Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Volume 75 , Issue 2
Showing 1-25 articles out of 25 articles from the selected issue
  • Masao Sugawara, Ayumi Hirano, Philippe Bühlmann, Yoshio Umezawa
    Type: scientific monograph
    2002 Volume 75 Issue 2 Pages 187-201
    Published: 2002
    Released: February 22, 2002
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    This paper reviews approaches to chemical sensing with receptor-modified electrodes that mimic the function of natural membranes containing biological and synthetic receptor channels. We highlight different types of ion-channel sensors, focusing on the working principle and the fundamental aspects, such as sensitivity and selectivity. It is demonstrated that biological receptors such as glutamate receptor ion channels and gramicidin, embedded in bilayer lipid membranes, have the potential as sensing elements for ion channel sensors with excellent sensitivity and selectivity. In addition, higher selectivities by improved receptor desigh, taking into account the particular advantages of interfacial analyte recognition at LB membranes and SAMs, are also shown with ion-channel sensors for antibodies, protamine, heparin, abasic DNA sites, and oligonucleotides.
  • Hiroaki Miyaoka, Yasuji Yamada
    Type: scientific monograph
    2002 Volume 75 Issue 2 Pages 203-222
    Published: 2002
    Released: February 22, 2002
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    This paper presents the total synthesis of bioactive marine terpenoids as conducted at this laboratory. The syntheses of marine sesquiterpenoid upial and marine diterpenoid sanadaol were conducted from D-mannitol via sequential Michael reaction and fragmentation reaction. The marine diterpenoid fuscol, its related compound, and phomactin D were obtained by sequential Michael reaction and oxidative cleavage of carbon–carbon double bond. The marine diterpenoid claenone was produced by sequential Michael reaction and retro-aldol reaction. Synthesis of the marine diterpenoid (+)-mayolide A involved the stereoselective introduction of a C2-unit and repeated Claisen rearrangement to construct the side chain as key steps. Synthesis of the marine diterpenoid (+)-halimedatrial involved stereoselective formation of the cyclopropane moiety and formation of the diformylcyclopentane moiety as crucial steps. The marine sesterterpenoid dysidiolide was synthesized by intramolecular Diels–Alder reaction as the key step to obtain the decalin moiety.
  • Jun-ichi Matsuo, Daisuke Iida, Kazuya Tatani, Teruaki Mukaiyama
    Type: technical report
    2002 Volume 75 Issue 2 Pages 223-234
    Published: 2002
    Released: February 22, 2002
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    Various primary and secondary alcohols were smoothly oxidized to the corresponding aldehydes and ketones by using a new oxidizing agent, N-t-butylbenzenesulfinimidoyl chloride (4a), in the coexistence of DBU or zinc oxide. The present oxidation proceeded under mild conditions via five-membered intramolecular proton-transfer of an alkyl arenesulfinimidate intermediate.
  • Natalia Wilke, Rodrigo Alejandro Iglesias, Sergio Gustavo Chesniuk, Se ...
    Type: Others
    Subject area: TP
    2002 Volume 75 Issue 2 Pages 235-240
    Published: 2002
    Released: February 22, 2002
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    Convective flux produced by stirring either the aqueous or the organic phase is proposed as a mechanistic tool to study the ion-transfer processes at ITIES. The dependence of the voltammetric response on the sweep rate and the rotation frequency was used to differentiate the simple transfer of TEA+ from the assisted transfer of K+ by DB18C6 at a water 1,2-dichloroethane interface.
  • Yuki Tanaka, Masaharu Tsuji
    Type: Others
    Subject area: TP
    2002 Volume 75 Issue 2 Pages 241-252
    Published: 2002
    Released: February 22, 2002
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    Chemical ionization of alkylbenzenes (PhCxH2x + 1 = M: x = 3–13) by the CH5+, C2H5+, and C3H5+ ions has been studied under a reactant-ion selective mode of an ion-trap type of GC/MS. The dominant product ions for short-chain reagents (x < 7) were [M + H]+, [PhH + H]+, and CxH2x + 1+ ions, produced through proton-transfer to benzene ring. On the other hand, the dominant product ions for long-chain reagents (x ≥ 7) were CyH2y + 1+ (y < x) and PhCyH2y+ (y ≤ x) ions. The former ions are produced through the attack of the reactant ions on the alkyl chain and/or the benzene ring, while the latter ones are exclusively formed through the attack of the reactant ions on the alkyl chain. Major formation processes of CyH2y + 1+ and PhCyH2y+ ions in each reaction were discussed on the basis of observed distributions and calculated thermochemical data.
  • Junhu Wang, Takafumi Kitazawa, Masami Nakada, Toshiyuki Yamashita, Mas ...
    Type: Others
    Subject area: AI
    2002 Volume 75 Issue 2 Pages 253-257
    Published: 2002
    Released: February 22, 2002
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    237Np Mössbauer spectra of two neptunyl(VI) trinitrato complexes, M[NpO2(NO3)3] (M = NH4+ 1 and K+ 2) were measured at 4.5 K, 10 K and 30 K, respectively. The spectra show magnetic hyperfine splittings similar to the spectrum of Rb[NpO2(NO3)3] 3 already reported. Since the SQUID data of 1 indicate that 1 is paramagnetic from 2 K to room temperature, the magnetic hyperfine splittings are due to slow paramagnetic relaxation. The crystal structures of 1 and 2 were refined by the Rietveld analysis, and the mean Np–O bond distances of 1 and 2 have been obtained. Almost the same Np–O bond distances of 1, 2 and 3 exhibit about the same δ values. This is consistent with the linear relationship between the δ values and the mean Np–O bond distances established for the neptunyl(VI) compounds.
  • Masakazu Hirotsu, Mutsumi Aoyagi, Masaaki Kojima, Wasuke Mori, Yuzo Yo ...
    Type: Others
    Subject area: AI
    2002 Volume 75 Issue 2 Pages 259-265
    Published: 2002
    Released: February 22, 2002
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    A hydroxo-bridged MnIIIMnIIMnIII trinuclear complex, [Mn3(L1)2(2,6-dcba)2(OH)2] (1), where H2L1 is N′,N&prime-bis-(2-hydroxybenzyl)-N′,N′-dimethylethylenediamine and H2,6-dcba is 2,6-dichlorobenzoic acid, was synthesized by the reaction of Mn(ClO4)2·6H2O with H2L1, H2,6-dcba, and a base in acetonitrile. The structure of 1 was determined by X-ray crystallography: 1 crystallizes in the monoclinic space group P21/c with a = 9.616(4) Å, b = 12.537(4) Å, c = 23.099(4) Å, β = 94.73(2)°, V = 2775(1) Å3, and Z = 2. The central MnII and terminal MnIII ions are bridged by phenolato, carboxylato, and hydroxo ligands to form a linear MnIII–MnII–MnIII arrangement. The bridging structure between MnIII and MnII is similar to that of analogous alkoxo-bridged complexes, [Mn3(L)2(carboxylato)2(alkoxo)2], where L is L1 or its derivatives. Most of the alkoxo-bridged complexes [Mn3(L)2(carboxylato)2(alkoxo)2] exhibit a weak ferromagnetic interaction between MnIII and MnII, while the hydroxo-bridged complex 1 exhibits a weak antiferromagnetic interaction. A comparison of the magnetic properties between the hydroxo- and alkoxo-bridged complexes was performed by density functional calculations of MnIIIMnII dinuclear model complexes.
  • Xiao-Yan Yu, Masahiko Maekawa, Tomonori Morita, Ho-Chol Chang, Susumu ...
    Type: Others
    Subject area: AI
    2002 Volume 75 Issue 2 Pages 267-275
    Published: 2002
    Released: February 22, 2002
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    Reactions of Rh and Ir hydrido complexes, [Rh(H)2(PPh3)2(solv)(EtOH)]ClO4 (solv = Me2CO, 1a; EtOH, 1b) and [Ir(H)2(PPh3)2(Me2CO)2]BF4 (2), with various N,N′-donor bridging ligands, such as pyrazine (pyz), 4,4′-trimethylenedipyridine (tmdp) and di(4-pyridyl) disulfide (dpds), in some solvents were examined, and their reaction products were characterized by X-ray crystal structure analysis, IR, 1H NMR and UV-vis spectra. Rh hydrido complexes, 1a or 1b, formed a dinuclear Rh complex, [Rh2(PPh3)2{(η6-C6H5)PPh2}2](ClO4)2·6CH2Cl2 (3·6CH2Cl2), in dichloromethane with a reductive elimination of hydrogen. The reactions of 1a or 1b with the pyz ligand in dichloromethane and tetrahydrofuran gave triangular Rh3 complexes, [Rh3(PPh3)6(pyz)3](ClO4)3·CH2Cl2 (5·CH2Cl2) and [Rh3(PPh3)6(pyz)3](ClO4)3·EtOH (5·EtOH), respectively, in contrast to the formation of a dinuclear Rh hydrido complex, [Rh2(H)4(PPh3)4(Me2CO)2(pyz)](ClO4)2·EtOH (4·EtOH), in acetone. The reactions of 1a or 1b with the tmdp ligand in dichloromethane and 3-methyl-2-butanone also afforded dinuclear Rh complexes, [Rh2(PPh3)4(tmdp)2](ClO4)2 (6) and [Rh2(PPh3)4(tmdp)2](ClO4)2·4MeCOCHMe2 (6·4MeCOCHMe2), respectively. On the other hand, Ir hydrido complex 2 reacted with pyz and dpds ligands in dichloromethane to afford dinuclear Ir complexes, [Ir2(H)4(PPh3)4(Me2CO)2(pyz)](BF4)2·3CH2Cl2 (7·3CH2Cl2) and [Ir2(H)4(PPh3)4(dpds)2](BF4)2·3CH2Cl2·H2O (8·3CH2Cl2·H2O), respectively, without any reductive elimination of hydrogen. Based on structural studies in solution and in the solid state, it was demonstrated that various Rh and Ir complexes were selectively produced depending on the choice of solvents and N,N′-donor bridging ligands.
  • Yasuhiro Yamada, Keiichi Katsumata, Hideo Shimasaki, Yuki Ono, Kayoko ...
    Type: Others
    Subject area: AI
    2002 Volume 75 Issue 2 Pages 277-281
    Published: 2002
    Released: February 22, 2002
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    The reaction of laser-evaporated iron atoms with methane gas was studied using a matrix-isolation technique, and the reaction products were observed by Mössbauer and infrared spectroscopy. The reaction produced CH3FeH in a CH4/Ar mixture, whereas Fe2H2(CH3)4 was also obtained in addition in a pure CH4 matrix. Molecular orbital calculations were performed in order to confirm the assignments.
  • Kazuaki Yamanari, Makiko Kida, Akira Fuyuhiro, Sumio Kaizaki
    Type: Introduction
    Subject area: AI
    2002 Volume 75 Issue 2 Pages 283-284
    Published: 2002
    Released: February 22, 2002
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    The novel tris(2-aminoethyl)aminecobalt(III) complex containing a dimerized ligand Hatuc-atuc (6-amino-5-[6-amino-4-oxo-(1H)-pyrimidin-2-yl]thio-2-thioxo-pyrimidin-4-onate(2-)) was prepared. The crystal structure revealed that Hatuc-atuc coordinates through the S/N donors and exhibits the intermolecular π–π stacking and the double N–H···O hydrogen bond interactions.
  • Toshio Itahara
    Type: Others
    Subject area: OB
    2002 Volume 75 Issue 2 Pages 285-290
    Published: 2002
    Released: February 22, 2002
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    The intramolecular hydrogen bond between the adenine and thymine rings of 9-[ω-(thymin-1-yl)alkyl]adenine was investigated in chloroform by means of NMR spectroscopy. The formation of the intramolecular hydrogen bond was dependent on the length of the polymethylene chains between adenine and thymine, and the thermodynamic parameters were estimated. The length of the polymethylene chains caused a marked difference in the physical properties of the compounds.
  • Hideki Jona, Hiroki Mandai, Warinthorn Chavasiri, Kazuya Takeuchi, Ter ...
    Type: Others
    Subject area: OB
    2002 Volume 75 Issue 2 Pages 291-309
    Published: 2002
    Released: February 22, 2002
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    A catalytic and stereoselective glycosylation of various glycosyl acceptors, such as methyl glycosides, thioglycosides, or a disarmed glycosyl fluoride, with benzyl-protected armed glycosyl fluoride was successfully carried out by using various protic acids in the presence of MS 5A. In the cases when trifluoromethanesulfonic acid (TfOH) or perchloric acid (HClO4) was used in diethyl ether (Et2O), α-glycosides were obtained as major products, while β-stereoselectivity was observed when tetrakis(pentafluorophenyl)boric acid [HB(C6F5)4] was used in a mixed solvent of trifluoromethylbenzene (BTF)–pivalonitrile (tBuCN) = 5 : 1. Stereoselectivity of this glycosylation was controlled by the properties of counter anions of the catalyst as well as by those of solvents. Also, one-pot trisaccharide synthesis was performed by successive addition of NIS and third-sugar to afford Glcα or β1–6Glcβ1–6Glc and Glcα or β1–6GlcNβ1–6Glc in excellent yields.
  • Ken Takaki, Yohei Shimasaki, Tetsuya Shishido, Katsuomi Takehira
    Type: Others
    Subject area: OB
    2002 Volume 75 Issue 2 Pages 311-317
    Published: 2002
    Released: February 22, 2002
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    Oxidation of 2,6-disubstituted 4-methylphenols with dioxygen by using a CuCl2-poly(4-methyl-4′-vinyl-2,2′-bipyridine) catalyst gave the corresponding 4-hydroxybenzaldehydes in high yields. The activity of the catalyst and the selectivity of the products significantly depended on the reaction conditions and the composition of the catalyst. When the molar ratio of the bipyridine unit of the polymer ligand to Cu was unity, i.e., N/Cu = 2, the best results were obtained. Moreover, the reaction is likely to be promoted by coordination of the products to the catalyst. Similarly, 2,3,6-trimethylphenol and related compounds were converted to p-benzoquinones selectively with a CuCl2-poly(4-vinylpyridine) catalyst. These polymer-supported catalysts were readily recovered and are reusable without noticeable decrease of their activity.
  • Akihiko Ishii, Hideaki Oshida, Juzo Nakayama
    Type: Others
    Subject area: OB
    2002 Volume 75 Issue 2 Pages 319-328
    Published: 2002
    Released: February 22, 2002
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    6-t-Butyl-6-phenylpentathiane was oxidized with trifluoroperacetic acid (CF3CO3H) or dimethyldioxirane (DMD) at -20 °C. Oxidation with CF3CO3H yielded pentathiane 3-oxide as the main product, whereas that of DMD gave 1- and 3-oxides. The structures of 1- and 3-oxides were finally determined by X-ray crystallographic analysis. DFT calculations of the NMR chemical shifts were performed on the chair and twist forms of the pentathiane and sixteen isomers of the monoxides with the GIAO method at the B3LYP/6-31G* level. The calculated chemical shifts were verified to be in practical agreement with the experimental data of the pentathiane and the isolated 1- and 3-oxides.
  • Jun-ichi Yamaguchi, Yukihito Murayama, Takayuki Suyama
    Type: Others
    Subject area: OB
    2002 Volume 75 Issue 2 Pages 329-333
    Published: 2002
    Released: February 22, 2002
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    Degradation of N,N′-dialkyldiazenedicarboxamides with a copper(II) reagent, which was prepared from lithium 4-nitrophenoxide and copper(II) bromide in tetrahydrofuran, proceeded via formation of isocyanate to produce the corresponding 4-nitrophenyl N-alkylcarbamate with the evolution of nitrogen. Further, it was also found that 4-nitrophenyl N-alkylcarbamate reacted with primary or secondary amines to give the corresponding multisubstituted urea. Based on the above results, we developed a new method for the one-pot preparation of multisubstituted ureas from N,N′-dialkyldiazenedicarboxamides.
  • Dusan Hesek, Guy A. Hembury, Michael G. B. Drew, Yoshihisa Inoue
    Type: Others
    Subject area: OB
    2002 Volume 75 Issue 2 Pages 335-338
    Published: 2002
    Released: February 22, 2002
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    Reaction of rac-cis-Ru(Cl)2(bpy)2 with N,N-diethyl-4-nitrosoaniline (2) yields the compound rac-cis-[Ru(Cl)-(bpy)2(2)]Cl in 90–95% yield. Irradiation at 420 nm results in the novel specific substitution of the equatorial chloride ligand for MeCN, leaving the nitrosoarene ligand unaffected. X-ray analysis shows that the nitrosoarene ligand does not participate in an intramolecular π–π interaction with a bipyridine; molecular modelling confirms the relative instability of such a conformation. High thermal stability allows the Δ and Λ enantiomers to be separated and the circular dichroism spectra to be obtained; the anisotropy, or g, factors that are subsequently derived are found to be unexpectedly large.
  • Hideo Kitagawa, Tsuyoshi Shibata, Jun-ichi Matsuo, Teruaki Mukaiyama
    Type: Others
    Subject area: OB
    2002 Volume 75 Issue 2 Pages 339-345
    Published: 2002
    Released: February 22, 2002
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    Direct iodination and bromination of various aromatic compounds with 1.1–2.0 molar amounts of iodine monochloride (ICl) and 1.1–3.0 molar amounts of bromine proceeded smoothly to afford the corresponding aromatic iodides and bromides, respectively, in good to excellent yields by using 0.05 molar amount of ferrocenium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate, Cp2FeB[3,5-(CF3)2C6H3]4 (1), in the presence of ZnO. Iodination of toluene in the coexistence of 0.5 molar amount of DDQ also proceeded to give iodotoluenes in high yield.
  • Kazuyoshi Obitsu, Shojiro Maki, Takashi Hirano, Haruki Niwa
    Type: Others
    Subject area: OB
    2002 Volume 75 Issue 2 Pages 347-354
    Published: 2002
    Released: February 22, 2002
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    Seven deoxygenated neoanisatin derivatives were prepared from anisatin and neoanisatin by utilizing methoxalyl ester/tributylstannane (n-Bu3SnH) deoxygenation procedure coupled with a novel dehydration reaction of neoanisatin.
  • Takashi Sugimura, Satoshi Nakagawa, Akira Tai
    Type: Others
    Subject area: OB
    2002 Volume 75 Issue 2 Pages 355-363
    Published: 2002
    Released: February 22, 2002
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    Tartaric acid-modified Raney nickel (TA-MRNi) is a chiral heterogeneous catalyst for the hydrogenation of prochiral ketones. An optical yield (OY) of 86% with methyl acetoacetate (1) as a substrate was improved to 94–96% by employing β-keto esters having a proper bulkiness at the γ -position. The γ -bulkiness effect contributes to a high intrinsic enantio-differentiating ability (factor-i) of the TA-MRNi catalysis. Through the study, we found the best substrate, γ -cyclopropyl-β-keto ester, the hydrogenation of which resulted in 98.6% OY. This further improvement in the OY was ascribed to a smaller contribution of non-enantio-differentiating hydrogenation (N-site catalysis) due to the substrate-specific activation of the enantio-differentiating hydrogenation by the chiral modifier. The OY of the hydrogenation of 1 was analyzed by comparing with well-behaved β-keto esters, and the contribution of the factor-i and the N-site to the OY value was evaluated to deduce the origin of the enantiodifferentiation.
  • Dipak K. Mandal
    Type: Introduction
    Subject area: OB
    2002 Volume 75 Issue 2 Pages 365-366
    Published: 2002
    Released: February 22, 2002
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    A new and unifying approach based on a directional relationship between two arcs joining two ligands at either end of the stereogenic axis is presented for assigning stereogenic axis configuration, which is specified as Con (when both arcs are clockwise or counterclockwise) or Dis (when one arc is clockwise and the other counterclockwise). Con and Dis correspond, respectively, to the descriptors axial R and axial S for a chiral axis, and to E and Z for an achiral alkene axis.
  • Tsutomu Watahiki, Hisashi Kikumoto, Masaya Matsuzaki, Takeshi Suzuki, ...
    Type: Introduction
    Subject area: OB
    2002 Volume 75 Issue 2 Pages 367-368
    Published: 2002
    Released: February 22, 2002
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    Reaction of alcohols with dihydropyran in the presence of a catalytic amount of Sc(OTf)3 provides efficiently the corresponding tetrahydropyranyl ethers. After the reaction, the catalyst can be recovered quantitatively from the aqueous media and reused without loss of the activity.
  • Vilas. D. Athawale, Priti. S. Pillay
    Type: Others
    Subject area: AM
    2002 Volume 75 Issue 2 Pages 369-373
    Published: 2002
    Released: February 22, 2002
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    Hydrogenated castor oil was reacted with isophorone diisocyanate under different stoichiometric NCO/OH ratios to obtain polyurethanes. These polyurethanes were subsequently interpenetrated with butyl methacrylate monomer using ethylene glycol dimethacrylate as a crosslinker by radical polymerization using benzoyl peroxide as an initiator. Polyurethane/poly(butyl methacrylate) interpenetrating polymer networks (PU/PBMA IPNs) were obtained as tough films by casting in a glass mould. All IPNs were characterized for their resistance to thermal behavior, swelling (%), and mechanical properties. The morphology of the IPNs was studied by scanning electron microscopy. Enhanced mechanical properties were obtained with an increase in the NCO/OH ratios in addition to the regular trend obtained by increasing the polyurethane component in the blend.
  • Mamoru Ai
    Type: Others
    Subject area: AM
    2002 Volume 75 Issue 2 Pages 375-381
    Published: 2002
    Released: February 22, 2002
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    Iron(III) phosphates doped with a very small amount of molybdenum(VI) were found to be effective as catalysts for a vapor-phase oxidative dehydrogenation of ethylene glycol to glyoxal. The effects of the molybdenum(VI) content and of the reaction variables on the conversion of ethylene glycol and selectivity to glyoxal were studied. The optimum Mo/Fe atomic ratio was in the range from 0.002 to 0.01. The highest selectivity to glyoxal was obtained in the temperature range of 290 to 310 °C. The rate of ethylene glycol consumption increased almost in proportion to the oxygen concentration, while the selectivity to glyoxal increased only slightly as the oxygen concentration was increased. The selectivity to glyoxal increased markedly as the concentration of water was increased. It reached 37 and 32 mol% at ethylene glycol conversions of 60 and 80%, respectively. The one-pass yield of glyoxal reached 26.5 mol%.
  • Hirohisa Tamagawa, Fumio Nogata, Susumu Umemoto, Norimasa Okui, Suzana ...
    Type: Others
    Subject area: AM
    2002 Volume 75 Issue 2 Pages 383-388
    Published: 2002
    Released: February 22, 2002
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    Adhesion between anionic and cationic gels was observed. This adhesion force varied according to the pH and the ionic strength of solutions bathing the gels. A quite strong adhesion was observed in neutral and the ionic-strength solutions. The cause of this phenomenon was suggested to be due to electrostatic interaction between the anionic and cationic fixed groups on the respective gel surfaces, that is, the formation of salt-linkages between the dissociated –COOH and –NH2 groups, –COO-···+H3N–. They were also found in an amphoteric gel body, thus suggesting a great influence on the degree of hardness. Salt-linkages serve as crosslinkings in amphoteric gel in addition to the permanently formed chemical crosslinkings of N,N-methylenediacrylamide. The degree of amphoteric gel hardness can be controlled reversibly by their formation and disruption. Since a reversible hardness change was also observed in real human muscle, the use of salt-linkages is a new principle used to design practical artificial gel muscles.
  • Yutaka Amao, Ichiro Okura
    Type: Others
    Subject area: AM
    2002 Volume 75 Issue 2 Pages 389-391
    Published: 2002
    Released: February 22, 2002
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    A new optical molecular thermometer based on the fluorescence intensities of the fullerene C60 dispersed in poly(methyl methacrylate) (PMMA) film was developed. The fluorescence intensity of the C60 film decreased with increasing the temperature in the range from 260 to 373 K. The Arrhenius plot of ln[(I(T)/I(Tref))] versus 1/T for the C60 film exhibits considerable linearity supported by the correlation factor, r2, estimated to be 0.989 by the least squares method (Tref = 260 K). The E/R value of the C60 film is estimated to be 22.3 K. These results indicate that the C60 film provides a linear temperature response in the range 260 to 373 K.
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