Carbonyl Molecules Research Articles

Comparison and study on the asymmetric uranyl—salophen to the single carbonyl molecules

Theoretical study of the asymmetric uranyl−salophen (AUS) on the unsaturated aldehyde or ketone is a focus of present research. This study underlines the complexes of asymmetric uranyl−salophen (as modified by unilateral benzene) to single carbonyl molecules, including formaldehyde, acetone, cyclopentanone, and cyclohexanone, using the density functional theory of quantum chemistry. Our results suggest that the C=O double bond of the single carbonyl molecules is weakened by the asymmetric uranyl−salophen. Both the negative charge of oxygen atoms and the positive charge of carbon atoms from the C=O bond of the single carbonyl have increased, and the binding energies and stability between asymmetric uranyl−salophen and acetone, cyclopentanone, or cyclohexanone were higher than that of formaldehyde. These new findings could be used as an important reference for the study of other complexes that the asymmetric uranyl−salophen to the complex carbonyl molecules.

Perylenedianhydride-Based Polyimides as Organic Cathodes for Rechargeable Lithium and Sodium Batteries

Organic carbonyl molecules have recently been investigated as redox-active electrode materials in rechargeable organic batteries (ROBs), and although redox-active polymers offer high specific energ...

Organocatalysis Combined with Photocatalysis.

Over the past decade, the combination of visible light photocatalysis and organocatalysis has made remarkable progress in modern chemical synthesis. In these dual catalysis system, photocatalysts or photosensitizers absorb visible light to induce their photoexcited states which can activate unreactive substrates via electron or energy transfer mechanisms, and organocatalysts are usually employed to regulate the chemical reactivity of the other substrates. By doing so, two reactive species react with each in a selective-especially enantioselective-way, to provide the final products. This article summarizes the recent development of cooperative catalysis by the combination of organocatalysis and photocatalysis in asymmetric organic synthesis. These reactions are classified according to the manner of activation of the organocatalysts. Enamine/iminium catalysts are used to activate unreactive carbonyl molecules. Nucleophilic catalysts including nitrogen heterocycle carbene catalysts and tertiary amine catalysts are employed to reverse the reactivity of electrodeficient substrates including aldehydes and enals. Chiral Brønsted acid catalysts are used to activate substrates by forming key H-bonding complexes between substrates and catalysts.

Role of water in cyclopentanone self-condensation reaction catalyzed by MCM-41 functionalized with sulfonic acid groups

Water is ubiquitous in many catalytic reactions used in the upgrading of biomass. Therefore, quantifying and controlling the influence of water in activity, selectivity, and catalyst deactivation is essential for advancing this technology. Here, we report a kinetic study of the cyclopentanone self-condensation over functionalized MCM-41 catalysts with varying acid densities and in the presence of controlled amounts of water. It is observed that small amounts of water enhance the activity of these catalysts. A detailed analysis of the experimental data indicates that the rate limiting step is the enol formed via protonation and tautomerization of a cyclopentanone molecule attacks the electrophilic carbon of a second carbonyl. On catalyst with high density of sulfonic acid groups, the best fitting of the experimental data is obtained with a kinetic model in which the CC bond forming step mostly occurs with the second carbonyl molecule adsorbed (and polarized) by an adjacent acid site (Langmuir-Hinshelwood, L-H). By contrast, at a lower density of sulfonic acid groups, the number of active sites with enough proximity greatly decreases and the CC bond forming occurs with the second carbonyl in the liquid phase (Eley-Rideal, E-R). In this case, it is observed that when water is added to the reaction mixture, the best description of the kinetics switches from E-R to L-H. Evidently, the water can help bridging active sites remotely located on the surface, extending the polarizing effect of the second acid site.

Highly efficient Nb2O5 catalyst for aldol condensation of biomass-derived carbonyl molecules to fuel precursors

Aldol condensation is of significant importance for the production of fuel precursors from biomass-derived chemicals and has received increasing attention. Here we report a Nb2O5 catalyst with excellent activity and stability in the aldol condensation of biomass-derived carbonyl molecules. It is found that in the aldol condensation of furfural with 4-heptanone, Nb2O5 has obviously superior activity, which is not only better than that of other common solid acid catalysts (ZrO2 and Al2O3), more importantly, but also better than that of solid base catalysts (MgO, CaO, and magnesium-aluminum hydrotalcite). The detailed characterizations by N2 sorption/desorption, NH3-TPD, Py-FTIR and DRIFTS study of acetone adsorption reveal that Nb2O5 has a strong ability to activate the C=O bond in carbonyl molecules, which helps to generate a metal enolate intermediate and undergo the nucleophilic addition to form a new C–C bond. Furthermore, the applicability of Nb2O5 to aldol condensation is extended to other biomass-derived carbonyl molecules and high yields of target fuel precursors are obtained. Finally, a multifunctional Pd/Nb2O5 catalyst is prepared and successfully used in the one-pot synthesis of liquid alkanes from biomass-derived carbonyl molecules by combining the aldol condensation with the sequential hydrodeoxygenation.

Exploring Norrish type I and type II reactions: an ab initio mechanistic study highlighting singlet-state mediated chemistry.

Norrish reactions are important photo-induced reactions in mainstream organic chemistry and are implicated in many industrially and biologically relevant processes and in the processing of carbonyl molecules in the atmosphere. The present study reports multi-reference electronic structure calculations designed to assess details of the potential energy profiles associated with the Norrish type-I and type-II reactions of a prototypical ketone 5-methyl-hexan-2-one. We show that the well-established 'triplet state mediated' reaction pathways following initial population of a singlet excited state can be complemented by (hitherto rarely recognized) 'singlet state only' Norrish type-I and type-II reaction mechanisms that involve no spin-forbidden transitions along the respective reaction paths, and suggest how the efficiencies of such reactions might be affected by strategic substitutions at selected sites within the parent ketone.

Catalyst systems for the clean synthesis of nitrogen-containing fine chemicals based on the building and transformation of carbonyl-containing molecules

The clean synthesis of nitrogen-containing fine chemicals with wide applications in organic and pharmaceutical chemistry has attracted lots of attention. Meanwhile, the sustainable development for chemical industry is based on the clean conversion of fossil resource derived basic chemicals such as hydrocarbon, alcohols, CO, CO2 and amines. Therefore, it is very important to synthesize the nitrogen-containing fine chemicals by the effective and clean conversion of fossil resource derived basic chemicals. The synthesis of nitrogen-containing fine chemicals via building, activation and transformation of carbonyl-containing molecules is an effective way to realize it. The key point is to establish a highly active catalyst system for building and transformation of carbonyl-containing molecules. Our group has focused on the clean synthesis of the nitrogen-containing fine chemicals based on the building and transformation of carbonyl-containing molecules since 2008. Here, the main progress from our group in the catalytic amination based on the activation and conversion of C1 carbonyl molecules, the building of the intermediate containing carbonyl, and the establishment of the catalytic system bridging homogeneous and heterogeneous catalysis based on a catalytic cycle between C=O and CH–OH has been summarized.

Facile use of lignite as robust organic ligands to construct Zr-based catalysts for the conversion of biomass derived carbonyl platforms into alcohols

Use of lignite under mild conditions without destroying the natural functional groups and structures is a potential approach for the value-added utilization of lignite. Considering the abundant acidic functional groups in lignite, in this work, a novel and facile route using lignite as robust organic ligands to construct Zr-based catalysts was proposed, and the designed catalysts were applied in the conversion of biomass-derived carbonyl molecules into valuable chemicals. The universality of the proposed route for different rank coals and substrates with various structures were analyzed. Both the preparation conditions of the catalysts and the reaction parameters were systematically investigated. The obtained catalysts were characterized by SEM-EDS, XRD, FTIR, Raman, and TG, etc. The results demonstrated that the designed catalysts were highly efficient for the selective conversion of furfural into furfuryl alcohol. Under the optimized conditions, the conversion, yield, and selectivity were up to 93.4%, 81.0%, and 86.7%, respectively. Both the reaction conditions and the performances of the catalyst were competitive compared with analogous catalysts. It was proved that the catalyst was heterogeneous and the reusability could be improved through demineralization of lignite via acid washing before use, and the catalyst prepared by demineralized lignite had no obvious changes in both performances and structures after 5 reuses. The proposed route was also identified to be applicable for other low rank coals besides lignite, such as long flame coal and coking coal. The catalyst prepared using lignite was robustly effective for the conversion of various carbonyl compounds with different structures, indicating the broad universality for different substrates. Detailed characterization showed that the performances of the catalyst were jointly influenced by both Zr contents and surface areas of the catalyst. This novel route of constructing Zr-based catalysts using low rank coal as raw materials is highly potential for application in the utilization of low rank coals and biomass resources, with the advantages of high efficiency of the catalysts, low cost of raw materials, and simple preparing process.

Variability of free and glycosylated volatiles from strawberries destined for the fresh market and for processing, assessed using direct enzymatic hydrolysis

Free- and glycosylated-volatile profiles of 14 strawberry varieties, 9 for industrial processing (‘Darselect’, ‘Clery’, ‘Honey’, ‘Honeoye’, ‘Siabel’, ‘FCMO060’, ‘Fraise19’, 2 ‘Senga Sangana’) and 5 for fresh market (‘Gariguette’, ‘Charlotte’, ‘CIR121’, 2 ‘Clery’ (full-field and hydroponic)), were compared. All volatiles were analysed by GC-MS. Volatiles from glycosides were first released by direct enzymatic hydrolysis. The extraction method was optimised for furaneol, a key component of strawberry aroma. More than 60 volatile compounds were identified, the most abundant being butyl acetate (average: 17 mg/kg), furaneol (average: 2 mg/kg) and free hexanoic acid (average: 3 mg/kg). Free-volatile profiles showed a split between fresh market strawberries, distinguished by esters and carbonyl molecules like isobutyl acetate or hexanal, and strawberries for processing, distinguished by molecule like 3-penten-2-one and 1-butanol. The three ‘Clery’ profiles were different notably in their hexanal, 4-vinylguaiacol and 3-penten-2-one concentrations. The glycosylated volatile profiles were similar among most strawberry varieties with, as major glycosylated volatiles, hexanoic acid (average: 1.7 mg/kg), benzyl alcohol (average: 0.5 mg/kg), gamma-decalactone (average: 0.5 mg/kg) and coumaran (average: 2.5 mg/kg). The potential for volatile enhancement by deconjugation was different. Potentially fresh market strawberries had a volatile increase of 6% against 50% for strawberries for processing.

On the Mechanism of Trimethylphosphine-Mediated Reductive Dimerization of Ketones.

High-level single-reference calculations reveal that trimethylphosphine-mediated reductive dimerization of properly substituted (e.g., CF3) ketones proceeds via initial formation of an oxaphosphirane intermediate, with the oxygen atom occupying an equatorial position at phosphorus. In the "oxirane route", this oxaphosphirane intermediate loses a trimethylphosphine oxide unit, thus behaving as a carbene transfer agent toward a second carbonyl molecule and giving rise to a carbonyl ylide that cyclizates to the corresponding oxirane. This in turn transfers the carbene unit to a second phosphine molecule, with loss of acetone, affording a phosphorane. The latter undergoes typical Wittig reaction to the final homocoupling product through the oxaphosphetane intermediate. The alternative direct conversion of oxaphosphirane into phosphorane constitutes the lowest energy path as it skips the highest barrier oxirane → phosphorane conversion. The oxirane route is favored by the use of polar solvents and electron deficient carbonyl components. The lowest barrier most exergonic process from oxaphosphirane is the pericyclic cycloaddition of the acetone C═O bond along the endocyclic P-C bond, furnishing the stable 1,3,2-dioxaphospholane product.

Efficient Mukaiyama–Aldol Reaction with Aqueous Formaldehyde on a Hydrophobic Mesoporous Lewis Acid Polymer

AbstractThe design of robust water‐compatible solid Lewis acid catalysts in the efficient utilization of aqueous formaldehyde is a challenging task. Herein, we describe an ytterbium triflate containing ordered mesoporous polymer (Yb(OTf)2‐MP) that acts as a highly active and selective Lewis acid catalyst for the Mukaiyama–aldol reaction with aqueous formaldehyde. The unique capacity of hydrophobic surface and ordered mesoporosity was able to stabilize the hydrophilic and hydrophobic reactants simultaneously and catalyze the reaction selectively by minimizing water interference at active sites. Accordingly, it enabled a broad range of silyl enol ethers to be used to create structurally diverse β‐hydroxy carbonyl molecules efficiently. Notably, the process can be scaled up easily to achieve the gram‐scale production of the key intermediate of natural product sarkomycin. Additionally, it is stable under aqueous conditions and can be recovered easily and used repeatedly at least six times.

Entropy-Driven High Reactivity of Formaldehyde in Nucleophilic Attack by Enolates on Oxide Surfaces.

CH3OH dehydrogenation on a metal function occurs in tandem with C-C coupling of HCHO with enolates derived from alkanals or alkanones on acid-base pairs at anatase TiO2 surfaces with very high specificity for nucleophilic attack by enolates on HCHO over larger carbonyl molecules. The measured rate constants for enolate coupling with HCHO are >103-fold larger than for its coupling with acetone. Free energies derived from theoretical treatments of reactions between C2-C4 bound enolates and carbonyls show that such specificity for nucleophilic attack on HCHO reflects smaller entropy losses upon formation of the transition state (TS), instead of enthalpic effects caused by weaker steric effects or the stronger electrophilic character of HCHO compared with larger carbonyls. The easier steric access and higher electrophilicity of the carbonyl C atom of HCHO in C-C coupling with enolates are compensated by a later TS and by stronger van der Waals contacts for the corresponding reactions of the larger carbonyls. The preeminence of entropic effects over enthalpic stabilization reflects the greater structural organization imposed by surfaces on TS structures compared with similar reactions and structures in gaseous or liquid media. Such organization imposes significant entropic penalties that become least consequential for smaller electrophiles, thus enabling highly selective routes for sequential addition of C1 groups at nucleophilic C atoms in co-reactants using HCHO, whether added or formed in situ from CH3OH, as the monomer source. Such entropy-driven specificity is therefore a unique and unrecognized characteristic of reactions catalyzed by surfaces.

Enhanced adsorption of carbonyl molecules on graphene via π-Li-π interaction: a first-principle study

Carbonyl compounds with elements of C, H, and O and reversible redox-active centers are promising electrode materials in rechargeable batteries owing to their high theoretical capacity, structure flexibility and resources abundance. However, the low conductivity and the dissolution of active molecules in organic electrolyte limit the practical application. Immobilizing the carbonyls on graphene provides a simple approach to address these two issues. However, most reported interaction between carbon-based substrates and carbonyl compounds is weak π-π interaction, which is not strong enough to prohibit the detachment of active materials from carbon surface, and thus leading to undesirable cycling performance. Herein, we applied the first principle calculations to study the carbonyls-graphene interaction and found that the weak π-π interaction can be rationally converted to the strong π-Li-π interaction via introducing the groups containing Li atoms. The introduced Li atoms can cooperatively bind with the two aromatic π components through the covalent Li-carbonyl compounds interaction and Li-graphene interaction. The concept of π-Li-π interaction provides a versatile method to suppress the dissolution of active materials and increase the electronic conductivity at the same time, which gains insight into the design of organic electrode materials for rechargeable batteries with high performance.

Reaction behavior of the Collman reagent towards the nitrosyl carbonyls [CoNO(CO)3] and [Fe(NO)2(CO)2

Abstract Reactions of the Collman reagent, Na2[Fe(CO)4]·1.5 dioxane, towards the nitrosyl carbonyls [CoNO(CO)3] and [Fe(NO)2(CO)2] in THF as the solvent at room temperature were investigated. Thereby a quick transfer of one nitrosyl ligand from the nitrosyl carbonyl molecule to the iron carbonyl metalate was observed. The reaction with the cobalt compound afforded in high yields the well-known species [Co(CO)4]− and [FeNO(CO)3]− isolated by addition of two equivalents of [PPN]+Cl− ([PPN]+= bis(triphenylphosphane)iminium cation) and characterized by their known IR spectra, by elemental analysis and their characteristic colors and melting points. In the reaction of the Collman reagent with [Fe(NO)2(CO)2] a clean transformation to the tricarbonylnitrosylferrate(1−) as the only formed product was observed.

A theoretical study on the reaction mechanism and kinetics of allyl alcohol (CH2 = CHCH2OH) with ozone (O3) in the atmosphere

ABSTRACTVolatile organic compounds (VOCs) play a major role in the physical and chemical process of the tropospheric chemical reactions in both polluted and remote environments. A theoretical work has been presented on the VOC of allyl alcohol with O3 molecule is investigated using density functional theory methods. The reaction profile is initiated through the cycloaddition of ozone which leads to the formation of primary ozonide with minimal relative energy barrier of 1.31 kcal/mol which decomposes to form carbonyl molecule and carbonyl oxide. Carbonyl oxide, i.e. criegee intermediates reacts with various atmospheric species to produce more hazardous and toxic end products to the environment. The condensed form of Fukui function was calculated to predict reactive sites of the primary and secondary reaction profile. The rate coefficient using CVT with SCT over the temperature range of 258–358K is analysed and also to study the atmospheric effects of allyl alcohol in the atmosphere. The predicted rate coefficient for the favourable reaction pathway of kp1 found to be 1.190 ×10−15 cm3/molecule/sec and comparable with the experimental result at 298 K. The atmospheric lifetime of allyl alcohol was found to be around 10 hours in addition to that global warming potentials are compared with the CO2.

Effects of substituents and charge on the RCHO⋯X–Y {X = Cl, Br, I; Y = –CF3, –CF2H, –CFH2, –CN, –CCH, –CCCN; R = –OH, –OCH3, –NH2, –O−} halogen-bonded complexes

Noncovalent interactions involving halogen bonding interactions, one of the emerging interactions due to its directionality, have been a subject of interest for various researchers, owing to its role played in construction of supramolecular structures and crystal engineering. In this article, the RCHO⋯X–Y {X = Cl, Br, I; Y = –CF3, –CF2H, –CFH2, –CN, –CCH, –CCCN; R = –OH, –OCH3, –NH2, –O−} halogen-bonded complexes have been investigated with aid of quantum chemical calculations at MP2/aug-cc-pVDZ(-PP) level. The geometrical, spectroscopic and energetic properties have been analyzed for these complexes with QTAIM, MEP and NBO analyses. For same RCHO molecule, the interaction energies increase in the order of O⋯Cl < O⋯Br < O⋯I and for the same X–Y; the trend is (HO)CHO < (CH3O)CHO < (H2N)CHO. The present article also compares the neutral complexes involving (HO)CHO, (CH3O)CHO and (H2N)CHO carbonyl molecules with those of charged carbonyl species HCOO−. It has been found that strength of the latter complexes is highest among all of the four. The role of substituents in the complex formation has been analyzed on the basis of results obtained from MEP, QTAIM and NBO studies.

The copper carbonyl complexes revisited: Why are the infrared spectra and structures of copper mono and dicarbonyl so different?

New infrared absorption data have been obtained using isolation in solid argon and neon on copper carbonyl molecules, CuCO and Cu(CO)2, two very reactive molecules. For CuCO, all three fundamentals are now observed and it presents an unusually large matrix effect, in line with former results indicating a weak metal carbon interaction and a large total dipole moment. With help of isotopic effects, new data indicates unambiguously that Cu(CO)2 is linear and presents a notably stronger metal–carbon interaction than CuCO. Quantum chemical calculation have been carried out at the CCSD(T) level for determining energies and structural properties, as well as spectroscopic observables. The results enable an assessment of the high stability of the Cu(CO)2 molecule (first bond dissociation energy of 66kJ/mol) which suggest that observation at room temperature is possible and give a first evidence of Renner effect on a penta-atomic molecule.

Practical approach in surface modification of biaxially oriented polypropylene films for gravure printability

Abstract Biaxially oriented polypropylene (BOPP) film is one of the most popularly used materials for the gravure printing process in flexible packaging industry. The skin layers of BOPP film were associated with 3–6 weight % of propylene–ethylene copolymer. These films were completely biaxial-oriented by sequential stretching process after which the film surfaces were subjected to corona treatment integrated in the production line. The FT-IR results exhibited that polar functional groups as carbonyl molecules were established on the corona-treated BOPP film. The contact angles of these BOPP films were measured; the surface free energies (SFE) were then calculated. AFM topographical images also agreed well with the SFE which increased as the contents of propylene–ethylene copolymer increased. An approximated 20% increased SFE was obtained for the BOPP film that was associated with 6% propylene–ethylene copolymer. The printing quality on BOPP films was tested by light microscope which confirmed that the chromatic resolution of the printed images improved down to even more smaller groove sizes, 10 or 5 dot%. This improvement was also examined and found to correspond well with the interfacial tensions and work of adhesion between the inks and the modified BOPP films.

A novel square-planar Ni(II) complex with an amino-carboxamido-dithiolato-type ligand as an active-site model of NiSOD.

To understand the role of the unique equatorial coordination environment at the active center in nickel superoxide dismutase (NiSOD), we prepared a novel Ni(II) complex with an amino-carboxamido-dithiolato-type square-planar ligand (1, [Ni(2+)(L1)](-)) as a model of the NiSOD active site. Complex 1 has a low-spin square-planar structure in all solvents. Interestingly, the absorption wavelength and ν(C═O) stretching vibrations of 1 are affected by solvents. This provides an indication that the carbonyl oxygens participate in hydrogen-bonding interactions with solvents. These interactions are reflected in the redox potentials; the peak potential of an anodic wave (Epa) values of Ni(II)/Ni(III) waves for 1 are shifted to a positive region for solvents with higher acceptor numbers. This indicates that the disproportionation of superoxide anion by NiSOD may be regulated by hydrogen-bonding interactions between the carboxamido carbonyl and electrophilic molecules through fine-tuning of the redox potential for optimal SOD activity. Interestingly, the Epa value of the Ni(III)/Ni(II) couple in 1 in water (+0.303 V vs normal hydrogen electrode (NHE)) is similar to that of NiSOD (+0.290 V vs NHE). We also investigated the superoxide-reducing and -oxidizing reactions of 1. First, 1 reacts with superoxide to yield the superoxide-bound Ni(II) species (UV-vis: 425, 525, and ∼650 nm; electron paramagnetic resonance (EPR) (4 K): g// = 2.21, g⊥ = 2.01; resonance Raman: ν((16)O-(16)O)/ν((18)O-(18)O) = 1020/986 cm(-1)), which is then oxidized to Ni(III) state only in the presence of both a proton and 1-methylimidazole, as evidenced by EPR spectra. Second, EPR spectra indicate that the oxidized complex of 1 with 1-methylimidazole at the axial site can be reduced by reaction with superoxide. The Ni(III) complex with 1-methylimidazole at the axial site does not participate in any direct interaction with azide anion (pKa 4.65) added as mimic of superoxide (pKa 4.88). According to these data, we propose the superoxide disproportionation mechanism in superoxide-reducing and -oxidizing steps of NiSOD in both Ni(II) and Ni(III) states.

Fast and Sustainable Energy Storage in Flavins Inspired by Biological Energy Metabolism for Li Rechargeable Batteries

Cellular metabolism comprises energy transduction machineries that operate by a series of redox-active components for storing energies from nutrients, which are transduced into high-energy intermediates for cellular works such as chemical synthesis, transport, and movement.Biological energy transduction mechanism hints at the construction of a man-made energy storage system. Since the pioneering work by Tarascon et al.[1] towards a sustainable lithium rechargeable battery received significant resonance, organic materials such as carbonyl, carboxyl, or quinone-based compounds have been demonstrated to be bio-inspired organic electrodes [2, 3]. The imitation of redox-active plastoquinone and ubiquinone cofactors [4] through the utilization of redox active C=O functionalities in organic electrodes is a significant step-forward to biomimetic energy storage. However, the biological energy transduction is based on numerous redox centers of versatile functionalities available in nature, not limited to the simple redox active C=O functionalities. Consideration of how natural energy transduction systems function at organelle or cellular levels by elucidating the basic components and their operating principles selected by evolution will enrich the biomimetic strategy for efficient and green energy storage.Herein, we propose new-type of redox active organic molecules containing C=N functionality, where most interest in organic electrodes has focused on the molecules with C=O functionalities, such as carbonyl, carboxylate, or quinone-based molecules [5]. Flavins, a key redox element in respiration and photosynthesis, facilitate either one- or two-electron-transfer redox processes accompanying proton transfer at nitrogen atoms of diazabutadiene motif during cellular metabolism. We have discovered that the protonation sites of a riboflavin molecule can capture two lithium ions reversibly exhibiting a high capacity of 174 mAh/g, which is comparable to that of LiFePO4. The combined ex situ characterizations and density-functional theory(DFT)-based calculation revealed that the redox reaction occurs via the two successive single-electron transfer steps at nitrogen atoms of diazabutadiene motif, which is analogous to the proton-coupled electron transfer of flavoenzymes in nature. We also demonstrated that the capacity and voltage can be tuned by the substitution of flavin cofactors, which opens up new principles in electrode design. This kind of bio-electrode is particularly unprecedented for lithium rechargeable batteries.In terms of the practical use of organic-based electrodes, however, they suffer from sluggish kinetics and poor capacity retention, which originate from low electronic conductivity and dissolution of electroactive chemicals into electrolytes. To address this issue, we further demonstrate a novel and facile design strategy for organic electrodes possessing high energy and power densities combined with excellent cyclic stability [6]. Non-covalent nanohybridization of electroactive aromatic molecules with single-walled carbon nanotubes (SWNTs) leads to reassembly of electroactive molecules from bulk crystalline particles into molecular layers on conductive scaffolds. The simple fabrication of this nanohybrid electrode in the form of a flexible, free-standing paper (free of binder/additive and current collector) results in ultrafast kinetics delivering 510 Wh/kg within 30 minutes (204 mAh/g ≈ 98% of theoretical capacity) and 272 Wh/kg of energy even within 46 seconds. Moreover, the stable anchorage of electroactive organic molecules on the sidewall of SWNTs enables above 99% capacity retention upon 100 cycles, which was hardly achieved for organic electrodes. Our approach can be extended to other aromatic organic electrode systems, bringing bio-inspired organic materials a step closer to practical cathodes in rechargeable batteries.[1] H. Chen, M. Armand, G. Demailly, F. Dolhem, P. Poizot, J.M. Tarascon, ChemSusChem 2008, 1, 348.[2] Z. Song, H. Zhan, Y. Zhou, Chem. Commun. 2009, 448.[3] M. Armand, S. Grugeon, H. Vezin, S. Laruelle, P. Ribière, P. Poizot, J.M. Tarascon, Nat. Mater. 2009, 8, 120.[4] P. Poizot, F. Dolhem, Energy Environ. Sci. 2011, 4, 2003.[5] M. Lee, J. Hong, D.-H. Seo, D.H. Nam, K.T. Nam, K. Kang, C.B. Park, Angew. Chem. Int. Ed. 2013, 52, 8322[6] J. Hong, M. Lee, H. Kim, H.-D. Lim, C.B. Park, K. Kang, Adv. Mater., 2013, In press