The ability of organic macrocycles like gamma-cyclodextrin to encapsulate two small-molecule guests has already been explored. The resulting ternary complexes have been used for a wide variety of applications, including sensing and catalysis. With this background knowledge, we have been working on the synthesis of a new all-organic macrocycle which has electron-rich and electron-deficient segments, as well as fluorescent moieties incorporated directly into the macrocyclic backbone. The synthetic strategy employs multiple C-C coupling reactions like Sonogashira coupling, and Suzuki coupling to link a distinct electron-rich moiety (alkoxy-substituted pyrenes) with an electron-deficient moiety (1,4,5,8-napthalene tetracarboxylic diimide) in order to create an asymmetric electronic environment. Once synthesized, the macrocycle will be used for a number of applications, including the fluorescence-based detection of polycyclic aromatic hydrocarbons via proximity-induced energy transfer.

Electronically dissymmetric fluorescent organic macrocycle for the detection of polycyclic aromatic hydrocarbons

245th National Meeting (2013)

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