Anthraquinone Derivatives Research Articles

Toxicity of anthraquinone derivatives in relation to non-linear optical properties and electron correlation.

1,4-Dialkylamino -5,8-dihydroxy anthraquinones are investigated using density functional theory (DFT) and time-dependent DFT (TD-DFT) for their growth inhibitory potential. The frontier molecular orbital shows that the electron density is located at the anthraquinone core and at the substituents NH and OH in both HOMO as well as in LUMO. The chemical potential and electrophilicity index showed a direct relation, while hardness and hyperhardness had an inverse association with an energy gap. The results of the molecular docking analysis revealed that the anthraquinone molecules have a high affinity for the primary targets of the DNA topoisomerase IIα enzyme. The docking results showed good binding ability with extremely energetically stable scores ranging from -8.9 to -7.6 kcal/mol. Electron correlation descriptors showed a direct link with NLO properties and toxicity.

The study of the total antioxidant capacity of St. John’s Wort (Hypericum perforatum L.) herb

Aim. To determine the total antioxidant capacity of St. John’s Wort herb. Materials and methods. The content of phenolic compounds, anthraquinone derivatives, flavonoids, and derivatives of hydroxycinnamic acids was determined by the spectrophotometric analysis, while organic acids were identified by the alkalimetric method; the antioxidant activity of extracts obtained was evaluated by the potentiometric method. Results and discussion. The total antioxidant capacity of St. John’s Wort herb was 91.35 mmol-equiv/m dry weight, the total content of phenolic compounds was 22.70 mg of gallic acid/mL, anthraquinone derivatives – 0.46 mg of hyperecin/mL, flavonoids – 8.10 mg of rutin/mL, derivatives of hydroxycinnamic acids – 7.90 mg of chlorogenic acid/mL and organic acids – 10.80 mg of citric acid/mL in St. John’s Wort herb extracts obtained during the sequential exhaustive extraction. The correlation analysis showed a very high positive correlation between the antioxidant activity and the total content of phenolic compounds, flavonoids, hydroxycinnamic acid derivatives in St. John’s Wort herb extracts. Conclusions. The total antioxidant capacity of H. perforatum herb was 91.35 mmol-equiv./m dry weight. The results of the analysis of the BAS content and the antioxidant activity of H. perforatum herb extracts revealed that the aqueous extract had a significant content of phenolic compounds, flavonoids, hydroxycinnamic acids, organic acids and the antioxidant activity, while anthraquinone derivatives dominated in 96 and 60 % EtOH extracts. The quantitative analysis showed that flavonoids and hydroxycinnamic acids dominated among phenolic compounds. The results can be applied in developing optimal technologies for obtaining drugs based on the extract of H. perforatum herb.

Analysis of the components of Cassia nomame and their antioxidant activity

Cassia nomame, an annual herb belonging to the Leguminosae family, is traditionally consumed as tea in the form of dried whole herbs or beans. To deepen our understanding of the chemical constituents of C. nomame, we isolated 16 compounds, categorised as flavone derivatives (1–4), including a novel compound nomameflavone A (4), a chalcone derivative (5), an aurone derivative (6), a chromone derivative (7), a juglone derivative (8), anthraquinone derivatives (9–11), phenolic compounds (12–14), and sterol derivatives (15, 16). The structure of each compound was elucidated using NMR and MS. Compounds 2, 6, 7, 8, 12, 13, and 14 were successfully isolated from C. nomame for the first time. Furthermore, compounds 1, 3, 5, and 6 exhibited DPPH radical scavenging activities, and the bioactivity of 3 was discovered. The elucidation of the diverse chemical constituents of C. nomame underscores its potential functional ingredients.

Contribution of Protonation to the Dielectric Relaxation Arising from Bacteriopheophytin Reductions in the Photosynthetic Reaction Centers of Rhodobacter sphaeroides.

The pH dependence of the free energy level of the flash-induced primary charge pair P+IA- was determined by a combination of the results from the indirect charge recombination of P+QA- and from the delayed fluorescence of the excited dimer (P*) in the reaction center of the photosynthetic bacterium Rhodobacter sphaeroides, where the native ubiquinone at the primary quinone binding site QA was replaced by low-potential anthraquinone (AQ) derivatives. The following observations were made: (1) The free energy state of P+IA- was pH independent below pH 10 (-370 ± 10 meV relative to that of the excited dimer P*) and showed a remarkable decrease (about 20 meV/pH unit) above pH 10. A part of the dielectric relaxation of the P+IA- charge pair that is not insignificant (about 120 meV) should come from protonation-related changes. (2) The single exponential decay character of the kinetics proves that the protonated/unprotonated P+IA- and P+QA- states are in equilibria and the rate constants of protonation konH +koffH are much larger than those of the charge back reaction kback ~103 s-1. (3) Highly similar pH profiles were measured to determine the free energy states of P+QA- and P+IA-, indicating that the same acidic cluster at around QB should respond to both anionic species. This was supported by model calculations based on anticooperative proton distribution in the cluster with key residues of GluL212, AspL213, AspM17, and GluH173, and the effect of the polarization of the aqueous phase on electrostatic interactions. The larger distance of IA- from the cluster (25.2 Å) compared to that of QA- (14.5 Å) is compensated by a smaller effective dielectric constant (6.5 ± 0.5 and 10.0 ± 0.5, respectively). (4) The P* → P+QA- and IA-QA → IAQA- electron transfers are enthalpy-driven reactions with the exemption of very large (>60%) or negligible entropic contributions in cases of substitution by 2,3-dimethyl-AQ or 1-chloro-AQ, respectively. The possible structural consequences are discussed.

Discovery and optimization of anthraquinone derivatives containing substituted bisbenzyloxy groups as a novel scaffold damaged endoplasmic reticulum and against hepatocellular carcinoma cells

This paper reports the antitumor activity and possible mechanism of anthraquinone derivatives containing substituted bisbenzyloxy groups. Series of anthraquinone derivatives containing substituted bisbenzyloxy groups were designed and synthesized by etherification and esterification. The antitumor activities of the synthesized substituted bisbenzyloxy anthraquinone derivatives on liver cancer cell Huh7, triple negative breast cancer cell line MDA-MB-231 and lung cancer cell A549 were in the order of methoxy substitution > methyl substitution > chloral substitution. Among these, the Compound KA-MO-g showed strong antitumor activity, especially against liver cancer Huh7 cells. Further studies on the antitumor mechanism showed that the Compound KA-MO-g simultaneously activated three pathways of endoplasmic reticulum stress (ERS), also caused impairment of endoplasmic reticulum (ER) functions, such as glycoprotein synthesis and disulfide bond formation are impeded and caused calcium overload, then increased mitochondrial ROS, damaged of mitochondria, changed of apoptosis-related protein levels, activated Caspase 3, induced the apoptosis of Huh7 cells. Because KA-MO-g showed strong antitumor activity, it is expected to be a new candidate drug for treating liver cancer and is worth further study.

Penicitrisochromans A-C, new isochromans from the marine-derived fungus Penicillium citrinum PSU-MF100.

Three new isochroman derivatives, penicitrisochromans A-C (1-3), together with 25 known polyketides were isolated from the marine-derived fungus Penicillium citrinum PSU-MF100. Their structures were elucidated by extensive spectroscopic analysis. The absolute configurations of 1 and 2 were established by comparison of specific rotations and electronic circular dichroism (ECD) data with those of the known co-metabolite whereas those of 3 were assigned based on the ECD calculation and biosynthetic consideration. Among the isolated polyketides, three known anthraquinone derivatives, ω-hydroxyemodin, penicillanthranin A and emodin, displayed moderate to strong antibacterial activity against methicillin-resistant Staphylococcus aureus with MIC values of 32, 16 and 4 µg/mL, respectively. For antifungal activity, two known benzopyranones, coniochaetones A and C, exhibited moderate antifungal activity against Candida albicans NCPF3153 and Cryptococcus neoformans ATCC90112 with the respective MIC values of 16 and 64 µg/mL.

New developments in intrinsic black photosensitive polyimide for advanced display applications

To meet the requirements of low power consumption, long endurance, and cost-efficiency for mobile phones, a polarizer-less technology (Pol-Less) OLED with a color-on-encapsulation (COE) structure has been proposed. In this groundbreaking technology, black photosensitive polyimide (PSPI) serves as the pixel definition layer (PDL) and plays a crucial role. However, the addition of inorganic pigments, such as carbon black, significantly compromises the dielectric insulation properties of the PDL. Therefore, exploring intrinsic black photosensitive polyimide with outstanding light shielding performance and high dielectric insulation properties has garnered increasing attention. In this study, a derivative of anthraquinone, namely 2,4,5,7-tetraamino-1,8-dihydroxyanthraquinone (4NADA) is incorporated into the photosensitive polyimide chains, successfully producing an intrinsic black photosensitive polyimide with broad absorption in the visible light range. Experimental results revealed that by copolymerizing 50 % moles of 4NADA in the diamines in the photosensitive polyamide acid ester, a black photosensitive polyimide with a high optical density (OD) of 0.89 and a relatively low dielectric constant of 3.6 at 1000 kHz was obtained. Furthermore.

Electron Spin Dynamics of the Intersystem Crossing in Aminoanthraquinone Derivatives: The Spectral Telltale of Short Triplet Excited States.

We studied the excited state dynamics of two bis-amino substituted anthraquinone (AQ) derivatives, with absorption in the visible spectral region, which results from the attachment of a electron-donating group to the electron-deficient AQ chromophore. Femtosecond transient absorption spectra show that intersystem crossing (ISC) takes place in 190-320 ps, and nanosecond transient absorption spectra demonstrated an unusually short triplet state lifetime (2.06-5.43 μs) for the two AQ derivatives. Pulsed laser-excited time-resolved electron paramagnetic resonance (TREPR) spectra show an inversion of the electron spin polarization (ESP) phase pattern of the triplet state at a longer delay time after laser flash. Spectral simulations show faster decay of the Ty sublevel than the other two sublevels (τx = 15.0 μs, τy = 1.50 μs, τz = 15.0 μs); theoretical computation predicts initial overpopulation of the Ty sublevel, and rationalizes the short T1 state lifetime and the ESP inversion. Theoretical computations taking into account the electron-vibrational coupling, i.e., the Herzberg-Teller effect, successfully rationalize the TREPR experimental observations.

Combination of Metabolomics, Lipidomics, and Molecular Biology for the Investigation of the Metabolic Disturbance of Short-Term Administration of Emodin.

Emodin, a natural anthraquinone derivative, is an active ingredient in many Chinese traditional herbs. Interestingly, although it is generally considered to possess hepatoprotective activity, some studies have also reported that it has a certain degree of hepatotoxicity. Additionally, the underlying metabolic regulation of emodin remains uncertain. Therefore, we conducted a nontargeted metabolomic study based on UHPLC/Q-Orbitrap-MS and NMR. Data are available via ProteomeXchange with the identifier PXD055000. The results indicated a close association between the short-term administration of emodin and lipid metabolism. Moreover, a lipidomics investigation utilizing QTRAP 6500+ UHPLC-MS/MS was conducted, with a focus on determining the position of C═C double bonds in unsaturated lipids based on Paternò-Büchi (PB) reaction to discover the metabolic disturbance more precisely. Specifically, lipidomics revealed elevated levels of free fatty acids (FFA) alongside notable reductions in sphingomyelin (SM) and triacylglycerol (TAG) levels. Furthermore, the combination of PB reaction and molecular biology results indicated that short-term administration of emodin may lead to the accumulation of n-6 polyunsaturated fatty acids by up-regulating the expression of FASN, stearyl CoA desaturase 1 (SCD1), and cytosolic phospholipase A 2 (cPLA2). Simultaneously, up-regulation of cyclooxygenase-2 (Cox-2) expression was observed, potentially fostering the production of prostaglandin E2 (PGE2) and subsequent inflammation.

Tuning the composition of mixed anthraquinone derivatives towards an affordable flow battery negolyte

Having a long lifespan and being capable of scaling capacity and power independently, redox flow batteries (RFB) offer great opportunities for energy storage. However, the challenge lies in finding an ideal electrolyte. The most mature version of RFB utilizes vanadium solutions and suffers from rising and highly volatile prices of this metal. To address this, organic electrolytes are gaining attention, as they can be obtained from abundant feedstocks. Among those, Anthraquinone-2,7-disulfonic acid (2,7-AQDS) solutions are particularly prominent, demonstrating reversible and fast redox kinetics coupled with reasonable solubility. This paper explores the possibility of synthesizing 2,7-AQDS together with other electroactive compounds (2,6-AQDS, 2-AQS) through the reaction of anthraquinone sulfonation. It shows that obtained mixtures act as electrolytes without any purification or separation, while synthesis conditions can adjust mixture composition and hence their redox behavior. Although the performance of anthraquinone-bromine RFB utilizing these mixtures exhibits a trade-off between power and stability, the best of them are comparable or even superior to 2,7-AQDS. For instance, RFB with a mixture free of 2-AQS demonstrates an energy efficiency of 76.4 % and a capacity fade rate of 0.04 %/cycle at a current density of 75 mA cm−2. The specific capacity of such mixtures can reach 70 Ah L−1, which makes them promising and affordable RFB negolyte.

Aloe-emodin: Progress in Pharmacological Activity, Safety, and Pharmaceutical Formulation Applications.

Aloe-emodin (AE) is an anthraquinone derivative and a biologically active component sourced from various plants, including Rheum palmatum L. and Aloe vera. Known chemically as 1,8-dihydroxy-3-hydroxymethyl-anthraquinone, AE has a rich history in traditional medicine and is esteemed for its accessibility, safety, affordability, and effectiveness. AE boasts multiple biochemical and pharmacological properties, such as strong antibacterial, antioxidant, and antitumor effects. Despite its array of benefits, AE's identity as an anthraquinone derivative raises concerns about its potential for liver and kidney toxicity. Nevertheless, AE is considered a promising drug candidate due to its significant bioactivities and cost efficiency. Recent research has highlighted that nanoformulated AE may enhance drug delivery, biocompatibility, and pharmacological benefits, offering a novel approach to drug design. This review delves into AE's pharmacological impacts, mechanisms, pharmacokinetics, and safety profile, incorporating insights from studies on its nanoformulations. The goal is to outline the burgeoning research in this area and to support the ongoing development and utilization of AE-based therapies.

Emodin combined with 5-aminolevulinic acid photodynamic therapy inhibits condyloma acuminate angiogenesis by targeting SerRS.

Human papillomavirus (HPV) infection can cause condyloma acuminatum (CA), which is characterized by a high incidence and a propensity for recurrence after treatment. Angiogenesis plays an important role in the occurrence and development of CA. Seryl-tRNA synthetase (SerRS) is a newly identified, potent anti-angiogenic factor that directly binds to the vascular endothelial growth factor (VEGFA) promoter, thereby suppressing its transcription. Emodin is a natural anthraquinone derivative that can promote SerRS expression. This study aimed to investigate the effects of emodin on CA and explore combined treatment strategies. The HPV-infected cell line SiHa was treated with either DMSO, emodin, ALA-PDT or a combination of emodin and ALA-PDT. We observed the effects on cell proliferation, apoptosis and the SerRS-VEGFA pathway. Our findings demonstrated that emodin targets angiogenesis through the SerRS-VEGFA pathway, resulting in the inhibition of SiHa cell proliferation and promotion of apoptosis (p < 0.001). To verify the therapeutic effect of emodin combined with ALA-PDT on HPV-associated tumours invivo, we established an animal xenograft model by subcutaneously inoculating mice with SiHa cells (n = 4). The results showed that the combination of emodin and ALA-PDT significantly inhibited the expression of VEGFA to inhibit angiogenesis (p < 0.001), thus showing an inhibitory effect on tumour (p < 0.001). Furthermore, we determined that the mechanism underlying the decrease in VEGFA expression after emodin combined with ALA-PDT in CA may be attributed to the promotion of SerRS expression (p < 0.001). The combination of emodin and ALA-PDT holds promise as a novel therapeutic target for CA by targeting neovascularization in condyloma tissues.

Unveiling the multifaceted interactions of antitumor drug mitoxantrone with ct-DNA through biophysical and in silico studies

Mitoxantrone, an anthraquinone derivative, is a widely used anticancer drug with its well-known ability to engage in complex interactions with DNA. Although known for its intercalating ability, the enigma surrounding its binding modes with DNA persists. The existing corpus of literature primarily focuses on mitoxantrone-DNA interactions with short DNA sequences, thereby yielding insights into its interactive nature is limited to this specific sequence. This study aims to elucidate the diverse modes with which mitoxantrone interacts with calf thymus DNA using a combination of spectroscopy, calorimetry and in silico studies. The findings from spectroscopic, calorimetric and molecular dynamic results in correlation with existing literature, unveil a fascinating narrative: mitoxantrone intercalates at lower concentrations but promotes condensation at higher concentrations. Although intercalation with side chains positioned in the minor/major groove is the major binding mode in GC-rich sequences, molecular modelling studies hint at an alternative binding mode in AT-rich sequences where it exclusively displays pure electrostatic interaction. These findings underscore the pivotal role of both drug structure and base sequence in dictating binding mode and affinity. Such insights not only deepen the understanding of structure-activity relationships but also hold promise for guiding future drug design strategies.

Chemical constituents from the soil fungus Penicillium sp. DWS853 and their cytotoxic activity

A total of fourteen compounds, including two previously undescribed depside derivatives penicidepsides A (1) and B (2), three phenyl ether derivatives (3–5), three benzophenone derivatives (6–8), four anthraquinone derivatives (9–12), one flavonoid derivative (13), and one bisnaphthalene derivative (14), were isolated from the solid-state fermentation medium of fungus Penicillium sp. DWS853. The structures of these compounds were determined through comprehensive analysis of UV, HRESIMS, and 1D/2D NMR spectroscopic data, along with quantum-chemical calculations. In vitro bioactivity assays showed that questin (9) exhibits cytotoxicity against human colorectal cancer HCT116 cell line, and can induce apoptosis and inhibit its migration/invasion in a dose-depended manner. The potential target of the active compound was implied to be DNA topoisomerase II, using similarity ensemble search, molecular docking, and quantum chemical calculations.

Efficient thermally activated delayed fluorescence materials from symmetric anthraquinone derivatives for high-performance red OLEDs

Constructing efficient red thermally activated delayed-fluorescence (TADF) materials for high-performance organic light-emitting diodes (OLEDs) remains challenging due to the formidable barrier of energy gap law. In this work, a design strategy of connecting two donor units to the adjacent positions of electron acceptor is proposed for creating red luminescent materials, and four Y-shaped TADF molecules consisting of strong electron-withdrawing anthraquinone (AQ) acceptor and triphenylamine or acridine-based donors are designed and synthesized. They exhibit strong red emissions (604−618 nm) in toluene solutions and orange/red emissions (566−608 nm) with good photoluminescence quantum yields (43−68%) in doped films, and enjoy small singlet-triplet energy gaps (0.02−0.10 eV) and fast reverse intersystem crossing processes (1.5–7.3 × 105 s−1), which are attributed to the unique Y-shape structure. A maximum external quantum efficiency of 19.5% with an electroluminescence peak at 616 nm is achieved for AQ-PTPA-based red doped device, representing the highest level for red TADF-OLEDs based on AQ acceptor in the literature. This work can provide guidance for the design of efficient red delayed-fluorescence molecules for the application in OLEDs.

Exploring naphthoquinone and anthraquinone derivatives as antibiotic adjuvants against Staphylococcus aureus biofilms: Synergistic effects of menadione

Given the ability of Staphylococcus aureus to form biofilms and produce persister cells, making infections difficult to treat with antibiotics alone, there is a pressing need for an effective antibiotic adjuvant to address this public health threat. In this study, a series of quinone derivatives were evaluated for their antimicrobial and antibiofilm activities against methicillin-susceptible and methicillin-resistant S. aureus reference strains. Following analyses using broth microdilution, growth curve analysis, checkerboard assay, time-kill experiments, and confocal laser scanning microscopy, menadione was identified as a hit compound. Menadione exhibited a notable antibacterial profile (minimum inhibitory concentration, MIC = 4–16 μg/ml; minimum bactericidal concentration, MBC = 256 μg/ml) against planktonic S. aureus and its biofilms (minimum biofilm inhibitory concentration, MBIC50 = 0.0625–0.25 μg/ml). When combined with oxacillin, erythromycin, and vancomycin, menadione exhibited a synergistic or additive effect against planktonic cells and biofilms of two S. aureus reference strains and six clinical isolates, highlighting its potential as a suitable adjuvant for further development against S. aureus biofilm-associated infections.

An anthraquinone derivative for modulating the energy levels of polysulfide molecular orbitals to enhance the kinetics of redox reactions

The shuttle effect of lithium polysulfides (LiPSs) and the slow kinetics of sulfur redox reactions severely hinder the commercialization of lithium-sulfur (Li–S) batteries. In this study, 2,6-dihydroxyanthraquinone (DHAQ) is absorbed onto the surface of carbon materials through π-π interactions to facilitate the adsorption and catalytic conversion of LiPSs. Electrostatic potential (ESP) results indicate that introducing hydroxyl groups into the molecule enhances the carbonyl group's ability to adsorb LiPSs and thereby facilitates the formation of covalent Li-O bonds for their immobilization. The interaction between DHAQ and LiPSs results in a complex with a higher energy level for the highest occupied molecular orbital (HOMO) and a lower energy level for the lowest unoccupied molecular orbital (LUMO). This leads to enhanced redox activity, which accelerates the kinetics of LiPSs conversion reactions. Consequently, the S@DHAQ/C composite demonstrates a capacity decay rate of just 0.040 % per cycle after 600 cycles at 1 C. At a sulfur loading of 5 mg cm−2, it retains an initial discharge specific capacity of 643 mAh g−1 at 0.2 C. This work introduces a novel approach to improving polysulfide adsorption capacity through organic molecules while also accelerating the kinetics of redox reactions.

Antiviral Activity of Rhein against Enterovirus 71 through Inhibiting Viral Replication and Stability

Background: Enterovirus 71 (EV71) is one of the most prevalent pathogens responsible for hand, foot, and mouth disease in the Asia-Pacific region. Severe EV71 infections can be fatal in children under the age of 5. As of now, there are no proven anti-EV71 drugs available. Rhein is an anthraquinone derivative, mainly derived from rhubarb plants. Several beneficial pharmacological properties of rhein have been linked to anti-inflammatory, antioxidant, anticancer, and antiviral effects. Aim: This research aims to evaluate rhein’s antiviral activity against Enterovirus EV71 in vitro. Methods: The cytotoxicity of rhein was assessed using a Cell Counting Kit-8 kit. The antiviral activities of rhein were characterized by viral RNA level, protein expression level, and infectious ability using quantitative reverse transcription polymerase chain reaction, Western blot assay, and immunofluorescence assay, respectively. The mechanism by which rhein suppresses virus life cycles was examined utilizing a time-of-addition assay. An inactivation assay was performed to evaluate whether rhein directly impaired the virion stability. Results: The findings indicated that rhein exhibited anti-EV71 activity by reducing viral RNA synthesis, protein expression, and infectivity. Rhein demonstrates potent antiviral effects against EV71 at the late-life stage and inhibition of virion stability. Conclusion: Our findings strongly support further research into rhein as a potential treatment for EV71.

Intramolecular charge transfer dynamics of anthraquinone derivatives in the confined environments of reverse micelles

Reverse micelles (RMs) are considered important model systems for molecular dynamics and chemical reactions, where the nanopools of aqueous and nonaqueous polar cores are separated from the surrounding organic phase via a monolayer of surfactant molecules. Here, we report the intramolecular charge transfer (ICT) dynamics of anthraquinone derivatives in the methanol-in-oil RMs composed of nonionic surfactants Igepal by femtosecond transient absorption and fluorescence upconversion spectroscopy. The ICT dynamics slow down inside the RMs due to abnormally diminished solvent motions and restricted internal rotations of the (methyl)amino group during the ICT in the excited states. The micelle size-dependent dynamics of anthraquinone derivatives inside the RMs were compared with the results in bulk aliphatic alcohols and understood as the changes in the microenvironment properties such as microviscosity.

Two-electron sulfonyl(trifluoromethanesulfonyl)imide-anthraquinone redox electrolytes for high-energy density supercapacitors

Organic redox electrolyte-enhanced electrochemical double layer capacitors (ORECs) are potentially better solution for combining both high power and energy density. The critical factor of ORECs is to develop high-performance organic redox electrolytes. Anthraquinone (AQ) derivatives are the promising organic redox electrolyte candidates because of their low redox potential and fast two-electron redox kinetics. Low solubility and poor longevity in aprotic solvents of charged AQ species are main issues for effective enhancement. Here we report two-electron redox ionic compounds by functionalizing AQ with a robustly electron-withdrawing sulfonyl(trifluoromethanesulfonyl)imide (AQSTFSI) anion and pairing counter monovalent cations for high-performance ORECs. The highly electron-conjugate substitute markedly stabilizes the radical and 2e−-charged forms of AQ by decentralizing the electron density of the CO heads, preventing the adverse reaction of electrophilic/nucleophilic attack, revealing by theoretical simulation. Also, the STFSI− substituent enables AQSTFSI-compounds significantly improved solubility, thermostability, and redox reversibility. Consequently, the AQSTFSI-K applied in OREC shows all-roundly superior performance containing 3.2 V cell voltage, specific energy of 58 Wh kg−1 with 1.8 times of corresponding electrochemical double layer capacitors (EDLCs), specific power over 8 kW kg−1, cycling stability over 12,000 cycles, low self-discharge, and wide working-temperature range. This molecular strategy grounded on electron density modulation of redox electrolyte structures provides valuable insights into the design for high-performance ORECs in practical applications.