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Chemistry Lettershttp://www.csj.jp/journals/chem-lett/
Vol.39 No.3 CMLTAGMarch, 2010 ISSN 0366-7022
Copyright © 2010 The Chemical Society of Japan
Highlight Review
148 Carotenoid Radicals: Cryptochemistry ofNatural Colorants
Zeaxanthin
Spin density distribution in zeaxanthin radical cation
Lowell D. Kispert� and Nikolay E. Polyakovdoi:10.1246/cl.2010.148
This review examines the properties and uses of carotenoid radicals. Their mechanisms of action on the molecular level play acrucial role in electron transfer and light regulation processes in photosynthesis, in the design of improved artificial solar cells, andin the scavenging of toxic free radicals. There is a remarkable increase in the quantum yield and the lifetime of the charge-separatedstates of the carotenoid radical cations in the supramolecular “hosts” ¢-glycyrrhizic acid (GA) and arabinogalactan (AG).
Letter
156 Ratiometric Fluorescent Sensor for 2,4,6-Trinitrotoluene Designed Based on EnergyTransfer between Size-different QuantumDots
Tomohiro Shiraki, Youichi Tsuchiya, and SeijiShinkai�doi:10.1246/cl.2010.156Electronic Supporting Information
159 Size Effect of Silica-supported Gold Clustersin the Microwave-assisted Oxidation ofBenzyl Alcohol with H2O2
Yongmei Liu, Hironori Tsunoyama, TomokiAkita, and Tatsuya Tsukuda�doi:10.1246/cl.2010.159
162 QuinoneHydroquinone ³-ConjugatedRedox Reaction Involving Proton-coupledElectron Transfer Plays an Important Rolein Scavenging Superoxide by PolyphenolicAntioxidants
Tatsushi Nakayama and Bunji Uno�doi:10.1246/cl.2010.162
165 Halochromic Chiroptical Response of NovelBis(9-acridinyl)-type Fluorophores with aHelical ³ Framework
Four-way-output molecular response upon protonation of helical diacridines.
Tatsuo Nehira, Yasuyo Yoshimoto, KazuhisaWada, Hidetoshi Kawai, Kenshu Fujiwara, andTakanori Suzuki�doi:10.1246/cl.2010.165Electronic Supporting Information
168 Blue, Green, and Red Light Emission of1,8-Carbazole-based Conjugated Polymers
400 500 600 700 800
Inte
nsity
/ a.
u.
Wavelength / nm
N
C16H33
C6H13
C6H13
n
N
C16H33
S
S
n
N
C16H33
S
NSN
S
n
Tsuyoshi Michinobu,� Haruka Osako, KimieMurata, and Kiyotaka Shigeharadoi:10.1246/cl.2010.168Electronic Supporting Information
170 Chiral T-shaped Semiflexible CompoundExhibiting a Wide Temperature Range BluePhase III
C8H17O COO (CH2)5 OO
C6H13
O
CH3H
O
(CH2)5
O
O
CN
Hirotoshi Iwamochi, Tetsu Hirose, YutaroKogawa, and Atsushi Yoshizawa�doi:10.1246/cl.2010.170Electronic Supporting Information
Chemistry Letters Vol.39, No.3 (2010)C-20
http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan
172 A Cembranoid, Trocheliophorol, from theCultured Soft Coral Sarcophyton trochelio-phorum
O
HO
O O
H
Trocheliophorol
Jui-Hsin Su, Yi Lu, Wan-Yu Lin, Wei-HsienWang, Ping-Jyun Sung, and Jyh-Horng Sheu�doi:10.1246/cl.2010.172
174 Ultrastrong Gravity-induced Unusual Reac-tivity in Radical Addition of Bromotrichloro-methane to Ethyl Cinnamate
5 G
1 G
Yasuyuki Abe, Tsuyoshi Sawada, MakotoTakafuji, Tsutomu Mashimo, Masao Ono, andHirotaka Ihara�doi:10.1246/cl.2010.174Electronic Supporting Information
176 Regioselective Oxidation of Pyrrole Deriva-tives with DDQ and Its Synthetic Application
NH
CO2tBu
DDQAcOH
NH
CO2tBu
R1OAc
R1
NuBase
NH
CO2tBu
R1Nu
R2
R2 R2
NH
CO2tBu
R1O
R2DDQ
MeOHRyoji Iwamoto, Yutaka Ukaji,� and KatsuhikoInomata�doi:10.1246/cl.2010.176
178 Effects of Redox Potential ofMetallophthalo-cyanine Dye on Photocatalytic Activity ofKTa(Zr)O3 for Water Splitting
-1.0 -0.9 -0.8 -0.7 -0.60
10
20
30
40
50
60
Co
Fe
Cr
Mn
NiH2
form
atio
n ra
te /
µmol
gca
t-1h-1
Redox potential /V vs. SCE
N
N
N
N
NN
N
M
Optimum redox potential was observed around
perovskite photocatalyst for water splitting.−0.8V vs. SCE for dye modifying KTaO3
N
Hidehisa Hagiwara, Naoko Ono, and TatsumiIshihara�doi:10.1246/cl.2010.178Electronic Supporting Information
180 A Straightforward and Efficient Catalyst-free One-pot Synthesis of N-Acyl-1,3-diaryl-2-azaphenalene Derivatives via Multicompo-nent Reactions
Naser Foroughifar,� Akbar Mobinikhaledi, andHassan Moghaniandoi:10.1246/cl.2010.180Electronic Supporting Information
Chemistry Letters Vol.39, No.3 (2010) C-21
http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan
182 Novel Tube-like Y2Sn2O7:Tb3+ Crystals:Hydrothermal Synthesis and Photolumines-cence Properties
The pyrochlore structure Y2Sn2O7:Tb3+ crystals synthesized via hydrothermal route in aqueousammonia display a tube-like shape, and green emission.
Jinyu Yang, Yuchang Su,� and Lijian Lidoi:10.1246/cl.2010.182
184 Thermoresponsive Fluorescent Sensor Basedon Core/Shell Nanocomposite Composed ofGold Nanoparticles and Poly(N-isopropyl-acrylamide)
Core/shell nanocomposite fluorescent sensor which can sense the thermal change and work in areversible mode.
Jirarut Wongkongkatep,� Runchuan Ladadat,Woraphoj Lappermpunsap, PravitWongkongkatep, Pranee Phinyocheep, AkioOjida, and Itaru Hamachidoi:10.1246/cl.2010.184Electronic Supporting Information
186 One-dimensional Tube-like {51262}n WaterClusters Stabilized in a Molecular Nano-porous Framework
O
O
O
O
H
H
H
H
H
H
H
H
Tetradecahedron 5126 2 Unit
Clathrate-Hydrate Like
Large water nanotube clusters (WNTs) contained inone-dimensional (1-D) channels of molecular nanoporous
the same as that of the {51262}n water molecule clustercrystal are prepared. The structure of this WNT is almost
present in type-I clathrate hydrate.Makoto Tadokoro,� Chihiro Iida, TakahitoSaitoh, Takahiro Suda, and Yuji Miyazatodoi:10.1246/cl.2010.186Electronic Supporting Information
188 Preparation of Uniform-sized PolymerNanofibers by Extrusive Spinning UsingOrdered Anodic Porous Alumina
Takashi Yanagishita,� Ryoko Fujimura,Kazuyuki Nishio, and Hideki Masudadoi:10.1246/cl.2010.188
190 Capturing a Metastable Silver(I) Compoundof Pyrazine-2,3-dicarboxylic Acid A metastable 3D supramolecular compound
[Ag(NH3)2][Ag3(pzdca)2(NH3)4] (H2pzdca =pyrazine-2,3-dicarboxylic acid) (1) has beensynthesized and characterized crystallo-graphically. This study offers importantinformation to in-depth understanding of theself-assembly process involving AgI underammoniacal conditions and conforms that[Ag(NH3)2]
+-containing compounds are theintermediates during synthesis of some AgI
coordination polymers.
Di Sun, Geng-Geng Luo, Na Zhang, Zhan-HuaWei, Cheng-Feng Yang, Rong-Bin Huang,� andLan-Sun Zhengdoi:10.1246/cl.2010.190Electronic Supporting Information
Chemistry Letters Vol.39, No.3 (2010)C-22
http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan
192 Fabrication of Cu3V2O7(OH)2¢2H2O Nano-ribbons and Cu3V2O7(OH)2¢2H2O/PANINanocomposites Used in Supercapacitors
Cu3V2O7(OH)2·2H2O (CVO) nanoribbons (a) and CVO/PANI nanocomposites (b) are fabricated for use in supercapacitors.
Zhongjie Huang, Wenbin Ni, Huan Pang,Qingyi Lu, Dengchao Wang, and JianweiZhao�doi:10.1246/cl.2010.192
194 Lewis Acid-mediated Highly RegioselectiveRing-expansion of Methyl 2-Phenyl-1-(aryl-hydroxymethyl)cyclopropanecarboxylates
Ph CO2MeSc(OTf)3or BF3
.OEt2Ph
CO2Me
OH
R3R3
R1 R2 R1 R2
A novel ring-expansion of methyl (arylhydroxymethyl)cyclopropanecarboxylates 1 usingSc(OTf)3 or BF3·OEt2 afforded 1,2-dihydronaphthalene-3-carboxylic acid ester 2 in highto excellent yields.
Eri Yoshida, Kazufumi Nishida, Kei Toriyabe,Ryouta Taguchi, Jiro Motoyoshiya, andYoshinori Nishii�doi:10.1246/cl.2010.194Electronic Supporting Information
196 Selective Coupling at the ¡-Amino Group ofCysteine Using Transfer Active-ester-con-densation Technology to Synthesize a LinearOctadecapeptide Fmoc-Leu67-His-Leu-Val-Leu-Arg-Leu-Arg-Gly-Gly76-NHNH2
Fmoc-Ub67-76-NHNH2 H-mNGF110-117-OH2-CH-CO-Val-Leu-Ser-Arg-Lys115-Ala-Thr117-OH
SH
NH2
+ NH
NH2-CH-CO-Val-Leu-Ser-Arg-Lys115-Ala-Thr117-OH
S
Fmoc-Ub67-76
Fmoc-Ub67-76-mNGF110-117-OH H-Ub67-76-mNGF110-117-OH
NH2
TAEC
Yongxiang Liao, Yan Kong, Naifeng Hu, ZhiJin, and Pu Wang�doi:10.1246/cl.2010.196Electronic Supporting Information
198 Transesterification of Triolein to BiodieselFuel over Mordenite-supported CaO Cata-lysts
Syuhei Yamaguchi, Makiko Asamoto, SyunInoue, Satomi Kawahito, Yasuhiro Mieno,Kenji Ikushima, and Hidenori Yahiro�doi:10.1246/cl.2010.198
200 Deep Red Emission of Ca19Ce(PO4)14:Mn2+
Phosphor for Fluorescent Lamp and PDPApplications
Red-emitting (Ca 0.95Mn 0.05)19Ce(PO4)14 phosphor coating wasprovided on the interior surface of the helical fluorescentlamp, operating under a power of 11 W.
Te-Wen Kuo,� Hsiu-Pei Chung, and Teng-MingChen�doi:10.1246/cl.2010.200
Chemistry Letters Vol.39, No.3 (2010) C-23
http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan
202 Low-temperature Heteroepitaxy ofMorphol-ogy-controlled ZnO Mirco/Nanorod Arrayson GaN Substrates
The influence of GaN seed morphology on the growth of ZnO rods by solution-based process isinvestigated. The scale of ZnO rods is controlled with a wide size range from 130 nm up to2.5 µm in diameter. Our investigation demonstrates that the morphologies of GaN seedinglayers have strong influences on the features of the ZnO rods grown thereon.
Cha-Hsin Chao, Wen-Han Lin, Chang-HoChen, Ching-Hua Changjean, Chang-Chi Pan,and Ching-Fuh Lin�doi:10.1246/cl.2010.202
204 AcidBase Responsive Photoelectric Con-version of a Hydroxyazobenzene-appendedBipyridineCopper Complex System
CuO
O O
O
Cu Cu
Interligandπ-π stacking
UV
VisCu
OH
OH
CuHO
HO
OH
OH
OH
OH
CuCu
CuUV
Base Acid
O
O
O
O
-
- -
-
-
-
-
-
-
-
-
-
-
-
-
-Satoshi Umeki, Shoko Kume, and HiroshiNishihara�doi:10.1246/cl.2010.204Electronic Supporting Information
206 Facile Fabrication of Inorganic/PolymerJanus Microspheres by Miniemulsion Poly-merization
A facile method for the preparation of inorganic/polymer Janus microspheres was presented viaminiemulsion polymerization by taking full advantage of phase separation between the growingpolystylene particles and tetraethoxysilane.
Jianan Zhang,� Mingyuan Wu, Qingyun Wu,Jianjun Yang, Nannan Liu, and Zhilai Jindoi:10.1246/cl.2010.206Electronic Supporting Information
208 Pd-catalyzed DithioleneAryl Cross-couplingReaction of Aromatic Cyclopentadienyl-cobalt Dithiolene Complex
SCo
S B
O
ON
Br
+S
CoS N
Suzuki-MiyauraCross-Coupling
Pd(PPh3)4
Mitsushiro Nomura,� Kosuke Terada, AkihideOnozawa, Yoshiro Mitome, Toru Sugiyama,and Masatsugu Kajitani�doi:10.1246/cl.2010.208Electronic Supporting Information
210 An Unexpected Guanidine-catalyzed Amina-tion Reaction Leading to (Z)-¡-Aminocin-namamides
ONO
Ph
Ar
Guanidine
H2O
O
NNH
Ar
O Ph
Me
Me100 °C
O
H N+
A series of new (Z )- -aminocinnamamides derivatives have been prepared by unexpectedguanidine-catalyzed amination reaction between 4-arylidene-2-phenyloxazol-5-ones and DMFin water at 100 °C.
α
Bo Jiang and Shu-Jiang Tu�doi:10.1246/cl.2010.210Electronic Supporting Information
Chemistry Letters Vol.39, No.3 (2010)C-24
http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan
212 Copper-catalyzed Stereoselective Synthesisof Vinyl Selenides under Ligand-free Con-ditions
I
1.0 mmol 0.5 mmol
SePhCuO(1.5 mmol)
DMSO/KOH80 °C, 4 h
R R
PhSeSePh
Vutukuri Prakash Reddy, Akkilagunta VijayKumar, and Kakulapati Rama Rao�doi:10.1246/cl.2010.212
215 Laser Ablation of Micro-sized Organic DyeParticles in Solvents with Limited Solubilityfor the Dye: Formation of a SupersaturatedSolution
The absorbance of the free PTCDI-C8 molecules in solution obtained by laser irradiation wasunusually larger than that of the suspension before laser irradiation.
400 500 6000.0
0.2
0.4
0.6
0.8
1.0
1.2
1.4
Abs
orba
nce
Wavelength/nm
(2)
(3)
(4)
(1)
Laser
(1) (2) (2) = (3) + (4)
(4) > (1)
Akira Itaya,� Takumi Murakami, Nao Yokoi,Sadahiro Masuo, and Shinjiro Machidadoi:10.1246/cl.2010.215Electronic Supporting Information
218 Systematic Construction of Porous Coordi-nation Pillared-layer Structures and TheirSorption Properties
Cu2+
2D sheets[Cu(pzdc)]n
3D porous framework[Cu2(pzdc)2L]n
Dypyridyl Pillar Ligand (L)Hirotoshi Sakamoto, Ryo Kitaura, RyotaroMatsuda, Susumu Kitagawa,� Yoshiki Kubota,and Masaki Takatadoi:10.1246/cl.2010.218Electronic Supporting Information
220 Facile Surface Functionalization of Polysty-rene Substrates with Biomimetic Apatite byUtilizing Serum Proteins
Serum proteins adsorbed on polystyrene (PS) surfaces effectively induced hydroxyapatite(HAp) deposition under body fluid conditions, which resulted in formation of HAp-coatedPS surfaces.
Mineo Hashizume,� Atsushi Sakai, YuriSakamoto, Hisao Matsuno, and TakeshiSerizawadoi:10.1246/cl.2010.220Electronic Supporting Information
223 Highly Chemoselective Reduction of Nitro-aromatic Compounds Using a Hydrotalcite-supported Silver-nanoparticle Catalystunder a CO Atmosphere
Yusuke Mikami, Akifumi Noujima, TakatoMitsudome, Tomoo Mizugaki, KoichiroJitsukawa, and Kiyotomi Kaneda�doi:10.1246/cl.2010.223Electronic Supporting Information
Chemistry Letters Vol.39, No.3 (2010) C-25
http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan
226 Synthesis of Lipophilic Gold Nanosheetsby Using Reducing Stabilizers and TheirReversible Transformation between GoldenSolid
Au nanosheet
O
HN NH
O O
O
O
O
O
O
O
HN NH
O O
O
O
O
O
O
O
HN NH
O O
O
O
O
O
O
O
HN NH
O O
O
O
O
O
O
O
HN NH
O O
O
O
O
O
O
O
HNNH
OO
O
O
O
O
O
O
HNNH
OO
O
O
O
O
O
O
HNNH
OO
O
O
O
O
O
O
HNNH
OO
O
O
O
O
O
O
HNNH
OO
O
O
O
O
O
O
Rempei Kuwahara, Keita Kuroiwa, and NobuoKimizuka�doi:10.1246/cl.2010.226Electronic Supporting Information
228 An Excellent Method for Cbz-protection ofAmines
RN O Ph
O
R1
N H
R
R1 PhCH2OCOClH3PW12O40•x H2O (0.05 equiv)
CH2Cl2, rt
Cbz-protection of aliphatic and aromatic amines can be accomplished withbenzylchloroformate using a catalytic amount of dodecatungstophosphoric acid hydrate(0.05 equiv). The reaction is simple, fast, does not require aqueous work-up and givesexcellent yields.
Khiangte Vanlaldinpuia, H Atoholi Sema,Lalthazuala Rokhum, and Ghanashyam Bez�doi:10.1246/cl.2010.228
230 Photochromic Reaction of a Novel RoomTemperature Ionic Liquid: 2-Phenylazo-1-hexyl-3-methylimidazolium Bis(pentafluoro-ethylsulfonyl)amide
Novel liquid material [2PA-Hmim][Pf2N] undergoes photochromic reaction by visible lightirradiation.
NNC6H13 CH3
NN
NNC6H13 CH3
NN
+
+hν1
∆, hν2E form Z form
400 450 500 550 600-0.06
-0.04
-0.02
0.00
0.02
After irradiation time t1
0.5 min 2.0 min
10.0 min
Isosbestic point
∆{A
bs(t
=(t
1) -
Abs
(t =
0)}
Wavelength / nm400 450 500 550 600
-0.02
0.00
0.02
0.04
0.06At delay-time t
2
1 min 5 min
30 min 600 min
Isosbestic point
∆ {A
bs(t
=(t
2) -
Abs
(t =
t s)}
Wavelength / nm
Akio Kawai,� Daiki Kawamori, Tomoo Monji,Tooru Asaka, Nobuyuki Akai, and KazuhikoShibuya�doi:10.1246/cl.2010.230Electronic Supporting Information
232 Acceleration of Enantioselective Hydrogena-tion of Olefins over Pd/C by Cinchonidineas a Chiral Modifier. Comparison withCinchonine, Pseudoenantiomer
Ph Ph
COOH
Ph Ph
COOH
+ H2
N
HON
Hcinchonidine (CD)
cinchonine (CN)
N
HON
H
Ph Ph
COOH
+ Pd/C
H
H
83% ee
54% ee
CD is a better modifier than CN due to the ligand acceleration effect in addition to the higher intrinsic stereocontrollability
Takashi Sugimura� and Hiroyuki Ogawadoi:10.1246/cl.2010.232Electronic Supporting Information
234 Photoinduced Deformation of PolymerFibers with Anthracene Side Groups
Photomobile fibers were fabricated from
toward the actinic light upon irradiation
a precise shape into the polymer in advance
simple polymer structures. The fiber bent
with UV light. We succeed in programming
by photoirradiation.Mizuho Kondo,� Takehiro Matsuda, RyoheiFukae, and Nobuhiro Kawatsuki�doi:10.1246/cl.2010.234Electronic Supporting Information
Chemistry Letters Vol.39, No.3 (2010)C-26
http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan
236 Tri(quaternary ammonium) Surfactant witha Benzene Core as a Novel Template forSynthesis of Ordered Porous Silica R = (CH2)10N+(CH3)3Br-
TEOS
H2O
OR
RO OR
Columnarlyotropic liquid crystal Silica-template compositewith ordered structure
Yuki Fukasawa, Ayae Sugawara, HirotomoHirahara, Atsushi Shimojima, and TatsuyaOkubo�doi:10.1246/cl.2010.236Electronic Supporting Information
238 Fabrication of MetalPolymer Nanocompo-site with Beaded Structures Using OrderedAnodic Porous Alumina Template
Toshiaki Kondo, Kazuyuki Nishio, and HidekiMasuda�doi:10.1246/cl.2010.238
240 Synthesis and Photochemistry of StilbeneIonic Liquids
Ionic liquids having a photoresponsive stilbene chromophore were prepared and their propertieswere examined.
Hiroyasu Tamura, Yoshihiro Shinohara, andTatsuo Arai�doi:10.1246/cl.2010.240Electronic Supporting Information
242 Photocontrolled Size Changes of Doubly-threaded Dimer Based on an ¡-CyclodextrinDerivative with Two Recognition Sites
Shujing Li, Daisuke Taura, AkihitoHashidzume, Yoshinori Takashima, HiroyasuYamaguchi, and Akira Harada�doi:10.1246/cl.2010.242Electronic Supporting Information
244 Living Polymerization of PhenylacetyleneCatalyzed by a Cationic Rh Complex Bear-ing Tetrafluorobenzobarrelene
n
Rh
F
F
F
F PPh3
PPh3
BPh4
cationic Rh complex
Living Polymerization
excess iPrNH2
0 20 40 60 80Time/min
0
1
2
3
4
5
ln([
PA
] 0/[P
A])
Masashi Shiotsuki,� Naoya Onishi, FumioSanda, and Toshio Masudadoi:10.1246/cl.2010.244Electronic Supporting Information
Chemistry Letters Vol.39, No.3 (2010) C-27
http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan
246 A Rapid and Efficient Synthesis of AllylIodides from BaylisHillman Adducts: AFacile Synthesis of Semiplenamide D
NH
O
OH
Semiplenamide D
14( )R
OH
COOEtR
I
EWG
CHCl3, rt
R = C17H35
Et3SiH/I2
5 min
86-98%Biswanath Das,� Yallamalla Srinivas,Chithaluri Sudhakar, Kongara Damodar, andParigi Raghavendar Reddydoi:10.1246/cl.2010.246
248 Transition-metal-catalyzed Electrophilic Ac-tivation of 1,1-Difluoro-1-alkenes: OxindoleSynthesis via Intramolecular Amination
TsNF
RH2O
cat. PdCl2TMSOTf
(CF3)2CHOH
TsHN
R
CF2 HNO
R
R' R'R'
Hiroyuki Tanabe and Junji Ichikawa�doi:10.1246/cl.2010.248
250 Preparation of Nanoaggregates through Self-assembly of Amphiphilic Polyrotaxane Com-posed of PLLAPEGPLLA Triblock Co-polymer and ¡-Cyclodextrins
Koji Nagahama, Junpei Ohmura, HiromiSakaue, Tatsuro Ouchi, Yuichi Ohya,� andNobuhiko Yui�doi:10.1246/cl.2010.250Electronic Supporting Information
252 Self-assembly of Zn(II) Porphyrin1,2,3-Tri-azole Conjugate with Alcohol Glue
NN
NN
Ph
Ph
Ph
Ph
Zn
NN
N
EtO2C
O
H
CH3
NN
NN
Ph
Ph
Ph
Ph
Zn
NN
N
EtO2C
CH3OH
dimerization
Motoki Toganoh, Hiroyuki Harada, YoshiyaIkawa, and Hiroyuki Furuta�doi:10.1246/cl.2010.252Electronic Supporting Information
254 Fabrication of Thin Film Surface Templatesfrom Two Immiscible Polymers by PhaseSeparation and Phototethering
(b)(a)
1 µµ1 µ
A thin two-dimensional surface pattern (b) was obtained from a three-dimensionalphase-separated structure of two immiscible polymers (a) by photoirradiation andimmersion in a solvent.
Koichi Kawamura,� Kazuhiro Yokoi, andMitsuhiro Fujitadoi:10.1246/cl.2010.254
Chemistry Letters Vol.39, No.3 (2010)C-28
http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan
257 Preparation of Charge-transfer Host Com-plex Composed of [9,9¤-Biphenanthryl]-10,10¤-diol Having a Large and Widely ³-Conjugated Phenanthrene Ring
2,5Me-BQ
Me
MeO
O
OHOH +
CT Host System
Tatsuya Ukegawa, Takafumi Kinuta, TomohiroSato, Nobuo Tajima, Reiko Kuroda, YoshioMatsubara,� and Yoshitane Imai�doi:10.1246/cl.2010.257Electronic Supporting Information
260 High Performance of SiOTi Bonds forAnchoring Sensitizing Dyes on TiO2 Electro-des in Dye-sensitized Solar Cells Evidencedby Using Alkoxysilylazobenzenes
0 0.1 0.2 0.3 0.4 0.50
0.2
0.4
0.6
0.8
Cur
rent
/ m
A c
m−2
Photovoltage / V
η = 0.20%η η = 0.20%
η η = 0.15%η η = 0.15%
Alkoxysilyl dyeAlkoxysilyl dye
Carboxy dyeCarboxy dye
NN Si
Ph
OO
Ti
Ti
TiO
2
N
N C OO
Ti
stabilitystabilitystability << <<
TiO
2
Carboxy dye
Alkoxysilyl dye
Kenji Kakiage, Masaki Yamamura, EmiFujimura, Toru Kyomen, Masafumi Unno, andMinoru Hanaya�doi:10.1246/cl.2010.260
263 Reshuffling Activity of Protein DisulfideIsomerase Reduces Refolding Yield in theStructure-forming Step of the OxidativeProtein Folding Reaction
↔
3SNonnatbnd 3Snatbnd
Chemical Reshuffling rxn
Physical Conf.Folding rxn
~11x w/PDI
~8x w/PDI
Although PDI is known to
the conformational folding
catalytic potential in the ER.
accelerate the overallregeneration of proteins, asseen in RNase A, it hampers
step in oxidative regeneration.This feature limits its overallRituraj Pal, Veronica Gonzalez, and Mahesh
Narayan�doi:10.1246/cl.2010.263Electronic Supporting Information
266 Effects of Microwave Radiation on ProteinsCoexisting with Carbon Nanotubes
Hirokazu Horiguchi, Haruko Ohe, Ken Kato,and Masahito Sano�doi:10.1246/cl.2010.266Electronic Supporting Information
268 Effect of Phase Separation on ThermalAging Behavior of StyreneButadiene Rub-ber Vulcanizates Using Liquid Polyisopreneas Plasticizer
Phase-Separated Structure Homogeneous Structure
Thermal AgingTakeo Nakazono,� Anri Ozaki, and AkikazuMatsumoto�doi:10.1246/cl.2010.268
Chemistry Letters Vol.39, No.3 (2010) C-29
http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan
270 In Vivo Resonance Raman Detection ofFerrous Cytochrome c from Mitochondriaof Single Living Yeast Cells
Ram
an In
ten
sity
1600 1400 1200 1000 800 600Wavenumber / cm
−1
Excitation-wavelength
single living yeast cell
dependent components(Figure) of theRaman spectrum ofmitochondria in a
the resonance Ramanbands of ferrouscytochrome c.
agree excellently with
Chikao Onogi and Hiro-o Hamaguchi�doi:10.1246/cl.2010.270
272 Distribution of Fluorescent Dyes Dissolved inTernary Mixed Solvent in a Microchannelunder Laminar Flow Conditions Aqueous–organic carrier solutions containing fluorescent dyes,
perylene and Eosin Y, were delivered into a microchanneland the tube radial distribution of the dyes was monitoredusing a fluorescence microscope. When an organic solvent-richsolution was fed into the channel, perylene and Eosin Y weredistributed around the center and near the inner wall of thechannel, respectively. This observation consists with thespecific carrier solvent distribution previously proposed.Mari Murakami, Naoya Jinno, Masahiko
Hashimoto, and Kazuhiko Tsukagoshi�doi:10.1246/cl.2010.272
274 Unusual Phase Inversion Behavior in anEmulsion Polymerization System Caused byAmmonia
Two entirely different kinds of carbon materials were prepared by the polymerization of anO/W emulsion of Span 80-Tween 80/1iquid paraffin/water−resorcinol−formaldehyde (R/F) withNaOH and ammonia, respectively. Inferential evidence indicates that the O/W emulsion
emulsion or a transition structure depends on the R/F concentration within the aqueous phase.undergoes a phase inversion caused by ammonia; whether the phase inversion leading to a W/O
Mingxian Liu, Lihua Gan,� Zijie Xu, LongwuChen, Jun Hu, and Honglai Liu�doi:10.1246/cl.2010.274
276 Hydrophosphination of Propargylic Etherswith Diphenylphosphine in the Presenceof LiHMDS, N-Heterocyclic Carbene, andTi(NMe2)4
Hydrophosphination of propargylic ethers with Ph2PH, a difficult reaction by conventionalcatalysts, has been achieved very efficiently using a three-component catalyst.
Ryosuke Sakae, Yuta Yamamoto, KimihiroKomeyama, and Ken Takaki�doi:10.1246/cl.2010.276Electronic Supporting Information
278 Preparation of CpG ODN-encapsulatedAnionic Poly(amino acid) Nanoparticles forGene Delivery
Polycation
CpG ODN
γ−PGA−Phe
CpG ODN/Polycation(Polyplex)
Polyplex/γ−PGA−Phe NPsHyungjin Kim, Takami Akagi, and Mitsuru
Akashi�doi:10.1246/cl.2010.278
Chemistry Letters Vol.39, No.3 (2010)C-30
http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan
280 Zinc-mediated Alkylation and Acylation of1,3-Dicarbonyl Compounds
OO
O OBr
Zn, DMF, 60 °COO
O O
1 3a
2
J. S. Yadav,� B. V. Subba Reddy, and AnandKumar Mishradoi:10.1246/cl.2010.280
282 Absolute Measurements of Photolumines-cence Quantum Yields of 1-Halonaphtha-lenes in 77K Rigid Solution Using anIntegrating Sphere Instrument
Integrating sphere (IS)
Dewar
Spectrometer
Excitation light
Sample tube
Schematic diagram of an
for absolute measurements ofintegrating sphere instrument
luminescence quantum yieldsat 77K.Atsushi Kobayashi, Kengo Suzuki, Toshitada
Yoshihara, and Seiji Tobita�doi:10.1246/cl.2010.282Electronic Supporting Information
284 Photoabsorption Study of Pigments inMosses: Scopelophila ligulata Has an Abnor-mally High Formation Rate of Pheophytin
400 440 480 520 560 600 640 680 720
0
1
2Scopelophila ligulata
Average of other seven mosses
Rel
ativ
e ab
sorb
ance
Wavelength/nm Scopelophila ligulata in Chichibu, Saitama
Hiromitsu Nakajima,� Kiminori Itoh, HideakiOtake, and Kenjiro Fujimotodoi:10.1246/cl.2010.284
286 Effect of Coating by PerfluorosulfonatedIonomer Film on Electrochemical Behaviorsof Pt(111) Electrode in Acidic Solutions
Electrochemical behaviors of bare and Nafion-coated Pt(111) electrodes in acidicsolutions were compared. The Nafion-coated Pt(111) electrode did not show thecharacteristic anion adsorption−desorption peaks observed at the bare electrode,demonstrating the blocking of anion adsorption by Nafion film. Effects of oxideformation/reduction on the electrochemical behaviors were also investigated.
0.1 M H2SO40.1 M HClO4
Bare
Nafion-coated
0.0 0.2 0.4 0.6 0.8 1.0 1.2 1.4-200
-100
0
100
200
Cur
rent
den
sity
/ µA
cm
-2
Potential / V vs. RHE0.0 0.4 0.8 1.2
-100
-50
0
50
100
Cur
rent
den
sity
/ µA
cm
-2
Potential / V vs. RHE
0.0 0.2 0.4 0.6 0.8 1.0 1.2 1.4-200
-100
0
100
200
300
Cur
rent
den
sity
/ µA
cm
-2
Potential / V vs. RHE0.0 0.4 0.8 1.0 1.2
-400
-200
0
200
400
Cur
rent
den
sity
/ µA
cm
-2
Potential / V vs. RHE
0.2 0.6 1.0 1.4
0.2 0.6 1.4
Faridah Sonsudin, Takuya Masuda, KatsuyoshiIkeda, Hideo Naohara, and Kohei Uosaki�doi:10.1246/cl.2010.286
288 Influence of Conformation of 9,10-An-thrylene Rotors on Structures and Self-association Properties of Macrocyclic Ary-leneAlkynylene Oligomers
Dimer
RR
RR
R
R R
R
RR
Trimer
R R
R R
R
R
R
R
Tetramer
PlanarSelf-Association
Kazuaki Miyamoto, Tetsuo Iwanaga, and ShinjiToyota�doi:10.1246/cl.2010.288Electronic Supporting Information
Chemistry Letters Vol.39, No.3 (2010) C-31
http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan
291 Quantum Yield Measurements of FireflyBioluminescence Reactions Using a Commer-cial Luminometer
Quantum yields of firefly bioluminescence reactions were determined using a commerciallyavailable luminometer whose absolute sensitivity was calibrated with respect to the spatiallyand spectrally integrated photon flux emitted from the reaction solution.
0
2
4
6
8
10
Luminometer count value/ x106 counts
. s-1
Tot
al p
hoto
n flu
x/ x
109
phot
ons .
s-1
0 1 2 3 4 5
L. mingrelica
P. pyralis
L. cruciata
6.050.482.89566P. pyralis
6.020.432.60565L. cruciata
5.820.432.58571L. mingrelica
Responsivityc
/ ×10–4 counts .
photons–1Quantum
yieldPhotonb
/ ×1010λMax
a
/ nmLuciferase
a Luminescence maximum.b Number of photons emitted from 6.02 × 1010 D-luciferin molecules.c Responsivity of the luminometer.
Kazuki Niwa, Yoshiro Ichino, and YoshihiroOhmiya�doi:10.1246/cl.2010.291
294 Hydrothermal Synthesis of TiO2 NanorodBundles in the Presence of Tetramethyl-ammonium Hydroxide Highly crystallized anatase TiO2 nanorod
hydroxide for the first time. Many nanorods
nanorod bundle. The TiO2 particles show
bundles have been prepared by a hydrothermalmethod in the presence of tetramethylammonium
stick together in the middle, obtaining a special
relatively higher photocatalytic activity thanDegussa P25 evaluated via the degradationof phenol.
Teming Lai,� Long Yi, and Wenxia Yangdoi:10.1246/cl.2010.294
296 Effective Interaction Energies for WeaklyBound Dimers at Room Temperature:(H2O)2, (N2O)2, (CO2)2, and (HCHO)2 Effective interaction energies evaluated
analysis for weakly bound dimers of
agreement with experimental results
technique for rotational lines. ZPE
by the present simple theoretical
H2O, CO2, N2O, and HCHO are in good
derived from the pressure broadeningPotential welldepth : De
Effective interaction energy
ZPE
EffectiveThermal energy: <εv>
Dimerizationenthalpy: D0
stands for the zero-point energy.
Hirofumi Sato, Shigeyoshi Sakaki, YosukeSakamoto, and Masahiro Kawasaki�doi:10.1246/cl.2010.296Electronic Supporting Information
298 Reaction of Cage-opened Fullerene Deriva-tive with Grignard Reagents and SubsequentTransannular Cyclization
S
OO
H H RR
THF
(5.0 equiv)MeMgCl
S
O
H HRR
Me
toluene
(2.9 equiv)S
OO
H HRR
Me
H
−20 °C, 70 min
p -TsOH H2O.
110 °C, 12 h
HO
46% 75%
Michihisa Murata, Yuta Morinaka, KeiKurotobi, Koichi Komatsu, and YasujiroMurata�doi:10.1246/cl.2010.298Electronic Supporting Information
300 Pentaleno[1,2-c:4,5-c¤]dithiophene Deriva-tives: First Synthesis, Properties, and aMolecular Structure
SS
R
R
BrS
R NiCl2(PPh3)2-Zn
Toluene, 110 °C
R = SiMe3, Ph
Akihito Konishi, Takeru Fujiwara, NorikoOgawa, Yasukazu Hirao, Kouzou Matsumoto,Hiroyuki Kurata, Takashi Kubo, ChitoshiKitamura, and Takeshi Kawase�doi:10.1246/cl.2010.300Electronic Supporting Information
Chemistry Letters Vol.39, No.3 (2010)C-32
http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan
302 Optical Properties of 4-(Dicyanomethyli-dene)-6-(4-dimethylaminostyryl)-2-methyl-4H-pyran Nanoparticles Prepared by Reprecipi-tation
Zhao-Lin Yuan, Si-Lu Tao, Jun-Sheng Yu,� andYa-Dong Jiangdoi:10.1246/cl.2010.302
304 Size Control of Catalytic Reaction Space byIntercalation of Alkylcarboxylate Anionsinto NiZn Mixed Basic Salt Interlayer:Application for Knoevenagel Reaction inWater
Takayoshi Hara, Jun Kurihara, NobuyukiIchikuni, and Shogo Shimazu�doi:10.1246/cl.2010.304Electronic Supporting Information
306 Novel Counter Anion Effects of Added[Co(NH3)6]X3 (X¹ = Cl¹, Br¹, I¹, or ClO4
¹)on Surface Tension Reduction in AqueousSolutions of Anionic Surfactants Surface tension values (γ) of (A) [Co(NH3)6]X3
(2.50 mM) and plateaued values of surface tensions(γ*) for (B) SDS, or (C) SBS, aqueous solutions with[Co(NH3)6]X3 (2.50 mM) (X−
= Cl−, Br−, I− or ClO4−)
as a function of temperature (K).
30
40
50
60
70
290 295 300 305 310
γ* /
mN
m-1
T/K
Cl-
Br-
I-
ClO4-
Cl-
Br-
I-
ClO4-
Cl-
I-, ClO4-
(A) [Co(NH3)6]X3 (2.50 mM)
(B) SDS (0.03 mM) with [Co(NH3)6]X3 (2.50 mM)
(C) SBS (0.03 mM) with [Co(NH3)6]X3 (2.50 mM)
(X- = Cl
-, Br
-, I
-, or ClO4
-)
Br-
Sieng Sovanna, Takayoshi Suzuki, MasaakiKojima, Satoshi Tachiyashiki, and MasakazuKita�doi:10.1246/cl.2010.306
308 Tsukuba-green: A Fluorescent Dye thatEmits Green Fluorescence Useful for Live-cell Imaging
A new fluorescent dye, 4-ethoxycarbonylmethyl-2-methyl-7-hydroxyquinoline (TG) wasobtained unexpectedly from the BiCl3-catalyzed Pechmann condensation. TG emits greenfluorescence at 509 nm in water. For live-cell imaging applications, TG derivatives TG1–TG3were prepared. Under physiological conditions, HEp-2 cells were immediately stained uponaddition of a solution of TG3.
Naoko Senda, Yoshihiro Miwa,� Junko Tanaka,Atsuya Momotake, and Tatsuo Arai�doi:10.1246/cl.2010.308Electronic Supporting Information
Chemistry Letters Vol.39, No.3 (2010) C-33
http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan
