Hydroquinone/quinone redox couple is an essential part of life on earth, being involved in electron transport chains in both photosynthesis and cellular respiration. This robust redox system has received increased interest in recent years for potential applications in energy storage as search for lightweight and flexible battery materials intensified. The oxidation potential of a hydroquinone ring can be modulated simply by changing its substituents, making hydroquinone/quinone a versatile redox couple that can be tailored for many applications. We developed a new hydroquinone derivative functionalized with two pyridinium rings. The extended π conjugation of this compound makes it a unique chromophore addressable by either acid/base or redox agents. The optical and electronic properties of this hydroquinone derivative will be discussed, as well as how its properties change upon switching. Several new polycationic cyclophanes that employ the same hydroquinone motif and their host-guest complexes will also be presented.

Tuning properties of a hydroquinone chromophore

2019 Fall National Meeting

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