Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 65, Pages 16612-16620Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201703823
Keywords
aromatic imides; chiral dimerization; Diels-Alder reactions; electrochemistry; lithium; organic lithium batteries
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Funding
- National Natural Science Foundation of China [21572032, 51503038]
- Program for New Century Excellent Talents in Fujian Province University
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The search for high-performance electrode materials in organic rechargeable batteries remains a key challenge. Reported herein is a molecular structural modification of perylene imides, a promising class of redox-active electrode materials, for improved battery performance. The Diels-Alder extension of perylene imides at the lateral position led to the simultaneous incorporation of two electron-withdrawing carbonyl groups and extension of the pi system, which is supposed to favor high specific capacity, operating voltage, and electronic conductivity. After the chiral dimerization of the extended species with 1,2-diaminocyclohexane, it was anticipated that the porosity and coulombic interactions with lithium ions would be promoted, which would be beneficial for fast reaction kinetics and long cycling life. As expected, in lithium batteries, the obtained chiral and pi-extended tweezer, which features six imide groups and a porous solid-state network of 42.2% accessible cell volume, was found to deliver a reversible capacity of 92.1 mA hg(-1) at a charge/discharge rate of 1 C within an operating voltage window of 1.60-2.80 V versus Li+/Li, around 75 and 50% of which was maintained after 100 and 300 galvanostatic cycles, respectively, much better than those of unmodified species.
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