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

Vol.38 No.7 CMLTAGJuly, 2009 ISSN 0366-7022

Copyright � 2009 The Chemical Society of Japan

Highlight Review

634 Electro- and Photoactive Molecular Assem-blies of Liquid Crystals and Physical Gels

Takashi Kato and Kana Tanabedoi:10.1246/cl.2009.634

Self-organized structures of liquid crystals and self-assembled fibers have great potential as new functional materials.This article highlights self-organization of �-conjugated molecules, leading to the induction of photonic, electronic, and elec-trochemical properties.

640 Nonenzymatic Regioselective Acylation ofCarbohydrates

OOC8H17

OHHO

HO

HO

OOC8H17

OHHO

HO

i -PrCOO

99% selective98% yield

(i -PrCO)2O

1. TBDMSCl / imidazole2. 2-methoxypropene / PPTS3. (i -PrCO)2O / DMAP

4. CSA / MeOH5. separation of regioisomers

46% overall

1 mol%

NOO

HN

HN

O

OO

O

NHHN

N

4 4

Takeo Kawabata and Takumi Furutadoi:10.1246/cl.2009.640

A nonenzymatic one-step procedure for the chemo- and regioselective acylation of carbohydrates has been developed.With 1mol% of an organocatalyst, acylation of octyl �-D-glucopyranoside took place preferentially on the secondary hy-droxy group at C(4) among four hydroxy groups including the primary hydroxy group at C(6) in 99% selectivity and in98% yield. This could be alternatively achieved by a conventional protection/deprotection procedure via five steps and in46% overall yield. Thus, development of the present process is expected to contribute to extremely shorten synthetic routesfor carbohydrates.

C-80 Chemistry Letters Vol.38, No.7 (2009)

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

Letter

648 Near-infrared Luminescence from Ytter-bium(III) Ternary Complexes by Visible-light Excitation of Attached ChlorophyllDerivatives

Visible-light sensitization of carboxylatedchlorophyll ligands triggered near-infraredemission from Yb3+ in a supramolecule.

N

N

NH

N

HN

OO

NIR-lightemission

Energytransfer

N

N

OOO

O

OO

Yb

HVisible-lightexcitation

COOCH3

N

Qianming Wang, Shin-ichi Sasaki, and HitoshiTamiakidoi:10.1246/cl.2009.648Electronic Supporting Information

650 Glucose to Value-added Chemicals: An-hydroglucose Formation by Selective De-hydration over Solid Acid Catalysts

Selective dehydration of glucose to anhydroglucoses was performed over solid acids withsulfonic acid groups.

Glucose

Solid acid (-SO3H)

O

OH

OH

OH

OCH2

1,6-anhydroglucopyranose(Levoglucosan)

OO

OH

OH

HO

1,6-anhydroglucofuranose

dehydration

Atsushi Takagaki and Kohki Ebitanidoi:10.1246/cl.2009.650Electronic Supporting Information

652 Synthesis and Application of 20-ara-Fluoro-guanosine-substituted Cap Analog

HN

N

N

O

H2N N

O

O PO

OO P

O

OO P

O

OO

NH

N

N

O

NH2N

O

OHOH

CH3

OH

F

Anilkumar R. Kore, Irudaya Charles, andMuthian Shanmugasundaramdoi:10.1246/cl.2009.652

654 Crystal Structure and Proton Conductivityof a One-dimensional Coordination Polymer,{Mn(DHBQ)(H2O)2}

Shota Morikawa, Teppei Yamada, and HiroshiKitagawadoi:10.1246/cl.2009.654Electronic Supporting Information

656 Sandwich-type Electrochemical Immunoas-say for Carbohydrate Antigen-125 UsingMultifunctional Magnetic Beads with Ferro-cenyl-tethered Dendrimer as Label

This letter describes a new sandwich-type electrochemical immunoassay for carbohydrateantigen-125 (CA125) by using multifunctional magnetic beads with ferrocenyl-tethereddendrimer as labels.

Xiao-Hong Fudoi:10.1246/cl.2009.656

Chemistry Letters Vol.38, No.7 (2009) C-81

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

658 A Discovery of Tetravalent Ge4þ Ion Con-duction in Solids

Tetravalent Ge4+ ion conductionin solid was firstly demonstratedfor a NASICON-typeGe41/40NbP2.9Si0.1O12 solid.

Naoyoshi Nunotani, Shinji Tamura, andNobuhito Imanakadoi:10.1246/cl.2009.658Electronic Supporting Information

660 Water Droplets for the Symmetric Adhesionof Two Poly(methyl methacrylate) Films Poly(methyl methacrylate) films with thermally nontreated surface chains were successfully

adhered together using only water droplets as evaporative and unsubstantial adhesives.

Physicalcontact Adhesion

PMMA

H2O

H2OSwollen layer

Takaaki Date, Mizuki Ishikawa, Koichiro Hori,Keiji Tanaka, Toshihiko Nagamura, MakioIwahashi, and Takeshi Serizawadoi:10.1246/cl.2009.660Electronic Supporting Information

662 Development of a HPLC-ESR Spin-trappingSystem for Post-column On-line Detection ofSuperoxide Radical Scavenging Ability ofColumn Eluates

A new HPLC-ESR spin-trapping system was developed for post-column on-line detection ofthe superoxide radical scavenging activity of column eluates by using 5,5-dimethyl-1-pyrrolineN-oxide (DMPO) as a spin-trapping reagent. This system is suitable for screening superiorsuperoxide radical scavengers involved in plant extracts.

0 5 10 15 20 25 30

0.0

0.2

0.4

0.6

0.8

1.0

1.2

1.4

0

5

10

15

20

25

Retention time / min

Absorbance at 280 nm

/ mV

Con

cent

ratio

n of

DM

PO/O

2 / µ

M

a)

b)

* *Gal

Caf

Cou a) UV chromatogram of the solutionof Gal, Caf, and Cou (25 µM), observedat 280 nm.b) ESR chromatograms of 25 (solid line),50 (broken line), and 150 µM (doted line)of the same solution.

Yasuhiro Sakurai, Kiyoshi Kawai, RushiruKomatsu-Watanabe, Chie Morimoto, ShunjiSakamoto, Akira Nakajima, Kenji Kanaori,and Kunihiko Tajimadoi:10.1246/cl.2009.662

664 �-Amidobenzylation of Aryl and AlkenylHalides via Palladium-catalyzed Suzuki–Miyaura Coupling with �-(Acylamino)ben-zylboronic Esters

Pd(dba)2 (5 mol %)P(t-Bu)3 (10 mol %)

KF (3 equiv)H2O (2 equiv)

1,4-dioxane, 110 °C

HN

BO

O

Ac

HNAcX

R2

R2

PhBr

HNAc

Ph

R1

R1

(X = Br, Cl)

Toshimichi Ohmura, Tomotsugu Awano, andMichinori Suginomedoi:10.1246/cl.2009.664Electronic Supporting Information

666 Acidity Control by On/Off Switching ofan Intramolecular NH���O Hydrogen Bondby E/Z Photoisomerization of CinnamateFramework

Photoswitching of the intramolecular NH...O hydrogen bond by using E/Z photoisomerizationof cinnamate framework was achieved. After 313 nm irradiation, the acidity of carboxylicacid was reversed by opposite switching of hydrogen bonding.

Takashi Matsuhira, Hitoshi Yamamoto, andTaka-aki Okamuradoi:10.1246/cl.2009.666Electronic Supporting Information

C-82 Chemistry Letters Vol.38, No.7 (2009)

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

668 Phosphorofluoridic Acid-catalyzed Conden-sation Reaction of Carboxylic Acids with1-Arylalkyl Alcohols Leading to Estersunder Solvent-free Conditions

alkyl OH

O+

100 °C6 h O

PO

FHO

cat.cat.

alkyl O

O

Ar

under solvent-free conditions

HO Ar

Toshiaki Murai, Nagisa Tanaka, ShinjiHigashijima, and Hidetoshi Miuradoi:10.1246/cl.2009.668Electronic Supporting Information

670 Preparation and X-ray Structures of trans-5,6-Diaryl-5,6-dihydro-1,10-phenanthroline-5,6-diols: Formation of Supramolecular Rodby Hydrogen Bonds

The title molecules form one-diemensional chiral architecture in crystals which consist ofhomochiral diols with the same sense of helicity.

Takanori Suzuki, Youhei Miura, RyuuichiTamaki, Hidetoshi Kawai, and KenshuFujiwaradoi:10.1246/cl.2009.670Electronic Supporting Information

672 Synthesis of Zr-containing SBA-15 withHollow Spherical Morphology

Dong Liang, Jianjian Chen, Yan Wang,Jianhong Liu, and Ruifeng Lidoi:10.1246/cl.2009.672

674 Size-controlled Fabrication of PeriodicNanocrystal Arrays by Using the Hemi-spherical Metal Nanowells

A periodic array of NaCl nanocrystals is

by sputter deposition of Fe and Au layers overprepared using a metallic nanoreactor prepared

hexagonally close-packed 1-µm polystyrenebeads.

Apply NaCl solutionand fill the wells

Trapped solution

Si substrate

NaCl nanocrystal

Toluene wash andfilm isolation

Deposit Au (1.5 nm) and Fe (50 nm) films

Crystallization

TT

Self-assemblePS monolayer

Yumina Sato and Yoshihiro Koidedoi:10.1246/cl.2009.674

676 Preparation of CdSe Quantum Dots viaThermolysis of a Novel Single Source Cd/Se Precursor Derived from Cyclohexeno-1,2,3-selenadiazole

A novel single source molecular precursor [Cd(SeC6H8Br)2], has been derived fromcyclohexeno-1,2,3-selenadiazole via bromination of selenadiazole and its subsequesntreduction followed by reaction with cadmium chloride. Thermolysis of the so-obtainedprecursor in high boiling reaction medium resulted in formation of CdSe quantum dots.

Heat

0

50

100

150

200

400 450 500 550 600 650 700

Wavelength/nm

Inte

nsit

y (a

.u.)

PLUV570 nm

500 nmPawan K. Khanna, Priyesh More, RahulShewate, Rupinder K. Beri, A. Kasi Viswanath,Vidyanand Singh, and Bodh R. Mehtadoi:10.1246/cl.2009.676

Chemistry Letters Vol.38, No.7 (2009) C-83

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

678 NO Cations as Highly Efficient Catalysts forCarbon–Carbon Bond Forming Reactions

R1

NOR2

H

or

R3

N

H

N

O

cat. NOPF6+

OR4

R5 ON

R1

R2

OR4

or NN

R3 OR4

O

R5

Yasuhiro Yamashita and Shu Kobayashidoi:10.1246/cl.2009.678Electronic Supporting Information

680 Pseudo-intramolecular Cyclization of �-Ni-tro-�-keto Nitrile Leading to 2-Amino-3-ni-tro-1,4-dihydropyridines

N+

OC

N

O

O

_

_ NO2

CH

NOPrNH2

intimate pair

PrNH2+

H

∆

NH

NO2

NHPr

Nagatoshi Nishiwaki, Kengo Kakutani, MinaTamura, and Masahiro Arigadoi:10.1246/cl.2009.680Electronic Supporting Information

682 Fabrication of SmCo5 Alloy Magnetic Nano-particles by Assistance of Copper and TheirMagnetic Properties

A novel polyol route is described to prepare SmCo5 nanoparticles using copper and sodiumborohydride. The prepared particles had a mean diameter of 3.4 nm and a well-controlledCaCu5 structure. The particles presented sufficiently high coercivity and magnetization of1300 Oe and 15.7 emu/g, respectively, at room temperature.

Shiho Tokonami, the late Mutsuko Kinjo,Makoto Inokuchi, and Naoki Toshimadoi:10.1246/cl.2009.682

684 Phosphatidylserine-selective ConformationalChange of �-Helix Peptide, Td3717, and ItsAbility to Transfect Cancer Cells

V12,30

H13,31

L6,24

L15,33P8,26

L17,35

L4,22

S10,28Y3,21Q14,32

H7,25

W11,29

T1L19S37

Td3717:

TRYLRLHPRSWVHQLALRLRYLRLHPRSWVHQLALRS1 5 10 15 20 25 30 35 37

R 5,23

R 9,27

R 18,36

A16,34

R 2,20Td3717Shinichi Kuriyama, Kanako Nishimura,

Yasushi Taguchi, Kazutoshi Yanagibashi,Yoshiki Katayama, and Takuro Niidomedoi:10.1246/cl.2009.684

686 Voltammetric Determination of Tryptophanand Serotonin at Glassy Carbon Paste Elec-trodes in a Potential Region Free from Inter-fering Substances

Oxidation productsof analyte

analyte

interference

interference

The determination of analyte is difficult in thepresence of interference.

The concentration of analyte can be selectivelydetermined in the presence of interference byusing the peak of oxidation products.

Kazufumi Inada, Katsuhiko Nishiyama, andIsao Taniguchidoi:10.1246/cl.2009.686

C-84 Chemistry Letters Vol.38, No.7 (2009)

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

688 Photoinduced Outgrowth of Gold Nanotad-poles in Aqueous Bilayer Dispersions

Tetsuro Soejima, Toshio Hasegawa,Masa-aki Morikawa, and Nobuo Kimizukadoi:10.1246/cl.2009.688Electronic Supporting Information

690 Single-Molecule Imaging of a Micro-Brow-nian Motion of a Chiral Helical �-Conju-gated Polymer as a Molecular Spring Drivenby Thermal Fluctuations

Ken-ichi Shinohara, Noriyuki Kodera, andToshio Andodoi:10.1246/cl.2009.690Electronic Supporting Information

692 Hydrophobic Protic Ionic Liquid for Non-humidified Intermediate-temperature FuelCells

Tomohiro Yasuda, Atsushi Ogawa, MichihiroKanno, Kazuki Mori, Kazuhisa Sakakibara,and Masayoshi Watanabedoi:10.1246/cl.2009.692

694 Synthesis and Structural Characterization ofa Novel Three-dimensional Molybdenum–Oxygen Framework Constructed fromMo3O9 Units

A novel three-dimensional molybdenum

Mo3O9 units has been successfully

by IR spectrum, inductively coupled

diffraction (PXRD), X-ray photoelectron

oxide Mo3O9·H2O (1) constructed from

synthesized under hydrothermalconditions and structurally characterized

plasma (ICP) analysis, powder X-ray

spectroscopy (XPS), and single-crystalX-ray diffraction.

Junwei Zhao, Pengtao Ma, Jingping Wang, andJingyang Niudoi:10.1246/cl.2009.694Electronic Supporting Information

696 Application of Gas Chromatography/Com-bustion/Isotope Ratio Mass Spectrometryfor Studying Nutrition and Biosynthesis inPlants

0

10

20

30

40

50

0 20 40 60 80 100

15N

enr

ichm

ent i

n gl

utam

ic a

cid/

‰

15N enrichment of nutrient/‰

urea

ammonium

nitrate

Compound-specific isotope analysis of

chromatography/isotope ratio mass spectrometery

Here, as a primary application of this method for

nutrients, and evaluate the practical utility of

15N enrichment of nitrogenous molecules by gas

is a potential method for a quantitative access ofnitrogen flow in plant nutrition and biosynthesis.

plant nutrition studies, we demonstrate highlysensitive detection of 15N enrichment of aminoacids in white radish cultivated either with verya low level of 15N-labeled organic or inorganic

this method.

Mayu Yamamoto, Rumiko Nakashita, YaekoSuzuki, Takahiro Ichimiya, and TakashiKorenagadoi:10.1246/cl.2009.696

Chemistry Letters Vol.38, No.7 (2009) C-85

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

698 Fluorescence Sensor for Water Content inOrganic Solvents Based on Covalent Im-mobilization of Benzothioxanthene

Wavelength/nm

460 480 520 540 560 580

Flu

ores

cenc

e in

tens

ity

300

400

500

600

700

tetrachloromethane

ethanol

dioxane

acetonitrile

methanol

waterZhi-Zhang Li, Cheng-Gang Niu, Guang-MingZeng, and Pin-Zhu Qindoi:10.1246/cl.2009.698Electronic Supporting Information

700 Mukaiyama Aldol Reaction Catalyzed byMesoporous Aluminosilicate

+

(1.2 equiv)

R

SiO

R3

OSi

R3

OAl-MCM-41 (30 mg/mmol)

R

OR1

R2 R1 R2CH3CN (0.5 M), 0 °C or 30 °C

R = Aryl, AlkylSi = TMS, TES, TBDMS

67-99% yield

up to 3 times recycling

17 examples

H

Suguru Ito, Hitoshi Yamaguchi, YoshihiroKubota, and Masatoshi Asamidoi:10.1246/cl.2009.700

702 Oxygen Evolution from Water Catalyzedby Mononuclear Ruthenium Complexeswith a Triazamacrocyclic Ligand in a FacialFashion

N

N

Me

Me

Me

Ru

N N

OH2

R R

2+

O2-Evolving Catalyst

4Ce4+

4Ce3+

2H2O

O2 + 4H+

R = H Me OMe

Higher Catalytic Activity

Stronger Donating Ability

N

Masaki Yoshida, Shigeyuki Masaoka, and KenSakaidoi:10.1246/cl.2009.702Electronic Supporting Information

704 Mutual Chiral Discrimination between Tri-cationic and Trianionic Sulfur-bridged Tri-cobalt(III) Complexes

Hou Qun Yuan, Asako Igashira-Kamiyama,Kiyoshi Tsuge, and Takumi Konnodoi:10.1246/cl.2009.704Electronic Supporting Information

706 Periodic Structure in a Fluorene-based Poly-mer Prepared by Electrochemical Polymer-ization

A fluorene-based polymer film prepared by electrochemical polymerization in cholestericliquid crystal electrolyte solution displays a labyrinthine fingerprint texture, and diffractiongrating function.

Kohsuke Kawabata and Hiromasa Gotodoi:10.1246/cl.2009.706

C-86 Chemistry Letters Vol.38, No.7 (2009)

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

708 A Simple Access to Symmetric Diaryl-amines via Copper(II)-catalyzed Couplingof Aqueous Ammonia with ArylboronicAcids

Ar B(OH)2 + NH3·H2OEtCOOEt

Cu , PhCOOHAr2NH

Changfeng Zhou, Fan Chen, Dongpeng Yang,Xiaofei Jia, Lixue Zhang, and Jiang Chengdoi:10.1246/cl.2009.708Electronic Supporting Information

710 Ni0-catalyzed Direct Amination of AnisolesInvolving the Cleavage of Carbon–OxygenBonds

Ni0-catalyzed cross-coupling of aryl methyl ethers with amines is described. The use of an N-heterocyclic carbene as a ligand and NaOt-Bu as a base promotes the amination of anisolederivatives via the cleavage of normally unreactive aryl carbon–oxygen bonds.

OMe HN+

cat.Ni(cod)2, ligand

NNaOt -Bu

catalytic C-O bond cleavage

Mamoru Tobisu, Toshiaki Shimasaki, andNaoto Chatanidoi:10.1246/cl.2009.710Electronic Supporting Information

712 Phenanthroline Derivatives for Electron-transport Layer in Organic Light-emittingDevices

Novel electron-transport phenanthroline derivatives for OLEDs.

B(OH)2O

BrBr

Pd(PPh3)4Na2CO3

OON N

N N

NNH2

CHO

KOH/EtOH

Phen1Yan-Jun Li, Hisahiro Sasabe, Shi-Jian Su,Daisaku Tanaka, Takashi Takeda, Yong-JinPu, and Junji Kidodoi:10.1246/cl.2009.712

714 Syntheses and Physicochemical Properties ofNew Ionic Liquids Based on the Hexafluo-rouranate Anion

–HF

(FH)nF−UF6

−UF5

NNNN

Takatsugu Kanatani, Kazuhiko Matsumoto, andRika Hagiwaradoi:10.1246/cl.2009.714Electronic Supporting Information

716 Synthesis of Thermotropic Liquid Crystal-line Polyimides with Siloxane Linkages

n = 1 n = 3

OSi

OSi

ON

O

O

N

O

On

Yu Shoji, Tomoya Higashihara, JunjiWatanabe, and Mitsuru Uedadoi:10.1246/cl.2009.716Electronic Supporting Information

Chemistry Letters Vol.38, No.7 (2009) C-87

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

718 Intracellular Enzyme-responsive Fragmen-tation of Nonviral Gene Carriers Leads toPolyplex Destabilization and EnhancedTransgene Expression

Intracellular fragmentation of nonviral gene carriers in response to endogenous enzyme, furin,led to enhanced transgene expression.

EndosomeEndosome

FurinFurin

FragmentationFragmentation DestabilizedDestabilized

polyplexpolyplex

Enhanced expressionEnhanced expression

HighlyHighly

compactedcompacted

polyplexpolyplex

Tomoko Hashimoto, Yoichi Tachibana, HisaeNozaki, Osam Mazda, Takuro Niidome, AkiraMurakami, and Tetsuji Yamaokadoi:10.1246/cl.2009.718Electronic Supporting Information

720 Effect of Support on the Suppression of HotSpot Formation in the Partial Oxidation ofMethane

Ni/α-Al2O3

Ni/BaTiO3

Ni/LaAlO3

Ni/SrTiO3

Ni/CaTiO3

Hot spotformation

CH4 + 1/2O2 CO + 2H2Ni-based catalyst

"Suppression ofhot spot formation"

Tetsuya Shishido, Reina Morishima, YusukeYoshinaga, Sadao Hasegawa, and TsunehiroTanakadoi:10.1246/cl.2009.720

722 Enantioselective Reduction of AliphaticKetones Using Oxazaborolidine CatalystGenerated In Situ from Chiral LactamAlcohol and Phenoxyborane

RL RS

O

RL RS

OH

(10 mol%)

BH3-THF, p-I-PhOH

NH

ArAr

OHO

up to 98% eeAr = 3,5-Me2Ph

Yasuhiro Kawanami, Yudai Mikami, KatsuhiroHoshino, Mikiko Suzue, and Izumi Kajiharadoi:10.1246/cl.2009.722Electronic Supporting Information

724 Catalytic Cyclization of Alkenyl N,O-Acetalsby Fe(OTf)3

N OXPG

iron catalyst( )n

R

NPG

R( )n

OX = OH, OAc, OMePG = protecting groupKimihiro Komeyama, Ryoichi Igawa, Takayuki

Morimoto, and Ken Takakidoi:10.1246/cl.2009.724Electronic Supporting Information

726 High-sensitivity HPLC Quantification ofNonfluorescent but Photolabile Analytethrough Photoreversion in FluorescenceDetector

Masaki Nishijima, Takehiko Wada, KoushiNagamori, and Yoshihisa Inouedoi:10.1246/cl.2009.726Electronic Supporting Information

C-88 Chemistry Letters Vol.38, No.7 (2009)

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

728 Hydrolysis of Disaccharides byMetal Speciesin Neutral Homogeneous Solutions

Daisuke Takahashi, Sakiko Kobayashi, KanaTsumura, and Kazunobu Toshimadoi:10.1246/cl.2009.728

730 Rhodamine–Pyridyl Probe: A Selective Opti-cal Reporter for Biologically Important Zn2þ

A new Rhodamine-based probe, Rhoda-P affords remarkably selective chromo- as well asfluorogenic responses in the company of Zn2+ with the color of the probe turning fromcolorless (λmax=302 nm) to pink (λmax=528 nm), and the fluorescence output increased by 160-fold at 1.5 × 10−3

M of Zn2+.

Rhoda - P Rhoda - P + Zn2+

Sabir H. Mashraqui, Tabrez Khan, SubramanianSundaram, Rupesh Betkar, and MukeshChandiramanidoi:10.1246/cl.2009.730Electronic Supporting Information

732 Ene Reaction Using the Iminium Salt Gener-ated by the Oxidation of Aminoketene SilylAetal

Ene reaction of various olefins proceeded with the iminium salt generated by the oxidation ofaminoketene silyl acetal to give the addition products in good yields.

Bn2NOTMS

OEt NBn2

CO2EtArO-

NBn2

CO2Et

DDQ

+

R1

R2

R1

R2

Makoto Shimizu, Hiroyuki Itou, Takuya Iwao,and Yuki Umedadoi:10.1246/cl.2009.732

734 Synthesis of Cyano-substituted Through-space Poly(p-arylenevinylene)

CN

CN

RO

ORNC

CN

RO

ORNC

NC

OR

RO NC

CN

RO

OR

NC

Yasuhiro Morisaki, Lin Lin, and Yoshiki Chujodoi:10.1246/cl.2009.734Electronic Supporting Information

736 Cs2:5H0:5PW12O40 Nanoparticles Fixed onSilica Encapsulating Magnetic Iron Oxideas a Magnetically Separable Water-tolerantSolid Acid

+ C2H5OH

343 K, 2 h

waterO

O

O

OH

SiO2 FexOy

Cs2.5H0.5PW12O40Nanoparticle

magnet

Toshimitsu Goto, Yoshinori Sakamoto, andYuichi Kamiyadoi:10.1246/cl.2009.736Electronic Supporting Information

Chemistry Letters Vol.38, No.7 (2009) C-89

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

738 Direct Synthesis of Amino-substituted Aro-matic Phosphonates via Palladium-catalyzedCoupling of Aromatic Mono- and Dibro-mides with Diethyl Phosphite

HP(O)(OEt)2

Pd(OAc)2,

NR3,EtOHBr

+

P(O)(OEt)2

PPh3,NH2

NH2

Alla Bessmertnykh, Christiane MorkosDouaihy, and Roger Guilarddoi:10.1246/cl.2009.738Electronic Supporting Information

740 The Hardest Magnet from a CoordinationPolymer of Alternating Cobalt(II)–RadicalHeterospins

Yoshitomo Okamura, Takashi Nogami, andTakayuki Ishidadoi:10.1246/cl.2009.740Electronic Supporting Information

742 Electrochemiluminescence Devices Consist-ing of ZnO Nanorods Vertically Grown onSubstrate

ZnO nanorod

∼FTO

FTO

Ru complex (Rubpy) for emission layer

ECL device structure consisting of ZnO nanorods

Rubpy 50 µm

Tomohito Tanaka, Hiroshi Takishita, TakashiSagawa, Susumu Yoshikawa, and Shuzi Hayasedoi:10.1246/cl.2009.742

744 Development of an Off-axis Sample Intro-duction System for Use in Multiphoton Ion-ization/Time-of-flight Mass Spectrometry

An off-axis sample introduction technique was developed for improvement of mass resolutionin multiphoton ionization/time-of-flight mass spectrometry. This approach suppressed theexcessive collisions between analyte ions and carrier gas molecules that is responsible fordegradation of mass resolution.

Tomohiro Uchimura, Satoshi Yamaguchi, andTotaro Imasakadoi:10.1246/cl.2009.744

746 Synthesis of Hollow Nanospheres Consistingof Amphiphilic Block Copolymers

P(TMS-HEA)-grafted SiNP

SiNP70oC

initiator-modified SiNP PMMA-b-P(TMS-HEA)-

grafted SiNP

2-EBIB MMATMS-HEA

hydrophobic

hydrophilic

cross-linking hollow polymeric nanosphere

P(TMS-HEA)-grafted SiNP

HF etching

CuBr / 2dNbpy

AC

Et3NHideki Matsune, Daisuke Sakurai, SakaeTakenaka, and Masahiro Kishidadoi:10.1246/cl.2009.746Electronic Supporting Information

C-90 Chemistry Letters Vol.38, No.7 (2009)

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

748 4,5-Bis(diarylmethylene)-1,3-dithiole: ANovel Helical Electron Donor ExhibitingElectrochromic Behavior

1,1,4,4-Tetraaryl-1,3-butadiene unit is framed on a 1,3-dithiole skeleton to provide a chiralelectron donor exhibiting vivid color and geometrical changes upon redox reactions.

Takanori Suzuki, Shintaro Mikuni, YusukeIshigaki, Hiroki Higuchi, Hidetoshi Kawai,and Kenshu Fujiwaradoi:10.1246/cl.2009.748Electronic Supporting Information

750 Stability of Boronic Esters to Hydrolysis:A Comparative Study

O

OB

RB

R

OH

OH

HO

HO2 H2O

No hydrolysisR= i -Pr, Bn

+x

Raffaella Bernardini, Ambrogio Oliva,Alessandro Paganelli, Ernesto Menta, MarioGrugni, Sergio De Munari, and Luca Goldonidoi:10.1246/cl.2009.750Electronic Supporting Information