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

Vol.41 No.7 CMLTAGJuly, 2012 ISSN 0366-7022

Copyright © 2012 The Chemical Society of Japan

Highlight Review

658 Chemical Biology of Natural Products on theBasis of Identification of Target Proteins “Lock” A

“Lock” B “Lock” C

Minoru Uedadoi:10.1246/cl.2012.658

Letter

667 Preparation of Lipophilic Anionic PolymerNetworks Based on Tetraphenylborates

Yuki Furukawa, Kenta Kokado, and KazukiSada*doi:10.1246/cl.2012.667Electronic Supporting Information

669 Liquid-phase Deposition of Titanium OxideFilm on Silicon Substrate Mediated byPolydopamine

Junfei Ou, Fajun Wang, Mingshan Xue, YingWang, Junping Yao, and Wen Li*doi:10.1246/cl.2012.669Electronic Supporting Information

672 Theoretical Studies of Solvation Effects on2-(2-Hydroxyphenyl)benzimidazole

enol

Keto form is stable or not?

keto

Ayaka Kuroki, Hiroshi Ushiyama,* and KoichiYamashitadoi:10.1246/cl.2012.672

674 Effects of Alkoxy Substitution on the OpticalProperties of 9,10-Anthraquinone and An-thracene: 2,3,6,7-Tetrapropoxy-substitutedvs. 2,6-Dipropoxy-substituted Derivatives

600500400300Wavelength / nmA

bsor

banc

e / a

rb u

nit

600500400300Wavelength / nmA

bsor

banc

e / a

rb u

nit

O

OOPr

OPrPrO

PrO

O

O

OPr

PrO

O

OOPr

OPrPrO

PrO

OPr

PrO

Akira Ohta,* Kazuki Hattori, Yui Kusumoto,Takeshi Kawase, Takashi Kobayashi, HiroyoshiNaito, and Chitoshi Kitamura*doi:10.1246/cl.2012.674Electronic Supporting Information

677 Preparation and Reaction of Titania Par-ticles Encapsulated in Hollow Silica Shells asan Efficient Photocatalyst for StereoselectiveSynthesis of Pipecolinic Acid

Sheela Chandren and Bunsho Ohtani*doi:10.1246/cl.2012.677Electronic Supporting Information

680 Arrangement and Dispersion of Rh and PtAtoms on Graphene Oxide Sheets

Rh on carbon sheets Pt on carbon sheets

Rh atoms on graphene sheets arrange with a regular spacing of 0.50 or 0.45 nm and form squareor rectangular grid patterns, whereas isolated Pt atoms disperse on graphene sheets randomly.

Kazuma Gotoh,* Hideki Hashimoto, RyoKawai, Yuta Nishina, Eiji Fujii, TakahiroOhkubo, Atsushi Itadani, Yasushige Kuroda,and Hiroyuki Ishidadoi:10.1246/cl.2012.680Electronic Supporting Information

683 Study on Amino-functionalized GrapheneOxide/Poly(methyl methacrylate) Nanocom-posites

Reaction scheme of preparing amino-functionalized graphene oxide (AGO)/poly(methyl methacrylate) (PMMA) nanocomposites.

Jia-lin Yan, Guo-qiang Qi, Jun Cao, Yong Luo,Wei Yang,* Bang-hu Xie, and Ming-bo Yangdoi:10.1246/cl.2012.683

Chemistry Letters Vol.41, No.7 (2012)C-66

http://www.csj.jp/journals/chem-lett/Copyright © 2012 The Chemical Society of Japan

686 Surfactant-free Synthesis and FormationMechanism of Fe3O4 Nanospheres in MixedSolvent Ethylene Glycol­Water System

Uniform Fe3O4 nanospheres have been synthesized by a simple ethylene glycol−H2O system without the assistance of any additives. Compared with the literature, the reaction temperature of our polyol synthetic method is relatively low and the reactiom time is short. The control of the reaction temperature and the presence of a certain amount of water were necessary in the formation of Fe3O4 nanospheres. The relatively low temperature, short reaction time, and additive-free synthetic method can afford a low-cost and green synthesis route.

Yanyan Xu,* Yanyan Cao, Yaqiu Sun, GuoyingZhang, and Dongzhao Gaodoi:10.1246/cl.2012.686

689 One-pot Chemoenzymatic Route to Chitohepta-ose via Specific Transglycosylation of Chito-pentaose­Oxazoline on Chitinase-template

Naoki Yoshida, Tomonari Tanaka, MasatoNoguchi, Atsushi Kobayashi, Kumiko Ishikura,Tatsuya Ikenuma, Hiromu Seno, TakeshiWatanabe, Michinari Kohri, and Shin-ichiroShoda*doi:10.1246/cl.2012.689Electronic Supporting Information

691 Linking Magnetic Clusters: FerrimagneticInteractions in a Nonanuclear Nickel(II)Cluster

Fumichika Iijima, Koen Hasumi, Takuya Shiga,Graham N. Newton, and Hiroki Oshio*doi:10.1246/cl.2012.691Electronic Supporting Information

693 How Does Methanol Assist the HydrogenTransfer in Pd-catalyzed Cyclocarbonylationof Allylic Alcohols? Insights from a DFTStudy

A theoretical study is carried out on the mechanism of the carbonylation of allylic alcohol catalyzed by [PdHCl(bppm)] complex. The results indicate that the pathway with Pd(II) character is more favorable than that with Pd(IV) character, and methanol assistance plays a critical role in the reaction.

Mawia Hassan, Xin Zhang,* Wenchao Zhang,Xiaojia Guo, Biaohua Chen, and Ming Lei*doi:10.1246/cl.2012.693Electronic Supporting Information

696 Charge Transfer at the Interfaces betweenPoly(3,4-ethylenedioxythiophene):Poly(styrene-sulfonate) (PEDOT:PSS) and Pentacene asInvestigated by ESR

Typical ESR signals of organic thin films of PEDOT:PSS/pentacene fabricated with deposition speeds of pentacene of 0.7 (red line) and 0.07 Å s−1 (green line). ESR signal of PEDOT:PSS film (blue line) is also shown. Inset on the right hand side: Dependence of the peak-to-peak ESR intensity of pentacene on the deposition speed of pentacene. Two layered films were fabricated with the deposition speeds of 0.07, 0.21, and 0.7 Å s−1. Inset on the left hand side: The enlargement of the ESR signals in the main panel. 320.5 321 321.5 322

Magnetic Field/mT

PEDOT:PSS/pentaceneDeposition speed

0.7 Å s−1

0.07 Å s−1

PEDOT:PSS

320.5 321 321.5 322H/mT

0.2 0.4 0.6 0.8 1

2

4

6

8

0Deposition speed/Å s−1

ES

R in

t. (

arb

un

it)

Masaaki Ito and Kazuhiro Marumoto*doi:10.1246/cl.2012.696

Chemistry Letters Vol.41, No.7 (2012) C-67

http://www.csj.jp/journals/chem-lett/Copyright © 2012 The Chemical Society of Japan

699 Synthesis of Triple-ringed [14]Arene viaDynamic Covalent Chemistry Mechanismin Condensation Reaction of Phenols withm-Benzenedicarbaldehyde

H3CHO

OH HO CH3

OHOH

CH3HOOH

CH3HOOH

CH3

OH

OHH3C

HOHO

CH3

OH HOCH3

OH HOCH3

OH HO CH3

OH

Triple-ringed [14]arene (TRA[14])

Condensation reaction of 2-methylresorcinol with m-benzenedicarbaldehyde in the presence of HCl as a catalyst in n-propanol at 90 °C for 48 h proceeded via a dynamic covalent chemistry (DCC) mechanism to afford a triple-ringed [14]arene in 52% yield.

Hiroyuki Seki, Shingo Kuwabara, HirotoKudo,* and Tadatomi Nishikubodoi:10.1246/cl.2012.699Electronic Supporting Information

702 para-Benzihemiporphyrazine and Its Ex-panded [3 + 3]-type Analogue

A novel para-benzihemiporphyrazine was synthesized from a stepwise reaction of 1,3-diiminoisoindoline and para-phenylenediamine via a linear [2 + 1]-type compound, whereas its ring-expanded [3 + 3]-type analogue was obtained from a one-pot condensation reaction of the same starting materials.

Soji Shimizu,* Yuta Sato, and NagaoKobayashi*doi:10.1246/cl.2012.702Electronic Supporting Information

705 Cascade Synthesis of 3-Alkenylcoumarins byPalladium-catalyzed Reaction of Phenols andEthyl Propiolate

Tsugio Kitamura,* Kotaro Tatemoto, MarikoSakai, and Juzo Oyamadadoi:10.1246/cl.2012.705Electronic Supporting Information

708 Improvement of Thermal Stability of GoldNanoparticles by Synergistic InterligandInteractions

OO

S NH

O

OO

S NH

O

OO

S NH

O

Au

Amide bond

(Hydrogen Bonding)

Alkyl chain

(van der Waals force)

Aromatic ring

(π−π stacking)

Atsushi Okumura, Yoshitaka Tsuchido, KouYamada, Kenji Todori, and Shigeru Machida*doi:10.1246/cl.2012.708

711 Sequential Release of Single-stranded DNAsfrom Gold Nanorods Triggered by Near-infrared Light Irradiation

Hiromitsu Fukushima, Shuji Yamashita,Takeshi Mori, Yoshiki Katayama, and TakuroNiidome*doi:10.1246/cl.2012.711Electronic Supporting Information

Chemistry Letters Vol.41, No.7 (2012)C-68

http://www.csj.jp/journals/chem-lett/Copyright © 2012 The Chemical Society of Japan

713 Selective Hydroxylation of Cyclohexene inWater as an Environment-friendly Solventwith Hydrogen Peroxide over Fe­BipyridineEncapsulated in Y-type Zeolite

The selective hydroxylation of cyclohexene to 2-cyclohexen-1-ol with hydrogen peroxide in water was successfully achieved using [Fe(bpy)3]

2+ complexes encapsulated into Y-type zeolite ([Fe(bpy)3]

2+@Y).

Syuhei Yamaguchi, Tomohiro Fukura, ChiharuFujita, and Hidenori Yahiro*doi:10.1246/cl.2012.713Electronic Supporting Information

716 Spin Crossover and Light-induced ExcitedSpin-state Trapping Observed for an Iron(II)Complex Chelated with Tripodal Tetrakis-(2-pyridyl)methane

Naoki Hirosawa, Yuya Oso, and TakayukiIshida*doi:10.1246/cl.2012.716

719 The First Example for Cyanation of Aryl-boronic Acids with Nontoxic and InexpensiveK4[Fe(CN)6]

B(OH)2 + K4[Fe(CN)6]I2, Catalyst

6-24 h, 100-180 °CCNAr Ar

Nontoxic and inexpensive K4[Fe(CN)6] was first introduced as a cyanating agent to cyanation of arylboronic acids. The present method is simple, practical, and allowed a wide range of substrates including functionalized phenylboronic acids, 1-naphthylboronic acid as well as heterocyclic boronic acids to be smoothly converted into the corresponding products in moderate to high yields.

Xinzhe Tian,* Yanpei Sun, Chuanhua Dong,Kaixuan Zhang, Tengfei Liang, Yu Zhang, andChaodong Houdoi:10.1246/cl.2012.719Electronic Supporting Information

722 Novel Method of Producing Carbon Nano-particles on Benzene/Water Interface withFemtosecond Laser Plasma Filament

Tomoyuki Yatsuhashi,* Naoko Uchida, andKayo Nishikawadoi:10.1246/cl.2012.722

725 Photofuel Cells Using Allophane­TitaniaNanocomposites

titaniananocrystal

fuel material

ITO

hν

e–

e–

e–

adsorption

counter electrode

electrolytecontaining O2

ITO

oxidative degradation

allophane

with glucose

without glucose

0

20

40

60

80

100

120

0 0.2 0.4 0.6

Cur

rent

den

sity

/ µA

cm

-2

Applied voltage / V

titania allophane-titania

The observed photocurrent and CO2 production indicated that allophane effectively adsorbed glucose molecules and then transported them to the titania, on which their oxidative degradation induced the generation of electricity.

Hiromasa Nishikiori,* Masaaki Ito, Rudi AgusSetiawan, Ayaka Kikuchi, Tomohiko Yamakami,and Tsuneo Fujiidoi:10.1246/cl.2012.725

Chemistry Letters Vol.41, No.7 (2012) C-69

http://www.csj.jp/journals/chem-lett/Copyright © 2012 The Chemical Society of Japan

728 Isolation and Structure of a Novel BiindolePigment Substituted with an Ethyl Groupfrom a Metagenomic Library Derived fromthe Marine Sponge Halichondria okadai

halichrome A

NH

O

NH

Takahiro Abe,* Akira Kukita, KiyotakaAkiyama, Takayuki Naito, and DaisukeUemura*doi:10.1246/cl.2012.728

730 Retention Behavior of ¢-Cyclodextrin-bonded Stationary Phase Synthesized viaAtom-transfer Radical Polymerization andClick Chemistry

A new chiral stationary phase (CSP) was synthesized via surface-initiated atom-transfer radical polymerization (ATRP) and click chemistry. This CSP can facilitate the efficient separation of chiral compounds, as well as aromatic compounds, with HPLC.

Huaisong Wang, Qiwei Xie, Haiyan Wang,Diankui Zhu, and An Jiang*doi:10.1246/cl.2012.730Electronic Supporting Information

732 Preparation of Nanosheets by UltrasonicExfoliation with the Aid of SurfactantPoly(vinylpyrrolidone) Using poly(vinylpyrrolidone) (PVP) as

a stabilizing agent, graphite nanosheets (GNs) and molybdenum disulfide nanosheets (MNs) were conveniently obtained by ultrasonic exfoliation. The special UV spectra and Raman spectra of as-received nanosheets were studied and discussed.

Caixia Li, Qing Lv, Danyu Jiang, Lin Zhang,Jinfeng Xia, and Qiang Li*doi:10.1246/cl.2012.732Electronic Supporting Information

735 Repeatable Wettability Conversion betweenHydrophobic and Superhydrophilic Stateson Nonwoven Fabrics Based on ElectrospunTiO2­Poly(dimethylsiloxane) Fibers

Nonwoven fabrics based on composite fibers of TiO2 and poly(dimethylsiloxane) (PDMS) are prepared by electrospinning. Wettability conversion on the surface of the nonwoven fabrics can be changed by subsequent cycles of plasma irradiation and storage under ambient conditions.

Kazuya Nakata,* Munetoshi Sakai, BaoshunLiu, Tsuyoshi Ochiai, Taketoshi Murakami, andAkira Fujishimadoi:10.1246/cl.2012.735

738 SO42¹/CexZr1¹xO2-catalyzed Synthesis of N-

tert-Butylamides from Various Nitriles underSolvent-free Conditions The highly efficient synthesis of N-tert-butylamides using SO4

2−/CexZr1−xO2 catalysts under solvent-free conditions is reported.

R-CNO

O

R N

H

O

+ SO4

2−/CexZr1−xO2

110 °C, solvent-free 5 h

R= alkyl,arylSandeep S. Kahandal, Sandip R. Kale,Shamrao T. Disale, and Radha V. Jayaram*doi:10.1246/cl.2012.738Electronic Supporting Information

Chemistry Letters Vol.41, No.7 (2012)C-70

http://www.csj.jp/journals/chem-lett/Copyright © 2012 The Chemical Society of Japan

741 Control of Periodicity in Mesoporous SilicaFilms with Aligned Mesochannels Preparedby a Sol­Gel Process

C10

C12

C16

LCH

d01

Atsushi Komoto, Wataru Kubo, and HirokatsuMiyata*doi:10.1246/cl.2012.741Electronic Supporting Information

744 Pt-Catalyzed Oxidative Rearrangement ofCyclic Tertiary Allylic Alcohols to EnonesUsing Aqueous Hydrogen Peroxide

OHR

R

OPt black (0.01 equiv)30% H2O2 (3 equiv)

H2O, 90 °C, 3 hTakashi Nagamine, Yoshihiro Kon,* andKazuhiko Sato*doi:10.1246/cl.2012.744Electronic Supporting Information

747 An Improved Method to Increase the Con-centration of Graphene in Organic Solvent Graphene sheets are negatively charged in organic solvent and stabilized through electrostatic

repulsion.

Hao Zhang, Jiqiu Wen, Xiaopeng Meng,Yadong Yao,* Guangfu Yin, Xiaoming Liao,and Zhongbing Huangdoi:10.1246/cl.2012.747

750 A Sulfonated Polyaramide: Stir-inducedChirality in Its Aqueous Solution

Kunihiko Okano,* Kanami Machida, andTakashi Yamashita*doi:10.1246/cl.2012.750Electronic Supporting Information

Chemistry Letters Vol.41, No.7 (2012) C-71

http://www.csj.jp/journals/chem-lett/Copyright © 2012 The Chemical Society of Japan