Herein we report the synthesis of a dissymmetric, flexible organic macrocycle that can be used for a variety of applications. The macrocycle is synthesized using various C-C bond forming reactions such as Suzuki and Heck couplings. Electron deficient and electron rich segments are included in the dissymmetric macrocycle, so that it can form three-component complexes with two electronically-distinct small molecule guests.Two proposed applications for the macrocycle are the catalysis of challenging cycloaddition reactions and the fluorescent detection of toxic polycyclic aromatic hydrocarbons. Each of these applications relies on the formation of ternary complexes. For the catalysis of cycloaddition reactions, the macrocycle will bind the two small-molecule reactants, leading to proximity-induced rate accelerations. For the fluorescent detection of PAHs, the macrocycle will bind a PAH and a small-molecule fluorophore in its interior. The close proximity of the two guests will facilitate energy transfer, with excitation of the PAH resulting in energy transfer to and emission from the fluorophore. By utilizing a variety of small-molecule fluorophores, including squaraine compounds and rhodamine dyes, we will develop an array-based system for the detection of carcinogenic PAHs such as pyrene and benzopyrene.

Design and synthesis of a dissymmetric organic macrocycle

244th National Meeting (2012)

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