chemistry letters · 2013. 2. 5. · 140 new organic sensitizers with n-substituted or...
TRANSCRIPT
Chemistry Lettershttp://www.csj.jp/journals/chem-lett/
Vol.42 No.2 CMLTAGFebruary, 2013 ISSN 0366-7022
Copyright © 2013 The Chemical Society of Japan
Highlight Review
94 Heterocyclic CarbeneMetal-catalyzed Csp2Csp2 and CspCsp2 Couplings Using Non-metallic Substrates
HR3
R2
R4
HR2
+R1 NHC-Metalcomplex
XR1
R3
R2 R4
R1
R2or
Miguel Yus* and Isidro M. Pastor*doi:10.1246/cl.2013.94
The use of carbene ligands for transition-metal complexes has been developed in the last decades, being of special interest thosecarbenes derived from a nitrogen-containing heterocyclic system. An interesting variety of carbenemetal complexes has been testedin the MizorokiHeck reaction. In comparison, few examples can be found for the MatsudaHeck version of this coupling reaction.Additionally, the Sonogashira coupling has been also catalyzed with different carbenemetal catalysts.
Letter
109 Ethyl Imidazole-1-carboxylate (EImC) as aCarbonylating Agent: Efficient Synthesis ofOxazolidin-2-ones from Amino Alcohols
OHR2
NH
R3
R1
NO
R1
R2
R3
ON
N
O
O
K2CO3 / THF
R1 = Different alkyl groupsR2 = Different alkyl (or) aryl groupsR3 = Different alkyl (or) aryl groups
S. Veeraswamy, K. Indrasena Reddy, R. VenkatRagavan,* Satyanarayana Yennam, and A.Jayashreedoi:10.1246/cl.2013.109Electronic Supporting Information
112 Synthesis of Silyl-substituted AnthraceneDerivatives via Birch-type Silylation
Li (excess)Me3SiCl (12 equiv)
THF, rt, 24 h
Me3Si
Me3Si
SiMe3
1 (30%)
DDQ (3 equiv)
toluene80 °C, 12 h
SiMe3
SiMe3
5 (89%)
SiMe3
SiMe3
SiMe3
Ken-ichiro Kanno,* Yumika Maemura, NaotakaKobayashi, and Soichiro Kyushin*doi:10.1246/cl.2013.112Electronic Supporting Information
115 Elongation of Circulation Time of a Dia-tomic Molecule Receptor in Bloodstream byAttachment to Small Gold Nanoparticles
Keiichi Karasugi, Hiroaki Kitagishi, and KojiKano*doi:10.1246/cl.2013.115Electronic Supporting Information
118 Carbon Combustion over Synthetic Potas-sium Aluminosilicate with LIT Structure K
Si
AlH
Without catalyst
C + O2 CO220
10
0
CO
2 fo
rmat
ion/
μmol
min
–1
900800700600500Temperature/K
–LIT type zeolite
Norihito Hiyoshi,* Takuji Ikeda, and TakakoNagasedoi:10.1246/cl.2013.118Electronic Supporting Information
121 Internally Modified Halloysite Nanotubes asInorganic Nanocontainers for a Flame Re-tardant
flame retardant(BDP)
Al
PO OO
O P OO
O
OPOO
O
Hui Jing, Yuji Higaki, Wei Ma, Hui Wu,Weng On Yah, Hideyuki Otsuka, Yuri M.Lvov, and Atsushi Takahara*doi:10.1246/cl.2013.121Electronic Supporting Information
124 Quantitative Analysis of Coke Formationduring Steam Reforming of Methane on aNickelHydrotalcite Catalyst under PracticalOperation Conditions
Mg-Al oxide
Ni Ni Ni Ni
Ni-incorporated hydrotalcite
CH4
Mg-Al oxide
Coke
CO2
rem
ova
l
CH4
Water vapor
Tatsuya Takeguchi,* Hiroshi Watanabe, ToruMurayama, Hiroki Takahashi, and Wataru Uedadoi:10.1246/cl.2013.124
Chemistry Letters Vol.42, No.2 (2013)C-10
http://www.csj.jp/journals/chem-lett/Copyright © 2013 The Chemical Society of Japan
127 Systematic Exploration of Lipophilic TagsThat Allow Efficient Anchoring of Aptamersto Live Cell Surfaces
Takeshi Tokunaga, Kohei Kuwahata, andShinsuke Sando*doi:10.1246/cl.2013.127Electronic Supporting Information
130 Enhanced Tumor Targeting and Photo-cytotoxicity of FolatePoly(ethylene glycol)Chlorin Photosensitizer Mediated by FolateReceptor
A549HeLa
Hep-20
20
40
60
80 II+FAA+F
Flu
ore
scen
ce in
ters
ity
NH N
N HN
OH
OH
OH
CONH O NHR
A R = -Boc,
I R = -Fol,
n
n =75
F = folic acidDonghong Li,* Pengxi Li, Zonglin Jiang, andLinfeng Guodoi:10.1246/cl.2013.130Electronic Supporting Information
132 Localized Sn2+ Emission Center Independ-ent of the Optical Basicity of Zinc PhosphateGlass
We have demonstrated that emission of Sn2+ center is not affected by chemical composition of the glass, indicating that local coordination state of Sn2+ emission center is generated.
Sn2+
Ca2+
Mg2+
Sr2+
Ba2+
5.04.03.02.0Energy/eV
Nor
mal
ized
inte
nsity
(ar
b un
it)Mg
BaSr
Ca
Zn
PL PLE
Hirokazu Masai,* Toshiro Tanimoto, TakumiFujiwara, SyujiMatsumoto, Yomei Tokuda, andToshinobu Yokodoi:10.1246/cl.2013.132
135 A New Method for Estimating Surface BandEnergies of a Semiconductor Electrode inContact with an Electrolyte Solution
A new graphical method is presented to estimate surface band energies (or the flat-band potential, Ufb) of a semiconductor electrode unambiguously and consistently under conditions that various kinds of surface charges exist simultaneously. Surface band energies are a key quantity for knowing the reactivity of electrons and holes in bands, and the present method will be of fundamental importance in analyzing and developing high-performance semiconductor devices such as solar cells.Yoshihiro Nakato
doi:10.1246/cl.2013.135
137 (3-Fluoro-4-methoxyanilinium)+([18]Crown-6)Supramolecular Cation Salt of Ferromag-netic [MnIICrIII(oxalate)3]¹
Toru Endo, Kazuya Kubo,* Masashi Yoshitake,Shin-ichiro Noro, Tomoyuki Akutagawa, andTakayoshi Nakamura*doi:10.1246/cl.2013.137Electronic Supporting Information
Chemistry Letters Vol.42, No.2 (2013) C-11
http://www.csj.jp/journals/chem-lett/Copyright © 2013 The Chemical Society of Japan
140 New Organic Sensitizers with N-Substitutedor Nonsubstituted Pyrrole Units for Dye-sensitized Solar Cells
hνν
NN
CN
R n
O
O
n = 1~2R = H, Me, Bu, Oct, Dod
e
02468
1012
0 0.2 0.4 0.6 0.8Cu
rren
t d
ensi
ty /
mA
cm
-2
Voltage / V
n = 1, R = Hη = 5.1%TiO2
Masaki Hara, Daisuke Kondo, TomohiroShono, Yoshihito Kunugi, and HidenoriAihara*doi:10.1246/cl.2013.140Electronic Supporting Information
143 Inclusion Crystals of 3¡,7¡,12¡,24-Tetra-hydroxycholane with Haloaromatic Com-pounds: Pitches and Stability of HerringboneAssemblies in Channels
Wen-Tzu Liu, Yute Kin, Kazunori Nakano,Ichiro Hisaki,* Norimitsu Tohnai, and MikijiMiyata*doi:10.1246/cl.2013.143Electronic Supporting Information
146 Acetals of N,N-Dimethylformamides: Ambi-philic Behavior in Converting Carbon Di-oxide to Dialkyl Carbonates
Carbon dioxide is immobilized into dialkyl carbonate using acetals of N,N-dimethylformamide under atmospheric pressure. No special treatment with tailor-made catalysts is needed. Use of dimethyl sulfoxide as a solvent is critical. An ambiphilic mechanism is proposed for the direct synthesis of dialkyl carbonates from acetals and carbon dioxide.
Yuki Takada, Aki Matsuoka, Ya Du, HiroshiNaka, and Susumu Saito*doi:10.1246/cl.2013.146Electronic Supporting Information
148 Fabricating Perovskite BaHfO3 HollowNanospheres through a Mild Reflux Route
Yongzheng Lu, Hua Huang, Tiannan Ye,Jianguo Yu, Guodong Li, and Yongnan Zhao*doi:10.1246/cl.2013.148Electronic Supporting Information
150 Low-temperature Hydrothermal Synthesis ofBismuth Nanoflowers and Their Applicationfor Heavy Metal Detection Utilizing a low-temperature hydrothermal
method, pure bismuth nanoflowers were synthesized for the first time with remarkable productivity. The obtained nanostructures were used to prepare modified electrode, which have shown high sensibility for the detection of heavy metal ions in aqueous solution by stripping analysis.
Haifeng Yang, Yan Yan,* Junfang Li, XiaojingLu, Guangcheng Xi, Qing Zhang, and ChaoWangdoi:10.1246/cl.2013.150Electronic Supporting Information
Chemistry Letters Vol.42, No.2 (2013)C-12
http://www.csj.jp/journals/chem-lett/Copyright © 2013 The Chemical Society of Japan
153 Application of Graphene as a Sorbent forPreconcentration and Determination ofTrace Amounts of Cadmium
Scanning electron micrograph of graphene packed in SPE column at 30000 magnification.
Yunkun Wang, Yanli Dong, Jingwen Zhang,Chao Li, Jingci Li,* and Jingjun Ma*doi:10.1246/cl.2013.153
156 Titration Analysis of Electron Storage andDischarge Properties of Carbon Nanodots
Carbon nanodot
e-
Oxazine 725
Methylene blue
Thionine
Methyl viologen radical
Nile blue A
e-
e- e-e-
Ken-ichi Matsuoka,* Ryo Shibuya, andKatsuhiko Fujitadoi:10.1246/cl.2013.156Electronic Supporting Information
159 A Simple Synthetic Route for the Prepara-tion of Tetramethylglycolide from LacticAcid
Kohtaro Watanabe, Yoshito Andou,* YoshihitoShirai, and Haruo Nishida*doi:10.1246/cl.2013.159Electronic Supporting Information
162 Molecular Iodine in Aqueous Ammonia:Oxidative Fragmentation of Oxiranes toNitriles
R
OI2
Aqueous ammonia
Acetonitrile, 70 °CR
CN
R= alkyl, arylYield = 70-86 %19 examples
6-7 hRavindra R. Jadhav and Krishnacharya G.Akamanchi*doi:10.1246/cl.2013.162
165 Extraordinary Microwave Effect on atropo-Enantioselective Catalytic Reduction of Bi-aryl Lactones
O
CH3
O
OH3C
CH3
O
CH3
OHM MP
H3CH3C
NB
O
H PhPh
CH3
10 mol%
in THF 30 °C
Microwave2.45 GHz
Microwaveenhancement
Dynamic Kinetic Resolution
Reaction Acceleration
BH3•THF
86% yield, 92% eeConventional:
Microwave:82% yield, 91% ee
/ 4320 min
/ 20 minKeeping high enantioselectivity!!
OH
Kazuya Nushiro, Satoshi Kikuchi, and TohruYamada*doi:10.1246/cl.2013.165Electronic Supporting Information
Chemistry Letters Vol.42, No.2 (2013) C-13
http://www.csj.jp/journals/chem-lett/Copyright © 2013 The Chemical Society of Japan
168 Production of Oxidation-resistant CopperNanoparticles on Carbon Nanotubes byPhotoreduction
Naoki Nishida, Akira Miyashita, TatsuyaTsukuda, and Hideki Tanaka*doi:10.1246/cl.2013.168Electronic Supporting Information
171 Shape-controlled Synthesis of ZnSCuInS2AgInS2 Solid Solution Nanoparticles andTheir Photoluminescence Properties
ZnS−CuInS2−AgInS2 (Z-CAIS) nanoparticles with rod-like or spherical shapes were successfully synthesized, the band gap of which was dependent on the chemical compositions.
Meilin Dai, Taro Uematsu, Susumu Kuwabata,and Tsukasa Torimoto*doi:10.1246/cl.2013.171Electronic Supporting Information
174 Drawing Effect of Poly(vinyl alcohol) onCrystal Growth of Calcium Carbonate
The crystal form, morphology, orientation, and nucleation frequency of the calcium carbonate thin films which were formed on poly(vinyl alcohol) (PVA) have been changed by the drawing of PVA.
VateriteAragonite VateriteAragonite
nondrawn drawn
10μ μm 25 mNaoyuki Kubo and Masafumi Yamato*doi:10.1246/cl.2013.174
177 Facile Solubilization and Photovoltaic Ap-plication of C60 FullereneEthylenediamineAdduct
H2N
NH2
toluene
C60PC60
toluene
C9H19COCl
C60P-DC (n)
C60-EDA adduct particle
EDA DC
P3HT (p)S
C6H13
PEDOT:PSS(hole transportlayer)
S
OO
n SO3-
n
ITO (-)
TiO2
P3HT:C60P-DC
PEDOT:PSS
Au (+)
Brown Colored Solid
nTsuyoshi Akiyama,* Taiki Ueda, Yuji Ono,Kento Kimura, Ken-ichi Matsuoka, SunaoYamada, and Takeo Okudoi:10.1246/cl.2013.177Electronic Supporting Information
180 Primary ¢-Amino Acid Salt-catalyzed Asym-metric Michael Addition of Benzoylacetatesto Cyclic Enones and Its Application for theSynthesis of Enantioenriched 1,5-Diketones
LiO2C OTBDPS
NH2
Catalyst:
Ph
O
CO2t -Bu +( )n Ph
CO2t -Bu
O
O
*( )n
O
( )n Ph
O
O
*
Catalyst
yield up to 99%ee up to 98%
CF3CO2H
Masanori Yoshida,* Ami Kubara, and ShojiHaradoi:10.1246/cl.2013.180Electronic Supporting Information
Chemistry Letters Vol.42, No.2 (2013)C-14
http://www.csj.jp/journals/chem-lett/Copyright © 2013 The Chemical Society of Japan
183 Ligand-controlled Iron-catalyzed Cross Cou-pling of Benzylic Chlorides with ArylGrignard Reagents
Cl
MgBr
Fe
PAr2
Ar2P
Cl
Cl
PAr2
Ar2Pcat. A
cat. B
71% yield
86% yield
cat. A: Ar = 4-Me2NC6H4cat. B: Ar = 3,4,5-F3C6H4
MeO
MeO
cross/homo switching
Shintaro Kawamura and Masaharu Nakamura*doi:10.1246/cl.2013.183Electronic Supporting Information
186 Synthesis of Mordenite Nanocrystals byUsing a Hydrophobic Structure-directingAgent
(b)
100 nm
(a)
100 nm
Mordenite with micron or submicron size
Mordenite nanoparticlesRelatively hydrophobicstructure-directing agent(SDA)
A common SDA withless hydrophobicity
Higher catalytic activity
N+
N+N+
Satoshi Inagaki, Yasuhiro Watanabe, YujiNishita, and Yoshihiro Kubota*doi:10.1246/cl.2013.186Electronic Supporting Information
189 Solubilization of Chemically Reduced Gra-phene Oxide Using Coffee Catechol
HO
COOHO
OH
COOH
OOH
40 °C
Coffee Coffee/GO Coffee/RGO
ChlorogenicAcid (CA)
Jang Mi Lee, Geumbi Jeong, Mi Yeon Lee,So Yeon Kim, Young Ho Park, Sung YoungPark, Sang Chun Kim,* Byung-Gak Min,* andInsik In*doi:10.1246/cl.2013.189
191 Poly(dimethylsiloxane)-protected SilverNanowire Network for Transparent Conduc-tor with Enhanced Oxidation Resistance andAdhesion Properties
Sheet resistance on UV−ozone treatment of AgNW and PDMS-protected AgNW networks.
0 100 200 300 400 0
2000
4000
6000
8000
Sh
eet
Res
ista
nce
UV-Ozone Time/min
PET
PET
AgNWPDMS(Ω
/)
Won Jin Lee, Mi Yeon Lee, Arup Kumer Roy,Kang Seok Lee, Sung Young Park,* andInsik In*doi:10.1246/cl.2013.191
194 Colorimetric Chemosensor for BariumMetal Ions Using Tris(bipyridiniumcrownether) Conjugate
Haocheng Guo and Tetsuo Kuwabara*doi:10.1246/cl.2013.194
Chemistry Letters Vol.42, No.2 (2013) C-15
http://www.csj.jp/journals/chem-lett/Copyright © 2013 The Chemical Society of Japan
197 Facile Synthesis of OligosaccharidePoly(L-lactide) Conjugates Forming Nanoparticleswith Saccharide Core and Shell
OO
OH
n
Direct azidation
Click chemistry
+NN
Cl Cl-
OOH
HOHO
O
HOO
HOHO
O
HO
H
m
OO
OH
n
NN
NO
HOHO
O
HOO
HOHO
O
HO
H
m
Tomonari Tanaka,* Hiroyuki Fukuhara,Shin-ichiro Shoda, and Yoshiharu Kimuradoi:10.1246/cl.2013.197Electronic Supporting Information
200 Chemically Reduced Graphene Oxide withCrosslinked Shell Showing Enhanced Envi-ronmental Stability Using Thiol-graftedPluronic
HO
COOHO
OH
COOH
OOH
SH
SH
S-S S-S
GO RGO/Plu-S-S
Plu-SHSH
SHSH
O2
DTT
RGO/Plu-SH
pH
2
pH
12
eth
ano
l
pH
2
pH
12
eth
ano
l
Shell Crosslinked RGO
Geumbi Jeong, Hyun Gu Kim, Jeong A Nam,Sung Young Park,* and Insik In*doi:10.1246/cl.2013.200
Chemistry Letters Vol.42, No.2 (2013)C-16
http://www.csj.jp/journals/chem-lett/Copyright © 2013 The Chemical Society of Japan