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

Vol.37 No.7 CMLTAGJuly, 2008 ISSN 0366-7022

Copyright � 2008 The Chemical Society of Japan

672 Structural and Functional Model Systemsfor Analysis of the Active Center of NitrileHydratase

Proposed reaction mechanism for nitrile hydratase

HOH

RCN

H2O

H2O

H2O

RC(=O)NH2

M = FeIII or CoIIIMN

S

S

OH2

S

NO

OO

Cys

O

O

MN

S

S

S

NO

OO

Cys

O

O NCR

MN

S

S

S

NO

OO

Cys

O

O NCR

Takuma Yano, Tomohiro Ozawa, and HidekiMasudadoi:10.1246/cl.2008.672

We focused a unique active site structure of nitrile hydratase (NHase), where the central metal ion (CoIII or FeIII) issurrounded with two amide nitrogens in peptide backbone, one cysteine sulfur and two oxidized cysteine sulfurs (Cys–SOand Cys–SO2) as the donor set. In this review, the biological implication of the unique structure has been discussed inthe relation with the nitrile hydration mechanism by using model complexes.

Highlight Review

Letter

678 Two Neutral Open-framework Metal Phos-phites with Ten-ring Channels Constructedby Three-, Four-, and Five-connected Cen-ters

Yang Yang, Yongnan Zhao, Jianguo Yu, NanPang, Hao Su, and Sha Pangdoi:10.1246/cl.2008.678

C-86 Chemistry Letters Vol.37, No.7 (2008)

Copyright � 2008 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

680 Stable Halodilithiosilanes: Synthesis andReactivity of TsiXSiLi2 (X = Br and Cl)

SiTsi

X

X

X

2LiNp

-78 °C, THFSi

Tsi

X

Li

X

X=Cl, Br

SiTsi

X

Li

Li

2LiNp

-78 °C, THF

Tsi = -C(SiMe3)3

Myong Euy Lee, Young Mook Lim, Joo YoungSon, and Won Guk Seodoi:10.1246/cl.2008.680Electronic Supporting Information

682 Alternative Route to Metal Halide Free IonicLiquids

Koichiro Takao and Yasuhisa Ikedadoi:10.1246/cl.2008.682Electronic Supporting Information

684 Multicomponent Molecular Layers thatExhibit Electrochemical Potential Flip onAu(111) by Use of Proton-coupled Electron-transfer Reactions

E / V vs. Ag/AgClE / V vs. Ag/AgCl

[Proton-coupled Electron Transfer Layer]

[Redox–Active Template Layer]

Au(111)

low pH high pH–0.4 0.0 0.4–0.4 0.0 0.4

Reversible tuningHiromitsu Uehara, Tomohiko Inomata,Masaaki Abe, Kohei Uosaki, and Yoichi Sasakidoi:10.1246/cl.2008.684Electronic Supporting Information

686 Synthesis and Electroluminescent Propertiesof New Amorphous Cyclohexyl- and Hexyl-substituted Ter(9,9-dialkylfluorene)s

Eunhee Lim, Byung-Jun Jung, Sung Min Kim,Bong Ok Kim, and Hong-Ku Shimdoi:10.1246/cl.2008.686

688 Effect of Liquid Viscosity on the InternalFluidity of a Droplet Sliding on a Fluoro-alkylsilane Coating

Yuu Sakurada, Shunsuke Suzuki, MunetoshiSakai, Akira Nakajima, Yoshikazu Kameshima,and Kiyoshi Okadadoi:10.1246/cl.2008.688Electronic Supporting Information

Chemistry Letters Vol.37, No.7 (2008) C-87

Copyright � 2008 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

690 A Relationship between Molecular Orienta-tion and Current–Voltage Characteristics inPoly(3-hexylthiophene) Thin Film

0

10

20

Cur

rent

/mA ITO/P3HT/Al

(a)

1st2nd3rd

-0.02

-0.01

0

∆I/I

(b)

0 1 2 3 4 5

-0.004

0

Voltage/V

(c)

1

I/I 0Takeshi Komino, Hiroyuki Tajima, and Masaki

Matsudadoi:10.1246/cl.2008.690Electronic Supporting Information

692 Synthesis, Structure, and Luminescent Prop-erty of a 3D Polymer Containing Silver Ions

Yajuan Li, Huihua Song, Tao Wang, andMiying Jiadoi:10.1246/cl.2008.692Electronic Supporting Information

694 Synthesis and Magnetic Properties of Conju-gated Radical Polymer

Daisuke Kato, Katsuya Inoue, Jun Akimitsu,and Jiro Abedoi:10.1246/cl.2008.694Electronic Supporting Information

696 Dynamic Behavior of Cyclic Hemiacetals of2-Hydroxy-2-(2-hydroxyphenyl)-1,3-indan-dione Derivatives

OOH

OHO

O

O

HO

OH

Dynamic interconversionSuzumi Hashimoto, Natsumi Sakuma,Hidetsugu Wakabayashi, Hiroshi Miyamae,and Keiji Kobayashidoi:10.1246/cl.2008.696

698 Simultaneous On-chip Surface PlasmonResonance Measurement of Disease MarkerProtein and Small Metabolite Combinedwith Immuno- and Enzymatic Reactions

Kohei Nakamoto, Ryoji Kurita, NaoyukiSekioka, and Osamu Niwadoi:10.1246/cl.2008.698Electronic Supporting Information

C-88 Chemistry Letters Vol.37, No.7 (2008)

Copyright � 2008 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

700 Photoluminescence Enhancement of ZnS–AgInS2 Solid Solution Nanoparticles Layer-by-layer-assembled in Inorganic MultilayerThin Films

Tatsuya Kameyama, Ken-ichi Okazaki, YujiIchikawa, Akihiko Kudo, Susumu Kuwabata,and Tsukasa Torimotodoi:10.1246/cl.2008.700

702 Azobenzene–Helical Peptide Conjugate:Electronic Structure and Photoisomerizationin Solution and on Surface

UV

Vis or ∆

N

N

NN

δ +

δ -

δ -

δ -

δ -δ +

δ +

δ +

Mika Wakabayashi, Shigekatsu Fujii,Tomoyuki Morita, and Shunsaku Kimuradoi:10.1246/cl.2008.702

704 A Convenient Method for the Lewis Base-catalyzed Synthesis of �,�-UnsaturatedCarboxylic Esters Using Trimethylsilyl-ketene Ethyl Trimethylsilyl Acetal andCarbonyl Compounds

TMS

OTMS

OEtPh

O

H+

Lewis Base5 mol%

0 °C 1 hPh OEt

O

quant.E :Z = >99:1

+ TMS2O

easily removedby evaporation

Makoto Michida and Teruaki Mukaiyamadoi:10.1246/cl.2008.704

706 Growth of ZnO Single Crystals by AnnealingSol–Gel-derived Films with PDMS Pre-pressing

We demonstrate a simple and novel approach for the low-temperature (400 °C) solid-stategrowth of ZnO micro- and nanorods directly from sol-gel-derived Al-doped ZnO films onsilicon substrates without any catalyst. Hot pressing the films by a PDMS pad beforeannealing is found to be effective for the creation of ZnO rods. A possible nucleationmechanism of ZnO rods has also been proposed.

Jui-Chi Lee, Ing-Chi Leu, and Min-Hsiung Hondoi:10.1246/cl.2008.706

708 An Onium Salt-catalyzed Direct Polyconden-sation of Lactic Acid

Poly(L-lactic acid) of Mw ≈ 160000 (PDI = 1.6) was produced by direct polycondensation of water-containing lactic acid using triphenylphosphonium triflate as a catalyst.

Mw ≈ 160000Hisako Iwahashi, Tatsuya Oka, and AtsushiAbikodoi:10.1246/cl.2008.708

Chemistry Letters Vol.37, No.7 (2008) C-89

Copyright � 2008 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

710 Highly Selective NH3 Formation in a NO–CO–H2O Reaction over Pt/TiO2

0

100

200

300

400

500

300 350 400 450 500 550 600

NH

3 co

ncen

trat

ion

/ppm

Temperature /K

NO–CO–H2O

NO–H2

Tetsuya Nanba, Shouichi Masukawa, JunkoUchisawa, and Akira Obuchidoi:10.1246/cl.2008.710

712 Convenient Fabrication and Property Inves-tigations of Uniform TiN Hollow Nanocages

Crystalline TiN hollow nanocages with pure

of 68.13 m2/g and pore volume of 0.17 cm3/g.

using TiO2, N2H4·2HCl, and Mg as reactants

hollow nanocages mainly have diameters

20 to 35 nm. The product obtained with target

cubic phase were prepared in large scale

in autoclaves in 300–500 °C for 12 h. These

of 300 to 500 nm and shell thicknesses from

temperature of 500 °C has a BET surface areaJing Li, Liancheng Wang, Zhicheng Ju, LiqiangXu, and Yitai Qiandoi:10.1246/cl.2008.712

714 Preparation of Mesoscopic TiO2–SnO2 Com-posite Grains by Spinodal Decompositionunder 28GHz Microwave Irradiation

50 nm

TiO2–SnO2 composite grains having mesoscopicmodulated lamellar structure were successfully

thermally nonequilibrium condition induced byprepared by spinodal decomposition under

microwave selective heating.

Hirotsugu Takizawa, Akio Hagiya, TakuyaAoyagi, and Yamato Hayashidoi:10.1246/cl.2008.714

716 Chiral Bead-like Trimer of Tris(2,4-pentane-dionato)ruthenium(III)

The bead-like shape of a trimer is an essential factor in achieving chiral two-dimensional packing.

Hisako Sato, Jun Kameda, Yutaka Fukuda,Masa-aki Haga, and Akihiko Yamagishidoi:10.1246/cl.2008.716Electronic Supporting Information

718 Photoinduced Release of Oligonucleotide-conjugated Silica-coated Gold NanorodsAccompanied by Moderate MorphologicalChanges

Near-infrared pulsed-laser irradiation of silica-coated gold nanorods loaded with single-stranded oligonucleotides induced the release of the oligonucleotides without changing themorphology of the gold nanorods into spherical particles. Silica layers on the gold nanorodswere advantageous to realize the efficient release of the oligonucleotides.

Yukichi Horiguchi, Shuji Yamashita, TakuroNiidome, Naotoshi Nakashima, and YasuroNiidomedoi:10.1246/cl.2008.718Electronic Supporting Information

C-90 Chemistry Letters Vol.37, No.7 (2008)

Copyright � 2008 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

720 Mechanistic Investigation of the HydrationReaction of [Cr(�6-silabenzene)(CO)3]: Hy-drido(silacyclohexadienyl)chromium Com-plex as an Intermediate

H2O (2 equiv)

C6H6, r.t. Cr

SiOH

OC COH

Tbt

OC

D2O (excess)

C6H6, r.t.

Si

Tbt OHHDCr

Si Tbt

OCCO

COII

0

Tbt = 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl

a key intermediateYusuke Tanabe, Yoshiyuki Mizuhata, andNorihiro Tokitohdoi:10.1246/cl.2008.720Electronic Supporting Information

722 Fabrication of Urchin-like Bismuth Nano-structures via a Facile Solvothermal Route

Urchin-like bismuth nanosrcutres composed ofnanorods are fabricated via a facile solvothermalmethod for the first time.

Chunjuan Tang, Y. X. Zhang, Guozhong Wang,H. Q. Wang, and Guanghai Lidoi:10.1246/cl.2008.722

724 Ruthenium-catalyzed 1,4-Addition ofOrganoboronic Acids to �,�-UnsaturatedKetones

+ RB(OH)2

[RuCl2(p -cymene)]2(5 mol % Ru)

P(t -Bu)2(2-PhC6H4) (5 mol %)

KOH (1.0 equiv)Dioxane/H2O (100/1)

90 °C, 24 h

R1 R2

O

R1 R2

OR

up to 83% yield(4.0 equiv)

Ryo Shintani and Tamio Hayashidoi:10.1246/cl.2008.724Electronic Supporting Information

726 A Solid-state Chiral Fluorophore Obtainedfrom Achiral Fluorescent Biphenyl-4-carboxylic Acid and rac-PhenylmethylamineDerivatives

Yoshitane Imai, Katuzo Murata, HidekiMatsuno, Kensaku Kamon, Tomohiro Sato,Reiko Kuroda, and Yoshio Matsubaradoi:10.1246/cl.2008.726Electronic Supporting Information

728 Application of Magnetically Simulated Mi-crogravity for Preparation of Thin Filmswith Carbon Nanotubes

A PVA thin film in which multiwall carbonnanotubes were included was prepared insimulated microgravity created by a highmagnetic field.

Akio Katsuki, Hiromi Yamamoto, YoshihisaFujiwara, Masao Fujiwara, Morinobu Endo,and Yoshifumi Tanimotodoi:10.1246/cl.2008.728

Chemistry Letters Vol.37, No.7 (2008) C-91

Copyright � 2008 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

730 A General Hydrothermal Method to V2VI3Thermoelectric Nanomaterials Directly fromthe Corresponding Elements

A general hydrothermal method was developed for the preparation of V2VI3 (V = Sb and Bi;VI = S, Se, and Te) thermoelectric nanoparticles directly from the corresponding elements.

Bo Zhou, Jian-Ming Hong, and Jun-Jie Zhudoi:10.1246/cl.2008.730

732 Poly( p-phenyleneethynylene)–Silica Gel Hy-brids without Any Compatibilizer

OR

RO

P1: R = N(C2H5)2

N(C2H5)2C16H33Br

N N

N N

n

Br

NSO2CF3

SO2CF3

P2: R =

P3: R =

P4: R =

Silica Matrix Cationic PPESilica Matrix Cationic PPE

hν

OR

RO

P1: R = N(C2H5)2

N(C2H5)2C16H33Br

N N

N N

n

Br

NSO2CF3

SO2CF3

P2: R =

P3: R =

P4: R =Kenta Kokado and Yoshiki Chujodoi:10.1246/cl.2008.732

734 Particle-size Effects of Activated Carbon-supported Rhodium Catalysts on Hydroge-nation of Naphthalene in Supercritical Car-bon Dioxide Solvent

60

10

20

30

40

50

0 10 20 30Dispersion/%

TOF

/min

-1H2

Rh/AC

In scCO2

In n -heptaneNorihito Hiyoshi, Chandrashekhar V. Rode,Osamu Sato, Yoshio Masuda, AritomoYamaguchi, and Masayuki Shiraidoi:10.1246/cl.2008.734Electronic Supporting Information

736 One-step Fabrication of Nickel HierarchicalSuperstructures

0 50 100 150 200 250 3000.000

0.001

0.002

0.003

0.004

0.005

0.006

0.007

0.008

χ(e

mu/

mol

Oe)

T/K

20 K

-2 -1 0 1 2

-40

-20

0

20

40

M (

emu

g-1

)

H (kOe)

290 KZhe Chen, Minhua Cao, and Xiaoyan Hedoi:10.1246/cl.2008.736Electronic Supporting Information

738 Efficient I(5 2P1=2) Production by the Reac-tion of I2 with NCl3 Flame

800 900 1000 1100 1200 1300 14000

500

1000

1500

2000

2500

3000

3500

4000

4500

5000

5500

6000

6500

7000

800 900 1000 1100 1200 1300 14000

500

1000

1500

2000

2500

3000

3500

4000

4500

5000

5500

6000

6500

7000

without I2

with I2

λ /nm

λ /nm

Inte

nsity

/arb

. uni

t

The emission spectroscopic study

efficiently produced by the reactionshowed that the I(5 2P1/2) could be

of I2 with NCl3 autodecompositionflame. The probable mechanismsare discussed.

Liucheng Li, Liping Duo, and Bailing Yangdoi:10.1246/cl.2008.738Electronic Supporting Information

C-92 Chemistry Letters Vol.37, No.7 (2008)

Copyright � 2008 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

740 Manganese-catalyzed Synthesis of Hydan-toin Derivatives from Terminal Alkynesand Isocyanates

Ph Ph N C O

PhN

N

O

O Ph

PhMnBr(CO)5 (5.0 mol %)

Dioxane, 150 °C, 24 h+

91%(1.0 equiv) (2.2 equiv)

Yoichiro Kuninobu, Kou Kikuchi, andKazuhiko Takaidoi:10.1246/cl.2008.740Electronic Supporting Information

742 Synthesis and Properties of Electrophos-phorescent Conjugated Polymers ContainingIridium Complexes in Polymer Backbone

Yong Zhang, Yan Xiong, Chun Li, JunbiaoPeng, and Yong Caodoi:10.1246/cl.2008.742

744 Transesterification of Phosphotriester Para-oxon Catalyzed by ZnCl2 Supported on SilicaGel

OP

OO

O

NO2

+ZnCl2/SiO2 O

PO

O

O

Ph

+NO2HOHOCH2CH2Ph

Ismail O. Kadydoi:10.1246/cl.2008.744

746 Synthesis of Hierarchically Meso-/Macropo-rous Titanium Tetraphosphonate Materialswith Large Adsorption Capacity of HeavyMetal Ions The structural illustration of

tetraphosphonate materials with

the synthesized hierarchicallymeso-/macroporous titanium

intraframework ethylenediaminegroups.

Xue-Jun Zhang, Tian-Yi Ma, and Zhong-YongYuandoi:10.1246/cl.2008.746

748 Preparation of Superhydrophilic Mesopo-rous Silica Thin Films Containing Single-sitePhotocatalyst (Ti, V, Cr, Mo, and W oxidemoieties)

Yu Horiuchi, Kohsuke Mori, NorikazuNishiyama, and Hiromi Yamashitadoi:10.1246/cl.2008.748Electronic Supporting Information

Chemistry Letters Vol.37, No.7 (2008) C-93

Copyright � 2008 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

750 Mono-cyclopropanated Fullerene DimerC120O and Its Application in a Bulk Hetero-junction Solar Cell

A soluble, longish fullerene derivative 1 opening the possibility to make organic photoactivelayers of supra-molecular and anisotropic order was prepared, characterized, and applied.

Lars Weber, Steffi Sensfuss, Uwe Ritter, andPeter Scharffdoi:10.1246/cl.2008.750Electronic Supporting Information

752 Preparation of Plywood-like Fe3BO5 Nano-rods by a Facile Hydrothermal Method atLow Temperature

Single-crystalline plywood-like vonsenite (Fe3BO5) nanorods were prepared by a facilehydrothermal method with K4Fe(CN)6 and NaBH4 as starting materials. The Fe3BO5 nanorods,which are composed of 5 to 7 nanobelts, are identified to grow along the [001] direction.

Haiping Qi and Qianwang Chendoi:10.1246/cl.2008.752

754 Isotope Effect on Spin-crossover Transitionin a New Two-dimensional CoordinationPolymer [FeII(C5H5N)2][Au

I(CN)2]2, [FeII-(C5D5N)2][Au

I(CN)2]2, and [FeII(C5H515N)2]-

[AuI(CN)2]2

Takashi Kosone, Chihiro Kachi-Terajima,Chikahide Kanadani, Toshiaki Saito, andTakafumi Kitazawadoi:10.1246/cl.2008.754Electronic Supporting Information

756 Oxidation States of Antimony and Arsenic inMarine Ferromanganese Oxides Related toTheir Fractionation in OxicMarine Environ-ment As and Sb are pentavalent in

the ferromanganese oxides.

changed significantly duringThe As/Sb ratio is not

their incorporation intoferromanganese oxides.Teruhiko Kashiwabara, Satoshi Mitsunobu,

Anirban Das, Takaaki Itai, Masaharu Tanimizu,and Yoshio Takahashidoi:10.1246/cl.2008.756

758 Stabilization of DNA Multiassembly byAddition of a Phosphate Group at the 50-Sticky End

Aya Tanaka, Yasutaka Matsuo, KenichiNiikura, and Kuniharu Ijirodoi:10.1246/cl.2008.758Electronic Supporting Information

C-94 Chemistry Letters Vol.37, No.7 (2008)

Copyright � 2008 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

760 Spin-crossover Transition Coupled withAnother Solid–Solid Phase Transition forIron(II) Thiocyanate Complexes Chelatedwith Alkylated N-(Di-2-pyridylmethylene)-anilines

Yuya Oso, Daisuke Kanatsuki, Shuichi Saito,Takashi Nogami, and Takayuki Ishidadoi:10.1246/cl.2008.760Electronic Supporting Information

762 Hydrothermal Synthesis of GdVO4:Ho3þ

Nanorods with a Novel White-light Emission

Yiguo Su, Guangshe Li, Xiaobo Chen, JunjieLiu, and Liping Lidoi:10.1246/cl.2008.762Electronic Supporting Information

764 Miniaturization of Nanofibers Composedof Melamine-appended Perylene Bisimidesand Cyanurates

Optical transparency of organogels formed from melamine-appended perylene bisimides bysupramolecular polymerization through complementary hydrogen-bonding interactions withcyanurates is improved by elongating the length of alkyl linker moieties between perylenecore and melamine moieties.

Tomohiro Seki, Shiki Yagai, Takashi Karatsu,and Akihide Kitamuradoi:10.1246/cl.2008.764Electronic Supporting Information

766 Preparation, Characterization, and Field-effect Transistor Performance of Benzo-[1,2-d:4,5-d0]bisthiazole Derivatives

0 10VD / V

0

5E-006

1E-005

1.5E-005

2E-005

2.5E-005

I D /

A

VG = 50 V

VG = 45 V

VG = 40 V

VG = 35 V

VG = 30 V

N

S N

SS

S

F3C

CF3

20 30 40 50

Masashi Mamada, Jun-ichi Nishida, ShizuoTokito, and Yoshiro Yamashitadoi:10.1246/cl.2008.766Electronic Supporting Information

768 Bis(1-methylimidazole) Complex of Iron(III)Oxypyriporphyrin Adopting an Intermedi-ate-spin State

N

N

NN

H3CH2C CH2CH3

CH3CH3

CH3CH3

O

FeL

L

CN–

DMAP

HIm

1-MeIm

Ligand (L) Spin State

S = 1/2

S = 3/2Hajime Eguchi, Yoshiki Ohgo, Akira Ikezaki,Saburo Neya, and Mikio Nakamuradoi:10.1246/cl.2008.768

Chemistry Letters Vol.37, No.7 (2008) C-95

Copyright � 2008 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

770 Stereocontrolled Total Synthesis of (�)-Gleenol Using Claisen Rearrangement ofSterically Congested Dihydropyran

A stereocontrolled total synthesis of enantiomerically pure (–)-gleenol using stericallycongested dihydropyran to construct the spiro[4.5]decane through the Claisenrearrangement has been achieved.

OOSiEt3O

OSiEt3

OH

(−)-Gleenol

250 °C

triglyme

75% yield

single isomersterically congesteddihydropyran

Atsuo Nakazaki, Tomohiro Era, and SusumuKobayashidoi:10.1246/cl.2008.770Electronic Supporting Information

772 A New Amphiphilic and ThermoresponsivePolysilsesquioxane Having Alkoxyethyl-amide Group

SiO

O

NH

n

CO

(H3COH2CH2C)2N

SiO

O

HNCO

N(CH2CH2OCH2CH3)2

mTomonori Matsuoka, Shin-ichi Yamamoto, andOsamu Moriyadoi:10.1246/cl.2008.772

774 Autoxidation Resistant Cyclopentyl MethylEther ∆BH°(Bond Dissociation Energy)

MM3 Force Field Evaluation∆Hf°(Heat of Formation), Structure

O

H CH3 OCH3 + H

∆BH°298(C−H:ether) = ∆H°298(ether radical) ∆H°298(parent ether) + ∆H°298(H*)

393.3 kJ/mol by CBS-Q calculation

Hayato Hoshino, Kazuhisa Sakakibara, andKiyoshi Watanabedoi:10.1246/cl.2008.774Electronic Supporting Information

776 Hydrothermal Preparation of BiomineralBotallackite Cu2(OH)3Cl Hollow Nanoarchi-tectures Biomineral botallackite Cu2(OH)3Cl

hollow nanoarchitectures have beenobtained by hydrothermal methodsand the possible reaction mechanismis also discussed.

Zhitao Chen and Lian Gaodoi:10.1246/cl.2008.776

778 Influence of the Work Function of Chemical-ly Modified Indium–Tin–Oxide Electrodeson the Open-circuit Voltage of Heterojunc-tion Photovoltaic Cells

Chemical structures of donors (ZnPc, Rub, and SubPc) used to change ∆ph and chemicalmodifiers (H−, Cl−, and −P) used to tune the work function of ITO and thus built-in potentials.

Khayankhyarvaa Sarangerel, Chimed Ganzorig,Masamichi Fujihira, Masaru Sakomura, andKazuyoshi Uedadoi:10.1246/cl.2008.778Electronic Supporting Information

C-96 Chemistry Letters Vol.37, No.7 (2008)

Copyright � 2008 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

780 An Improved Synthesis of Methyl Protodio-scin: Tautomerization and Direct Access tothe 3-O-Substituted Kryptogenin

O

O

OH

ROO

O

O

RO

OH

O

O

OPiv

O

BzOBzO

BzO

PivOO

O

BzOBzO

BzO

Zn/KI/HOAc

R = TPS, TBS,

3-O-substituted kryptogenin

4Qing-Chun Xu, Yang Liu, Jiao Liu, Chun-XianHe, Mao-Cai Yan, and Mao-Sheng Chengdoi:10.1246/cl.2008.780Electronic Supporting Information

782 Photoreduction of 1,2-Diarylcyclopropanesby Hydroxide Ion

R R

i -PrOH

hν , NaOH

R RYasuharu Yoshimi, Naohisa Wada, KoichiSasamoto, Tatsuya Itou, and Minoru Hatanakadoi:10.1246/cl.2008.782Electronic Supporting Information

784 Synthesis and Properties of Cyclic [5]meta-Phenyleneacetylene and Its CorrespondingCyclophane Polyone, [25](1,3)Cyclophanede-caone

O

O

O

O

OO O O

O

O

[5]CMPA (5PAM)

A rigid fluorescent moleculeA mobile colorless

molecule

X-ray structure of the dione

Jun Yamakawa, Masanori Ohkoshi, FutoshiTakahashi, Tomohiko Nishiuchi, YoshiyukiKuwatani, Tohru Nishinaga, Masato Yoshida,and Masahiko Iyodadoi:10.1246/cl.2008.784Electronic Supporting Information

786 Extended Pummerer Reaction of ArylketeneDithioacetal Monoxides with AromaticCompounds by Means of Trifluoromethane-sulfonic Anhydride

PhS

SO

+

PhS

STf2O (1.5 equiv)

(1.5 equiv)CH3NO2

25 oC, 1 h

RR

50−92%Suguru Yoshida, Hideki Yorimitsu, andKoichiro Oshimadoi:10.1246/cl.2008.786

788 Single-component CT Crystals Based on1,4-Benzoquinone Derivatives and TEMPORadical

Recrystallization(X=Cl)

O

O

X

X

O

X

NO

Mitsunori Nobusawa, Hiroki Akutsu, Jun-ichiYamada, and Shin’ichi Nakatsujidoi:10.1246/cl.2008.788Electronic Supporting Information

Chemistry Letters Vol.37, No.7 (2008) C-97

Copyright � 2008 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

790 Continuous Supercritical Low-temperatureMethanol Synthesis with n-Butane as aSupercritical Fluid

CO + CO2 + H2

2-Butanol

Cu/ZnO, 443 K, 60 bar

Undersupercritical n-butane

COCO2

Total carbon

Withoutsupercritical n-butane

CH3OH

CH3OH

0 6 12 15 180

20

40

60

Con

vers

ion

/ %

Time on stream/h

0 3 6 9 12 15 18-15

-10

-5

0

5

10

Time on stream/h

Co

nver

sion

/ %

3 9

Prasert Reubroycharoen, Jun Bao, Yi Zhang,and Noritatsu Tsubakidoi:10.1246/cl.2008.790

792 On-site Determination of Trace Nickel inLiquid Samples for Semiconductor Manu-facturing by Highly Sensitive Solid-phaseColorimetry with �-Furil Dioxime

A new, highly sensitive colorimetry for trace nickel(II) at the parts per billion level has beendeveloped. The proposed method has been successfully applied to the 48% NaOH solutionsused for silicon wafer etching.

0 1 2 5 10 25 50

Nickel(II) content/µg L-1

Hitoshi Mizuguchi, Yan-Fan Zhang, HirofumiOnodera, Saori Nishizawa, and Junichi Shidadoi:10.1246/cl.2008.792

794 Iron Salt-cataltzed Multipoint Alkylation ofPyrrole with Vinyl Ketones

Motoi Kawatsura, Masamune Fujiwara,Hiroyuki Uehara, Shun Nomura, ShuichiHayase, and Toshiyuki Itohdoi:10.1246/cl.2008.794Electronic Supporting Information

796 Palladium-catalyzed Cross-coupling of Ben-zylic Carbonates with Organostannanes

OCOMeR1

+

Bu3Sn R2 1 2% cat. [Pd] DPPPent

DMF, 80 °C

R1 R2

Ph2P PPh2

DPPPent =

O

Masato Ohsumi and Ryoichi Kuwanodoi:10.1246/cl.2008.796Electronic Supporting Information

798 High Electroconductivity of Wood Char Ob-tained by Iron-catalyzed Carbonization

Tsutomu Suzuki, Hiroshi Matsuzaki, KyokoSuzuki, Yukie Saito, Sei-ichi Yasui, NoriyasuOkazaki, and Tetsuo Yamadadoi:10.1246/cl.2008.798

C-98 Chemistry Letters Vol.37, No.7 (2008)

Copyright � 2008 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/

800 Iron(II) Chloride-mediated Addition of Di-alkylmagnesium to Carbonyl Compounds

O

OHMe

FeCl2 + Me2Mg0 °C

5 min 0 °C, 30 min70%

Addition reactions to carbonyl compounds with a complex reagent, prepared from

1,2-addition nucleophile to an easily enolizable ketone such as f-tetralone; it added to ketoester chemoselectively.

βorganomagensium species and iron(II) chloride, were examined. The complex reagent works as

Mutsumi Sada and Seijiro Matsubaradoi:10.1246/cl.2008.800

802 Crystal Structure of Boryllithium with TwoTHF Molecules and DFT Analysis of ItsProperty as a Boryl Anion

Makoto Yamashita, Yuta Suzuki, YasutomoSegawa, and Kyoko Nozakidoi:10.1246/cl.2008.802Electronic Supporting Information

804 Formation of Incompletely Condensed Oli-gosilsesquioxanes by Hydrolysis of Com-pletely Condensed POSS via Reshuffling

SiO O

O

SiO

SiOSi

O Si OPh

SiSi OSi

O

OPhO

PhPh

Ph

PhPh Ph

OH2O/NaOH

2-propanolreflux

+

SiO O

O

SiO

SiOSi

O Si OR

SiSi OSi

O

ORO

RR

R

RR R

O

SiOO

O

SiO

SiONa

ONaSi

OR'

Si SiOSi

O

O R'ONa

R'

R'

R'R'R'

O

R' = Phenyl or

+NaO

NaOSi

O O

O

SiO

SiOSi

O Si OR'

SiSi OSi

O

OR'

R'R'

ONaONaR'

R' R' R'

D

DD

D D

R = D

DD

D D

Ze Li and Yusuke Kawakamidoi:10.1246/cl.2008.804Electronic Supporting Information