Highly efficient non-covalent energy transfer in all-organic macrocycles

Rationally Designed Supramolecular Organic Hosts for Benzo[a]pyrene Binding and Detection

“…[16] Synthesis of 17b: Compound 15b (1.00 g, 1.872 mmol, 1.0 equiv.) [16] Synthesis of Macrocycle 5: Compound 19a was prepared according to the published procedure. was dissolved in anhydrous ethanol (16 mL), and sodium carbonate (1.984 g, 18.726 mmol, 10 equiv.)…”

“…[14] Previous research in our group has focused on the use of cyclodextrins as supramolecular hosts for a variety of highimpact applications, including the detection of PAHs and other carcinogens, [7b-7e] the extraction of toxicants from complex oils, [7f-7h] and the development of selective arraybased detection procedures. [16] Despite the importance of such performance enhancements using the synthetic macrocycles, previous work in our group did little to explain why these macrocycles are better suited for supramolecular applications, in particular the binding and detection of benzo[a]pyrene, nor was effort made to expand the scope of macrocycle architectures to develop key structure-property relationships. [16] Despite the importance of such performance enhancements using the synthetic macrocycles, previous work in our group did little to explain why these macrocycles are better suited for supramolecular applications, in particular the binding and detection of benzo[a]pyrene, nor was effort made to expand the scope of macrocycle architectures to develop key structure-property relationships.…”

“…[15] We have also demonstrated the ability to synthesize organic macrocycles using straightforward, high-yielding procedures, and that these macrocycles can in some instances demonstrate improved application performance compared to the cyclodextrin derivatives. [16] Despite the importance of such performance enhancements using the synthetic macrocycles, previous work in our group did little to explain why these macrocycles are better suited for supramolecular applications, in particular the binding and detection of benzo[a]pyrene, nor was effort made to expand the scope of macrocycle architectures to develop key structure-property relationships. Reported herein is the rational design and synthesis of 6 new macrocycles, resulting in a minilibrary of 10 macrocycles with significant structural variability (Figure 1).…”

Photoinduced processes in macrocyclic isoalloxazine–anthracene systems

“…They undergo intramolecular conformational changes in the excited state that give rise to a reshaping of the fluorescence spectrum on the nanosecond timescale. A recent example of complexation of anthracene by an organic macrocycle led to significant changes in the energy transfer rates due to orientation of donor and acceptors [38].…”

Cyclodextrin-promoted energy transfer for broadly applicable small-molecule detection

“…We recently reported that cyclodextrin-promoted energy transfer occurred from polycyclic aromatic hydrocarbons (PAHs) (compounds 1 – 5 , Figure 2) and polychlorinated biphenyls (compounds 14 – 19 , Figure 2) to three fluorophores (two of which are shown in Figure 3) (22–24). Proximity-induced energy transfer between the analytes and the fluorophores occurred in the cavity of γ-cyclodextrin, resulting in up to 35% energy transfer efficiencies.…”