐covalent energy transfer from benzo[ a ]pyrene to a BODIPY fluorophore, with energy transfer efficiencies ranging from 32 % to 398 %. These differences can be explained using a variety of computational investigative techniques, which highlight the flexibility of the macrocycle architectures to accommodate benzo[ a ]pyrene and to promote close donor–acceptor interactions.