Ethyl cellulose was grafted with ionic liquids in optimal yields (62.5–64.1%) and grafting degrees (5.93–7.90%) by the esterification of the hydroxyl groups in ethyl cellulose with the carboxyl groups in ionic liquids. In IR spectra of the ethyl cellulose derivatives exhibited C=O bond stretching vibration peaks at 1760 or 1740 cm⁻¹, confirming the formation of the ester groups and furnishing the evidence of the successful grafting of ethyl cellulose with ionic liquids. The ethyl cellulose grafted with ionic liquids could be formed into membranes by using the casting solution method. The resulting membranes exhibited good membrane forming ability and mechanical properties. The EC grafted with ionic liquids-based membranes demonstrated PCO₂/PCH₄ separation factors of up to 18.8, whereas the PCO₂/PCH₄ separation factor of 9.0 was obtained for pure EC membrane (both for CO₂/CH₄ mixture gas). The membranes also demonstrated an excellent gas permeability coefficient PCO₂, up to 199 Barrer, which was higher than pure EC (PCO₂ = 46.8 Barrer). Therefore, it can be concluded that the ionic liquids with imidazole groups are immensely useful for improving the gas separation performances of EC membranes.

Corn straw is an agricultural waste. The system for extracting cellulose from corn straw at a high temperature has been widely reported by researchers. However, the system for extracting cellulose from corn straw at a low temperature has been rarely reported. In this paper, a new system for extracting cellulose from corn straw at a low temperature was reported for the first time. This new system is designated as the low temperature laccase system (LTLS). Cellulose was successfully extracted from corn straw by the LTLS, and the used solution could be recycled. Therefore, the low temperature laccase system is an environmentally-friendly system. The cellulose content in corn straw is 30–40%. The yield of cellulose extracted by LTLS was 33%. The obtained cellulose product was creamy white. The extracted cellulose samples were characterized by using infrared spectroscopy (IR), thermogravimetry (TG), and X-ray diffraction (XRD). The results were consistent with that of standard cellulose. We confirmed that the LTLS extracted cellulose from corn straw with high purity.

A new polymer prepared by polymerization of 3,5-bis(hydroxymethyl)phenylacetylene having a chiral menthyl group via a very long and rigid spacer by an achiral rhodium complex with triethylamine as an initiator showed strong CD absorptions assigned to the main chain in spite of the long distance (23 Å) between the chiral group and the polymerizing group in the monomer. This distance is the longest to the best of our knowledge. In addition, switching between the two chiralities of the resulting polymer was realized in the CD spectrum.

Two kinds of novel nanoporous polycondensates (sc(Rf)) have been synthesized by two new preparation methods consisting of polycondensation and highly selective photocyclicaromataization of 1/3 helical cis-cis polyphenylacetylenes with polymerizable groups. By the original methods, new well-defined sheet polymers having nanopores or nanospaces have been synthesized for the first time. Their composite membranes, containing small amounts (1.0 wt%) of sc(Rf), had ultrahigh oxygen permeability (Po₂ > 1000 barrer), and their plots were beyond the Robeson’s upper bound line in the graph of oxygen permselectivity (α = Po₂/P_N2) versus Po₂. Both α and Po₂ values were enhanced by adding only small amounts (1.0 wt%) of sc(Rf). One of the sc(Rf)s synthesized on the base membrane surface showed the best performance, i.e., Po₂ = 5300 barrer and α = 2.5. The membrane surface was effectively covered by sc(Rf), judging from the contact angle values. It is thought that nanopores and nanospaces created in and between sc(Rf) molecules played an important role for the enhancement of both α and Po₂/P_N2.

A soluble and stable one-handed helical poly(substituted phenylacetylene) without the coexistence of any other chiral moieties was successfully synthesized by asymmetric-induced polymerization of a chiral monomer followed by two-step polymer reactions in membrane state: (1) removing the chiral groups (desubstitution); and (2) introduction of achiral long alkyl groups at the same position as the desubstitution to enhance the solubility of the resulting one-handed helical polymer (resubstitution). The starting chiral monomer should have four characteristic substituents: (i) a chiral group bonded to an easily hydrolyzed spacer group; (ii) two hydroxyl groups; (iii) a long rigid hydrophobic spacer between the chiral group and the polymerizing group; (iv) a long achiral group near the chiral group. As spacer group a carbonate ester was selected. The two hydroxyl groups formed intramolecular hydrogen bonds stabilizing a one-handed helical structure in solution before and after the two-step polymer reactions in membrane state. The rigid long hydrophobic spacer, a phenylethynylphenyl group, enhanced the solubility of the starting polymer, and realized effective chiral induction from the chiral side groups to the main chain in the asymmetric-induced polymerization. The long alkyl group near the chiral group avoided shrinkage of the membrane and kept the reactivity of resubstitution in membrane state after removing the chiral groups. The g value (g = ([θ]/3,300)/ε) for the CD signal assigned to the main chain in the obtained final polymer was almost the same as that of the starting polymer in spite of the absence of any other chiral moieties. Moreover, since the one-handed helical structure was maintained by the intramolecular hydrogen bonds in a solution, direct observation of the one-handed helicity of the final homopolymer has been realized in CD for the solution for the first time.

Three new phenylacetylene monomers having one or two carbamate groups were synthesized and polymerized by using (Rh(norbornadiene)Cl)₂ as an initiator. The resulting polymers had very high average molecular weights (Mw) of 1.4–4.8 × 10⁶, with different solubility and membrane-forming abilities. The polymer having two carbamate groups and no hydroxy groups in the monomer unit showed the best solubility and membrane-forming ability among the three polymers. In addition, the oxygen permeability coefficient of the membrane was more than 135 times higher than that of a polymer having no carbamate groups and two hydroxy groups in the monomer unit with maintaining similar oxygen permselectivity. A better performance in membrane-forming ability and oxygen permeability may be caused by a more extended and flexible cis-transoid conformation and lower polarity. On the other hand, the other two new polymers having one carbamate group and two hydroxy groups in the monomer unit showed lower performances in membrane-forming abilities and oxygen permeabilities. It may be caused by a very tight cis-cisoid conformation, which was maintained by intramolecular hydrogen bonds.