Organic compounds offer new possibilities for high energy/power density, cost-effective, environmentally friendly, and functional rechargeable lithium batteries. For a long time, they have not constituted an important class of electrode materials, partly because of the large success and rapid development of inorganic intercalation compounds. In recent years, however, exciting progress has been made, bringing organic electrodes to the attention of the energy storage community. Herein thirty years' research efforts in the field of organic compounds for rechargeable lithium batteries are summarized. The working principles, development history, and design strategies of these materials, including organosulfur compounds, organic free radical compounds, organic carbonyl compounds, conducting polymers, non-conjugated redox polymers, and layered organic compounds are presented. The cell performances of these materials are compared, providing a comprehensive overview of the area, and straightforwardly revealing the advantages/disadvantages of each class of materials.

Organic Electrode Materials for Rechargeable Lithium Batteries

Sodium-ion batteries (SIBs) receive significant attention for electrochemical energy storage and conversion owing to their wide availability and the low cost of Na resources. However, SIBs face challenges of low specific energy, short cycling life, and insufficient specific power, owing to the heavy mass and large radius of Na(+) ions. As an important component of SIBs, cathode materials have a significant effect on the SIB electrochemical performance. The most recent advances and prospects of inorganic and organic cathode materials are summarized here. Among current cathode materials, layered transition-metal oxides achieve high specific energies around 600 mW h g(-1) owing to their high specific capacities of 180-220 mA h g(-1) and their moderate operating potentials of 2.7-3.2 V (vs Na(+) /Na). Porous Na3 V2 (PO4 )3 /C nanomaterials exhibit excellent cycling performance with almost 100% retention over 1000 cycles owing to their robust structural framework. Recent emerging cathode materials, such as amorphous NaFePO4 and pteridine derivatives show interesting electrochemical properties and attractive prospects for application in SIBs. Future work should focus on strategies to enhance the overall performance of cathode materials in terms of specific energy, cycling life, and rate capability with cationic doping, anionic substitution, morphology fabrication, and electrolyte matching.

Recent Advances and Prospects of Cathode Materials for Sodium‐Ion Batteries

Most organs and biological tissues are soft viscoelastic materials with elastic moduli ranging from on the order of 100 Pa for the brain to 100 000 Pa for soft cartilage. Biocompatible synthetic materials already have many applications, but combining chemical compatibility with physiologically appropriate mechanical properties will increase their potential for use both as implants and as substrates for tissue engineering. Understanding and controlling mechanical properties, specifically softness, is important for appropriate physiological function in numerous contexts. The mechanical properties of the substrate on which, or within which, cells are placed can have as large an impact as chemical stimuli on cell morphology, differentiation, motility, and commitment to live or die.

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Soft biological materials and their impact on cell function

C2-Symmetric Chiral Bis(Oxazoline) Ligands in Asymmetric Catalysis

The fundamental challenge of the 21st century that mankind has to face is definitely energy supply, its storage and conversion in a way that necessarily protects the environment. For 250 years, the tremendous development of humanity has been founded on the harnessing of fossil fuels (coal, crude oil then natural gas) as primary energy due to their high energy density values and the easiness of access. However, this global pattern of energy supply and use is unsustainable. Global warming and finite fossil-fuel supplies call for a radical change in the energy mix to favour renewable energy sources. Without being exhaustive, we tackle in this article the tricky energy question and associated environmental issues as personally perceived. The eminent role of electric energy produced from decarbonized sources in a future sustainable economy is particularly highlighted as well as the issues of its needed storage. The possible and foreseen hindrances of electrochemical energy storage devices, focusing on the lithium-ion technology, are presented in parallel with the possible pathways to make such a technology greener in synergy with the rise of a biomass-based industry.

Clean energy new deal for a sustainable world: from non-CO2 generating energy sources to greener electrochemical storage devices

A novel type of optically active N-[4-N′-(α-methylbenzyl)aminocarbonylphenyl]maleimide [(R)-MBCP] was synthesized from maleic anhydride, p-aminobenzoic acid, and (R)-methylbenzylamine. Radical homopolymerization of (R)-MBCP was performed in tetrahydrofuran (THF) at 50 and 70°C for 24 h to give optically active polymers having [α]25D = -141° and -129°, respectively. Anionic polymerization of (R)-MBCP with n-butyllithium in THF and N,N-dimethylformamide gave an optically active polymer having −78 to −81° of [α]25D. Radical copolymerizations of (R)-MBCP (M1) were performed with styrene (ST, M2) and methyl methacrylate (MMA, M2) in THF at 50°C. The monomer reactivity ratios (r1, r2) and the Alfrey-Price Q-e values were determined as follows: r1 = 0.009, r2 = 0.091, Q1 = 1.30, e1 = 1.87 in the (R)-MBCP-ST; r1 = 0.27, r2 = 1.21, Q1 = 0.93, e1 = 1.46 in the (R)-MBCP-MMA system. Chiroptical properties of the polymers were also investigated. © 1992 John Wiley & Sons, Inc.

Synthesis and polymerization of N‐[4‐N′‐ (α‐methylbenzyl)aminocarbonylphenyl]maleimide

A set of thermoplastic expandable microspheres was investigated with respect to their crosslinking density and expandable property. The crosslinking efficiencies of dipentaerythritol hexaacrylate in a set of thermoplastic expandable microspheres were measured. As expandable properties, expansion curves were measured by using a thermomechanical analyzer, and they also were shown by measuring the change of thickness of the coated compound consisting of ethylene–vinyl acetate copolymer resin emulsion and CaCO3 with thermoplastic microspheres on paper. In view of the expansion ratio and heat resistance, as crosslinking density, a swelling ratio of about 20–25 is needed to achieve optimum expansion without collapse and rupture of microspheres. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 93: 505–512, 2004

Synthesis and properties of thermoplastic expandable microspheres: The relation between crosslinking density and expandable property

The effects of various additional non-nitrile-containing monomers on the heat resistance of thermoplastic expandable microspheres containing acrylonitrile and methacrylonitrile were investigated to determine the correlation between the chemical structure and expandable properties. Thermoplastic expandable microspheres were synthesized by suspension polymerization, with acrylonitrile and methacrylonitrile as the main ingredients and seven kinds of methacrylic acid derivatives, methacrylic acid, and acrylic acid as non-nitrile-containing monomers. The expandable properties, that is, the maximum expansion temperature, the expansion start temperature, and the maximum dimension change, were measured with thermomechanical analysis. For the development of heat-resistant microspheres, polymer structures with smaller functional free volumes, higher glass-transition temperatures, and higher cohesive energy densities, such as methyl acrylic acid, were applied as non-nitrile-containing monomers. Molecular structures such as COOH groups with strong electrostatic interactions and hydrogen-bonding forces were found to be suitable for high heat resistance. © 2005 Wiley Periodicals, Inc. J Appl Polym Sci 96: 1306–1312, 2005

Effects of the chemical structure on the heat resistance of thermoplastic expandable microspheres

Polyaniline (PANI)-poly (p-styrenesulfonic acid) (PSS) composite was prepared by thermal post-polymerization of PANI-p-styrenesulfonic acid (SSA) composite. A PANI–SSA composite was prepared by mixing PANI/N-methyl-2-pyrrolidinone solution with SSA aqueous solution. The PANI–SSA composite film was prepared by casting the composite onto an ITO glass plate. The cast film was converted to PANI-PSS film by heating at 100°C for 3h (post-polymerization process). The PANI–PSS modified ITO electrode showed electrochemical responses based on the redox reaction of PANI–PSS composite in the organic electrolyte solution, for example, propylene carbonate containing 1moldm−3 LiClO4. The PANI–PSS composite was a cation -doping polymer composite. The composite was also modified on a porous carbon material (Reticulated Vitreous CarbonTM, RVC, Energy Research and Generation, Inc.). The PANI–PSS modified RVC electrode showed similar electrochemical behaviour as the PANI–PSS modified ITO electrode. Model secondary lithium cells, Li|1moldm−3 LiClO4-propylene carbonate|PANI–PSS modified RVC electrode, were constructed and charge–discharge cycling tests were carried out. The cell showed about 60% coulombic efficiency under high current density cycling conditions (3.8Ag−1, per gram of PANI–PSS modified RVC electrode).

Preparation of polyaniline-poly (p-styrenesulfonic acid) composite by post-polymerization and application as positive active material for a rechargeable lithium battery

Asymmetric anionic homopolymerizations of achiral N-substituted maleimide (RMI:  R = cyclohexyl (CHMI), R = phenyl (PhMI), R = tert-butyl (TBMI)) were carried out with n-butyllithium (n-BuLi)−chira...

Tsutomu Oishi

Papers

Synthesis and polymerization of N‐[4‐N′‐ (α‐methylbenzyl)aminocarbonylphenyl]maleimide

Synthesis and properties of thermoplastic expandable microspheres: The relation between crosslinking density and expandable property

Effects of the chemical structure on the heat resistance of thermoplastic expandable microspheres

Preparation of polyaniline-poly (p-styrenesulfonic acid) composite by post-polymerization and application as positive active material for a rechargeable lithium battery

Asymmetric anionic polymerization of N-substituted maleimides with n-butyllithium-methylene-bridged 2,2-bis(oxazoline) complexes