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

Vol.38 No.6 CMLTAGJune, 2009 ISSN 0366-7022

Copyright � 2009 The Chemical Society of Japan

512 Synthesis of Several Types of BridgedNucleic Acids O

Y

B

P OO

Z

2',4'-BNA (LNA): X = Y = Z = O3'-Amino-2',4'-BNA: X = Z = O, Y = NH 5'-Amino-2',4'-BNA: X = Y = O, Z = NH2'-Amino-LNA: X = NH, Y = Z = O

2'4'

X

OBO

2'4'

OP OO

XY

2',4'-BNACOC: X = Y = OPrNA: X = O, Y = C

OBO

2'4'

OP OO

XY

ENA: X = O, Y = CAza-ENA: X = NH, Y = C2',4'-BNANC: X = O, Y = N

O

O

O

O T

OO B

O

3',4'-BNA

trans -3',4'-BNA

O

P

P

OO

OO

O

N

O

T

P OO

5'-Amino-3',5'-BNA

O T

2',5'-BNAON

ON

OP OO

N-type BNAs

5' 3'

S-type BNAs

3'

4'

4'

3'

3'

5'

5'

2'S. M. Abdur Rahman, Takeshi Imanishi, andSatoshi Obikadoi:10.1246/cl.2009.512

A number of bridged nucleic acids with conformationally locked sugar moiety were synthesized from the readily acces-sible sugar derivatives. The conformations of the sugar moiety of the bridged nucleic acids (BNAs) are locked to eitherN-type or S-type sugar puckering. This article summarizes the synthesis of these nucleic acid analogues.

Highlight Review

Letter

518 Preparation of Cu@Ag Core–Shell Nanopar-ticles Using a Two-step Polyol Process underBubbling of N2 Gas

Masaharu Tsuji, Sachie Hikino, YoshiyukiSano, and Misao Horigomedoi:10.1246/cl.2009.518

C-64 Chemistry Letters Vol.38, No.6 (2009)

Copyright � 2009 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

520 Mass Spectrometric Detection of GaseousHydrogen Peroxide in Ambient Air Using Di-electric Barrier Discharge as an ExcitationSource

MS

A.C. H.V.

DC bias

SampleHelium

Innerelectrode

Outer electrode

Dielectricquartz tube

Innerelectrode

He*

Dielectricquartz tube

m /z20 40 60 80 100 120 140

[H2O2]O2−

66

48

Lee Chuin Chen, Hiroaki Suzuki, KunihikoMori, Osamu Ariyada, and Kenzo Hiraokadoi:10.1246/cl.2009.520

522 Selective Uptake of Aromatic Compoundsfrom Aqueous Solutions by Mg–Al LayeredDouble Hydroxide Intercalated with 2,7-Naphthalenedisulfonate Brucite-like layer

–O3S SO3–

Xe-

Ye-

Brucite-like layer

2,7-NDS•Mg-Al LDH

π -π stackinginteraction

Tomohito Kameda, Takashi Yamazaki, andToshiaki Yoshiokadoi:10.1246/cl.2009.522

524 Expeditious Construction of Quinazolinesvia Brønsted Acid-induced C–H Activation:Further Extension of ‘‘tert-Amino Effect’’

A rapid access to the quinazolineskeleton is acheived by exploitingthe “tert-amino effect.” A catalyticamount of Brønsted acid (TsOH•H2O)worked as an effective activator forthe expeditious construction of aquinazoline framework from o-formylN,N-dialkyl-substituted anilines andamines.t-amino effect

6-endo-trigcyclization

H

N

N

Ph

H

O

N N

N

H

HN

N+

PhH

mineformation

5 mol%TsOH•H2O

Benzenereflux, 8 h

73%

H2N

Ph Ph

Ph Ph

6 additional examples

PhPh

Ph Ph

H+

Keiji Mori, Yoshitaka Ohshima, KensukeEhara, and Takahiko Akiyamadoi:10.1246/cl.2009.524Electronic Supporting Information

526 Drastic Change in Dimensional Structures ofD-Penicillaminato (AuI2Pt

II2Zn

II)n Coordi-nation Polymers by Moderate Change inSolution pH

Takumi Konno, Nobuto Yoshinari, MaiTaguchi, and Asako Igashira-Kamiyamadoi:10.1246/cl.2009.526Electronic Supporting Information

528 Extension of Frozen-orbital Analysis to theTamm–Dancoff Approximation to Time-dependent Density Functional Theory

Schematic picture of excitation-energy levels of CO.

Yutaka Imamura, Takeshi Baba, and HiromiNakaidoi:10.1246/cl.2009.528

Chemistry Letters Vol.38, No.6 (2009) C-65

Copyright � 2009 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

530 Biological Activity of Some CyanobiphenylDerivatives

An amphiphilic compound with a nematic phaseexhibits anticancer activity against A549 humanlung carcinoma cells without toxity againstWI-38 nomal fibroblast cells.

Atsushi Yoshizawa, Yuuka Takahashi, AyumiNishizawa, Kazuhito Takeuchi, MasanobuSagisaka, Kenji Takahashi, Masaharu Hazawa,and Ikuo Kashiwakuradoi:10.1246/cl.2009.530Electronic Supporting Information

532 A Novel Method for Preparing Silanols fromSilylmethanols

MeSi

R

MeOH

MeSi

R OH

MeTEMPO, NaOCl, KBr

silylmethanol silanol

acetone, NaHCO3(aq)

Daisuke Takeda, Ryo Oyama, and ShozoYamadadoi:10.1246/cl.2009.532Electronic Supporting Information

534 Internal Alkyne-to-vinylidene Isomerizationat Cationic Ruthenium and Iron Complexes

Cp

MPh2PPPh2

ClArPh

NaBArF4 Cp

MPh2PPPh2

•

BArF4

Ar

PhM = Ru, Fe

Formation of Vinylidens from Common Internal AlkynesYuichiro Mutoh, Yousuke Ikeda, YusukeKimura, and Youichi Ishiidoi:10.1246/cl.2009.534Electronic Supporting Information

536 Pulse Frequency-dependent Regulation ofLysozyme Reactivity under Pulsed Ultra-sound Irradiation

Takayoshi Kawasaki, Momoko Toyoda, andYoshio Okahatadoi:10.1246/cl.2009.536Electronic Supporting Information

538 Pulsed Ultrasound Effect on DNA Polymer-ase Reaction Monitored on a QCM

Takayoshi Kawasaki, Momoko Toyoda, YuHoshino, and Yoshio Okahatadoi:10.1246/cl.2009.538

C-66 Chemistry Letters Vol.38, No.6 (2009)

Copyright � 2009 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

540 Promoting Effect of Re Addition to Rh/SiO2

on Glycerol Hydrogenolysis

0

20

40

60

80

Yie

ld /

%

Degradation

2-Propanol

1-Propanol

1,2-Propanediol

1,3-Propanediol

393 K ↑ ↑ 453 K

Rh/SiO2

Rh-ReOx /SiO2

Rh-MoOx /SiO2

Rh-WOx /SiO2

Ru/C+Amberlyst

Rh/C+H2WO4

Raney Ni

Reaction temperature

20% glycerol aq8.0 MPa H25 h

Modification of Rh/SiO2 with ReOx promotedthe glycerol hydrogenolysis and suppressed thedegradation. In particular, the formation of

Rh–ReOx /SiO2.1,3-propanediol became more favorable on the

Akira Shimao, Shuichi Koso, Naoyuki Ueda,Yasunori Shinmi, Ippei Furikado, and KeiichiTomishigedoi:10.1246/cl.2009.540

542 Preparation of Long Conjugated PorphyrinPolymers with Gold Nanoparticles at BothEnds as Electronic and/or Photonic Mole-cular Wires

100 nm

Hiroaki Ozawa, Masahiro Kawao, HirofumiTanaka, and Takuji Ogawadoi:10.1246/cl.2009.542Electronic Supporting Information

544 Properties of Protic Ionic Liquids Composedof N-Hexylethylenediaminium and N-(2-Ethylhexyl)ethylenediaminium Cations withBis(trifluoromethanesulfonyl)amide Anion

Protic ionic liquid of (a) monoprotic N-hexylethylenediaminium (=HexH)(TFSA) salt tendsto crystallize on cooling while that of (b) monoprotic N-(2-ethylhexyl)ethylenediaminium(= EtHexH)(TFSA) salt assumes only a glassy state in solid. In the liquids, the HexH salt ismore fluid than the EtHexH salt.

Masayasu Iida, Emi Syouno, SayakaKawakami, and Miyuki Hanaidoi:10.1246/cl.2009.544

546 External Electric Field Effects on Emissionof a Dendrimer-encapsulated Gold Nano-cluster in a Polymer Film

Emission spectrum

Electroemission spectrum at 0.8 MV cm–1

Ruriko Ohshima, Takakazu Nakabayashi,Tatsuo Hamada, and Nobuhiro Ohtadoi:10.1246/cl.2009.546

548 Highly Stable Mesoporous Aluminosilicateswith a Dual Pore System: Simultaneous For-mation of Mesophase with Zeolitic BuildingUnits

Al-MCM-48-type mesoporous materials containngzeolitic subunits on the mesopore walls and strongacid sites were fabricated by a direct one-pothydrothermal synthesis. These novel materials, whichpossess dual micro- and mesoporosities, were foundto exhibit superior thermal, hydrothermal andmechanical stabilities compared to conventionalAl-MCM-48. They are presumed to have BEA subunitsand are of practical interest as solid acid catalysts forindustrial applications.250 200 150 100 50 0 -50 -100

298 K

280 K

260 K

240 K

220 K

200 K

180 K

160 K

MesoporesMicropores

Chemical Shift (δ )

HP 129Xe NMR spectra of Al-MCM-48-SUB

Subhash C. Laha, Ayyamprmaul Sakthivel,Kenichi Komura, Shing-Jong Huang, Pei-HaoWu, Shang-Bin Liu, Yukichi Sasaki, MidoriKobayashi, and Yoshihiro Sugidoi:10.1246/cl.2009.548Electronic Supporting Information

Chemistry Letters Vol.38, No.6 (2009) C-67

Copyright � 2009 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

550 Influence of Surface Energy and Roughnessof Substrate on Thin Pentacene and C60

Films Prepared by Vacuum DepositionSurface roughness of substrate predominantly

deposited thin films while surface energy of the

was obtained on substrate with the lower roughness

influenced grain size of pentacene in vacuum-

substrate did not, i.e., the larger pentacene grain

instead of the lower surface energy.Hu Yan, Takuya Uchida, Tsubasa Kagata, YuIriyama, and Hidenori Okuzakidoi:10.1246/cl.2009.550

552 Hydrotreatment of Jatropha Oil to ProduceGreen Diesel over Trifunctional Ni–Mo/SiO2–Al2O3 Catalyst

Green diesel and LPG fuel were produced by hydrotreating Jatropha oil (containing 15 wt %free fatty acids) over Ni–Mo/SiO2–Al2O3 catalyst with functions of hydrogenation,deoxygenation, and isomerization/hydrocracking.

CH2–O–CO–C17=

CH–O–CO–C17=

CH2–O–CO–C15

C3H8

n-C18H38 + n-C17H36

n-C16H34 + n-C15H32

Isomerization/Hydrocracking

SiO2-Al2O3

Diesel

LPG

C17H33COOH n-C18H38 + n-C17H36

+H2; –O

Ni-Mo

+H2; –O

Ni-MoYanyong Liu, Rogelio Sotelo-Boyas, KazuhisaMurata, Tomoaki Minowa, and KinyaSakanishidoi:10.1246/cl.2009.552

554 A Novel Tailoring Route for the Fabricationof Different Hierarchical CuS Superstruc-tures

Different hierarchical CuS superstructures havebeen prepared firstly by a novel “ion-tailoring”method with clear advantages over the traditionalcomplex approachs for the production of 1Dsuperstructured nanomaterials.

Peng Gao, Xiaona Wang, and Yujin Chendoi:10.1246/cl.2009.554Electronic Supporting Information

556 Preparation of Perfluorocarbon/FluoroalkylPolymer Nanodroplets for Cancer-targetedUltrasound Contrast Agents

Masamichi Nishihara, Kenji Imai, andMasayuki Yokoyamadoi:10.1246/cl.2009.556Electronic Supporting Information

558 Facile Preparation of Red Luminescent Sili-con Nanocrystals via Controlled ChemicalEtching

Keisuke Sato, Hiroaki Tsuji, Naoki Fukata,Kenji Hirakuri, and Yusuke Yamauchidoi:10.1246/cl.2009.558Electronic Supporting Information

C-68 Chemistry Letters Vol.38, No.6 (2009)

Copyright � 2009 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

560 Selective Conversion of Glycerol into 1,2-Propanediol at Ambient Hydrogen Pressure

OHHO

OH

HO

OH- H2O

0.1 MPa H2

Satoshi Sato, Masaki Akiyama, Kanichiro Inui,and Masahiro Yokotadoi:10.1246/cl.2009.560

562 Synthesis of Thiol-capped Gold Nano-particles with Organometallic Reagents as aNew Class of Reducing Agent

HAuCl4·4H2O

HS-C12H25

Alkyl Metal

S C12H25AuS C12H25

S C12H25

Au nanoparticle

+(Metal = Mg, Li, Zn, Al)

TEM image

reduction byalkyl organometallic reagent

Atsushi Sugie, Tomomi Hatta, Kiyoshi Kanie,Atsushi Muramatsu, and Atsunori Moridoi:10.1246/cl.2009.562Electronic Supporting Information

564 Gallium(III) Chloride-catalyzed Sakurai Re-action of �-Amido Sulfones with Allyltri-methylsilane: Access to Synthesis of 2,6-Di-substituted Piperidine Alkaloid Derivatives

R SO2Tol

NHCbz

R

NHCbzGaCl3 (5 mol %)

DCM, rt, 3 h+ Me3Si

1 2 3

R. Sateesh Chandra Kumar, G. VenkateswarReddy, K. Suresh Babu, and J. MadhusudanaRaodoi:10.1246/cl.2009.564Electronic Supporting Information

566 Low Driving Voltage of a Liquid Crystal De-vice Fabricated from 40-Pentyl-4-biphenyl-carbonitrile Doped with EnvironmentallyFriendly ZnO Nanoparticles

The dirving voltage of LCD fabricated by 5CB decreases about 30% by doping with ZnOnanoparticles.

0.0 0.5 1.0 1.5 2.0 2.5 3.0 3.5 4.00

20

40

60

80

100

120V

th=0.9 V

Vd=1.7 V

Pure 5CB

Opt

ic tr

ansm

ittan

ce/%

Applied voltage (V/RMS)

20Hz 40Hz 60Hz 80Hz 100Hz 200Hz 400Hz 600Hz 800Hz 1KHz 2KHz 5KHZ

0.0 0.5 1.0 1.5 2.0 2.5 3.0 3.5 4.00

20

40

60

80

100

120V

th=0.4 V 5CB doped with ZnO

(0.5 wt%)

Vd=1.2 V

Applied voltage (V/RMS)

20Hz 40Hz 60Hz 80Hz 100Hz 200Hz 400Hz 600Hz 800Hz 1KHz 2KHz

Hui Jiang and Naoki Toshimadoi:10.1246/cl.2009.566

568 Alkylated 2,6-Bis(dicyanomethylene)-2,6-di-hydrobenzo[1,2-b:4,5-b0]dithiophenes: NewSoluble n-Channel Organic Semiconductorsfor Air-stable OFETs

5 10 15 20 250

200

400

600

800

1000

2θ / °

Inte

nsity

/ cp

s

d = 14.1 Å

S

S

CnH2n+1

CnH2n+1

NC

NC

CN

CN

S

S

NC

NC

CN

CN

0

1 10-6

2 10-6

3 10-6

4 10-6

5 10-6

0 10 20 30 40 50 60

I d / A

Vd / V

Vg = 60 V

50 V

40 V

30 V

20 V

10 V0 V

0

2 10-7

4 10-7

6 10-7

8 10-7

1 10-6

1.2 10-6

1.4 10-6

0 10 20 30 40 50 60

I d /A

Vd /V

Vg

= 60 V

50 V

40 V

30 V

20 V

10-0 V

0

100

200

300

400

500

5 10 15 20 25 30 35 40

Inte

nsity

/ cp

s

2θ / °

d = 3.3 Å

vapordeposition

spin coating

CNBDT

Cn-CNBDT(n = 8, 10, 12)

Tomoya Kashiki, Eigo Miyazaki, and KazuoTakimiyadoi:10.1246/cl.2009.568Electronic Supporting Information

Chemistry Letters Vol.38, No.6 (2009) C-69

Copyright � 2009 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

570 Face-on and Columnar Porphyrin Assem-blies at Solid/Liquid Interface on HOPG

A new strategy is proposed for new types of assemblies of porphyrins on surfaces. One of theresulting assemblies consists of highly ordered 1D columns of porphyrins.

Joe Otsuki, Kazuhiko Namiki, Yuki Arai,Makoto Amano, Hirokazu Sawai, ArataTsukamoto, and Toshiki Hagiwaradoi:10.1246/cl.2009.570Electronic Supporting Information

572 Ruthenium Nanoparticles Supported on Car-bon Nanotubes for Selective Hydrogenolysisof Glycerol to Glycols

OHOH

HO + H2

Ru/CNTs OHOH

OHHOOthers+ +

Juan Wang, Sihe Shen, Bodong Li, HaiqiangLin, and Youzhu Yuandoi:10.1246/cl.2009.572Electronic Supporting Information

574 Fritsch–Buttenberg–Wiechell (FBW) Reac-tion of 1-Halovinyllithium Carbenoids: AComputational Study

H

H

X

Li

H

H

X

Li

H

+

LiX

H

Lawrence M. Pratt, Ngan Van Nguyen, andOhyun Kwondoi:10.1246/cl.2009.574Electronic Supporting Information

576 An Efficient Ionic Liquid Additive for Pro-line-catalyzed Direct Asymmetric Aldol Re-actions between Cyclic Ketones and Aro-matic Aldehydes

An ionic liquid [EMIm][CF3COO] proved to be an efficient additive for proline-catalyzeddirect asymmetric aldol reactions between cyclic ketones and aromatic aldehydes in[BMIm]BF4 at room temperature.

Yunbo Qian, Xin Zheng, Xu Wang, ShiyongXiao, and Yongmei Wangdoi:10.1246/cl.2009.576

578 Tin–Chromium-modified Nickel/ActivatedCarbon Catalyst for Vapor-phase Carbon-ylation of Methyl Acetate to Acetic Anhy-dride

O

O

OO

O+ CO

Ni Sn

Cr

Qinglong Jia, Yisheng Tan, and Yizhuo Handoi:10.1246/cl.2009.578

C-70 Chemistry Letters Vol.38, No.6 (2009)

Copyright � 2009 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

580 Droplet Size Dependence of Line Tension foran Ionic Liquid on a Smooth Silane Coating

Line Tension

Hydrostatic Pressure0

Tsutomu Furuta, Akira Nakajima, MunetoshiSakai, Toshihiro Isobe, Yoshikazu Kameshima,and Kiyoshi Okadadoi:10.1246/cl.2009.580Electronic Supporting Information

582 The Effect of Zn Addition to La1�xSrxScO3��

Systems as a B-site Dopant

0.8 1.0 1.2 1.4 1.6–4

–3

–2La

0.8Sr

0.2Sc

0.95Zn

0.05O

3-δ (d = 0.954)

La0.8

Sr0.2

Sc0.975

Zn0.025

O3-δ

(d = 0.825)

La0.8

Sr0.2

ScO3-δ

(d = 0.641)La

0.9Sr

0.1ScO

3-δ (d = 0.779)

Temperature / oC400500600700800900

log{

σ(S

/ cm

)}

103 –1 –1T /K

Naoki Ito, Hiroshige Matsumoto, YuyaKawasaki, Sachio Okada, and Tatsumi Ishiharadoi:10.1246/cl.2009.582Electronic Supporting Information

584 An Eco-friendly, Convenient, and PracticalConversion of Arylamines to Oxazolidinones

A one-step procedure for efficient synthesis of oxazolidinone only using ethylene carbonate(EC) and aryl amines in the presence of 1,4-diazabicyclo[2,2,2]octane (DABCO) wasdeveloped. In most cases, moderate to high yield of products was obtained. The reaction can beconsidered a carbon dioxide fixation reaction, since ethylene carbonate is synthesizedvia reaction of ethylene oxide with carbon dioxide.

Hang Gong, Nian-Fa Yang, Guo-Jun Deng, andGuang-Yi Xudoi:10.1246/cl.2009.584Electronic Supporting Information

586 Efficient and Rapid Stereoselective Synthesisof trans-4,5-Diaminocyclopent-2-enones byAcidic Ionic Liquid under Solvent-free Con-ditions

O

N

NR'

R''

R'

R''NH

R'R''O

H

O+

[HMim][BF4]

solvent free5 to 10 minD. Ramesh, T. Srikanth Reddy, M.

Narasimhulu, S. Rajaram, N. Suryakiran, K.Chinni Mahesh, and Y. Venkateswarludoi:10.1246/cl.2009.586Electronic Supporting Information

588 TEMPO-based Redox-sensitive FluorescentProbes and Their Applications to EvaluatingIntracellular Redox Status in Living Cells

NB

N

F F

O O

NR

R

R

R

O

(R=H or Me)Yang Liu, Shanlin Liu, and Yanguang Wangdoi:10.1246/cl.2009.588Electronic Supporting Information

Chemistry Letters Vol.38, No.6 (2009) C-71

Copyright � 2009 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

590 One-pot Tandem Synthesis of a Coumarin/Naphthoquinone Monoimine-based Oxaza-bicycle and Its Fluorescence Redox-switch-ing Properties

O

O

O

N

O

CF3

H

N O

O

O

NH

OH

CF3

H

N

NaBH4

DDQ

fluorescentnonfluorescent

Jiun-Ting Lai, Chun-Han Lin, Yu-Ju Yang,and Ding-Yah Yangdoi:10.1246/cl.2009.590Electronic Supporting Information

592 Charge Carrier Transport Properties ofBiphenyl Liquid Crystals with a DimerStructure

1,8-Bis[4-(4′-octylbiphenyl)]octane (8BP8BP8) exhibits an enhanced hole mobility in thesmectic Bhex phase which is about 5 times higher than that of its corresponding monomer.

10−4

10−3

10−2

10−1

25 30 35 40 45 105 110 115 120 125 130 135 140

8BP8BP88BP4

Temperature/°C

Sm BSm B(8BP4)(8BP4)

Sm BSm B(8BP8BP8)(8BP8BP8)

Mob

ility

/cm

2 V−1

s−1

Jiang Wu, Takayuki Usui, Akira Ohno, andJun-ichi Hannadoi:10.1246/cl.2009.592Electronic Supporting Information

594 Diastereoselective Coupling of 1,3-Diene,Ketone, and Organometallic Reagents byNickel Catalyst: Stereoselective Construc-tion of Tetrasubstituted Carbon Centers

R

cat. Ni(cod)2-Ligand

Cs2CO3, CPMER RL

Ph HO1,3-anti

R RL

Ar HO1,3-syn

Ligand =

Ligand = P(p -tolyl)3

13

13

+

O

RSRL

Ar B(OH)2

HOPhMe2Si

N N MesMes

RL = Larger groupRS = Smaller group

RS

RSNozomi Saito, Tetsuro Yamazaki, andYoshihiro Satodoi:10.1246/cl.2009.594Electronic Supporting Information

596 Highly Regioselective and Active Rh–2,20-Bis(dipyrrolylphosphinooxy)-1,10-(�)-bi-naphthyl Catalyst for Hydroformylation of2-Octene

A rhodium catalyst bearing 2,2′-bis(dipyrrolylphosphinooxy)-1,1′-(±)-binaphthyl (ligand 1)shows high regioselectivity and activity for the hydroformylation of 2-octene. The introductionof pyrrolyl groups in the ligand greatly improves the yield of the linear aldehyde. Theregioselectivity up to 97.5% is obtained under mild conditions (100 °C, 0.7 MPa CO/H2).

O

O

P N

N

P

N

N

R[Rh/ligand 1]

CO/H2 R CHO+ R CHO

linear aldehydebranched aldehyde

ligand 1

Wenjing Liu, Maolin Yuan, Haiyan Fu, HuaChen, Ruixiang Li, and Xianjun Lidoi:10.1246/cl.2009.596

598 Experimental Study of SOF Oxidation Cata-lysts under Plasma Discharge Conditions Oxidative activities of eight different transition-

metal oxides and two different noble metalstoward soluble organic fraction (SOF) includedin diesel particulate matter (PM) have beeninvestigated under plasma discharge conditions.The oxidation rate with ZnO has shown thehighest value 99% higher than that without acatalyst and has exceeded that with the noblemetals. A mechanism of catalytic SOFoxidation under plasma discharge conditionshas been proposed.

OO O

OON

ON

OO

OO C

C O

SOFSOF

IntermediateIntermediate

Zn2+Zn2+

ZnZn

ReductionReduction

OxidationOxidation

PlasmaO atomsRadicalsElectrons

PlasmaO atomsRadicalsElectrons

Shin Yamamoto, Shuiliang Yao, SatoshiKodama, Chieko Mine, and Yuichi Fujiokadoi:10.1246/cl.2009.598

C-72 Chemistry Letters Vol.38, No.6 (2009)

Copyright � 2009 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

600 Preparation, Crystal Structure, and Solid-state Fluorescence of a CH2Cl2-solvatedCrystal of 6,13-Bis(t-butylphenyl)-2,3,9,10-tetrapropoxypentacene

1·CH2Cl2crystalline form

Slow evaporationfrom CH2Cl2

Standing in air

OPr

OPr

PrO

PrO

tBu

tBu

1 powder form

0

200

400

600

800

500 600 700 800 900

Flu

ores

cenc

e in

tens

ity /

a.u.

Wavelength / nm

1·CH2Cl2

1

Chitoshi Kitamura, Takao Naito, Akio Yoneda,Takashi Kobayashi, Hiroyoshi Naito, andToshiki Komatsudoi:10.1246/cl.2009.600Electronic Supporting Information

602 Synthesis of Doubly Locked 5Zs15Za-Biliver-din Derivatives and Their Unique SpectralBehavior

NN

N

N

OMe

O

CO2R CO2R

Et Me A

BC

D

Me

ZsZa

N

N

OMe

CO2Allyl

MetBuO2CCHO

NHNO

CO2Allyl

Et Me

R = Allyl, H

A

BC

D 15

10

5ZsZa + H+

Liyi Chen, Hideki Kinoshita, and KatsuhikoInomatadoi:10.1246/cl.2009.602

604 Spin-crossover Transition in a MesophaseIron(II) Thiocyanate Complex Chelated with4-Hexadecyl-N-(2-pyridylmethylene)aniline

Yuya Oso and Takayuki Ishidadoi:10.1246/cl.2009.604

606 Gel–Flocculation Transition of a Supra-molecular Hydrogel Induced by DepletionEffect of Polymers

Mitsutoshi Masuda, Keiko Sumitomo, HiroyukiMinamikawa, Naohiro Kameta, YoshinoriYamaguchi, and Toshimi Shimizudoi:10.1246/cl.2009.606Electronic Supporting Information

608 Synthesis of Dense and Pinhole-free Y-zeolitefor Separation Membrane Using a ModifiedHydrothermal Method SEM images of Y-zeolite membranes prepared

(b) 7 wt % zeolite, (c) 15 wt % zeolite. Cross

method with various concentration mixtures.

(e) 7 wt % zeolite, (f) 15 wt % zeolite.

by a double-layered capsule hydrothermal

Surface views of samples: (a) 1 wt % zeolite,

section views of samples: (d) 1 wt % zeolite,

Atsushi Nakahira, Hidezumi Nagata, TakamasaOnoki, Yuki Yamasaki, and Toshiyuki Hashidadoi:10.1246/cl.2009.608

Chemistry Letters Vol.38, No.6 (2009) C-73

Copyright � 2009 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

610 Preparation of Thin Macroporous TiO2

Films Using PMMAMicrospheres and TheirPhotoinduced Hydrophilicities

0

20

40

60

80

0 2Con

tact

ang

le o

f wat

er (

θ) /

degr

ee

Irradiation time / h

20

40

60

80

00

6 12 18

θ/ d

egre

e

Storage time in the dark / hm-TiO2/Q

m-TiO2/Q

TiO2/Q

TiO2/Q

Thin macroporous TiO2 films (m-TiO2/Q)

Thin macroporous TiO2 films exhibited good photoinduced hydrophilicity after short period ofUV light irradiation and maintained lower water contact angle compared to those onthin nonporous TiO2 films.

1 3

Takashi Kamegawa, Norihiko Suzuki, andHiromi Yamashitadoi:10.1246/cl.2009.610

612 Hybrid Photoreactive Magnet Obtainedfrom Fe3O4/TiO2 Composite Nanoparticles

200 400 600 800

0.0

0.3

0.6

0.9

1.2

1.5

1.8

700 C

750 C

600 C

500 C

400 C annealing

Anatase TiO2

Abs

orba

nce

Wavelength (nm)

Hyon Min Song, Jang Myoun Ko, and Jeong HoParkdoi:10.1246/cl.2009.612Electronic Supporting Information

614 A Simple H2O2-assisted Method for the Syn-thesis of Intestine-like SnO2 Nanostructuresat Room Temperature A simple organic-free H2O2-assisted approach

hollow interior at room temperature. In the

has been developed to synthisizing theintestine-like SnO2 nanostructures with

synthesis, H2O2 fulfills important functions inboth forming the intestine-like morphologyand promoting the generation of hollowstructure.Shunqiang Liu, Mingjiang Xie, Yanxing Li,

Xuefeng Guo, Weijie Ji, and Weiping Dingdoi:10.1246/cl.2009.614

616 Fluorescence-based Indicator DisplacementAssay for Phosphosugar Detection UsingZinc(II) Dipicolylamine-appended Phenyl-boronic Acid

B

HN

N

NNZn2+

·(NO3 –)2

OO

OO SO3

–

400 450 500 550 6000

50

100

150

200

250

300

Wavelength / nm

Flu

ores

cenc

e in

tens

ity

HO

F6P

F6P = D-fructose-6-phosphate

HEPES bufferwith 10 mM of NaCl

Shoichi Horie and Yuji Kubodoi:10.1246/cl.2009.616Electronic Supporting Information

618 Effects of Bubbling N2 or O2 Gas in Synthe-ses of Gold Nanocrystals Using a PolyolMethod

500 nm

Gold nanowires

Masaharu Tsuji, Daisuke Ueyama, and Md.Jahangir Alamdoi:10.1246/cl.2009.618Electronic Supporting Information

C-74 Chemistry Letters Vol.38, No.6 (2009)

Copyright � 2009 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

620 Magnetic Properties of Iron(II) and Co-balt(II) Complexes of Tetrakis(2-pyridyl)-methane. Spin-crossover Behavior in the Co-balt(II) Complex

A gradual spin crossover to the high-spin state above 300 K is observed in the cobalt(II)complex of tetrakis(2-pyridyl)methane (C(py)4); [Co{C(py)4}2]•(ClO4)2

•2CHCl3 (2), while thecorresponding iron(II) complex [Fe{C(py)4}2]•(ClO4)2

•2CHCl3 (1), exhibits no spin transitionto the high-spin state between 5 and 400 K.

Ryuta Ishikawa, Kouzou Matsumoto, KojiOnishi, Takashi Kubo, Akira Fuyuhiro, ShinyaHayami, Katsuya Inoue, Sumio Kaizaki, andSatoshi Kawatadoi:10.1246/cl.2009.620Electronic Supporting Information

622 Chemical Synthesis of Aluminum NitrideNanorods in an Autoclave at 200 �C

Aluminum nitride nanorods with diameters ranging from 50 to 100 nm and lengths up toseveral micrometers have been prepared via a chemical reaction from Al, I2, and NaN3 inan autoclave at 200 °C.

Li Fu, Liqiang Xu, Junling Duan, Ting Li,Lishan Yang, and Yitai Qiandoi:10.1246/cl.2009.622

624 Palladium-catalyzed Mizoroki–Heck Reac-tions of 2-Methylene-1,3-dithiane 1-Oxidewith Aryl Iodides

S

S+

O–IR

+

cat. Pd(OAc)2cat. DPPEK2CO3, TBAB

DMF, 100 °C, 24 h

S

S+

O–R

Eiji Morita, Masayuki Iwasaki, SuguruYoshida, Hideki Yorimitsu, and KoichiroOshimadoi:10.1246/cl.2009.624

626 Synthesis of Hydroxyapatite–Zeolite Compo-site Material from Disposed Steel Slag andInvestigation of Its Structural and Physico-chemical Characteristics

Hydroxyapatite–zeolite composite material (HAP–ZE) was successfully synthesized from steelslag via a convenient route. The structural analyses and the adsorption test of VOCs clarifiedthat the HAP–ZE contains both HAP and faujasite-type zeolite phases blended in microscaleand is applicable for practical use as an adsorbent.

Steel slag

+ H3PO4

+ NaOH

Hydroxyapatite-zeolitecomposite material

(HAP-ZE)

Aging at 90 °C

Hydroxyapatite (HAP)Ca10(PO4)6(OH)2

Faujasite-type ZeoliteNa64[(AlO2)64(SiO2)128]·276H2O

CaOPOH

Chemical composition (wt%)

CaO: 41.5 SiO2: 35.8 Al2O3: 15.3MgO: 5.48 Fe2O3: 1.58 MnO: 0.28

OSi or Al

Yasutaka Kuwahara, Tetsutaro Ohmichi,Takashi Kamegawa, Kohsuke Mori, and HiromiYamashitadoi:10.1246/cl.2009.626

628 Dual Functionalization of Allene: FacileConstruction of Heteropolycycles Mediatedby Brønsted Acid

A facile construction of a heteropolycyclic framework is developed by exploiting the dualfunctionalization of allene. On treatment of phenethyl alcohol or amine bearing a terminalallene with the Brønsted acid, two consecutive reactions to allene, nucleophilic addition ofheteroatom and the Friedel–Crafts reaction, occurred to give 2-oxa- or azabicyclo[2.2.2]octaneskeleton.

·RX RX

Nu

RR RRX – H

H

H

O

Ph

OH

PhPh ·

TfOH (20 mol%)

CH2Cl2reflux, 5 h

80%

TsN

Ph

NHTs

PhPh ·

TfOH (150 mol%)

CH2Cl20 °C, 3 h

68%

H+

X = O, NR'

H+ RX+

R

H

Nu – HH+

additionfirst second

addition

Keiji Mori, Shosaku Sueoka, and TakahikoAkiyamadoi:10.1246/cl.2009.628Electronic Supporting Information

Chemistry Letters Vol.38, No.6 (2009) C-75

Copyright � 2009 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

630 Extraction of Actinides and Fission Productsby the New Ligand, N,N,N0,N0-Tetraoctyl-3,6-dioxaoctanediamide O

H2C

H2C CH2

CONC8H17

C8H17

O CH2

CO N

C8H17

C8H17

Structure of DOODA-C8

New reagent, N,N,N ′,N ′-tetraoctyl-3,6-dioxaoctane-diamide (DOODA-C8), wassynthesized and examinedfor actinide and fissionproduct extractions. Itwas found that DOODA canextract UVI, PuIV, AmIII,lanthanides (Ln)III, and TcVII

from HNO3 to n-dodecane.Yuji Sasaki, Yasuji Morita, Yoshihiro Kitatsuji,and Takaumi Kimuradoi:10.1246/cl.2009.630

Additions and Corrections

632 Size-controlled Preparation of Poly(allyl-amine)-stabilized CdS Nanoparticles bySolution pH

Junjiro Hayashi, Mitsumi Nishi, and MioWanakadoi:10.1246/cl.2009.632