18
Chemistry Letters http://www.csj.jp/journals/chem-lett/ Vol.34 No.3 CMLTAG March, 2005 ISSN 0366-7022 Copyright Ó 2005 The Chemical Society of Japan 276 Hydrothermal Synthesis and Characteriza- tion of Zeolites Sodalite cage D6R D4R Faujasite Zeolite A Sodalite cage Toru Wakihara and Tatsuya Okubo Zeolites have been widely utilized in industry and in household products, for example as adsorbents, ion-exchangers, and catalysts, and have attracted considerable attention as host materials for various nanotechnology applications. Recent devel- opments in analytical methods have enabled detailed studies on the crystallization mechanism of zeolites. The purpose of this review is to give a survey of recent progress in hydrothermal synthesis and characterization of zeolites. Highlight Review Letter 282 Chemical Recycling of Polycarbonate to Raw Materials by Thermal Decomposition with Calcium Hydroxide/Steam When Ca(OH) 2 was added to PC at 500 °C, the yield of the low boiling fraction increased irrespective of the existence of steam. When the molar ratio (Ca(OH) 2 /PC) was 0, the yield of the low boiling fraction at a steam concentration of 86 vol % was 17 wt %, and at the molar ratio (Ca(OH) 2 /PC) of 5 was 31 wt %, the yield of the high boiling fraction was 67, 49 wt %, respectively. Moreover, the addition of Ca(OH)2 led to a high selectivity for phenol (70 mol %) irrespective of steam concentration. 100 20 40 60 80 composition of liquid / mol% others 0 35 86 steam conc. (%) Ca(OH) 2 /PC 0 0 5 0 5 phenol p-methylphenol p-ethylphenol p-vinylphenol tetramethylbenzene bisphenol A Toshiaki Yoshioka, Katsuya Sugawara, Tadaaki Mizoguchi, and Akitsugu Okuwaki

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Page 1: Chemistry Letters · C-34 Chemistry Letters Vol.34, ... Copyright 2005 The Chemical Society of Japan  ... (crystallized sample) (glassy sample) H

Chemistry Lettershttp://www.csj.jp/journals/chem-lett/

Vol.34 No.3 CMLTAGMarch, 2005 ISSN 0366-7022

Copyright � 2005 The Chemical Society of Japan

276 Hydrothermal Synthesis and Characteriza-tion of Zeolites

Sodalitecage

D6RD4R

FaujasiteZeolite A

Sodalite cage

Toru Wakihara and Tatsuya Okubo

Zeolites have been widely utilized in industry and in household products, for example as adsorbents, ion-exchangers, andcatalysts, and have attracted considerable attention as host materials for various nanotechnology applications. Recent devel-opments in analytical methods have enabled detailed studies on the crystallization mechanism of zeolites. The purpose of thisreview is to give a survey of recent progress in hydrothermal synthesis and characterization of zeolites.

Highlight Review

Letter

282 Chemical Recycling of Polycarbonate to RawMaterials by Thermal Decomposition withCalcium Hydroxide/Steam

When Ca(OH)2 was added to PC at 500 °C,the yield of the low boiling fraction increased irrespective of the existence of steam. When themolar ratio (Ca(OH)2/PC) was 0, the yield of the low boiling fraction at a steam concentration of 86 vol % was 17 wt %, and at the molar ratio (Ca(OH)2/PC) of 5 was 31 wt %, the yield of thehigh boiling fraction was 67, 49 wt %, respectively.Moreover, the addition of Ca(OH)2 led to a high selectivity for phenol (70 mol %) irrespective of steam concentration.

100

20

40

60

80

com

posi

tion

of li

quid

/ m

ol%

others

0 35 86steamconc. (%)

Ca(OH)2/PC 0 05 0 5

phenol

p-methylphenol

p-ethylphenol

p-vinylphenoltetramethylbenzene

bisphenol A

Toshiaki Yoshioka, Katsuya Sugawara, TadaakiMizoguchi, and Akitsugu Okuwaki

Page 2: Chemistry Letters · C-34 Chemistry Letters Vol.34, ... Copyright 2005 The Chemical Society of Japan  ... (crystallized sample) (glassy sample) H

C-34 Chemistry Letters Vol.34, No.3 (2005)

Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

284 Phosphor-doped Titania —a Novel Photoca-talyst Active in Visible Light

A novel phosphor-doped titania prepared by a

simple modified sol–gel method shows a

narrower band gap than pure titania and an

absorption tail in the visible range, which

results in its effective photocatalytic

degradation of 4-chlorophenol under

visible-light (>420 nm) irradiation.0 30 60 90 120

0.2

0.4

0.6

0.8

1.0

P-doped TiO2 - vis

pure TiO2 - vis

P-doped TiO2 - UV

pure TiO2 - UV

Ct /

C0

Time / min

Li Lin, Wei Lin, Yuexiang Zhu, Biying Zhao,and Youchang Xie

286 Dendritic Nanoreactor Encapsulating RhComplex Catalyst for Hydroformylation

RhCl

PPh2

-O2CHN+

N

N

N

N

N

N NHCO(CH2)mCH3

NHCO(CH2)mCH3

NHCO(CH2)mCH3

NHCO(CH2)mCH3

NHCO(CH2)mCH3

NHCO(CH2)mCH3

NHCO(CH2)mCH3

NHCHO(CH2)mCH3

Ph

CN

CO2Et Ph

CN

CO2Et

CO + H2

+

dendrimer encapsulated Rh complex

Tomoo Mizugaki, Yasuaki Miyauchi, MakotoMurata, Kohki Ebitani, and Kiyotomi Kaneda

288 A Mixed-metal Single-molecule Magnet:[Mn8Fe4O12(O2CCH2Cl)16(H2O)4]

2 3 5 64 70.00

0.05

0.10

0.15

0.20

χ M"

/ em

u m

ol–1

Temperature / K

10000 Hz 7500 Hz 5000 Hz 2500 Hz 1000 Hz 500 Hz 250 Hz 100 Hz

The out-of-phase components of

[Mn8Fe4O12(O2CCH2Cl)16(H2O)4] showfrequency-dependent peaks, predominantpeaks in the region 2 to 3 K as wellas minor peaks at 3 to 6 K.

ac susceptibilities of complex

Chen-I Yang, Hui-Lien Tsai, Gene-Hsiang Lee,Ching-Shuei Wur, and Shwu-Fen Yang

290 Novel Family of Molecular Glasses Based onSilicon-containing Compounds

(crystallized sample)

(glassy sample)

H3C Si CH3

7

0 10 20θ / degree2

30 40 50 60

Inte

nsity

Ichiro Imae and Yusuke Kawakami

292 The First S-Bridged CoIIICdIICoIII andCoIIICdII2Co

III Structures Controlled byChirality of Mono(thiolato)-Type Cobalt(III)Units

CdCl2 CdCl2

CoN

N N

S

N

N[∆/Λ] [Λ]

[∆]

[Λ]

[Λ][Λ]

Takashi Aridomi, Tatsuya Kawamoto, AsakoIgashira-Kamiyama, and Takumi Konno

Electronic Supporting Information

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Chemistry Letters Vol.34, No.3 (2005) C-35

Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

294 Simple and Practical Semi-wet Protein/Pep-tide Array Utilizing a Micelle-mixed AgaroseHydrogel In an agarose hydrogel, triton X-100

formed a micelle. The micelle-mixed

agarose gel was successfully applied

to fabricate a semi-wet protein/peptide

array for the enzyme/enzyme inhibitor

assay in a high throughput manner. BSA

substrate

Enzyme/protein assaysemi-wet protein/peptide

array

enzyme

substrate; DANS-Phe-Lys-Ser-Ser-Lys-Ser

no enzyme chymotrypsin trypsin V8 protease

Shun-ichi Tamaru, Satoshi Yamaguchi, andItaru Hamachi

Electronic Supporting Information

296 Control of Morphology and Reaction Activ-ity of CeO2–TiO2 Composite Nanostructuresby Changing the Mole Ratio of Cerium toTitanium Alkoxides

Crystallized CeO2–TiO2 composite nanostructures with differentmorphology, i.e., nano-network structure (Ce/Ti = 75/25) andnanorods (Ce/Ti = 25/75) were synthesized by changing the moleratio of metal alkoxides.

Ce/Ti =75/25 Ce/Ti =25/75

Keizo Nakagawa, Yusuke Murata, MasahiroKishida, and Motonari Adachi

298 Magnetic Mullite–iron Composite Nanopar-ticles Prepared by Solid Solution Reduction

0 50 100 150 200 250 3000.14

0.15

0.16

0.17

0.18

0.19

0.20

Mag

net

izat

ion

(em

u/g

)

Temperature (K)

FC

ZFCTBReduced at 1300°C , H2

Washed in HNO3

Grain of mullite-iron oxidesolid solution

Intra-granular nanocomposite ofiron embedded in mullite grain

Superparamagnetism

Hao Wang, Tohru Sekino, and Koichi Niihara

300 Changing Mixed-valence State of HexacobaltCluster by Substituting Central Metal Ionand by Electrochemical Reduction —Differ-ent Mixed-valence States of [M{Co-(prolinato)2g6]

4þ(M ¼ Ba2þ and La3þ)

Ba La [BaCoIII

2CoII4(prolinato)12]

4+ [LaCoIIICoII5(prolinato)12]

4+

Takashi Komiyama, Satoshi Igarashi,Yoshimasa Hoshino, and Yasuhiko Yukawa

Electronic Supporting Information

302 The Preparation and ElectrochemicalBehavior of Density-controlled Gold Nano-particle Self-assembled Interface abundance in SAMs.

The modified interfaceelectrodetheonnanoparticlesofdensityalteringcan 4,4′-bis(sulfanylmethyl)biphenylbycontrolledbe

Baokang Jin, Shounian Ding, KiyokazuKametani, and Toshio Nakamura

Electronic Supporting Information

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C-36 Chemistry Letters Vol.34, No.3 (2005)

Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

304 Polymorphism, Photoluminescence, andElectroluminescence of Diaminodicyanopyr-azine

Red Crystal Yellow crystalPhotoluminescence from red and yellowcrystals of the dye under a UV lightHisayoshi Shiozaki, Yotaro Inoue, and

Yoshiaki Sakurai

306 Organic Radical Crystals Based on aTEMPO–substituted Pyridinium with Radi-cal Anions

Ph N

Ph

Ph

N

XComposition/Polymorphism

Magnetic Property

OKen-ichi Kanbara, Kazumi Tsureishi, HirokiAkutsu, Jun-ichi Yamada, and Shin’ichiNakatsuji

Electronic Supporting Information

308 DNA-photocleaving Activities of Water-solu-ble Carbohydrate-containing Nonionic Ho-mooxacalix[3]arene.[60]fullerene Complex

OO

But

O

O

O

But

HN

HN

O

O

OHNO

HN

HN

NHO

But

O

O

But

N

N

O

O

OHNO

NH

NH

HNBut

O

OO

OHOH

HOHOHO

OHOH

OOHO

O

HOHOHO

HOHO

OH

OH

OHO

O

O

O OH

OH

HO

HOHO

OH

OH

O

OH

O

OHOH

OH OHOH

HO HO

OOH

O

OHO

HO

OH

OHOH

HO

HO

O

HO

O

OH OHOH

OHOH

HO

HO

OOH

O

O

Visible Light

DNA Photocleavage

Atsushi Ikeda, Akinori Ejima, Koji Nishiguchi,Jun-ichi Kikuchi, Takahiro Matsumoto,Tsukasa Hatano, Seiji Shinkai, and MasahiroGoto

310 Unusual Solvatochromism Based on Intra-molecular Hydrophobic Interaction inWater-soluble Azobenzene Dendrimers

Atsuya Momotake and Tatsuo Arai

312 Imidazolium Ionic Liquid-Grafted 2,20-Bi-pyridine—ANovel Ligand for the RecyclableCopper-catalyzed Selective Oxidation ofAlcohols in Ionic Liquid [bmim][PF6]

R1 R2

OH

R1 R2

OTEMPO, CuCl

O2, [bmim][PF6], 65 °C

PF6- PF6

-

N NN N

N N

A novel imidazolium ionic liquid-grafted 2,2′-bipyridine ligand has been prepared andsuccessfully employed in the copper-catalyzed oxidation of alcohols in [bmim][PF6]under mild conditions. Effective reuse has been demonstrated.

Xue-E Wu, Li Ma, Meng-Xian Ding, andLian-Xun Gao

Electronic Supporting Information

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Chemistry Letters Vol.34, No.3 (2005) C-37

Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

314 A Simple, Efficient and Solvent-Free Proto-col for the Friedlander Synthesis of Quino-lines by Using SnCl2 .2H2O

O

NH2

Cl

Ph

O O

OEtN

O

OEt

Ph

Cl+

SnCl2.2H2O

Neat, rt

18 examples Yield > 90%Pandurangan Arumugam, GanesanKarthikeyan, Raji Atchudan, D. Muralidharan,and Paramasivan T. Perumal

316 Stereoselective �-Hydrazination of �,�-Un-saturated Carboxylates Catalyzed by Man-ganese(III) Complex with Dialkylazodicar-boxylate and Phenylsilane

R

O

N

HN

BocBoc

Xc*

SO2

N

Xc*R

O+

PhSiH3

cat. Mn(dpm)3

Xc* =

diastereoselectivity91 99%

NCOt-But-BuOCNO O

Mitsuo Sato, Yasuhiko Gunji, Taketo Ikeno,and Tohru Yamada

318 Lewis Base-catalyzed Strecker-type Reactionbetween Trimethylsilyl Cyanide and N-Tosy-limines in Water-containing DMF

Ph H

NTs

Me3SiCN Ph CN

HNTs

DMF−H2O (Volume ratio 5:1)

6 h, −45 °C

+H+

AcOLi(10 mol%)

92 %

Eiki Takahashi, Hidehiko Fujisawa, ToshiharuYanai, and Teruaki Mukaiyama

320 Supramolecular Polymers from a Cyclodex-trin Dimer and Ditopic Guest Molecules

Kahori Ohga, Yoshinori Takashima, HirokazuTakahashi, Masahiko Miyauchi, YoshinoriKawaguchi, Hiroyasu Yamaguchi, and AkiraHarada

322 Photosensitizing Properties of Diazapor-phyrin Derivatives for Singlet OxygenGeneration

M

N

N

N N

N

NC6H13C6H13

C6H13 C6H13

3O21O2

hνHideyuki Shinmori, Fumiaki Kodaira, SeiichiMatsugo, Shigeki Kawabata, and AtsuhiroOsuka

Page 6: Chemistry Letters · C-34 Chemistry Letters Vol.34, ... Copyright 2005 The Chemical Society of Japan  ... (crystallized sample) (glassy sample) H

C-38 Chemistry Letters Vol.34, No.3 (2005)

Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

324 Water-induced Acceleration of TransportProperties in Hydrophobic 1-Butyl-3-meth-ylimidazolium Hexafluorophosphate IonicLiquid

Di / 10_12 m2 s

_1

0 10

Λ

Λ

Λ

/ S m_1

0 5 10 15 20 25

water-saturateddried

Dcation

Danion

Dcation

Danion

25 °C

40 °C

20 30 40 50 60Mitsuhiro Kanakubo, Tatsuya Umecky,Takafumi Aizawa, and Yoshiaki Kurata

326 A Co-reduction–Silicification Route to�-Ni2Si Nanowire

A co-reduction−silicification route hasbeen developed to synthesizeNanowires with diameters ranged in10−100 nm and lengths up to several tensmicrometers.

δ -Ni2Si

Baojun Yang, Hanmei Hu, Yucheng Wu, TaoLuo, Xiaogang Yang, and Yitai Qian

328 A Simple Method for Fabrication of Mesopo-rous Films Using a Rapid Heating Process

Takeo Yamada, Haoshen Zhou, Itaru Honma,Yuko Ueno, Tsutomu Horiuchi, and OsamuNiwa

330 Ab Initio Study of the Electronic Spectrum of7-Hydroxyquinoline

State ∆E/eV fππ* 3.65ππ* 4.93ππ* 5.20σπ* 5.28ππ* 5.47πσ* 5.87ππ* 6.08σπ* 6.44

0.070.060.130.0060.030.0060.10.0002

Calculated electronic transition energies (∆E) and oscillator strengths (f) of the cis-7HQ.

Jan Franz, Sigrid D. Peyerimhoff, MichaelHanrath, Oh-Hoon Kwon, and Du-Jeon Jang

332 Application of Bis(terpyridine)ruthenium(II)to N-Terminal Amino Acid Sequencing

A novel N-terminal labeling reagent [(tpy)RuII(tpyCONSu)]2+ (= <Ru>-COONSu) provides anefficient and effective N-terminal sequencing of peptides and proteins in MALDI-TOF-MS/MS(PSD) analysis, which shows an fragments predominantly without any C-terminal-fragment ion.

Taka-aki Okamura, Taku Iwamura, Akihiro Ito,Maki Kaneko, Minoru Yamaguchi, HitoshiYamamoto, Norikazu Ueyama, HirokiKuyama, Eiji Ando, Shigemi Norioka,Takashi Nakazawa, Ryoji Masui, and SeikiKuramitsu

Electronic Supporting Information

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Chemistry Letters Vol.34, No.3 (2005) C-39

Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

334 Two Trans and Two Cis Isomers in Caprylo-lactam in Mixed Solvent of Methanol andWater

181.0181.5182.0182.5 ppm

283 K

303 K

323 K

361 K

cis2 C1cis1 C1 trans2 C1 trans1 C1

Yu Tsutsumi, Hiroshi Nakanishi, and KaoriChiba-Kamoshida

336 Sulfate-promoted Titania Photocatalyst forHigh Efficiency Gas Phase Toluene Degrada-tion

UV

CO2

Toluene

H2O

A regenerable, halide-free, sulfate-promoted titania photocatalyst was developedfor the high-efficiency, room temperature gas phase photodegradation of tolueneat higher than trace concentrations.

Elodie Barraud, Florence Bosc, Nicolas Keller,and Valerie Keller

338 Acceptor Number of Room TemperatureIonic Liquid Determined by the RamanSpectrum of Diphenylcyclopropenone

40

30

20

10

0

AN

164016301620

ν / cm-1

O

1680164016001560

Raman shift / cm-1

CHX

EtOAc

CF

MeOH

[TMPA][TFSI]

[BMIN][BF4]

The Raman spectrum of diphenylcyclopropenone has been measured in various liquids includingroom temperature ionic liquids. We found a good linear correlation between the acceptor number ofliquid and the vibrational frequency of the C=C and C=O stretching mode. From the correlation,we have successfully determined acceptor number of several room temperature ionic liquids.

Yoshifumi Kimura, Masanori Fukuda,Tomotsumi Fujisawa, and Masahide Terazima

340 Co2(CO)8 as Novel and Water-tolerantReagent for the Conversion of Azides toAmines in Aqueous Media

O

N3

Co2(CO)8

O

NH2

H2O

J. S. Yadav, B. V. S. Reddy, G. Satheesh, and K.Raghavender Rao

342 Preparation of Anodic Porous AluminaMask with Ideally Arranged Holes on InPSingle Crystals

Kenji Yasui, Yasuhisa Sakamoto, KazuyukiNishio, and Hideki Masuda

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C-40 Chemistry Letters Vol.34, No.3 (2005)

Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

344 Ruthenium(II) Tricarboxyterpyridyl Com-plex with a Fluorine-substituted �-Diketona-to Ligand for Highly Efficient Dye-sensitizedSolar Cells

N

Ru NN

OHO

O

TBAO

O O

NC

FF

F

S

O

OTBA

F

Phot

ocur

rent

den

sity

/ m

A c

m 2

Voltage / V0 0.1 0.2 0.3 0.4 0.5 0.6 0.7

5

10

15

20

Ashraful Islam, Firoz A. Chowdhury, YasuoChiba, Ryoichi Komiya, Nobuhiro Fuke,Noriaki Ikeda, and Liyuan Han

346 Novel Approach for the Preparation of MetalContaining Mesoporous Silica Using Solubi-lization of Fatty Acid Salt

Aritomo Yamaguchi, Masahito Yokoyama,Taku Ogura, Kenichi Oyaizu, Makoto Yuasa,Takahiro Ohkubo, Hideki Sakai, and MasahikoAbe

348 Gelator and Thickener Derived from Di-methyl 5-Aminoisophthalate

HN

O

HN

O

HN

O

3

Temperature dependence of viscosity oftoluene solution of 3 (15 mg/mL).

Vis

cosi

ty (

cP)

Temperature/°C

00

10000

20000

30000

40000

10 20 30 40 50 60

Daisaku Inoue, Yasuhiko Sakakibara, MasahiroSuzuki, Hirofusa Shirai, Akio Kurose, andKenji Hanabusa

350 Triple-stranded Helicates as a SyntheticTemplate: Synthesis of Pyridine-containingMacrocyclic Compounds

AR

AR AR

ARAR AR

8 9

10

RCMARO

nO

n

Cu(I)

AR NN N N

Triple-stranded helicate

Tomikazu Kawano, Masataka Nakanishi,Takahiro Kato, and Ikuo Ueda

352 Total Synthesis of (�)-Arohynapene B

OH

CO2H

(±)-Arohynapene B

OAc

CO2Me

CO2MeCO2Me

CO2Me

+ 8 steps∆O

3 steps

Hideyuki Sugimura and Yuki Uchida

Page 9: Chemistry Letters · C-34 Chemistry Letters Vol.34, ... Copyright 2005 The Chemical Society of Japan  ... (crystallized sample) (glassy sample) H

Chemistry Letters Vol.34, No.3 (2005) C-41

Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

354 Triton X-100-Assisted Assembly of 5-nm AuNanoparticles by DNA Hybridization

A Triton X-100-assisted method isdeveloped to assemble small Au

oligonucleotides on 5-nm Au

nanoparticles by DNA hybridization,in which the non-specifc adsorption of

nanoparticles is overcome by shieldingthe Au nanoparticle with a Triton X-100layer.

Jun Yang, Jim Yang Lee, Heng-Phon Too,Gan-Moog Chow, and Leong M. Gan

356 Molecular Design of Sweet Tasting Com-pounds Based on 3�-Amino-3�-deoxy-18�-glycyrrhetinic Acid: Amido FunctionalityEliciting Tremendous Sweetness

(AH)

(B)

OH C

N O

OH

H

COO-

CO

(B)

2.5~4.0 Å

Possible Sweet Taste Sensation Model.So Ijichi and Seizo Tamagaki

358 Photochemical Immobilization of Protein onInner Wall of Microchannel

Position selective immobilization of protein on inner wall of microchannel.

UV light

Photo-reactive group

Protein

Amine-reactive group

Reactive group on innerwall of microchannel

Hizuru Nakajima, Satomi Ishino, HironoriMasuda, Takuya Shimosaka, TatsuroNakagama, Toshiyuki Hobo, and KatsumiUchiyama

360 Swelling Behaviors of an OrganosilylatedLithium Potassium Titanate in OrganicSolvents

Chloroform Benzene Toluene n -Decane n -Octanol Ethyl acetateYusuke Ide and Makoto Ogawa

362 Alkylation of Nonbridging Thiolato Groupsin an S-bridged CoIIIPdIICoIII TrinuclearComplex: Control of Geometrical Isomerismby Tuning Trans Influence Due to SulfurDonors

Yu Chikamoto, Masakazu Hirotsu, TatsuyaKawamoto, and Takumi Konno

Electronic Supporting Information

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C-42 Chemistry Letters Vol.34, No.3 (2005)

Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

364 A Strategy to Protect Al2O3-based PFCDecomposition Catalyst from Deactivation

Xiu-Feng Xu, Jong Yeol Jeon, Mi Hwa Choi,Hee Young Kim, Won Choon Choi, andYong-Ki Park

Electronic Supporting Information

366 Improved Thermal Stability of EuropiumComplex Nanoclusters Embedded in SilicaColloidal Spheres

Optically active hybrid spheres with core-shell structure.Improved thermal stability of europium complex nanoclusters in hybrid spheres.

0 20 40 60 80 100

0

20

40

60

80

100

Eu Hybrid spheres

Eu complex

Rel

ativ

e E

mis

sion

Int

ensi

ty (

%)

Aging Time (hour)

Dan Zhao, Weiping Qin, Jisen Zhang, GejihuDe, and Jishuang Zhang

368 Application of the Criegee Rearrangement inSinglet Oxygen Reaction: A High Yield of Di-osone from the Photooxygenation of Pseudo-diosgenin Diacetate O

AcO 53

1

6

16

1720

21

22

9

26

O

OO

O

AcO

OOH

AcOAcO

O

OO

AcO

1

2

3

4

pseudodiosgenin diacetate

diosone

14

a

a b

a. hv/sensitizer b. pyridine and acetic anhydride

Photochemically generated singlet oxygen adds selectively to C20−C22 rather than C5−C6

double bond of pseudodiosgenin diacetate to give diosone 4 and ene product 3 at roomtemperature. 3 was separated and characterized by 1H and 13C NMR as well as IR. Using theCriegee rearrangement of 3 can yield a high collection yield (80% in acetonitrile) of 4.

Yan Zhang, Zhang-Hua Zeng, Yong-Yong Liu,Xue-Xin Cheng, Xue-Song Wang, andBao-Wen Zhang

Electronic Supporting Information

370 Marked Inhibitory Effects of Extracts fromBarley-Koji Miso Encapsulated in HybridLiposomes on the Growth of HumanStomach Tumor Cells in Vitro

A remarkably high inhibitory effect of extracts from barley-koji miso (extract “E”)with ethanol encapsulated in hybrid liposomes (HL) on the growth of humanstomach tumor cells in vitro was obtained.

0

0.50

1.00

HL HL/Extract “E”

AM

ean/

A Con

trol

0.01Yutaka Kadota, Taiki Ibuki, Koichi Goto, YokoMatsumoto, and Ryuichi Ueoka

372 Stereoselective Synthesis of �-Amino-�0-

Hydroxy-�,�-Unsaturated Esters by theSamarium(II) Iodide-mediated Aldol Reac-tion of Aldehydes with �,�-Aziridiny-�,�-Unsaturated Esters

2 SmI2 / THF

RCHOR1

NTs

O

R1

ONTs SmI2

ON

O

Bn

R1

O

ON

ONHTs

R OHBn

syn / anti = >95 / <5

ON

O

Bn

SmI2

Yasuyuki Ogawa, Kiichi Kuroda, and TeruakiMukaiyama

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Chemistry Letters Vol.34, No.3 (2005) C-43

Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

374 Electrochemical Fabrication of Pd–Au Het-erogeneous Nanocontact Showing StableConductance Quantization under ApplyingHigh Bias Voltage

A very stable Pd−Au heterogeneous nanocontanct

high bias was fabricated by electrochemical method.showing conductance quantization under applying

Jingze Li, Yoshihiro Nakato, and KeiMurakoshi

376 First Example of Cationic Ring-OpeningPolymerization of �-Thionobutyrolactone

p

S

O

O

Scationic initiator

Hirofumi Kikuchi, Norio Tsubokawa, andTakeshi Endo

Electronic Supporting Information

378 Solution of a SAT Problem on a Photochem-ical DNA Computer

The sequence in MARK operation for each cycle

TACCCA

ATGCTG

ATGGGT

ACGACSAAAAASAAAAA

GCTGGTGCGGT

ACGCCA

ATGCTG

ATGCACGCTGGTTGCGGT

ACGACSAAAAASAAAAA

ACGCCA

ATGCTG

ATGGGTGCTGGTTGCGGT

ACGACSAAAAASAAAAA

AAAA

cvU cvU cvU

V V V

C P G[111][011][111]

cycle 2

TACCCA

ATGCTG

ATGGGT

ACGACSAAAAASAAAAA

GCTGGTGCGGT

cvU

V

[111]

ACGGTG

ATGCTG

Not used

final answer

cycle 3

TACGTG

ATGCTG

ATGCAC

ACGACSAAAAASAAAAA

GCTGGTTGCCACAAAAAAAAAAAA

TACGTG

ATGCTG

ATGCAC

ACGACSAAAAASAAAAA

GCTGGTTGCGGTAAAA

ACGCCA

ATGCTG

ATGCACGCTGGTTGCGGT

ACGACSAAAAASAAAAA

ACGCCA

ATGCTG

ATGGGTGCTGGTTGCGGT

ACGACSAAAAASAAAAA

AAAA

cvU cvU cvU cvU

V V V V

C P G[111][011][011][010]

Photochemical ligation

answer-ODN

template -ODN

anchor-ODN

spacer region

cycle 1Shinzi Ogasawara and Kenzo Fujimoto

380 Vanadium-catalyzed Isomerization of Cyclo-propanemethanols to Homoallylic AlcoholsInvolving C–C Bond Cleavage

Some vanadium compounds work as effective catalysts for the isomerization ofcyclopropanemethanols to the corresponding homoallylic alcohols. This reactionmay proceed via [3,3]sigmatropic rearrangement involving an oxovanadiumcyclopropanemethanolate accompanied by the C–C bond cleavage.

R1

R2OH

R1

R2 OH

up to 91%

VOXn

1 2

cat.V

OR1

R2

OXn-1

Yasunari Maeda, Takahiro Nishimura, andSakae Uemura

Electronic Supporting Information

382 X-ray Absorption Fine Structure Studies onthe Local Structures of Ni Impurities in aCarbon Nanotube

Ni in CNT

Kiyotaka Asakura, Wang-Jae Chun, KazuyukiTohji, Yoshinori Sato, and Fumio Watari

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C-44 Chemistry Letters Vol.34, No.3 (2005)

Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

384 Fabrication of MgOHierarchical Nanostruc-tures by a Thermal Evaporation Method MgO hierarchical nanostructures were

prepared through a simple thermalevaporation method. Scanning electronmicroscopy (SEM) image reveals the4-fold symmetric MgO hierarchicalmorphologies.

Peng Yan, Changhui Ye, Xiaosheng Fang,Jianwei Zhao, ZhenyangWang, and Lide Zhang

386 Effect of Ag Nanoparticles for Electrochemi-cal Sensing of Brilliant Cresyl Blue

S

S

CH2

CH2

S

S

CH2

CH2

S

S

CH2

CH2

Pretreated electrodeGold electrode

Active Agnanoparticles

HSCH2

CH2SH

S

HS

CH2

CH2

S

HS

CH2

CH2

S

HS

CH2

CH2

The modification of gold electrode by 1,4-benzenedimethanethiol (BDT)self-assembled monolayer and Ag nanoparticles was prepared and itselectrochemical sensing of brilliant cresyl blue (BCB) was observed.

Mao-Guo Li, Ying-Chun Gao, Xian-Wen Kan,Guang-Feng Wang, and Bin Fang

388 Fabrication of Polyaniline/EthylcelluloseComposite Microspheres by Microencapsu-lation

Polyaniline/ethylcellulose composite microsphereswere prepared by microencapsulation technique viaa modified emulsion−solvent evaporation method. Thecore was gained through the polymerization of aniline,while the shell was formed by the solidification ofethylcellulose under the condition of the evaporationof organic solvent. Microscopic study showedthat composite particles were all spherical in shapewith micron size. In scanning electron microscopeobservation, it can be seen that the size distribution ofcomposite particles is fairly narrow. The surface ofshell is rough and has some macropores. The structuresof composite microspheres were further characterizedby Fourier transform infrared spectra and UV–visspectra.

Fuyong Yang, Ying Chu, Lei Huo, Yang Yang,and Yang Liu

Electronic Supporting Information

390 Synthesis and CO Oxidation Catalytic Char-acter of High Surface Area Ruthenium Diox-ide Replicated by Cubic Mesoporous Silica

A high surface area ruthenium dioxide with partial ordered structure has beenreplicated by cubic Ia3d mesoporous silica KIT-6, and the replica shows highcatalytic activity for the oxidation of CO to CO2 at relatively low temperature.

Weihua Shen, Jianlin Shi, Hangrong Chen,Jinlou Gu, Yufang Zhu, and Xiaoping Dong

Electronic Supporting Information

392 Organic Field-effect Transistor Based onBiphenyl Substituted TTF

Bunpei Noda, Mao Katsuhara, Isao Aoyagi,Takehiko Mori, Tomohiro Taguchi, TakuyaKambayashi, Ken Ishikawa, and Hideo Takezoe

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Chemistry Letters Vol.34, No.3 (2005) C-45

Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

394 Synthesis of Highly Ordered MesoporousTantalum Oxide

Optimization

Ordered mesoporous structure

10 nm

Wormhole-like structure

10 nm

Kiyotaka Nakajima, Michikazu Hara, KazunariDomen, and Junko N. Kondo

396 Controllable Synthesis of One-dimensionalSingle-crystalline TiO2 Nanostructures

The high-magnification TEM and ED images ofas-synthesized titania nanoribbons indicate that thesynthesized nanoribbons are structurally uniform with aninterplanar spacing of about 0.35 nm, which correspondsto the distance between two (101) planes of anatase phaseTiO2. The clear lattice fringes further confirm that thenanostructures are single-crystalline and the structure isperfect.

Baomei Wen, Chunyan Liu, and Yun Liu

398 Distribution of Acid Sites in MordeniteBrønsted acid sites of mordenite

are preferentially located on the

site of 8-member ring, and these

were stronger than on the 12-

member ring, as found from

IRMS-TPD of ammonia.

Katsuki Suzuki, Naonobu Katada, and MikiNiwa

400 Effective One-pot Synthesis of H type 1 and2 Trisaccharide Derivatives Using GlycalEpoxide

XO

HOO OR

I

II

ORORRO

O

OH

OHO

HO

O OH

OHHO

H-disaccharide

OORO

OORRO

RO

O

Hiroshi Tanaka, Nobuatsu Matoba, and TakashiTakahashi

Electronic Supporting Information

402 Formation of a Ligand-based Mixed-valenceCluster Triggered by Dehydration Conden-sation of Semiquinonates with o-Phenylene-diamines

ligand-based mixed-valence cluster

N

N

Cl

Cl

H2N

H2N

Cl

Cl

Co

O

O

2 4

homovalent cluster

Ho-Chol Chang, Nao Nishida, and SusumuKitagawa

Electronic Supporting Information

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C-46 Chemistry Letters Vol.34, No.3 (2005)

Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

404 One Pot Synthesis of Isometrically Pure 5-Carboxy-sulforhodamines and Their Appli-cation for Labeling Proteins

N+

R2

O N

SO3H

CO2H

R1R1

R2

R3 R3

New reactive fluorescent dyeswere prepared by one potsynthesis. The application oftheir labeling proteins had beenaddressed.

Zhi-Qiang Wang, Zhenjun Diwu, JeannieFrancisco-Reyes, and George G. Yi

406 Direct Amination of Toluene with Hydroxyl-amine in the Presence of Vanadium-basedCatalysts

CH3

+ NH2OHCat.

CH3

NH2+ H2O

The amination of toluene to toluidines with hydroxylamine hydrochloride wasinvestigated over vanadium-based catalysts supported on different carriers. Thereaction was carried out in different reaction media with or without the presence ofair. 56% touidine yield with 87% selectivity were obtained at optimized conditions.This provides a new approach in accordance with the trends towards a sustainabledevelopment. Tianhua Yu, Changwei Hu, and Xueqin Wang

408 Unprecedented Ligand Dependent SN20

Mechanism on the Palladium-catalyzedNucleophilic Substitution to Bicyclic DienylAcetates AcO

OAc

Pd+L

Pd+L

Nu

Nu

Pd cat.

Pd cat.

Nu-

Nu-

SN2

(2R,4aR)

(2S,4aS)

SN2' SN2'(2R,4aR)

(2S,4aS)SN2

SN2SN2

Hisashi Daimon, Takahiro Kitamura, TamotsuKawahara, and Isao Shimizu

410 Flexible Hexagonal Tube Framework of aNew Nickel Complex Assembled from Inter-molecular Hydrogen Bonds

A new nickel complex with a tubular framework assembly, [Ni(ima)2(MeOH)2]•2MeOH (where ima =4-imidazoleacetato), and its nonmethanolated complex, [Ni(ima)2], have been synthesized. The dried,nonmethanolated compound selectively reacts with methanol to reconstruct the initial porous framework,which induces a porous function connected with the reconstruction of the tubular framework assembly.

40

35

30

25

20

15

10

5

00 24 48 72 96 120

24 25 26 270

10

5

time / hour

/hour

addition of MeOH

rela

tive

vo

lum

e o

f ad

sorb

ed e

than

ol

and

met

han

ol m

ole

cule

s / %

addition of MeOH

MeOH

EtOH

Mitsuru Kondo, Takahiro Iwase, YumikoFuwa, Tomonori Horiba, Makoto Miyazawa,Tetsuyoshi Naito, Kenji Maeda, Sachie Yasue,and Fumio Uchida

412 Solid Surface Enhancement Effects onChemiluminescence: Effects of Number ofCationic Species in Solid Media

Effects of number of cationic species (Na+

or K+) on solid surface chemiluminescencehas been shown. The more sodium ions

Rel

ativ

e C

L I

nten

sity

0

10

20

30

40

50

60

SA SHC PHP TSP MSP DPP ENa4 E SS SC PP PA DSP TPP MPP ENa2

(or potassium ions) are included in thesolid media, the stronger the CL intensity.

Tetsutaro Yoshinaga, Shigekazu Akimoto,Teijiro Ichimura, Hiroshi Hiratsuka, MikiHasegawa, Michio Kobayashi, and ToshihikoHoshi

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Chemistry Letters Vol.34, No.3 (2005) C-47

Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

414 Preparation of Aligned Amorphous SilicaNanowires

Highly aligned amorphous silica nanowireshave been prepared on silicon substrate.The strong blue emission peaked at 401 and440 nm under 274 nm excitation wavelengthwas observed.

Yajie Xu, Chuanbao Cao, Bing Zhang, andHesun Zhu

416 Enzymatic Synthesis of Gold NanoparticlesWrapped by Glucose Oxidase

β-D-glucose

glucono-lactone

GODRED

GODOX

(FADH)

(FAD )+AuIII

c.a. 14.5 nm

Kei Yasui and Nobuo Kimizuka

Electronic Supporting Information

418 Hydrothermal Synthesis of Highly Crystal-lized Lepidocrocite Nanosheets of TiO2 un-der Low Temperature DDA

DDA

DDA

DDA

alcohol

TBAOH

Lamella multisheets monosheetFumin wang, Jinting Jiu, Lihua Pei, KeizoNakagawa, Seiji Isoda, and Motonari Adachi

420 Quaternary Ammonium Dendrimers asLewis Base Catalysts for Mukaiyama–AldolReaction

OSiMe3

OMe

N+ I-

CH3

NH

O

RCO2Me

OSiMe3

RCHO +

16n = 8, 14

n

quaternarized dendrimer

Tomoo Mizugaki, Casey E. Hetrick, MakotoMurata, Kohki Ebitani, Michael D. Amiridis,and Kiyotomi Kaneda

422 Lewis Base-catalyzed Trifluoromethylationof Aldimines with (Trifluoromethyl)trime-thylsilane

H

N

CF3Me3SiCF3

(1.4 equiv.)

+

AcOLi (10 mol%)

DMF, −20°C

16 h 93 % yield

TsHN

Ts

Yoshikazu Kawano, Hidehiko Fujisawa, andTeruaki Mukaiyama

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C-48 Chemistry Letters Vol.34, No.3 (2005)

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424 Enhanced Selectivity to Decalin in Naphtha-lene Hydrogenation under SupercriticalCarbon Dioxide

Rh/C in scCO2

H2

Norihito Hiyoshi, Ritsuko Miura,Chandrashekhar V. Rode, Osamu Sato, andMasayuki Shirai

426 Fluorous Glycopeptide Synthesis withoutProtection of Sugar Hydroxy Groups

C8F17

N C8F17

N C8F17

O

O

C8F17

N C8F17

N C8F17

O

O

N

NN

O

O

OO

OFmoc-Leu

Fluoroussynthesis

OHOOH

HOAcHNH-Ile-Asn-Ala-Thr-Leu-OH

Mamoru Mizuno, Kohtaro Goto, and TsuyoshiMiura

428 Synthesis of Porous Nickel Oxide Nanofiber

Akihiko Nakasa, Eiji Suzuki, Hisanao Usami,and Hitoshi Fujimatsu

430 A Novel Way for Preparing Cu Nanowires

Copper nanowires with lateral dimensions of50–200 nm were successfully synthesized by thepyrolysis of copper oxalate hydrate in thepresence of CO2 at 220 °C. The phase andmorphology of the products were analyzed byX-ray powder diffraction (XRD) andtransmission electron microscopy (TEM).The possible mechanism and future applicationwere proposed.

Changle Chen, Zhengsong Lou, and QianwangChen

432 Study on Disulfur-backboned Nucleic Acid:Part 2. Efficient Synthesis of 30,50-Dithiothy-midine

N

NH

O

OOHO

HO

N

NH

O

OOHS

HS

1. TsCl, Pyridine2. MsCl, Pyridine

OTsO

N

N

O

O

4. AcSH, reflux5. AcSK, Dioxane

6. LiAlH4, THF or EtSNa, EtSH3. DBU, acetnitrile

Hua Wang, Changmei Cheng, HongchaoZheng, Xiaohong Liu, Chang Fang, ShanshanXu, and Yufen Zhao

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Chemistry Letters Vol.34, No.3 (2005) C-49

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434 Helical Stereocontrol of 2,6-Bis{(2-arylcar-bamoylphenyl)carbamoylgpyridine Deriva-tives by Use of Chiral Auxiliaries

The predominance of left- and right-handed stereochemistry of 1 is governed by thesteric bulkiness of substituent R1 and R2.

N

O

NH

H

ON

O

Z

N

O

NH

H

O

N

O

NH

H

ON

O

Z

O

Z

(M )-form of 1

N

O

NH

H

O

O

Z

(P )-form of 1

HH H H

R1 R2 R1 R2 R1R2 R1 R2

(Z = NH, O)

Tatsuya Minami, Shigeru Koyamoto, MasayukiKobayashi, Rika Tanaka, and Yasuo Hatanaka

Electronic Supporting Information

436 Formation and Optical Properties of Thinand Wide Tin-doped ZnO Nanobelts

Thin and wide ZnO nanobelts doped with 5 atom % tin (Sn) have been achieved onthe tin-coated silicon substrate via chemical vapor deposition of Zn powders at700 °C, and the growth orientation and optical property can be altered by doping.

Xiao-Sheng Fang, Chang-Hui Ye, Li-De Zhang,Yan Li, and Zhi-Dong Xiao

438 A Library Synthesis of Pyrazoles by Azome-thine Imine Cycloaddition to the Polymer-supported Vinylsulfone Ar2 N

N

NH2

OHN

O R1

NN

Ar2

RinkNH

OHN

O

p-tolSO2

2) DBU, CH2Cl2, rt, 1 h

3) 25% TFA / CH 2Cl2

R1

Ar3

Ar3

ClNEt3, CH2Cl2

1)

Nobuhiro Fuchi, Takayuki Doi, and TakashiTakahashi

440 Mercury(II) ion Potentiometric Sensor Basedon a Sulfur Schiff’s Base 1-(2-Hydroxy-1,2-diphenylethylidene)thiosemicarbazide asIonophore

N

HN

S

NH2

OH

A PVC membrane sensor for Hg(II) ion based on a sulfur Schiff ’s base1-(2-hydroxy-1,2-diphenylethylidene)thiosemicarbazide (HDPET) asionophore.

Lan Xu, Ruo Yuan, and Ya-Qin Chai

442 Self-assembled N-Alkylimidazolium Per-fluorooctanesulfonates Thermostability of a smectic A phase composed of N-alkylimidazolium

heptadecafluorooctanesulfonate was improved by the formation ofnonpolar layer composed of mixed perfluoroalkyl and aliphatic chains.

Tomohiro Mukai, Masafumi Yoshio, TakashiKato, and Hiroyuki Ohno

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C-50 Chemistry Letters Vol.34, No.3 (2005)

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444 A New One-pot Synthesis of �-Amino Phos-phonates Catalyzed by Butyldimethyl(1-phenylethyl)ammonium Bromide

H3COP

OCH3

OCH3O

OCH3

OCH3C

NHR1R

H

RCHO+ R1NH2 +

1 2 3

P

4 a o

Catalyst(0.3

DCM/Reflux, 2.5 3.5 h.

0.5 mol%)

K. Rosi Reddy, K. Srinivasa Reddy, Ch.Venkateshwar Reddy, M. Mahesh, P. V. K.Raju, and V. V. Narayana Reddy

446 Controlling Chemoselectivity in Reactions ofUnprotected Naphthalene-1-carboxylic Acidwith Strong Bases

(M= Li, K)

CO2H

5

7

SiMe3

CO2M CO2M CO2M

MM M

M

4 6

CO2H

1

CO2H

R

EH

3

David Tilly, Anne-Sophie Castanet, andJacques Mortier

Electronic Supporting Information

448 Synthesis of a Misfit-layered MagnesiumManganese Hydroxide Oxide

Yaohua Xu, Noriaki Nakayama, KeikoFujiwara, Tadato Mizota, and Seishi Goto

450 Novel Unsymmetrical Achiral Banana-shap-ed Molecules Having Different Lengths ofAlkyl Terminal Chains

The SmCAPA layer structure for the B2 phase was found in 2{4,10}, 2{4,11}, 2{4,12}, and 2{6,14}.

OO

O O

NN

OCn2H2n2+1H2n +1Cn1O

P(n1, n2)-O-PIMB 2{n1, n2} (n1 ≠ n2)1

Kumiko Ogino, Sungmin Kang, Takayuki Doi,Takashi Takahashi, Hideo Takezoe, and JunjiWatanabe

Additions and Corrections

452 Catalytic Asymmetric Syntheses of ICI-199441 and CP-99994 Using Nitro-MannichReaction NMe

N

OCl

Cl

ICI-199,441

HN

HN

OCH3

CP-99,994Natsuko Tsuritani, Ken-ichi Yamada, NaokiYoshikawa, and Masakatsu Shibasaki