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Chemistry Lettershttp://www.csj.jp/journals/chem-lett/
Vol.34 No.4 CMLTAGApril, 2005 ISSN 0366-7022
Copyright � 2005 The Chemical Society of Japan
454 Iminium Alkaloids from Marine Inverte-brates: Structure, Biological Activity, andBiogenesis
MeMe
HNCOO–
OHO O
O
O
Me
OMe
OH
H
Pinnatoxin A
+HN
OSO3–
OH
H
H
H
Me
Symbioimine
O
Me
OMe
N+
Me
O
Me
MeCOOH
Norzoanthamine hydrochloride
Cl–
Masaki Kita and Daisuke Uemura
The discovery of new natural products frequently triggers a breakthrough in basic sciences. This review features marineiminium alkaloids, which control biologically and physiologically intriguing phenomena. Pinnatoxins, potent shellfish poi-sons purified from the Okinawan bivalve Pinna muricata, activate Ca2þ channels. Norzoanthamine hydrochloride, isolatedfrom the colonial zoanthid Zoanthus sp., suppresses decreases in bone weight and strength in ovariectomized mice. Symbio-imine, an amphoteric iminium metabolite from the dinoflagellate Symbiodinium sp., inhibits osteoclast differentiation. Thelatter two compounds are good candidates for antiosteoporotic drugs.
Highlight Review
Letter
460 Kinetic Study of Dehydrogenation betweenH–Siloxane and Ti–OH on TiO2
TiO2 Ti–OH
TiO2Ti O Si CH3
O
O
CH3
CH3
H3C Si CH3
H3C Si CH3
Ti
H2O
H-O
H O-HH
SiH
k(free)
k(H2O)
Decreasing nucleophilicity of TiOH group by hydration
k(free) >> k(H2O)
H–O :
Si +
–δ
–δ
δ
The solid-liquid reaction between titanium dioxide (TiO2) and H-siloxane involved twodehydrogenation condensation; one between Ti-OH groups and Si-H groups, and theother between hydrated Ti-OH groups and Si-H groups.
H3C Si
CH3
CH3
O Si O Si
CH3
CH3
CH3
H
CH3 H–O :
Ti–O–Si H2+
Ti–O–Si H2+Ti H
+δ
Akira Nakabayashi, Junko N. Kondo,Michikazu Hara, and Kazunari Domen
C-56 Chemistry Letters Vol.34, No.4 (2005)
Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/
462 Templated Synthesis of Mesoscopic TubeSilicates Using Aqueous Mixtures of Naph-thalenediol and Ammonium Surfactants
Rod-like aggregates are formed from the
mixture of CTAB and 2,3-DHN in pure
water, and they act as templates for
directing the sol−gel synthesis of tube
structures.100 nm
Munetoshi Isayama, Kazuko Nomiyama,Tadatsugu Yamaguchi, and Nobuo Kimizuka
464 Selective Extraction of EndohedralMetallofullerenes Using a Mixed Solvent ofTriethylamine and Acetone
A mixed solvent of triethylamine andacetone was used to extract endohedralmetallofullerenes from raw soot. Theefficiency of extraction was investigated byextracting Ce-containing metallofullerenes,Ce@C82 and Ce2@C80. The resultantextract contained little or no emptyfullerenes, that is, the Ce-matallofullereneswere selectively extracted.
Takeshi Kodama, Korenari Higashi, TakafumiIchikawa, Shinzo Suzuki, Hiroyuki Nishikawa,Isao Ikemoto, Koichi Kikuchi, and YohjiAchiba
466 Stereoselective Tandem Aldol-TishchenkoReaction with Acylsilanes
LDA
R2 SiMe3
OHO R2
OR2CHO
(2.5 equiv.)
SiMe3
OR1
R1
SiMe3
OLi
R1
Mitsunori Honda, Ryota Iwamoto, YoshieNogami, and Masahito Segi
468 Lewis Base-catalyzed DiastereoselectiveMannich-type Reaction between Ketene SilylAcetals and Chiral Sulfinimines
OMe
OSiMe3 S
O
p-Tol
Ph
NH
OMe
O
THF, −78 °C24 hPh H
NS p-Tol
OAcONn-Bu4
(1 mol%)
+
d.r. = 96:4 quant.
Eiki Takahashi, Hidehiko Fujisawa, ToshiharuYanai, and Teruaki Mukaiyama
470 Application of Organocerium Reagents forthe Efficient Conversion of Z-�,�-Unsaturat-ed Weinreb Amides to Z-�,�-UnsaturatedKetones
PO
NOMe
2) R1CHO (2)
O
R2OR2O
R1
O
NOMe
1) base, THF, -78 °C
31b: R2=o-tolyl
1c: R2=CF3CH2
R1
O
R3
R3Li, CeCl3 THF
4
Satoshi Kojima, Tsugihiko Hidaka, and AtsushiYamakawa
Chemistry Letters Vol.34, No.4 (2005) C-57
Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/
472 A Novel Modification for Silicalite-1 withHigh Stability and Selectivity in Vapor PhaseBeckmann Rearrangement of Cyclohexa-none Oxime
We report a novel modification for zeolite silicalite-1 with hydrofluoric acid solution,which exhibited remarkable improvements in stability and selectivity for Beckmannrearrangement of cyclohexanone oxime to caprolactam.
5 10 15 20 25 30 35 40 45 50 55
65
70
75
80
85
90
95
100
FS-1
NS-1
S-1
Co
nve
rsio
n /
%
Time on stream / h
Weichuan Tao, Dongsen Mao, Jianchao Xia,Qingling Chen, and Ying Hu
474 Synthesis of Box-shaped Pentaporphyrinwith Cobalt(II) Porphyrin in the Center;Reversible O2 Binding in the Box
N
NN
NN
N
N
N
Co
Rh
Rh
Rh
Rh
N
OO
=Rh NN
N
N RhCl
Keirei Uruma, Kiyoshi Tsuge, Yoichi Sasaki,and Taira Imamura
Electronic Supporting Information
476 Laser-induced Structural Conversions of Sil-ver Nanoparticles in Pure Water —Influenceof Laser Intensity—
Takeshi Tsuji, Takanori Higuchi, and MasaharuTsuji
478 Reaction of (4-Nitorophenyl)nitrene withMolecular Oxygen in Low-temperature Ma-trices: First IR Detection and Photochemis-try of Aryl Nitroso Oxide
ArNO2
O2 / 50 K
>590 nm / -O2
>415 nmAr N Ar N
OO
Ar NOO
ArNO+
+ O (3P)
cis trans
First IR Detection of Aryl Nitroso Oxide
(Ar = 4-nitrophenyl)
Hiroshi Inui, Masatoshi Irisawa, and ShigeroOishi
Electronic Supporting Information
480 New Method for Preparation of IsolableN-tert-Alkoxyarylaminyl Radicals
Ph
NPhO R80 °C, 0.5−4 h
in benzeneNO
Ph
Ph N NR
R
R = C(Me2)COOMe, C(Me)(CN)CH2CHMe2, C(Me)(CN)CH2C(Me2)OMe
+
Stable N-tert-alkoxyarylaminyls were prepared by the reaction of2,4-diphenyl-6-tert-butylnitrosobenzene with azo compounds. They could beisolated in 18−49% yields, after column chromatography.
Yozo Miura and Yoshikazu Muranaka
Electronic Supporting Information
C-58 Chemistry Letters Vol.34, No.4 (2005)
Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/
482 Synthesis of Fine Mg1�xCaxFe2O4 FerritePowder Having High Heat Ability underAC Magnetic Field
Fine Mg1-xCaxFe2O4 ferrite powders for localthermal coagulation therapy were synthesizedby a reverse coprecipitation method. Thefigure shows the typical results for heatability under an AC magnetic field (370 kHz,4 kA/m). The enhancement of temperature(∆T) was improved by the partial Ca2+
substitution. This material has the best heatability in reported materials.
0
20
40
60
80
100
120
0 5 10 15 20
∆ T
/o C
Time/min.
Mg0.5
Ca0.5
Fe2O
4
Mg0.3
Ca0.7
Fe2O
4
MgFe2O
4
Hiromichi Aono, Hideyuki Hirazawa, TakayukiOchi, Takashi Naohara, Kensaku Mori,Yasumasa Hattori, Tsunehiro Maehara,Hiroyuki Kikkawa, and Yuji Watanabe
484 Stilbene-extended Trithienylmethano-phanes: A Novel C3-Symmetric Cage Mole-cule Capable of Accommodating an OrganicMolecule As Well As Three Silver(I) Ions
S
S
R
S
S
S
R
S
S
S
R
S
S
S
R
S
Ag+
Ag+ Ag+
AgOTf
Hiroyuki Kurata, Kenji Haruki, and Masaji Oda
486 The First Isolation of 1,3-Diaza-2-sila-4-cy-clopentene Radical Cation Salt: The X-rayStructure and Electronic Properties
Shintaro Ishida, Tohru Nishinaga, and KoichiKomatsu
Electronic Supporting Information
488 Degradation of p-Chlorophenol by �-Radiol-ysis: Radiolytic Intermediates and Theoreti-cal Calculations
Three transition states (TS1-3) and a
prereaction complex (PC) related to
TS3 were found through a Density
Functional Theory (DFT) study on
the reaction between hydroxyl radical
and p-CP molecule. This indicates
that the main p-CP degradation
pathway was the formation of
4-chlorocatechol.
Shao-Yang Liu, You-Peng Chen, Han-Qing Yu,and Qian-Rong Li
490 Microenvironments in Faujasite-type Fe–AlZeolites Probed by Europium Luminescence
Europium photoluminescence spectrain water (a) and in Eu3+-exchangedhydrated faijasite (b).
Yasushi Nakamura, Masatoshi Hasaegawa, andKazuko Katsuki
Chemistry Letters Vol.34, No.4 (2005) C-59
Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/
492 Photochromic and Fluorescence Propertiesof a Hemiindigo in the Presence of BovineSerum Albumin
The hemiindigo derivative having a pyrrole ring exhibited photochromic and thermochromicproperties in the presence of bovine serum albumin (BSA) in phosphate buffer solution.
K∆∆
hν
hνFluorescence
hν
hν
NH
O
NH
hν NH
O NH
∆
BSA
Masashi Ikegami and Tatsuo Arai
494 Preparation of Organic Light-emittingField-effect Transistors with AsymmetricElectrodes
Tomo Sakanoue, Eiichi Fujiwara, Ryo Yamada,and Hirokazu Tada
496 Efficient Decomposition of NO2 into N2 andO2 by 193-nm ArF Laser in N2 Atmosphere 193 nm ArF laser photolysis of NO2 in N2 at 1 atm
NO2
Major final products
NO + O2
N2 + O2
High NO2 concentration
Low NO2 concentration
Masaharu Tsuji, Kenji Noda, Hiroshi Sako,Taro Hamagami, and Takeshi Tsuji
498 Synthesis, Structure, and Fluxional Behaviorof �1-O-Enolatoiron(II) Complexes Derivedfrom 1,3-Dicarbonyl Compounds
PEt2
Et2P Fe
PEt2Et2P
N NR1
O
R2
O
− N2
H
FeP P
P P
O R1
O
R2
−
+Et2 Et2
Et2 Et2
1a: R1 = R2 = Me (59%)1b: R1 = R2 = OMe (71%)1c: R1 = Me, R2 = OMe (80%)
Sayori Kiyota, Jun-ichi Tamuki, NobuyukiKomine, Masafumi Hirano, and SanshiroKomiya
Electronic Supporting Information
500 A High Voltage Dye-sensitized Solar Cellusing a Nanoporous NiO Photocathode
electolyte
Powergeneration
Powergeneration
photoanode photocathode
TiO2/Dye1 NiO/Dye2
Akihiko Nakasa, Hisanao Usami, SeiichiSumikura, Satoshi Hasegawa, Toshiki Koyama,and Eiji Suzuki
C-60 Chemistry Letters Vol.34, No.4 (2005)
Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/
502 Thermal Stability of the Hydration Structureof Short-chain Poly(oxyethylene) in CarbonTetrachloride: An Infrared SpectroscopicObservation of the Breakdown of HydrogenBonds
O O
O
OH H
Bidentate H-bonded
O O
O
OH
H
Monodentate H-bonded
Temperature
Unbonded
O O
O
OHH
Md. Ruhul Matin, Shaheda A. Wahab, YukiteruKatsumoto, Hiroatsu Matsuura, and KeiichiOhno
504 Ruthenium-catalyzed Hydrative Dimeriza-tion of Allenes
•
OR
RR
O
+ R
Ru3(CO)12 (2 mol%, Ru)CF3COOH (10 mol%)
iPrOH - H2OH H
H
H
Shinichi Saito, Naotomo Dobashi, and YasuoWakatsuki
506 Energies of Low-lying Excited States andReactivity of Giant Polycyclic AromaticHydrocarbons with a Hole Inside
By studying the lowest singlet and triplet
excitations of series of large polycyclic aromatic
hydrocarbons (PAHs) by means of ZINDO and
MO/8E methods, there appear blue shifts for
those holed PAHs, in contrast to the ordinary
π-conjugated systems with simple red shifts. In
all investigated PAHs the even-layered holed
PAHs show higher aromatic character. In
addition, there is larger global softness in this
kind of widely delocalized π-systems from
reactivity indices.
20 30 40 50 60 70 80 90 1000.0
0.5
1.0
1.5
2.0
2.5
3.0
3.5
ω
S0-S
1
Number of Six-Membered Rings
Exc
itatio
n E
nerg
ies
/ eV
0.04
0.06
0.08
0.10
0.12
0.14
0.16
Rea
ctiv
ity in
dex
ω /a
.u.
Xia Yang, Balazs Hajgato, Megumi Yamada,and Koichi Ohno
508 Optical Properties of Long-range-ordered,High-density Gold Nanodot Arrays PreparedUsing Anodic Porous Alumina
Highly ordered Au nanodot array 200 nm
Au nanodot
Futoshi Matsumoto, Masahiro Ishikawa,Kazuyuki Nishio, and Hideki Masuda
510 Wet Chemical Synthesis of Ag NanowiresArray at Room Temperature
reduction of AgNO3 by NaBH4 solutions
and their arrays.
A new simple and rapid method to prepare
silver nanowires arrays by direct chemical
at process,reported.room temperature was In the
no adscititious seeds and stabilizers were needed.
The controlto andpresent method was easy
andlow-cost, can be extended to prepare 1D
nanostructureorganic cable-likeinorganicand
Ju Weigang, Zhang Xiaohong, and Wu Shikang
Chemistry Letters Vol.34, No.4 (2005) C-61
Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/
512 Preparation of Nanostructured Li1:4Al0:4-Ti1:6(PO4)3 Glass-Ceramics by a CitrateProcess
Nanostructured Li1.4Al0.4Ti1.6(PO4)3 glass-
ceramics were obtained for the first time by
heat-treating its precursor powders which were
successfully synthesized by a citrate process. The
FESEM image of the specimen heat-treated at
900 °C for 6 h showed that the specimen was very
dense, and the grain size was uniform with average
size under 100 nm.Xiaoxiong Xu, Zhaoyin Wen, Zhonghua Gu,Xiaohe Xu, and Zuxiang Lin
514 Stereoselective Synthesis of trans-3,4-Dihy-dropyran-2-ones by Phenoxide ion-catalyzedTandemMichael Addition and Lactonization
R3OPh
OSiMe3Bu4NOPh
R1
O
R2
OR1 O
R2
+(cat.)
R3
OR1 O
R2R3+
trans cis
Takashi Tozawa, Yoshinobu Yamane, andTeruaki Mukaiyama
516 A Stable Hexagonal Mesoporous Alumino-phosphate Assembled from Preformed Alu-minophosphate Precursors
Assembly Calcination
Assembly of preformed
aluminophosphate precursors
with surfactant of CTAB
Hexagonal arrays
of mesopores
Thermally stable mesoporous
aluminophosphate containing
zeolite-like connectivity
+
Kaifeng Lin, Lifeng Wang, Zhenhua Sun, QingYang, Yan Di, Daliang Zhang, Dazhen Jiang,and Feng-Shou Xiao
518 Synthesis and Characterization of Water-Soluble Multi-walled Carbon NanotubesFunctionalized with Polycystine
heat lamp.
Water-soluble multi-walled carbon
nanotubes functionalized(MWNTs)
with achievedpolycystine byare
solid-state reactionpolycondensation
under the irradiation of the infrared
Tao Wang, Guang-Chao Zhao, and Xian-WenWei
520 Surface Conductivity in Methyl-monolayer/Si Heterojunction Structure in the Presenceof Water
I d/ m
A
Vd / V
-2.0
-1.6
-1.2
-0.8
-0.4
00 -0.2 -0.4 -0.6 -0.8 -1.0
gm : 2.8 x 10-3 A/V
in presence of water
V = 0 V
V = 0.2 V
V = 0.4V
V = 0.6 V
g
g
g
g
Daisuke Niwa, Hiroshi Fukunaga, TakayukiHomma, and Tetsuya Osaka
C-62 Chemistry Letters Vol.34, No.4 (2005)
Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/
522 The High Thermoelectric Properties of Con-ducting Polyaniline with Special Submicron-fibre Structure
Conducting polyaniline withspecial submicron-fibre structurewas prepared and it exhibited20 times higher thermoelectricpower factor at 300 K thanthe sample with general grainstructure.
Qin Yao, Lidong Chen, Xiaochuan Xu, andChunfen Wang
524 Small-angle X-ray Scattering from Multi-walled Carbon Nanotubes (CNTs) Dispersedin Polymeric Matrix
10-4
10-2
100
102
104
I(q)
/a.u
.
0.12 3 4 5 6 7 8 9
12 3
q/nm−1
experiment
theory
r
410
ρ
Toru Inada, Hiroyasu Masunaga, ShinichiKawasaki, Masahiro Yamada, Kana Kobori,and Kazuo Sakurai
Electronic Supporting Information
526 Hydrothermal Synthesis and StructuralCharacterization of a Manganese(II) WireMade Up of Octahedral and Square Pyrami-dal Mn(II) Ions
Hydrothermal reaction between Mn(II) ion and acidα-phenylcinnamic α-phenylcinnamate).yields 1D-chain complex, [Mn5L8(OH)2] (L =
[Mn5L8(OH)2] consists of incomplete double cuboidal motifs in whichoctahedral {MnO6} and square pyramidal {MnO5} Mn(II) ions linked
motifs are linked by octahedral Mn(II) ions to form 1D-chain structure.µ-carboxylate ligands. The double cuboidalµ3-hydroxide and through
Hitoshi Kumagai, Motoko Akita-Tanaka,Satoshi Kawata, and Katsuya Inoue
528 Stereospecific Electrochemical Carboxyla-tion of �-Bromostyrene by Use of Nickel(II)Catalyst
0.1 MBu4NBF4-DMF
(E )-1
PhBr
Ph
Br(Z )-1
PtCO2
from (E )-1 71%, E/Z=99/1from (Z )-1 78%, E/Z=1/99
Ph
CO2H
PhCO2H
(E )-2+
(Z )-2
Mg
"20 mol% NiBr2 bpy"
3F/mol, 10 mA/cm2, -10°C
Chunxiang Kuang, Qing Yang, HisanoriSenboku, and Masao Tokuda
530 Reductive Coupling of Aryl Bromides UsingCat. Pd/TDAE System in Ionic Liquids
Ar ArAr Brcat. PdCl2(PhCN)2, TDAE
BdmimBF4 or BdmimTf2N60 °C
22
1
Manabu Kuroboshi, Toshiyuki Takeda, RyotaMotoki, and Hideo Tanaka
Chemistry Letters Vol.34, No.4 (2005) C-63
Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/
532 Ultrastable Steroidal Nanotube Formed inOrganic Solvents
Jong Hwa Jung, Soo Jin Lee, Sung-Hwan Han,Seiji Shinkai, and Toshimi Shimizu
534 Stepwise Preparation of Linear �-Conjuga-ted Bis(terpyridine)metal Polymer Chains atGold Surface
Katsuhiko Kanaizuka, Masaki Murata,Yoshihiko Nishimori, Ichiro Mori, KazuyukiNishio, Hideki Masuda, and Hiroshi Nishihara
536 Low-Temperature Synthesis of c Axis Ori-ented Submicrometer-scale ZnO Cones
20 40 60 800
400
800
1200
1600
(002
)(1
00)
(101
)
(102
)
(110
)
(103
)
Rel
ativ
e In
tens
ity /
A.U
.
Two Theta / deg
(004
)
R. S. Mane, Seung Jae Roh, and Sung-HwanHan
538 [3+2] Cycloaddition Reactions of Cyclopro-pylmethylsilanes and �-Keto Aldehydes:Trans- and Cis-selective Formation of 2-Silylmethyltetrahydrofurans R1
3SiR2
HO
O
CH2Cl2
OR1
3Si R2
O
1.5 equiv.
+1.2 equiv. SnCl 4
0 °C; 43 - 90%, trans only
−78 °C; 54% - Quant., cis : trans = 7 : 3R = aryl and alkoxy groups2
Kohei Fuchibe, Yuji Aoki, and TakahikoAkiyama
540 MUSASHI: NMR Pulse Width Determina-tion Method by Nonlinear Least SquareCurve Fitting
1H- NMR Nutation Experiment
Curve Fitting by MUSASHI
τ90 (90° pulse width) = 7.10µs
Fitting Result
−70
0
70
0 10 20 30 40Pulse Width / µs
Inte
nsity
/ ar
bitr
ary
unit
Pulse Width / µs
2 4 6 8 10 12 14 16 18 20 22 24 26 28 30 32 34 36 38 40 42
Tomomitsu Kurimoto, Katsuo Asakura,Chiharu Yamasaki, and Nobuaki Nemoto
C-64 Chemistry Letters Vol.34, No.4 (2005)
Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/
542 Formation of Self-assembled TubularStructures by Mixing Cyclodextrin andPolymers without Solvents
Akira Harada, Miyuko Okada, and YoshinoriKawaguchi
Electronic Supporting Information
544 Decomposition of Monolayer Coverage onGold Nanoparticles by UV/ozone Treatment
TEM image demonstrates that the UV/ozone process only affects adsorbedsurface species and not move the distributions of gold nanoparticles.
UV/O3
40 nm
2-Dimentional monolayers of Au nanoparticles, covered with cationic dichainsurfactant on the whole surface, were treated with UV/ozone.
Shufeng Pang, Yousuke Kurosawa, TakeshiKondo, and Takeshi Kawai
546 Perhydroxylation of Chiral CycloheptatrieneRing through Stepwise Oxidation underRegio- and Stereocontrol
O O
O
O
OOO
O
CHO
OHC
or
OOO
O
HO
OMe
OOO
O
O O X
XX = H or OH
1
2 3
oxidation from back oxidation from front
Takashi Sugimura, Masami Kagawa, NaokoOhuchi, Aya Inoue, and Tadashi Okuyama
548 Monodisperse SiO2/TiO2 Core-shell Colloi-dal Spheres: Synthesis and Ordered Self-as-sembling
SiO2
TiO2
Self-assembling
Renxiao Liu, Peng Dong, and Sheng-Li Chen
550 Synthesis of 3,4-Disubstituted Quinolin-2(1H)-ones via Palladium-catalyzed Regiose-lective Cross-coupling Reactions of 3-Bromo-4-trifloxyquinolin-2(1H)-one with Arylboro-nic Acids
Palladium-catalyzed regioselective cross-coupling reactions of 3-bromo-4-trifloxy-quinolin-2(1H)-one with arylboronic acids provide an efficient and practical routefor the synthesis of 3,4-disubstituted quinolin-2(1H)-ones.
N O
CH3
Br
OTf
N O
CH3
Ar2Ar1
1) [Pd], Ar1B(OH)2, RT
2) [Pd], Ar2B(OH)2, 60°CJie Wu, Liang Zhang, and Xiaoyu Sun
Electronic Supporting Information
Chemistry Letters Vol.34, No.4 (2005) C-65
Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/
552 Effect of Corona Poling during Film CastingProcess of Photorefractive Polymers
The new film fabrication technique, corona poling, was examined during the film castingprocess to educe an uniaxial orientation of non-linear optic (NLO) compounds in thephotorefractive polymer film.
2. Corona charging
3. Evaporation of solvent
V
heater
V8 kV
+ +++
+ ++
+++
heater
Corona Charger Spacer
1. Cast of solution
Eched ITO Electrode
NLO
4. Hot Press Press
heater
Shin-ya Tanaka, Norio Nagayama, and MasaakiYokoyama
554 Molecular Design of Squaraine Dyes forEfficient Far-red and Near-IR Sensitizationof Solar Cells
The introduction of short carboxyl anchoring groups into anilino-squaraines resulted in a muchimproved photosensitization on nanocrystalline TiO2 electrode over far-red/near-IR region, yieldinga maximum monochromatic incident photon-to-current conversion efficiency of 73% at 670 nm.
400 500 600 700 8000
10
20
30
40
50
60
70
80
90
100
IPC
E
Wavelength/nm
SQ1 SQ2 SQ4 SQ3
Unefficient
CB
SQ4+
SQ4*
SQ2+
SQ2*
I3-I-
Efficient
Fast SlowSQ2
SQ4
TiO2Chao Li, Weibo Wang, Xuesong Wang,Baowen Zhang, and Yi Cao
Electronic Supporting Information
556 Controlled Synthesis of SnO2 Hollow Micro-spheres via a Facile Template-free Hydro-thermal Route
Hollow rutile-like SnO2
microspheres were synthesizedvia a facile template-freehydrothermal method at 160 °Cfor 5−28 h.
Weiping Shao, Zhenghua Wang, YuanguangZhang, Jianhua Cui, Weichao Yu, and YitaiQian
558 Cooperative Reorientation of Dichroic DyesDispersed in Photo-cross-linkable PolymerLiquid Crystal and Application to LinearPolarizer
Linear polarizer was fabricated from aphoto-cross-linkable polymer liquid crystal(PLC) film doped with a dichroic dye basedon a large cooperative photoinduced
with orthogonal polarization direction wasdemonstrated.
reorientation using linearly polarized UVlight. By adjusting the reorientation directionusing a photomask, a patterned polarizer
Nobuhiro Kawatsuki and Keita Fujio
560 Vesicle–Micelle Transition of N-Acyl Phenyl-alaninate Salt in Very Dilute AqueousSolution
O-O
NH
O
O OH
HN
O
acid-soap dimer
ionic(major)
nonionic(minor)
hydrogen bond
π −π interaction
micelle
vesicle
concentrationAkio Ohta, Kumiko Tani-i, Aoi Hoshiba,Tsuyoshi Asakawa, and Shigeyoshi Miyagishi
C-66 Chemistry Letters Vol.34, No.4 (2005)
Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/
562 Formation of Single-wall Carbon Nanotubesby Using Porous Glass
100 150 200 250 300 350
Inte
nsity
/ ar
b.un
its
Raman shift / cm−1
Diameter / nm1.60 1.21 1.02 0.800.96
16 nm
10 nm
6 nm
Single-wall carbon nanotubes (SWNTs) were
by controlling the condition of phase separation. By
increases from 6 to 10 nm and 16 nm. On the other
under the same ambient temperature.
prepared by several kinds of porous glass, withdifferent inner pore size, each of which was prepared
applying alcohol CCVD technique, it was found thatthe yield of SWNTs was enhanced when the pore size
hand, the diameter distribution of SWNTs wasinvariant in all porous glasses under investigation,
Yosuke Aoki, Shinzo Suzuki, Shingo Okubo,Hiromichi Kataura, Hiroshi Nagasawa, andYohji Achiba
564 Controlled Synthesis of Novel Flower-shapedBaCrO4 Crystals
Well-defined BaCrO4 flowers arefabricated for the first time via a facilePSMA-mediated precipitation reaction
ambient temperature.of BaCrO4 from aqueous solution at
Shengwei Liu, Jiaguo Yu, Bei Cheng, andQingjie Zhang
Electronic Supporting Information
566 ANew Sol–Gel Route to Synthesize YPO4:Tbas a Green-emitting Phosphor for the PlasmaDisplay Panels
This work adopts a novel and low-cost sol–gel route to synthesize Tb3+-doped YPO4 as agreen-emitting phosphor for the plasma display panel (PDP). The phosphor obtained by thisroute shows improved luminescence performance in vacuum ultraviolet (VUV) excitation,compared with that obtained by a solid-state reaction.
450 500 550 600 650
sol-gel route
solid state reaction
Inte
nsity
/ a.
u.
Wavelength / nm150 200 250
sol-gel route
solid state reaction
Inte
nsity
/ a.
u.
Wavelength / nm
Weihua Di, Xiaojun Wang, Baojiu Chen, andXiaoxia Zhao
568 Synthesis of MCM-48 Single Crystals withCube Morphology
MCM-48 single crystals with cube morphologyhave been synthesized by using the ternary
rate of the hydrolysis of Si source.surfactant templating route and controlling the
Lingdong Kong, Su Liu, Xuewu Yan, QuanzhiLi, and Heyong He
570 Preparation of Chiral Poly(dipyridylamine).Its Metal Complex-controlled Steric Struc-ture, and Its Light Emitting Properties
N N
N
n
*
coordination sitesfor Cu2+ and Ni2+
A new polyaniline derivative with pyridyl coordinationsites and a chiral side chain was prepared. CD spectrasuggest formation of helix, whose structure wascontrolled by the coordination with metal ions. Thepolymer showed a PL component with a rather long lifetime of 700 ms.
Masaki Horie, Isao Yamaguchi, AkitoshiTanimoto, and Takakazu Yamamoto
Chemistry Letters Vol.34, No.4 (2005) C-67
Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/
572 Dye-sensitized Solar Cells with an ExtremelyThin Liquid Film as the Redox ElectronMediator
Schematic diagram showing the construction of a dye-sensitized solar cell with anextremely thin redox electrolytic film.
Thin liquid film redox mediator
Conducting glass substrate
Graphite layer
Dye-coated TiO2 film
G. R. Asoka Kumara, Shoji Kaneko, AkinoriKonno, Masayuki Okuya, and KirthiTennakone
574 Photochromic Cyan Dyes of Fulgide Deriva-tives in Polymer Film
1.5
1.0
0.5
0.0
Abs
orba
nce
800700600500400300Wavelength / nm
Photochromic polymer films dopedwith 3–4 wt% fulgide derivatives ascyan dyes exhibit high fatigue
UV
VIS
resistances as well as good colorproperty suitable for rewritable colordisplay or printing materials.
Ryoka Matsushima, Yoshiro Ito, Ken-ichiYamashita, Kanako Yamamoto, and YoshiumiKouno
576 Aldol Condensation in Water Using Poly-ethylene Glycol 400
ArCHO Ar'COCH3 CH CHCOAr'Ar+
PEG400NaOH
H2O
O
nn = 1, 0
O
n
ArAr2 ArCHO +
PEG400NaOH
H2OKiyoshi Tanemura, Tsuneo Suzuki, YokoNishida, and Takaaki Horaguchi
Electronic Supporting Information
578 Synthesis and Structure of a Molecular Met-al Propeller with Three Leaves, a Tetranu-clear Silver(I) Cluster Formed by 2-Mercap-tobenzoate and Triphenylphosphine Ligands A propeller-type Ag4 cluster is
constructed with an axis ofAg4… 3-S1 (C3 axis) and threeµ
µ µleaves of Ag( 3-S)( 2-S)P unitsaround the axis.Ryusuke Noguchi, Akihiro Hara, Akiyoshi
Sugie, Sawako Tanabe, and Kenji Nomiya
Electronic Supporting Information
580 Highly Aqueous-dispersible Carbon BlackGrafted with SAS and AA Copolymers nCH2 = CH
COOH
+ mCH2 = CH
CH2SO3Na
+CB
CB
COOH CH2SO3 Na
Schematic ReactionTransmission for suspension of modified CB,higher transmission means lower dispersibility
0 40 80 120 160 2000
20
40
60
80
100
AA+SAS-grafted
AA-grafted
ungrafted
Tran
smis
sio
n/%
Time /min
Jian-Yi Zhao and Cheng-Yang Wang
C-68 Chemistry Letters Vol.34, No.4 (2005)
Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/
582 Reaction of Dilithiosilane R2SiLi2 and Dili-thiogermane R2GeLi2 (R = SiMetBu2) withMesBCl2 (Mes = 2,4,6-trimethylphenyl):Evidence for the Formation of SilaboreneR2Si=BMes and Germaborene R2Ge=BMes
MesBCl2E
tBu2MeSi SiMe tBu2
Li Li
E = Si , Ge
BEtBu2MeSi
tBu2MeSiMes
O
BEO
tBu2MeSi
tBu2MeSiMes
Norio Nakata, Rika Izumi, Vladimir Ya. Lee,Masaaki Ichinohe, and Akira Sekiguchi
584 Catalyst-free Gas-phase Epoxidation ofAlkenes
The epoxidation of a series of alkenes (butadiene, styrene, cyclohexene, allyl acetate, methylmethacrylate, and allyl alcohol) in the gas phase in the absence of a catalyst is described.
(NO2)O3 + NO2 N(V)-oxide + O2
R3
R2
R4
R1
R3
R2
R4
R1
ON(V)-oxide + + xNO2 (2)
(1)
selectivity to the epoxide up to 97%Torsten Berndt and Olaf Boge
586 Excess Oxygen in 12CaO.7Al2O3 Studied byThermogravimetric Analysis
Katsuro Hayashi, Masahiro Hirano, and HideoHosono
588 Lewis Base-catalyzed [2,3]-Wittig Rear-rangement of Silyl Enolates Generated from�-Allyloxy Ketones
DMF, rt, 1 h
OSiMe3
OO
OHH+
LiN
O
93% Yield
(20 mol%)
Yoshinori Sato, Hidehiko Fujisawa, andTeruaki Mukaiyama
590 Hexagonal Ring Submicro- and Nanocrystalsof a La–Hexacyanoferrate CoordinationPolymer
200 nm
Hexagonal disk crystals of a La–hexacyanoferrate coordination polymerwere obtained by reversed micelletechnique. The {001} surface capping ofthe surfactants leads to the hexagonaldisk shape evolution with the completelydeveloped {001} surface. The hexagonaldisks are changed into hexagonal ringsthrough spontaneous and anisotropicsurface etching along the [001] directionfrom both sides of the hexagonal disk.
Nobuyuki Kondo, Masato Kurihara, MamiYamada, Mikio Miyake, Masahiko Nishijima,Tetsu Ohsuna, Fujio Mizukami, and MasatomiSakamoto
Chemistry Letters Vol.34, No.4 (2005) C-69
Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/
592 Preparation, Characterization, and Electro-luminescence Characteristics of �-Diimine-type Platinum(II) Complexes with Perfluori-nated Phenyl Groups as Ligands
Jun-ichi Nishida, Akihiro Maruyama, TakeshiIwata, and Yoshiro Yamashita
Electronic Supporting Information
594 Chlorotrimethylsilane as a Mild and Effec-tive Source of Acid Catalyst in ReductiveBenzylation
R OHTMSCl R OTMS
CHOCH OR
CH2 OR
TMSOHEt3SiH
+
HCl+ Cl-
Minoru Izumi and Koichi Fukase
596 Control of Pore Size in Mesoporous Silicaby Incremental Surface Modification UsingTetramethyl Orthosilicate
Si Si Si
O OO O
OHOH
MeO–Si–OMe
OMe
OMe
Si Si Si
O OO O
OO
Si Si Si
O OO O
OO
MeO–Si–OMe
MeO
Si
OMe
OMe
MeO
Si
HO
Si
OH
OOO
TMOS H2ORyohei Ishimaru, Yusuke Shibasaki, MichikazuHara, Mitsuru Ueda, Kazunari Domen, andJunko N. Kondo
598 White-emitting Long-lasting PhosphorSr2SiO4:Dy
3þA white-emitting afterglowphosphor Sr2(1-x)Dy2xSiO4 is reportedin this letter. Long-lastingphosphorescence from Dy3+ wasobserved with the naked eye formore than 1 h in the dark clearlyeven after the short UV light hasbeen removed.
400 500 600 700
Phosphorescence
For 10 min
For 5 min
For 2 min
Inte
nsity
/a.u
.
Wavelength/nmJinyong Kuang and Yingliang Liu
600 Fabrication of Ferroelectric Self-assembledFluorinated Polyether Monolayer on Hydro-gen-terminated Si(111) Surface
Takashi Okano, Hirofumi Inari, TakahiroIshizaki, Nagahiro Saito, Wataru Sakamoto,and Osamu Takai
C-70 Chemistry Letters Vol.34, No.4 (2005)
Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/
602 Hydrothermal Synthesis and Structure ofZero-dimensional Organic–inorganic Perov-skites
200 250 300 350 400 450 500 550 600
2-D0-D
Abs
orba
nce
/ a. u
.
Wavelength / nm 0-D
Yuko Takeoka, Keisuke Asai, MasahiroRikukawa, and Kohei Sanui
604 Lewis Base-catalyzed DiastereoselectiveStrecker-type Reaction between Trimethyl-silyl Cyanide and Chiral Sulfinimines
Me3SiCNDMF−THF (2:1)
−78 °C
H+N
Hi-Pr
Sp-Tol HN
CNi-Pr
Sp-Tol
+(1.2 equiv.)
1
AcONn-Bu4 (5 mol%)
quant.
2 (Ss,R)
82% d.e.
O O
Eiki Takahashi, Hidehiko Fujisawa, ToshiharuYanai, and Teruaki Mukaiyama
606 A New and Facile Route for the Synthesisof Thiocarbamates from Aniline, CarbonMonoxide, and Thiols Mediated by Selenium
NH2 + RSHSe COEt3N
NHCOSR ++ + H2Se
H2Se 1/2 O2 H2O++ Se
Xiaopeng Zhang and Shiwei Lu
Electronic Supporting Information
608 Optically Transparent Thin Film of LayeredNiobate (K4Nb6O17) Intercalated withTris(2,20-bipyridyl)ruthenium(II)
Optically Transparent [Ru(bpy)32+]xK4-2xNb6O17 Thin Film
Zhiwei Tong, Shinsuke Takagi, HiroshiTachibana, Katsuhiko Takagi, and Haruo Inoue
610 Structural Control of Mesoporous Silica by aBicontinuous Microemulsion-aided Process
OilWater
Mesoporous silicaBicontinuous microemulsion
Sol-gel reaction Mesopores
Silica wall
Isamu Moriguchi, Yuki Shono, HiromiTachikawa, Hirotoshi Yamada, Tetsuichi Kudo,Yasutake Teraoka, and Taisei Nishimi
Chemistry Letters Vol.34, No.4 (2005) C-71
Copyright � 2005 The Chemical Society of Japan http://www.csj.jp/journals/chem-lett/
612 Crystal Engineering with [Mo36O112-(H2O)16]
8� Anion as Nanosized BuildingBlock
Kazuo Eda and Yuichi Iriki
Electronic Supporting Information
614 Lithium Acetate-catalyzed Crossed AldolReaction between Aldehydes and Trimethyl-silyl Enolates Generated from Other Alde-hydes
90 − 91% yield
H
OSiMe3
Ar H
O
DMF or DMF−H2O
NaBH4
Ar H
Me3SiO O
Ar OH
HO
+
(1.4 equiv.)
AcOLi (10 mol%)
Ar = 4-NCC6H4
1N HCl aq
rt.
−45 °C
Yoshikazu Kawano, Hidehiko Fujisawa, andTeruaki Mukaiyama
616 Preparation of Visible Light-responsive TiO2
Thin Film Photocatalysts by an RF Magne-tron Sputtering Deposition Method andTheir Photocatalytic Reactivity
UV−vis spectra of TiO2 thin films prepared on quartzsubstrates by a radio-frequency magnetron sputteringdeposition method at various substrate temperatures.
100
0
50
200 400 600 800
Wavelength / nm
Tran
smitt
ance
/ %
473K
673K
873K
Visible light-responsive TiO2 (Vis-TiO2) thin
the O/Ti ratio from surface (O/Ti = 2.00)
solution under visible light irradiation.
films were successfully developed by aradio-frequency (RF) magnetron sputteringdeposition method. These Vis-TiO2 thinfilms exhibited a declined composition of
to bottom (O/Ti = 1.93), enabling theabsorption of visible light. Pt-loaded Vis-TiO2
was, thus, found to decompose waterinvolving methanol or a 0.05 M silver nitrate
Masaaki Kitano, Masato Takeuchi, MasayaMatsuoka, John M. Thomas, and MasakazuAnpo
618 Host to Guest Energy Transfer in a Self-assembled Supramolecular Nanocage Ob-served by Picosecond Fluorescence Quench-ing
acridineLPd 46 ⊃Haruko Hosoi, Shoichi Yamaguchi, and TaheiTahara
620 Structure and Magnetic Properties of a Hon-eycomb-like Copper(II) Complex Containing4-Aminopyrimidine and Methoxide Bridges
Keita Osanai, Takayuki Ishida, and TakashiNogami
Electronic Supporting Information