Ring Linkage Research Articles

Structural, electronic and optical properties of Halogen (F and Cl) atoms doped Graphdiyne

Abstract This paper reports the results of a density functional theory investigation of structural, electronic, and optical properties of halogen (fluorine and chlorine) atoms doped graphdiyne. Graphdiyne is doped with fluorine and chlorine with three different doping configurations each where one, two and three atoms of fluorine and chlorine were doped into Graphdiyne at benzene ring and acetylene linkages. The most stable doped structure was determined using the results of formation energy. Monolayers for fluorine and chlorine doped graphdiyne uniformly display metallic characteristics except where two atoms were incorporated shows semiconductor characteristics. PDOS shows that the energy band near the Fermi level is mainly contributed by the C 2p orbitals. Doped configurations shows higher peak intensities and good absorption in the UV, visible light region and IR region. These findings offer a fundamental basis for the understanding and manipulation of electrical and optical properties for doped graphdiyne with halogen atoms atoms and it is suitable for promoting the potential application of graphdiyne based electronic and opto-electronic device applications operating mainly in infrared and ultraviolet range.

New oligomeric terpenoids fused with an oxazoline ring linkage from cones of Taxodium ascendens and their biological activities

Taxodascaloids A-C (1–3), three uncommon oligomeric terpenoids featuring an oxazoline ring linkage, were purified from the cones of Taxodium ascendens. Compounds 1 and 2, a unique pair of stereoisomers, represented the first identified diterpenoid-monoterpenoid adducts linked by an oxazoline ring. Compound 3 was an uncommon dimeric diterpenoid and composed of a seco-abietane unit and an abietane unit, also containing an oxazoline ring. The planar structures and absolute configurations of these compounds were determined using extensive spectroscopic analysis and X-ray diffraction techniques. Compounds 1 and 2 demonstrated potent anticancer activity against human colon cancer HCT cells, with the IC50 values of 25.7 and 40.1 μM, respectively. Further research indicated that compound 1 could induce both ferroptosis and apoptosis in HCT-116 cells. Additionally, compound 3 showed notable α-glucosidase inhibitory activity in a mixed-type manner with an IC50 value of 2.9 μM.

Changing Benzoxazole Ring into Nonring Imine Linkages on Covalent Organic Frameworks with Tuning H2O2 Photosynthesis Performance.

Two π-conjugated covalent organic frameworks (COFs) with nonring imine or benzoxazole ring linkages were prepared by reacting 3,3'-dihydrooxybenzidine (BDOH) with 3,5-triformylbenzene (Tb) in the presence or absence of benzimidazole (BDOH-Tb-IM and BDOH-Tb-BO). Although two COFs indicated similar composition, crystalline structures, and morphologies, imine-based BDOH-Tb-IM exhibited a photocatalytic H2O2 production rate of 2490 μmol·g-1·h-1 in sacrificial reagent-free pure water, higher than that of benzoxazole-based BDOH-Tb-BO-a (1168 μmol·g-1·h-1). The higher photocatalytic activity of BDOH-Tb-IM was attributed to its more efficient photoinduced charge separation and utilization efficiency and different 2e- ORR active sites over the two COFs. This study demonstrated an available ring effect to adjust photocatalytic performance between π-conjugated COFs.

Biphenyls embedded Schiff base-bis esters: self-assembling behaviour, impact of additional aromatic ring and ester linkage and their DFT investigations

ABSTRACT In the present investigation, two series of biphenyl embedded Schiff base-bis esters alkyl-(E)-4-(((4’-(decyloxy)-[1,1’-biphenyl]-4-yl)methylene)amino)-benzoate, BPK-(2–18) and alkyl-(E)-4-(((4’-((4-(decyloxy)benzoyl)oxy)-[1,1’-biphenyl]-4-yl)-methylene)amino)benzoate, BPEK-(8–18) containing either terminal alkoxy biphenyl core or central biphenyl core have been synthesised and studied for their self-assembling behaviour. The compounds of both series demonstrated enantiotropic liquid crystal properties, displaying typical calamitic mesophases (Smectic A (SmA), Smectic C (SmC)) across a broad temperature range and with high thermal stability. The bimorphic behaviour of new molecules has been investigated by VT-XRD analysis. The density function theory has been done to illustrate the experimental results of the mesomorphic properties of the studied compounds. Several parameters have been calculated such as molecular geometry, dipole moment, polarisability, aspect ratio, etc. The results showed that more planar compounds will attain more packed structures leading to the formation of more ordered smectic phases.

Pyridine‐Based Covalent Organic Frameworks with Pyridyl‐Imine Structures for Boosting Photocatalytic H2O2 Production via One‐Step 2e− Oxygen Reduction

AbstractBipyridine‐based covalent organic frameworks (COFs) have emerged as promising contenders for the photocatalytic generation of hydrogen peroxide (H2O2). However, the presence of imine nitrogen alters the mode of H2O2 generation from an efficient one‐step two‐electron (2e−) route to a two‐step 2e− oxygen reduction pathway. In this work, we introduce 3,3′‐bipyridine units into imine‐based COF skeletons, creating a pyridyl‐imine structure with two adjacent nitrogen atoms between the pyridine ring and imine linkage. This unique bipyridine‐like architecture can effectively suppress the two‐step 2e− ORR process at the single imine‐nitrogen site, facilitating a more efficient one‐step 2e− pathway. Consequently, the optimized pyridyl‐imine COF (PyIm‐COF) exhibits a remarkable H2O2 production rate of up to 5850 μmol h−1 g−1, nearly double that of pristine bipyridine COFs. This work provides valuable insight into the rational design of functionalized COFs for enhanced H2O2 production in photocatalysis.

Pyridine-Based Covalent Organic Frameworks with Pyridyl-Imine Structures for Boosting Photocatalytic H2O2 Production via One-Step 2e- Oxygen Reduction.

Bipyridine-based covalent organic frameworks (COFs) have emerged as promising contenders for the photocatalytic generation of hydrogen peroxide (H2O2). However, the presence of imine nitrogen alters the mode of H2O2 generation from an efficient one-step two-electron (2e-) route to a two-step 2e- oxygen reduction pathway. In this work, we introduce 3,3'-bipyridine units into imine-based COF skeletons, creating a pyridyl-imine structure with two adjacent nitrogen atoms between the pyridine ring and imine linkage. This unique bipyridine-like architecture can effectively suppress the two-step 2e- ORR process at the single imine-nitrogen site, facilitating a more efficient one-step 2e- pathway. Consequently, the optimized pyridyl-imine COF (PyIm-COF) exhibits a remarkable H2O2 production rate of up to 5850 μmol h-1 g-1, nearly double that of pristine bipyridine COFs. This work provides valuable insight into the rational design of functionalized COFs for enhanced H2O2 production in photocatalysis.

Synthesis and interaction with growth factors of sulfated oligosaccharides containing an anomeric fluorinated tail

Compounds that mimic the biological properties of glycosaminoglycans (GAGs) and can be more easily prepared than the native GAG oligosaccharides are highly demanded. Here, we present the synthesis of sulfated oligosaccharides displaying a perfluorinated aliphatic tag at the reducing end as GAG mimetics. The preparation of these molecules was greatly facilitated by the presence of the fluorinated tail since the reaction intermediates were isolated by simple fluorous solid-phase extraction. Fluorescence polarization competition assays indicated that the synthesized oligosaccharides interacted with two heparin-binding growth factors, midkine (MK) and FGF-2, showing higher binding affinities than the natural oligosaccharides, and can be therefore considered as useful GAG mimetics. Moreover, NMR experiments showed that the 3D structure of these compounds is similar to that of the native sequences, in terms of sugar ring and glycosidic linkage conformations. Finally, we also demonstrated that these derivatives are able to block the MK-stimulating effect on NIH3T3 cells growth.

Unprecedented Benzoquinone Motifs Reveal Post-Oligomerizational Modification of Proanthocyanidins.

Proanthocyanidins (PACs) are complex flavan-3-ol polymers with stunning chemical complexity due to oxygenation patterns, oxidative phenolic ring linkages, and intricate stereochemistry of their heterocycles and inter-flavan linkages. Being promising candidates for dental restorative biomaterials, trace analysis of dentin bioactive cinnamon PACs now yielded novel trimeric (1 and 2) and tetrameric (3) PACs with unprecedented o- and p-benzoquinone motifs (benzoquinonoid PACs). Challenges in structural characterization, especially their absolute configuration, prompted the development of a new synthetic-analytical approach involving comprehensive spectroscopy, including NMR with quantum mechanics-driven 1H iterative functionalized spin analysis (HifSA) plus experimental and computational electronic circular dichroism (ECD). Vital stereochemical information was garnered from synthesizing 4-(2,5-benzoquinone)flavan-3-ols and a truncated analogue of trimer 2 as ECD models. Discovery of the first natural benzoquinonoid PACs provides new evidence to the experimentally elusive PAC biosynthesis as their formation requires two oxidative post-oligomerizational modifications (POMs) that are distinct and occur downstream from both quinone-methide-driven oligomerization and A-type linkage formation. While Nature is known to achieve structural diversity of many major compound classes by POMs, this is the first indication of PACs also following this common theme.

Design, Synthesis, and Anti-tumor Activity of Novel 2-Aryl Benzimidazole Compounds.

Combretastatin A-4 (CA-4) is a natural product isolated from the bark of the South African bush willow tree Combretum caffrum, which exerts tubulin inhibition, but its clinical application is limited due to poor stability and water solubility. 2-aryl benzimidazoles are excellent pharmacological skeletons with many activities, especially in tumor inhibition, and better pharmacokinetic properties. Several scaffold CA-4 analogs have been synthesized to date possessing antitumor activities. The benzimidazole was applied as the core moiety to replace the B ring and unstable linkage of CA-4, and the 5-aryl acetenyl group was introduced to improve the antitumor activity. MCF-7, A549, Caco-2, Siha, and Eca-109 tumor cell lines were used to study inhibition by these agents in vitro. The benzimidazole structure was constructed from the oxidation of o-nitroaniline and aldehyde and the following schemes, and the structural characterization was carried out. The antitumor effects were evaluated in vitro through MTT assay, cell cycle arrest, and apoptosis assay. Molecular docking with tubulin (Protein ID: 1SA0) was analyzed for the structure-activity relationship. Among these derivatives, 4a-4h series (with 6-methoxy group) compounds inhibited the tumor cell lines much stronger than the CA-4 and cisplatin, especially compound 4f showed prominently inhibitory activity in Siha cell with IC50 value as 0.61 μmol/L. The further assay showed that the cell cycle was arrested at the G0/G1 phase as well verified in apoptosis assay. Molecular docking indicated that 4f had stronger affinity energy and hydrogen bond than CA-4. The compound 4f has the potency to be used as an anti-tubulin agent and the 2-trimethoxyphenyl benzimidazole skeleton deserves further study as an antitumor structure.

Primary Structure of Glycans by NMR Spectroscopy.

Glycans, carbohydrate molecules in the realm of biology, are present as biomedically important glycoconjugates and a characteristic aspect is that their structures in many instances are branched. In determining the primary structure of a glycan, the sugar components including the absolute configuration and ring form, anomeric configuration, linkage(s), sequence, and substituents should be elucidated. Solution state NMR spectroscopy offers a unique opportunity to resolve all these aspects at atomic resolution. During the last two decades, advancement of both NMR experiments and spectrometer hardware have made it possible to unravel carbohydrate structure more efficiently. These developments applicable to glycans include, inter alia, NMR experiments that reduce spectral overlap, use selective excitations, record tilted projections of multidimensional spectra, acquire spectra by multiple receivers, utilize polarization by fast-pulsing techniques, concatenate pulse-sequence modules to acquire several spectra in a single measurement, acquire pure shift correlated spectra devoid of scalar couplings, employ stable isotope labeling to efficiently obtain homo- and/or heteronuclear correlations, as well as those that rely on dipolar cross-correlated interactions for sequential information. Refined computer programs for NMR spin simulation and chemical shift prediction aid the structural elucidation of glycans, which are notorious for their limited spectral dispersion. Hardware developments include cryogenically cold probes and dynamic nuclear polarization techniques, both resulting in enhanced sensitivity as well as ultrahigh field NMR spectrometers with a 1H NMR resonance frequency higher than 1 GHz, thus improving resolution of resonances. Taken together, the developments have made and will in the future make it possible to elucidate carbohydrate structure in great detail, thereby forming the basis for understanding of how glycans interact with other molecules.

A computational insight into the intrinsic, Si-decorated and vacancy-defected γ-graphyne nanoribbon towards adsorption of CO2 and O2 molecules

In this study, the effects of decorating a silicon (Si) atom and applying a single vacancy defect on an armchair γ-graphyne nanoribbon (A-γ-GyNR) are investigated toward CO2 and O2 molecules adsorption. The magnetic and electronic transport properties, including the calculation of adsorption energy, charge transfer, magnetic moment, band structure, phonon dispersion and density of state (DOS), have been studied using the spin-polarized density functional theory (DFT) method. The stability of the proposed substrates is measured and different positions for gas molecules are considered. The results reveal that the highest amounts of adsorption energy of CO2 (0.63 eV) and O2 (2.2 eV) molecules belong to the substrate decorated with the Si atom in the 12-membered ring (H1) and acetylene linkage (B3), respectively. In addition, the removal of a carbon atom with sp hybridization improves the O2 molecule adsorption by 3.34 times compared to the primary substrate (P-GyNR). According to the recovery time calculations, the most appropriate desorption time is related to T1-M1 model. The current–voltage characteristic confirms that the resistance of the introduced sensors fully changed after sensing. This work can be considered as an effective step toward understanding and developing A-γ-GyNR-based gas sensors.

Design, synthesis, characterization, antioxidant, antiproliferative activity and molecular docking studies of new transition metal complexes of 1,2,4-triazole as combretastatin A-4 analogues

In the present work, we introduce new transition metal complexes. The complexes are designed to have 3,4,5-trimethoxyphenyl and 2‑hydroxy-4-methoxyphenyl groups connected by 1,2,4-triazole ring and imine linkage to be proper analogues for the anti-tubulin agent combretastatin A-4. FT-IR, 1H NMR, 13C NMR, mass spectrometry, CHNS, thermal gravimetric analysis (TGA-DSC), magnetic susceptibility, conductivity measurements, UV–Vis spectrophotometry, and flame atomic absorption spectroscopy have been used for the characterization of the synthesized compounds. The observed analytical and spectral data confirmed the octahedral environment around cobalt(II), platinum(IV) and square planar around nickel(II), copper(II) and palladium(II) ions. The antioxidant activity of the synthesized complexes was assessed by the DPPH assay, the obtained results showed that C4 is the most active one, with a scavenging capacity of 87.6% in comparison with ascorbic acid as a reference antioxidant agent at 50 µg/mL. The new metal complexes were screened for anticancer activity by the MTT assay against the breast cancer cell line MCF-7 and normal cell line WRL-68. The obtained results revealed that the lowest IC50 24.38 µM was recorded for palladium complex (C4) against the cancer cell line MCF-7,and an IC50 value of 90.2 µM against the normal cell line WRL-68. The synthesized compounds were also subjected to theoretical DFT studies, the obtained results came in agreement with the experimental results. The new ligand and its metal complexes were subjected to molecular docking studies, the structures were docked with the colchicine binding site (PDB: 1SA0), and good docking scores were recorded.

Phenolic Foams Toughened with Triethylene Glycol by In Situ Polymerization and Prepolymerization Processes

The current work presents the study of the toughening effect of in situ polymerization modification process (In-MP) and prepolymerization modification process (Pre-MP) on triethylene glycol (TEG)-modified phenolic foams (PFs). TEG in situ polymerization-modified phenolic resin (T-In-PR) and TEG prepolymerization-modified phenolic resin (T-Pre-PR) with different molecular structures have been synthesized by two processes using TEG as a modifier. The comparison of the molecular structure and properties of the resins shows that the molecular weight distribution of T-Pre-PR is uniform and its basic properties of resin are better than T-In-PR. The number of benzene ring linkage bridges in the T-Pre-PR structure increases from three to four, which can improve the toughness while stabilizing the intermolecular connection strength. The TEG-modified PFs prepared with TEG-modified phenolic resins exhibit excellent toughness. The fracture displacement of T-Pre-PF was 85.13% higher than those of ordinary PFs, and the pulverization rate was 55.85% lower than those of ordinary PFs. Compared with T-In-PF, the cell shapes of T-Pre-PF were uniform polygonal structures and formed a stable honeycomb-like structure. The cell size distribution of T-Pre-PF was more concentrated than those of T-In-PF and ordinary PFs, and the level of damage of cell wall was low. The maximum bending strength of T-Pre-PF was 0.263 MPa, and the maximum compression strength was 0.160 MPa, which were higher than those of T-In-PF. The findings demonstrate that Pre-MP is more suitable for the preparation of PFs with internal toughening modification by TEG than In-MP.

Prediction of oil-fired boiler emissions with ensemble methods considering variable combustion air conditions

Exhaust gases emitted from ships in ports pose a number of concerns. Together with the increasing trend of logistics transportation by ships, air pollutants generated from ships in ports cannot be ignored. Therefore, in this study, an oil-fired boiler in a training ship, continuously operating in a port was subjected to various air/fuel ratio conditions, and its emissions were measured. The air/fuel ratio was adjusted by changing the position of the adjustment ring and air damper linkage of the boiler burner. Installing expensive equipment, such as gas analyzers in boilers is economically prohibitive for shipping companies; thus, emission prediction using data-driven modeling can be an alternative method. The collected ship and exhaust gas data were compressed in three ways to create three different datasets, and ensemble data were created by combining them. The support vector machine (SVM), XGBoost, artificial neural networks (ANN), and least squares SVM (LS-SVM) were used as base model, and base ensemble models were created. Furthermore, double ensemble models were created by using the base ensemble models as the foundation. It was confirmed that the ensemble data and the double ensemble method yielded significant predictions of the emissions. Moreover, these results were verified through a new dataset, confirming the superiority and generalization of the proposed method.

Sonocatalytic degradation of ciprofloxacin by BiOBr/BiFeO3

A novel BiOBr/BiFeO3 heterojunction sonocatalyst was prepared and characterized. The sonocatalytic activity of BiOBr/BiFeO3 composite was evaluated by the catalytic degradation of ciprofloxacin. BiOBr/BiFeO3 composite combined with persulfate had excellent sonocatalytic activity for ciprofloxacin degradation under ultrasonic irradiation, and the degradation rate was 73.64% ± 7.96%. The formation of Z-type heterojunction of BiOBr/BiFeO3 and the generation of hydroxyl radical, superoxide anion and hole were the key to the catalytic activity of BiOBr/BiFeO3. Free radicals will attack the positions of piperazine ring, cyclopropyl, C-F bond, carboxyl group and ethylenic linkage in ciprofloxacin structure, and gradually degrade ciprofloxacin through multiple paths. After the sonocatalytic degradation, the bacteriostatic effect of the solution decreased significantly and the environmental pollution decreased significantly. As a sonocatalyst, BiOBr/BiFeO3 composite has good degradation and removal effect on ciprofloxacin and has practical application potential. Meanwhile, it lays a foundation for the further practical application of sonocatalytic degradation technology.

Synchrotron X-ray assisted degradation of industrial wastewater by advanced oxidation process

Various methods for the degradation and detoxification of textile effluents have been developed in recent years and among these, advanced oxidation processes (AOPs) have been proven to be a successful way of degrading organically contaminated water into a useful form. The synchrotron X-ray (3–20 keV) irradiation-assisted AOP has been developed for the degradation of single and mixed colored industrial wastewater solution. Irradiation experiments were conducted on industrial effluents obtained straight from the cloth industries. The efficiency of AOP was measured by characterizing irradiated industrial wastewater solutions with optical, chemical, and biological characterization techniques. The UV-Vis spectroscopy and chemical oxidation demand (COD) results revealed that the wastewater was degraded and the degradation efficiency could be tailored by varying the X-ray dose. The complete decolorization and ∼ 85% removal in COD was obtained at the X-ray dose of 15000 mAs. Chemical species present in pristine and irradiated wastewater were analyzed using FTIR techniques. The FTIR spectra revealed the destruction of the aromatic ring and nitrogen linkage of wastewater under X-ray irradiation. The technique of liquid chromatography-mass spectroscopy (LC-MS) was employed to identify and quantify the unknown compounds present in pristine as well as X-ray irradiated wastewater solutions. Toxicity assays on gram-negative Escherichia coli (DH5α) clearly show detoxification of X-ray irradiated solutions. This study demonstrates a fast and effective approach for completely degrading and detoxifying industrial wastewater, and has a wide range of applications in environmental remediation.

Potent biological investigation into a new class of sulfone derivatives endowed with quinolinyl–cyclopropane analogue

Novel series of quinoline derivatives incorporating cyclopropyl ring and sulfone linkage as substituents have been synthesized, and oxidation of ethyl-2-cyclopropyl-4-(substituted phenylthio)quinoline-3-carboxylate was carried out to set ethyl-2-cyclopropyl-4-(substituted phenyl sulfonyl)quinoline-3-carboxylate. An ecofriendly synthesis of sulfone derivatives was carried out by the reaction of glacial acetic acid and 30% hydrogen peroxide at room temperature. The synthesized quinoline incorporating sulfone linkage derivatives was evaluated for their anticipated antimicrobial activity as well as characterized by their melting point, mass spectra, IR, 1H NMR and 13C NMR spectra. For proving the structural biological activity, herein we have carried out SAR and HOMO–LUMO studies. From these studies, we have found some best results as their energy gap is very low which makes their activity higher, i.e. compounds 11a, 11b, 11h, 11k and 11m.Graphical abstract

Trimeric and dimeric Aspidosperma-type alkaloids from leaves of Tabernaemontana divaricata 'Dwaft'

Continued interest in bioactive monoterpenoid indole alkaloids and the purpose to explore the artificial cultivation influence on the chemical composition in the same plant species, 8 undescribed Aspidosperma-type alkaloids including two unprecedented trimers, taberdivarines A–B (1–2), and six new dimers, taberdivarines CH (3–8), together with 9 known bisindoles were isolated from the leaves of Tabernaemontana divaricata 'Dwaft'. Notably, taberdivarines A and B were the first cases of Aspidosperma-Aspidosperma-Aspidosperma-type alkaloids with furan ring linkage patterns of the natural products. Their structures were elucidated by comprehensive spectroscopic analyse. Compounds 1–8 were screened for the cytotoxicity against three human cancer cell lines, SMMC-7721, HT-29 and A549. Among them, Compound 6 exhibited significant activity against three cell lines with IC50 values of 0.30, 0.75 and 3.41 μM, respectively (IC50 = 3.02, 0.14 and 2.23 μM for the positive control, vinorelbine). Compound 1, 3, 4, 6, 7 and 8 also expressed varying degrees of activity. The structure–activity relationships (SARs) of these alkaloids were discussed.

High-Voltage-Tolerant Covalent Organic Framework Electrolyte with Holistically Oriented Channels for Solid-State Lithium Metal Batteries with Nickel-Rich Cathodes.

By introducing lithiophilic groups and electrochemically stable quinolyl aromatic ring linkages, we prepared covalent organic frameworks (COFs) exhibiting a large band gap with an ultralow HOMO value (-6.2 eV under vacuum) and oxidative stability up to 5.6 V (versus Li+ /Li) as solid-state electrolytes (SSEs). The obtained flexible COF SSE thin films showed a holistically oriented arrangement along the (001) facet with remarkable ionic conductivity up to 1.5×10-4 S cm-1 at 60 °C and excellent mechanical strength with a high Young's modulus of 10.5 GPa. Molecular dynamic simulations showed that lithium ions are transmitted in this COF SSE by directional hopping paths with fast drift velocity. The COF SSE film was used to assemble all-solid-state lithium metal batteries with nickel-rich cathodes (NMC811). The batteries demonstrated stable cycling performance over 400 cycles, high coulombic efficiency (>99 %), and could also withstand abuse tests, such as folding.

High‐Voltage‐Tolerant Covalent Organic Framework Electrolyte with Holistically Oriented Channels for Solid‐State Lithium Metal Batteries with Nickel‐Rich Cathodes

AbstractBy introducing lithiophilic groups and electrochemically stable quinolyl aromatic ring linkages, we prepared covalent organic frameworks (COFs) exhibiting a large band gap with an ultralow HOMO value (−6.2 eV under vacuum) and oxidative stability up to 5.6 V (versus Li+/Li) as solid‐state electrolytes (SSEs). The obtained flexible COF SSE thin films showed a holistically oriented arrangement along the (001) facet with remarkable ionic conductivity up to 1.5×10−4 S cm−1 at 60 °C and excellent mechanical strength with a high Young's modulus of 10.5 GPa. Molecular dynamic simulations showed that lithium ions are transmitted in this COF SSE by directional hopping paths with fast drift velocity. The COF SSE film was used to assemble all‐solid‐state lithium metal batteries with nickel‐rich cathodes (NMC811). The batteries demonstrated stable cycling performance over 400 cycles, high coulombic efficiency (>99 %), and could also withstand abuse tests, such as folding.