<br/>Inspired by natures enzymes, the design of supramolecular hosts to recognize and achieve chemistries on specific guest molecules is an important challenge in modern chemistry and biochemistry. The electron poor (cationic) viologen moiety has been used in several molecular-host designs, and even to promote some limited catalysis. Here, a series of viologen dimers are synthesized with the para, meta, and ortho linkers and characterized in terms of both host-guest and electrochemistry. Upon addition of a dihydroxynapthalene (DHN) guest to the dicationic methyl viologen dimer, <sup>1</sup>H NMR shifts reveal that the meta linker is optimal for guest binding followed by the para and ortho linkers, respectively. In addition to host-guest chemistry, the redox chemistry of these organic dimers is characterized using reduction potential data, displaying that the ortho dimer is the most electrochemically stable. Furthermore, a novel synthesis for a water soluble methyl viologen-linked-napthalene diimide (NDI) dimer with para, meta, and ortho linkers is also presented. This molecular design potentially enhances the intramolecular folding interactions and optimizes di-radical stability by taking advantage of both the spin-spin and Colombic attractions between the two compounds. Both the host-guest and electrochemistry of these newly synthesized dimers are evaluated.

Synthesis of organic dimer ligands for radical host-guest chemistry

2019 Spring National Meeting

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