Hisanori Ando

National Institute of Advanced Industrial Science and Technology, Икеда, Ōsaka, Japan

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Publications (39)50.58 Total impact

  • [show abstract] [hide abstract]
    ABSTRACT: An X-ray absorption fine structure (XAFS) study has been conducted to reveal the local structure and chemical state of the copper in the complex of an acetylacetonate-based ligand (L1) and copper ion in acetonitrile solution. The copper ion in the complex was found to be divalent from the Cu K-edge X-ray absorption near-edge structure (XANES) spectrum. The FEFF (ab initio multiple scattering calculations of XAFS) were performed with the model compounds, whose structures were optimized by using MOPAC program with AM1 Hamiltonian. The comparative study of the experimental XAFS spectra and theoretical calculations from FEFF gave the perspectives for clarifying the coordination structure of the complex of L1 and copper ion.
    Journal of Inclusion Phenomena 01/2011; · 1.40 Impact Factor
  • Hisanori ANDO, Keiko TAWA, Mutsuo TANAKA
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    ABSTRACT: A new acetylacetone-based ligand (Ligand 1) bearing pyrene unit was synthesized and the fluorescence and metal-ion recognition properties were investigated in the presence of a different metal ion in acetonitrile solution. The fluorescence emission of Ligand 1 was strongly quenched by complexation with Cu2+ while no significant change was observed in the presence of other metal ions. The metal-ion selectivity changed from Cu2+ to Ni2+ when glycine moiety (–NH–CH2–CO–) was introduced into Ligand 1 as spacer. This result implies that hydrogen-bonding induced by the glycine moiety affects the binding ability of ligands to metal ions, resulting in change of the metal-ion selectivity.
    Journal of Environmental Sciences. 01/2009; 21.
  • [show abstract] [hide abstract]
    ABSTRACT: Oxymethylcrowned spirobenzopyran 1 and pyrenylspirobenzopyran 2 were synthesized, and fluorescence emission of their corresponding merocyanine form was examined in the presence of metal ions. For 2, fluorescence emission derived from the pyrene moiety was completely quenched by photoinduced electron transfer (PET) of the nitrogen atom when the merocyanine form was not produced, namely, without metal ions. However, when 2 was converted to the merocyanine form by the complexation of its crown ether with a metal ion, fluorescence resonance energy transfer (FRET) from the pyrene to the merocyanine moieties took place to produce fluorescence emission. This result demonstrates that the spirobenzopyran isomerization can function as a fluorescence emission switch. Fluorescence quantum yield measurement for 1 and 2 showed that fluorescence emission depends on the binding metal ion in which the fluorescence quantum yield generally increased with the increase of metal ion radius.
    Tetrahedron. 01/2004; 60(28):6029-6036.
  • [show abstract] [hide abstract]
    ABSTRACT: Chromene derivatives bearing oxymethyl-12-crown-4 (1), -15-crown-5 (2), -18-crown-6 (3) ether moieties, and non-cyclic analogue (4) were synthesized, and their metal ion binding properties and photochromism were examined. NMR titration with alkali metal ions revealed that 1 formed a 1:2 complex (metal ion: ligand) with Na+, while Li+ afforded a 1:1 complex of 1. In cases of K+ and Rb+, the complexes were a mixture of 1:1 and 1:2 complexes, but the formation of 1:1 complex was observed again with Cs+. Under UV irradiation, however, the complex stoichiometry of 1 with all alkali metal ions was 1:1. As a comparison of NMR spectra between the Li+ and Na+ complexes of 1 indicated considerable upfield shift for the chromene moiety of the Na+ complex, π–π stacking of the chromene moiety seems to induce formation of the 1:2 complex. These results indicate that the chromene moiety is not only to show photochromism but also to induce aggregation to form the 1:2 complex resulted in switching of the complex stoichiometry by UV irradiation. The formation of 1:2 complex appeared only with 1 because flexibility of the crown moieties for 2 and 3 interfered the formation of 1:2 complex. Studies on photochromism in the presence of a metal ion demonstrated that the chromene derivatives bearing crown ether moieties show ion-responsive photochromism depending on the metal ion binding ability of their crown ether moieties.
    Tetrahedron. 01/2004; 60(14):3211-3220.
  • [show abstract] [hide abstract]
    ABSTRACT: Crowned chromenes − four novel naphthopyrans (chromenes) bearing monoaza-12-crown-4, -15-crown-5, -18-crown-6, and a noncyclic analogue at the 5-position − were synthesized, and their photochromism in acetonitrile was examined in the presence of alkali and alkaline-earth metal ions. Incorporation of crown ether units to chromene moieties facilitated to a great extent both the thermal isomerization and photoisomerization of the chromene moiety, reflecting the metal-ion-binding ability of the crown ether moiety. Comparison of the crowned chromenes with the corresponding crowned spirobenzopyrans reveals that photochromism of the crowned chromene reflects an interaction between the metal ion and the crown ether moiety that is stronger than that of the crowned spirobenzopyran, and shows only positive photochromism with significant red-shifts in the UV/Vis absorption spectra, in contrast to the crowned spirobenzopyrans reported previously. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
    Annalen der Chemie und Pharmacie 06/2003; 2003(13):2437 - 2442. · 3.10 Impact Factor
  • [show abstract] [hide abstract]
    ABSTRACT: Novel t-butylcalix[4]arenes bearing several chromene molecules were synthesized, and their photochromism and metal-ion binding ability were examined with alkali and alkaline-earth metal ions. While the metal-ion binding ability of the t-butylcalix[4]arene moiety facilitated the photoisomerization of the chromene moiety to a great extent, the chromene moiety influenced the metal-ion binding ability of the t-butylcalix[4]arene moiety through lariat effect. Therefore, the metal-ion that induced the most facilitated photoisomerization of the chromene moiety was shifted drastically from Li+ to Ba2+ with the increase of the incorporated chromene number. Even without metal ions, the interaction among the chromene moieties derived from the cone-conformation of the t-butylcalix[4]arene moiety also facilitated the photoisomerization.
    Tetrahedron. 01/2003; 59(23):4135-4142.
  • [show abstract] [hide abstract]
    ABSTRACT: Spirobenzopyrans bearing monoazathiacrown ethers and noncyclic analogues were synthesized, and their ion-responsive photochromism depending on the dual metal ion interaction with the crown ether and the phenolate anion moieties was examined using alkali and alkaline-earth metal ions, Ag(+), Tl(+), Pb(2+), Hg(2+), and Zn(2+). The prepared spirobenzopyrans showed a selective binding ability to Mg(2+) and Ag(+) with negative and positive photochromism, respectively. Among the metal ions, only Ag(+) facilitated photoisomerization to the corresponding merocyanine form. Depending on the ring size of the monoazathiacrown ether moieties, soft metal ions such as Hg(2+) and Ag(+) showed significant shifts in the UV-vis absorption spectra, while hard metal ions such as Mg(2+), Zn(2+), and Pb(2+) did not afford any meaningful shift. This result reflects that the monoazathiacrown ether and phenolate anion moieties prefer soft and hard metal ions, respectively. Therefore, the Mg(2+) and Ag(+) selectivities are mainly derived from the phenolate anion and monoazathiacrown ether moieties, respectively. On the other hand, a spirobenzothiapyran bearing 3,9-dithia-6-monoazaundecane showed a remarkable selectivity to Ag(+).
    The Journal of Organic Chemistry 05/2002; 67(7):2223-7. · 4.56 Impact Factor
  • Journal of Organic Chemistry - J ORG CHEM. 04/2002; 58(11).
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    ABSTRACT: The influence of metal ion interaction with crowned spirobenzopyrans on the photoisomerization behavior was investigated through the use of various solvents, crowned spirobenzopyrans, and metal ions. Studies on the photoisomerization behavior of crowned spirobenzopyrans in various solvents revealed that solvation of the phenolate anion moiety in the merocyanine form induced photoisomerization back to the spiropyran form, giving rise to negative photochromism. Metal ion interaction with the phenolate anion moiety similarly caused photoisomerization back to the spiropyran form, while that with the crown ether moiety just produced a polar environment and its influence on photoisomerization behavior was dependent on the affinity of the metal ion captured by the crown ether moiety for the phenolate anion. Therefore, photochromic switching of crowned spirobenzopyrans between positive and negative to control the metal ion interaction with the phenolate anion moiety through the crown ether moiety is possible. This finding suggests a molecular design method for crowned spirobenzopyrans showing desired ion-responsive photochromism.
    Annalen der Chemie und Pharmacie 01/2002; 2002(4):655 - 662. · 3.10 Impact Factor
  • [show abstract] [hide abstract]
    ABSTRACT: Synthetic procedures for monoazathiacrown ethers were explored, and monoazatrithia-12-crown-4, monoazatetrathia-15-crown-5, and monoazapentathia-18-crown-6 were obtained in moderate yields by the reaction of bis(2-chloroethyl)amine with the appropriate dithiols in the presence of lithium hydroxide in THF. To evaluate metal-ion binding properties of the monoazathiacrown ethers by solvent extraction, lipophilic dodecyl and dodecanoyl groups were incorporated onto the monoazathiacrown ethers. The solvent extraction experiments suggested that monoazathiacrown ethers have Ag(+) and Hg(2+) selectivities and that the relative selectivity between Ag(+) and Hg(2+) depends on their nitrogen atom properties and numbers of sulfur atoms reflecting the respective affinities of nitrogen and sulfur atoms to Hg(2+) and Ag(+). An interesting ability to bind Mg(2+) was observed in the case of N-dodecyl monoazatrithia-12-crown-4.
    The Journal of Organic Chemistry 11/2001; 66(21):7008-12. · 4.56 Impact Factor
  • [show abstract] [hide abstract]
    ABSTRACT: Spirobenzopyran derivatives carrying an oxymethylcrown ether moiety were synthesized, and their photochromism was studied in the presence of various metal ions in acetonitrile. The metal ion complexing ability of the crown ether moiety in crowned spirobenzopyrans affects both thermal isomerization and photoisomerization of their spirobenzopyran moiety to a great extent. When the interaction of the crown ether moiety with a metal ion was strong enough to cause thermal isomerization of the spirobenzopyran moiety to its corresponding merocyanine form and to suppress UV-induced isomerization to the merocyanine form, a negative photochromism appears. On the other hand, a relatively weak interaction of the crown ether moiety with a metal ion affords a positive photochromism. This phenomenon enables us to switch the photochromic behavior between positive and negative photochromisms.
    The Journal of Organic Chemistry 04/2001; 66(5):1533-7. · 4.56 Impact Factor
  • [show abstract] [hide abstract]
    ABSTRACT: Ultrafine palladium particles supported on cerium oxide by the coprecipitation method effectively catalyzes the methanol synthesis from carbon monoxide and hydrogen, while the catalytic activity increases in the initial stage. The Pd K-edge EXAFS (extended X-ray absorption fine structure) of the catalyst shows that a small part of palladium is still oxidized after the pretreatment with hydrogen at 573 K for 1 h. During the reaction the palladium particles in the catalyst are further oxidized due to the formation of Pd–O–Ce bonding which may stabilize the cationic palladium species being active to the reaction.
    Catalysis Letters 08/2000; 68(3):181-183. · 2.24 Impact Factor
  • [show abstract] [hide abstract]
    ABSTRACT: Spirobenzothiapyrans bearing monoaza-12-crown-4, -15-crown-5, -18-crown-6, and oligooxyethylene moieties were synthesized, and their photochromism was examined in the presence of cations in acetonitrile. The cation complexation by their crown ether moieties cannot induce thermal isomerization to their corresponding colored merocyanine form, unlike the corresponding spirobenzopyran derivatives. The UV-light-induced isomerization was, however, facilitated by the cation complexation of the crown ether moieties and the affinity of the merocyanine thiophenolate anion to metal ions, especially in the presence of Li(+) and Ag(+). The presence of Ag(+) brought about the most remarkable effect in the facilitation of photoisomerization of the spirobenzothiapyrans and the thermal stability of the colored merocyanine form mainly due to the powerful interaction of the thiophenolate anion with the soft metal ion.
    The Journal of Organic Chemistry 08/2000; 65(14):4342-4347. · 4.56 Impact Factor
  • Applied Organometallic Chemistry - APPL ORGANOMETAL CHEM. 01/2000; 14(12):831-835.
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    ABSTRACT: Hydrogenation of CO2 to hydrocarbons over iron catalysts reduced with hydrogen at 350°C and 500°C has been compared with that of CO. The space time yield of hydrocarbons from CO2 at 250°C is significantly lower than from CO and the selectivity to olefin compounds is also lower from CO2. During the reaction with CO, χ-Fe2.2C is formed, and the surface, which is oxidized even after the reduction at 500°C, is further reduced. On the other hand, formation of the carbide species is slight in hydrogenation of CO2 while the surface is rather oxidized. The formation of the carbide species, which is probably the active site of hydrocarbon formation, is suppressed in the presence of CO2.
    Journal of Molecular Catalysis A-chemical - J MOL CATAL A-CHEM. 01/2000; 154(1):23-29.
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    ABSTRACT: The hydrogenation of carbon dioxide was examined over various composite catalysts composed of Fe−Zn−M catalyst and zeolite. Fe−Zn−Zr/HY composite catalyst was confirmed to be efficient for the highly selective production of isobutane, which is regarded as a synthetic intermediate of MTBE (methyl tert-butyl ether). The composite catalyst of Fe−Zn−Zr catalyst with H-ZMS-5 formed C5+ hydrocarbons in good yield. The ratios of branched hydrocarbons in C5+ ones, which are suitable for high-octane gasoline, were over 90%.
  • [show abstract] [hide abstract]
    ABSTRACT: The hydrogenation of carbon dioxide to methane can be catalyzed over an intermetallic compound of LaNi5 at 250–350°C. The catalytic activity at 250°C increases during the reaction while X-ray diffraction (XRD) analyses show that the structure of the compound decomposes to La(OH)3, LaCO3OH, and metallic nickel. Formation of metallic nickel species during the reaction also takes place in a nickel–lanthanum oxides catalyst prepared by a coprecipitation method, however, the activity is not so high as the former catalyst. Surface analyses by X-ray photoelectron spectroscopy (XPS) suggest that new nickel species interacting with lanthanum cation, possibly Ni–O–La, are formed in LaNi5 during the reaction, and the species are supposed to be rather active than metallic nickel.
    Journal of Molecular Catalysis A-chemical - J MOL CATAL A-CHEM. 01/1999; 144(1):117-122.
  • [show abstract] [hide abstract]
    ABSTRACT: A spirobenzothiapyran derivative bearing a monoaza-12-crown-4 moiety affords significant thermal stability enhancement in the UV light induced colored merocyanine form of its photochromic moiety by metal-ion complexation of its crown ether moiety, although the complexation hardly induces the isomerization without photoirradiation.
    Chemical Communications 01/1999; · 6.38 Impact Factor
  • [show abstract] [hide abstract]
    ABSTRACT: The Gattermann−Koch formylations of diphenyl, diphenylmethane, dibenzyl, and 1,3-diphenylpropane were studied in HF−SbF5, −TaF5, −BF3, −NbF5, and CF3SO3H−SbF5. While usual high para regioselectivity was obtained for diphenyl, diphenylmethane, and 1,3-diphenylpropane, unprecedented ortho regioselectivity was observed for dibenzyl which increased with decreasing the SbF5/dibenzyl molar ratio and with strength of Lewis acids used in HF. A sandwich-like complex for monoprotonated dibenzyl resulting in ortho regioselectivity via the intracomplex reaction was suggested; therefore, the conformations of protonated diphenylmethane, dibenzyl, and 1,3-diphenylpropane and their proton-transfer dynamics were probed by semiempirical calculation (PM3). The calculation predicted that ortho monoprotonation was slightly preferable for dibenzyl, and remarkable preference of dibenzyl over other aromatic compounds was observed in ortho−ortho intramolecular inter-ring proton transfer via a fan-shaped complex rather than a sandwich-like complex. The experimental and theoretical data for dibenzyl are compatible with the intracomplex reaction, whereby CO is protonated by the ortho σ-complex undergoing rapid inter-ring proton transfer to generate formyl cation in the vicinity of the ortho position leading to ortho regioselectivity.
    Journal of Organic Chemistry - J ORG CHEM. 05/1998; 63(13).
  • Studies in Surface Science and Catalysis - STUD SURF SCI CATAL. 01/1998; 114:327-332.

Publication Stats

98 Citations
50.58 Total Impact Points


  • 2001–2011
    • National Institute of Advanced Industrial Science and Technology
      • • Research Institute for Ubiquitous Energy Devices
      • • Research Center for Stem Cell Engineering
      Икеда, Ōsaka, Japan
  • 2003
    • Assiut University
      • Faculty of Science
      Asyūţ, Muhafazat Asyut, Egypt
  • 2000
    • Wakayama University
      Wakayama, Wakayama, Japan
  • 1996
    • Osaka Institute of Technology
      Ōsaka, Ōsaka, Japan