Perylene-Based All-Organic Redox Battery with Excellent Cycling Stability

Abstract

Organic materials derived from biomass can constitute a viable option as replacements for inorganic materials in lithium-ion battery electrodes owing to their low production costs, recyclability, and structural diversity. Among them, conjugated carbonyls have become the most promising type of organic electrode material as they present high theoretical capacity, fast reaction kinetics, and quasi-infinite structural diversity. In this letter, we report a new perylene-based all-organic redox battery comprising two aromatic conjugated carbonyl electrode materials, the prelithiated tetra-lithium perylene-3,4,9,10-tetracarboxylate (PTCLi6) as negative electrode material and the poly(N-n-hexyl-3,4,9,10-perylene tetracarboxylic)imide (PTCI) as positive electrode material. The resulting battery shows promising long-term cycling stability up to 200 cycles. In view of the enhanced cycling performances, the two organic materials studied herein are proposed as suitable candidates for the development of new all-organic lithium-ion batteries.

Molecular Engineering with Organic Carbonyl Electrode Materials for Advanced Stationary and Redox Flow Rechargeable Batteries

“…In addition, the easily dissolved carbonyls (raw materials or radical products) are shuttled to the Li anode with side reactions, resulting in low Coulombic efficiency and poor cycling stability. One is by increasing the molecular weight through polymerization (Figure 8), [119][120][121][122][123][124][125][126][127] and the other is by enhancing the polarity through salt formation (Figure 9). Therefore, most research interests so far have focused on solving this problem and enhancing the stability of carbonyls and extending cycling life.…”

“…The superior electrode performance motivated researchers to further study this intriguing class of PIs(8-16, 8-20 to 8-24) [119,133,138,139]. The superior electrode performance motivated researchers to further study this intriguing class of PIs(8-16, 8-20 to 8-24) [119,133,138,139].…”

From an Enhanced Understanding to Commercially Viable Electrodes: The Case of PTCLi4 as Sustainable Organic Lithium‐Ion Anode Material

“…[6][7][8]14] Following these considerations, studies on carbonyl-based alternative anodes cover the whole range from lithium/sodium terephthalates [15][16][17][18][19][20][21][22] and benzenediacrylate [23] over naphthalene carboxylates [15,[24][25][26] to perylene carboxylates. [27][28][29][30] Although such an extension of the aromatic core to more than one phenyl ring leads to a decrease in specific capacity as a direct result of the increasing molecular mass, the amelioration of the π-electron delocalization positively affects the rate capability and cycling stability. [28,30] As these latter characteristics are eventually more important for practical battery applications than short-term available higher specific capacities, we have selected tetra-lithium perylene-3,4,9,10-tetracarboxylate (PTCLi 4 ) as model compound for our investigation of the lithium reaction mechanism and the impact of the utilized conductive additive.…”

“…[27][28][29][30] Although such an extension of the aromatic core to more than one phenyl ring leads to a decrease in specific capacity as a direct result of the increasing molecular mass, the amelioration of the π-electron delocalization positively affects the rate capability and cycling stability. [28,30] As these latter characteristics are eventually more important for practical battery applications than short-term available higher specific capacities, we have selected tetra-lithium perylene-3,4,9,10-tetracarboxylate (PTCLi 4 ) as model compound for our investigation of the lithium reaction mechanism and the impact of the utilized conductive additive. In fact, from the practical point of view, PTCLi 4 has the additional advantage of being easily synthesized in a one-pot hydrolysis/lithiation reaction using 3,4,9,10-perylene-tetracarboxylic-dianhydride (PTCDA) also considered as organic cathode material [31][32][33] as low-cost, commercially available precursor.…”

A Novel High‐Capacity Anode Material Derived from Aromatic Imides for Lithium‐Ion Batteries

“…It has been proved to be electrochemically active in 1987, but until recently, aromatic imides have turned up as active materials in lithium/sodium‐ion batteries, possibly owing to its well‐known characteristics of being insulating . Currently, the research on aromatic imides is mostly investigated as cathode material with the core structure of benzene, naphthalene, or perylene, delivering a maximum capacity of 200 mA h g −1 (237 mA h g −1 , theoretically) with a voltage plateau of 1.2–2.75 V versus Li + /Li . And there are some sporadic reports on aromatic imides being explored as anode material in sodium ion battery with a voltage plateau of 0.9–2 V versus Na + /Na .…”