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Fusing Thiadiazole and Terephthalate: A Concept to Promote the Electrochemical Performance of Conjugated Dicarboxylates

Von Wiley-VCH zur Verfügung gestellt

Merging two redox systems: Annellation of a thiadiazole heterocycle to a terephthalate boosts the redox kinetics of the conjugated dicarboxylate in the reversible storage of electrons. The maintained aromaticity as well as the improved coordination of the Li ions increases the stability of the reduced form.


Organic electrode materials based on conjugated dicarboxylate moieties are particularly attractive to develop metal-ion organic batteries. Exhibiting good stability properties in liquid electrolytes, such organic electrode materials can reversibly store alkali metal ions (Li, Na or K) at low working potential. Although many molecular designs have been investigated in the last decade, conjugated dicarboxylates are impeded by low coulombic efficiencies, especially at the first cycle, and sluggish kinetics in most cases. Herein, a new strategy in the design of conjugated carboxylates by fusing a thiadiazole heterocycle to the terephthalate core is reported. The synthesis and electrochemical performance of dilithium-2,1,3-benzothiadiazole-4,7-dicarboxylate (Li2-DCBTZ) as positive electrode material is investigated for the first time. Next to being a new structural design, the presence of the thiadiazole ring enables (i) a better conjugation of π-n electrons leading to a benefit in terms of rate capability, and (ii) a better stabilizing coordination network for Li ions through both oxygen and nitrogen atoms. In addition, the reduced state in Li4-DCBTZ is stabilized due to a maintained aromaticity in the heteroaromatic core in comparison to the parent terephthalate. Theoretical calculations on the Li-ion storage mechanism and bonding character support the experimental work.

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