1452822-76-2Relevant academic research and scientific papers
Rationally Designed Supramolecular Organic Hosts for Benzo[a]pyrene Binding and Detection
Radaram, Bhasker,Levine, Mindy
, p. 6194 - 6204 (2015)
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. A series of 10 organic macrocycles were designed, synthesized, and evaluated for their ability to bind benzo[a]pyrene and facilitate benzo[a]pyrene to BODIPY energy transfer. These results highlight the relationship between structural features of hosts, their overall conformations, and their ability to participate in intermolecular interactions and supramolecular applications.
Highly efficient non-covalent energy transfer in all-organic macrocycles
Radaram, Bhasker,Potvin, Joshua,Levine, Mindy
supporting information, p. 8259 - 8261 (2013/09/12)
The use of aromatic organic macrocycles as supramolecular hosts for non-covalent energy transfer is reported herein. These macrocycles lead to stronger binding and more efficient energy transfer compared to commercially available γ-cyclodextrin. This energy transfer was particularly efficient for the highly toxic benzo[a]pyrene with a fluorescent BODIPY acceptor, with up to a 5-fold increase in the fluorophore emission observed.
