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 × 10⁴ 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.

Reported herein is the highly efficient quenching of fluorescent organic nanoparticles by 2,4-dinitrotoluene and 2,4,6-trinitrotoluene. These fluorescent nanoparticles are formed from the hydrophobic collapse of fluorescent polymer chains and display quenching efficiencies that are in line with the highest reported literature values. Moreover, the fluorescent quenching occurs only for the fluorescent nanoparticles, and not for the precursor polymer solutions, which display marked insensitivity to the presence of nitroaromatics. This aggregation-dependent fluorescent quenching has numerous applications for the detection of small-molecule electron-deficient analytes. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 4150–4155