9
Chemistry Letters http://www.csj.jp/journals/chem-lett/ Vol.39 No.11 CMLTAG November, 2010 ISSN 0366-7022 Copyright © 2010 The Chemical Society of Japan Highlight Review 1118 Overview of the Mechanistic Work on the Concerted Metallation-Deprotonation Path- way David Lapointe* and Keith Fagnou doi:10.1246/cl.2010.1118 The cleavage of aromaticC-H bonds promoted by a metal and an intramolecular base has been described over 50 years ago. Herein, discussion of selected mechanistic studies provides a description of the concerted metallation-deprotonation (CMD) mechanism in the functionalization of heteroarene C-H bonds promoted by transition metals. Letter 1127 PEG-mediated Facile Protocol for N-Boc Protection of Amines N NH R R 1 + (Boc) 2 O R R 1 PEG-400 RT Boc R 1 R, = H, alkyl, aryl 32 examples V. Siddaiah,* G. M. Basha, G. Padma Rao, U. Viplava Prasad, and R. Suryachendra Rao doi:10.1246/cl.2010.1127 http://www.csj.jp/journals/chem-lett/ Copyright © 2010 The Chemical Society of Japan

Chemistry Letters...R N H R N CHO cat. Au:PVP/ base MeOH-H2O/80 C or formalin/EtOH-H2O/27 C under air R' R' Au:PVP is active and selective catalysts for N-formylation of amines under

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Page 1: Chemistry Letters...R N H R N CHO cat. Au:PVP/ base MeOH-H2O/80 C or formalin/EtOH-H2O/27 C under air R' R' Au:PVP is active and selective catalysts for N-formylation of amines under

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

Vol.39 No.11 CMLTAGNovember, 2010 ISSN 0366-7022

Copyright © 2010 The Chemical Society of Japan

Highlight Review

1118 Overview of the Mechanistic Work on theConcerted Metallation­Deprotonation Path-way

David Lapointe* and Keith Fagnoudoi:10.1246/cl.2010.1118

The cleavage of aromatic C­H bonds promoted by a metal and an intramolecular base has been described over 50 years ago.Herein, discussion of selected mechanistic studies provides a description of the concerted metallation­deprotonation (CMD)mechanism in the functionalization of heteroarene C­H bonds promoted by transition metals.

Letter

1127 PEG-mediated Facile Protocol for N-BocProtection of Amines

NNHR

R1

+ (Boc)2OR

R1

PEG-400

RTBoc

R1R, = H, alkyl, aryl 32 examples V. Siddaiah,* G. M. Basha, G. Padma Rao, U.Viplava Prasad, and R. Suryachendra Raodoi:10.1246/cl.2010.1127

http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan

Page 2: Chemistry Letters...R N H R N CHO cat. Au:PVP/ base MeOH-H2O/80 C or formalin/EtOH-H2O/27 C under air R' R' Au:PVP is active and selective catalysts for N-formylation of amines under

1130 High-grafted Surface Modification of SilicaGel Particles with Urushiol

R

TEOSSol-gel reaction OH

HO

urushiolSiO2

Urushiol layer

55.4%

7.4%

1.7%

6.5%

4.4%

15.0%

1.5%

4.5%Others 3.6%

urushiol Content

O

OSiO2 SiO2

SiO2

OHOH

OHOH

OHOH

OHOH

OHOH

OHOH

OHOH

OHOH

High-grafted surface modification of silica gel particles was prepared by using silica gel obtained by traditional avenue as precursor. 10 wt % urushiol was added to the silica gel, and the reaction occurred between silanol (Si−OH) groups of silica gel and the hydroxy groups on the phenyl ring of urushiol to obtain soil-gray product. The urushiol moieties were found to be highly adhesive to the surfaces of silica particles, and the grafting ratio added up to 15.35 ± 0.05 wt %.

Jianrong Xia, Jinhuo Lin,* and Yanlian Xudoi:10.1246/cl.2010.1130

1132 Stereoselective Synthesis of 3-(1-Cyanoalkyl-idene)oxindoles by Palladium-catalyzed Cy-clization Reaction of 2-(Alkynyl)aryl Isocya-nates with Copper(I) Cyanide

NCO

R1

+

NC

CNR1

O

H

cat.Pd(0)/dppf

CuCN

The palladium-catalyzed reaction of 2-(alkynyl)aryl isocyanates with copper(I) cyanide gives stereochemically defined 3-alkylideneoxindoles incorporating a cyano group on the alkylidene unit.

Tomoya Miura, Takeharu Toyoshima, OsamuKozawa, and Masahiro Murakami*doi:10.1246/cl.2010.1132Electronic Supporting Information

1134 Redox Behavior of Ruthenium(Bipyridine)-(Terpyridine)(Carbonyl) Complex-modifiedCarbon Electrode and Reactivity towardElectrochemical Reduction of CO2

Electrochemical reduction of a diazonium complex [Ru(bpy)(trpy-ph-N2+)(CO)](PF6)3

([1](PF6)3) (bpy = 2,2′-bipyridine, trpy-ph-N2+ = 4-(2,2′:6′,2′′-terpyridine-4′-yl)benzenediazo-

nium) using a GC electrode forms multi-layer films of the complexes on the electrode surface, on which the reduced form of the comple showed strong affinity toward CO2.

Yuhei Tsukahara, Tohru Wada, and KojiTanaka*doi:10.1246/cl.2010.1134Electronic Supporting Information

1136 A Variational Monte Carlo Study of Posi-tronic Compounds Using InhomogeneousBackflow Transformations

The electronic and positronic molecular orbitals of [Li–;e+] obtained at the Hartree–Fock level. The positron affinity (PA) and two-photon annihilation rate (Γ2) from various methods are also shown. The Slater–Jastrow-backflow trial wave function (VMC(SJB)) greatly improves the positron affinity and two-photon annihilation rate.

Yukiumi Kita,* Masanori Tachikawa,Neil D. Drummond, and Richard J. Needsdoi:10.1246/cl.2010.1136

1138 Z-Selective Horner­Wadsworth­Emmons-type Reaction Using a 10-P-5 PhosphoraneBearing Bidentates Derived from 1-Naphthol

O

P

O

CH2CO2Et1) base

2) RCHO

R

CO2Et

R

CO2Et

Z E86:14 to 99:1Satoshi Kojima,* Jun-ya Arimura, and

Kazumasa Kajiyamadoi:10.1246/cl.2010.1138

Chemistry Letters Vol.39, No.11 (2010)C-124

http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan

Page 3: Chemistry Letters...R N H R N CHO cat. Au:PVP/ base MeOH-H2O/80 C or formalin/EtOH-H2O/27 C under air R' R' Au:PVP is active and selective catalysts for N-formylation of amines under

1140 Template Synthesis of Monodisperse Meso-porous Titania Spheres

A simple method was presented to synthesize monodisperse mesoporous titania by using PSMAA spheres as the templates. The as-prepared mesoporous titania spheres displayed an average diameter of about 130 nm, and their pore size distribution was centered around 4 nm when 220 nm PSMAA particles were used.

Peng Wang,* Shu-Hua Teng, and Fang-QiongTangdoi:10.1246/cl.2010.1140Electronic Supporting Information

1142 Preparation and Properties of Low ViscousTriazolate-based Ionic Liquids ContainingTwo Cyano Groups

NN

N

NC CN

Ag+ WaterN

NN

NC CN

+ AgI[emim][I]

NN

H3C

CH2CH3

liquid at room temperaturelow viscosity

Satoshi Kitaoka, Kaoru Nobuoka, NaokiYoshiiwa, Thomas Harran, and YuichiIshikawa*doi:10.1246/cl.2010.1142Electronic Supporting Information

1144 Photoinduced Phase Transitions in ChiralBinaphthyl-diol-doped Smectic Liquid Crys-tals by a Photochromic Azobenzene

500 1000 1500 2000 25000

102030405060708090

100

0s 10s 30s 60s 180s 300s

UV irradiation

Tra

nsm

issi

on/%

Wavelength/nm

Guojie Wang,* Mingzhi Zhang, Qiang Yang,Fang Liu, Zihui Cheng, Renwei Guo, and HuaiYang*doi:10.1246/cl.2010.1144Electronic Supporting Information

1146 Electrocatalytic O2 Evolution from Waterat an ITO Electrode Modified with [Ru-(terpy){4,4¤-(CH2PO3H2)2-2,2¤-bpy}(OH2)]2+:Evidence for a Unimolecular Pathway

Electrocatalytic O2 evolution at one Ru site

ITO electrode

2H2O

O2 + 4H+

4e-

N

N

N

NN

Ru

P

P

O

O

OH

OH OHHO

OH2

2+

Josaku Kiyota, Junpei Yokoyama, MasakiYoshida, Shigeyuki Masaoka,* and Ken Sakai*doi:10.1246/cl.2010.1146Electronic Supporting Information

1149 MnCl2¢4H2O-catalyzed Potential Protocolfor the Synthesis of Aryl/Vinyl Sulfides

I

MnCl2·4H2O(15 mol%)

TMEDA,DMSO, KOH 110 °C, 15h

MnCl2·4H2O(15 mol%)

TMEDA,DMSO, KOH 110 °C, 24h

SR

I

R-SHSR

R1, R = aryl, alkyl

R1

R1 R1

R1

Madhav Bandaru, Narayana Murthy Sabbavarpu,Ramesh Katla, and Venkata Durga NageswarYadavalli*doi:10.1246/cl.2010.1149Electronic Supporting Information

Chemistry Letters Vol.39, No.11 (2010) C-125

http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan

Page 4: Chemistry Letters...R N H R N CHO cat. Au:PVP/ base MeOH-H2O/80 C or formalin/EtOH-H2O/27 C under air R' R' Au:PVP is active and selective catalysts for N-formylation of amines under

1152 Electrochemical Investigation of DynamicSolution Structures of Bicontinuous Micro-emulsion at Solid Interfaces

Dynamic solution structure of a three-phase interface (oil/water/solid) of a bicontinuous microemulsion (BME) was evaluated electrochemically with apparent diffusion coefficients (Dapp’s) from cyclic voltammograms. With hydrophilic (ITO) and lipophilic (pyrolytic graphite) electrodes, Dapp’s were much smaller than with an amphiphilic (Au) electrode. The Dapp ratios of ITO:PG-b in the BME were larger than those in a homogeneous aqueous solution. These results indicate that BME solution structures around hydrophilic and lipophilic electrodes adopt alternately layered structures but not simple graded structures.Yuichi Makita, Shinobu Uemura, Nagayoshi

Miyanari, Takaaki Kotegawa, ShintaroKawano, Taisei Nishimi, Masato Tominaga,Katsuhiko Nishiyama, and Masashi Kunitake*doi:10.1246/cl.2010.1152Electronic Supporting Information

1155 Binding Properties of Calixarene-based Co-facial Bisporphyrins

PrO

PrO

PrO

NH N

N HN

NH

NH NN HN

ONH

O

t -bu

t -bu

t -bu

t -bu

(CH2)n

(CH2)n

t -bu

t -bu

OO

PrO

O

OAkihiko Tsuge,* Toshiyuki Kunimune, YutakaIkeda, Tetsuji Moriguchi, and Koji Arakidoi:10.1246/cl.2010.1155Electronic Supporting Information

1158 Bright White Upconversion Luminescence in¢-NaGd0.794Yb0.20Ho0.001Tm0.005F4 Nanopar-ticles

-NaGd0.74Yb0.20Ho0.001Tm0.005F4 nanoparticles crystallized well and exhibited nearly hexagonal and ellipsoidal sphere morphology, as characterized by X-ray powder diffraction, transmission electron microscopy, and high-resolution transmission electron microscopy. The nanoparticles have an average size of about 23 nm. Room-temperature bright white upconversion luminescence in

-NaGd0.794Yb0.20Ho0.001Tm0.005F4 nanoparticles was obtained under single-wavelength diode laser excitation of 980 nm.

β

βGejihu De,* Menggenqilavuqi Yu, and SiqinBaodoi:10.1246/cl.2010.1158

1160 Solubilization of Reduced Graphene inWater through Noncovalent Interaction withDendrimers

Solubilization of reduced graphene using dendrimers.

Seyoung Yoon and Insik In*doi:10.1246/cl.2010.1160Electronic Supporting Information

1162 Synthesis and Optoelectronic Properties ofCompletely Carbazole-substituted Double-decker-shaped Silsesquioxane

Michinari Kohri, Jun Matsui, Akira Watanabe,and Tokuji Miyashita*doi:10.1246/cl.2010.1162Electronic Supporting Information

Chemistry Letters Vol.39, No.11 (2010)C-126

http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan

Page 5: Chemistry Letters...R N H R N CHO cat. Au:PVP/ base MeOH-H2O/80 C or formalin/EtOH-H2O/27 C under air R' R' Au:PVP is active and selective catalysts for N-formylation of amines under

1164 Human Mesenchymal Stem Cell Behavior onConcentrated Polymer Brushes PresentingDifferent Surface Stiffness ATRP initiator (BHE)

Silane coupling agent (OTS)Same in contour chain length

Similar hydrophilicity

Nanometer-level smooth

Same type of polymer

Stiffness

Monomer

Concentrated brush (>0.1 chains/nm2)

ATRP

Polymer

BHE

OTS

Si

OEtEtO

EtO

SiO

OEtEtO

EtOBr

O

Kwangwoo Nam, Rie Fukaya, YoshihideHashimoto, Yukiko Ito, Tsuyoshi Kimura, andAkio Kishida*doi:10.1246/cl.2010.1164Electronic Supporting Information

1166 Solution-phase Assembly of a RhodiumComplex via Specific Hydrogen Bondingbetween Barbituric Acid and Triaminopyr-imidine Moieties

Solution-phase assembly of a Rh complex using specific hydrogen bonding between BA and TAP moieties was achieved by tuning the substituent on TAP to control the solubility of the assembly.

N N

HN

HN

N

H H

HHNN

O

O

O

HHN N

HN

HN

N

H H

HHNN

O

O

O

HH

Rh Rh

R R

Masataka Kondo, Takuya Kochi, Mitsuo Sato,Aki Kitajima, and Fumitoshi Kakiuchi*doi:10.1246/cl.2010.1166Electronic Supporting Information

1168 Screen-printed Cu2S-based Counter Elec-trode for Quantum-dot-sensitized Solar Cell

Minghui Deng, Shuqing Huang, QuanxinZhang, Dongmei Li, Yanhong Luo, Qing Shen,Taro Toyoda, and Qingbo Meng*doi:10.1246/cl.2010.1168

1171 Structural Control of Three-dimensionalAssemblies of Anisotropic Gold Nanopar-ticles Based on Their Different Shapes

Yutaka Kuwahara,* Daigou Mizoguchi,Keishiro Yoshimori, Hiroaki Endo, MioIwanaga, Tomoki Iwanaga, Tsuyoshi Sawada,Motonobu Goto, Hideto Shosenji, and SunaoYamadadoi:10.1246/cl.2010.1171Electronic Supporting Information

1174 N-Formylation of Amines Catalyzed byNanogold under Aerobic Oxidation Condi-tions with MeOH or Formalin

RNH

RNCHO

cat. Au:PVP/ base

MeOH-H2O/80 °Cor

formalin/EtOH-H2O/27 °C

under air

R'R'

Au:PVP is active and selective catalysts for N-formylation of amines under aerobic oxidation using methanol or formalin as a formyl source.

Patcharee Preedasuriyachai, Hiroaki Kitahara,Warinthorn Chavasiri, and Hidehiro Sakurai*doi:10.1246/cl.2010.1174Electronic Supporting Information

Chemistry Letters Vol.39, No.11 (2010) C-127

http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan

Page 6: Chemistry Letters...R N H R N CHO cat. Au:PVP/ base MeOH-H2O/80 C or formalin/EtOH-H2O/27 C under air R' R' Au:PVP is active and selective catalysts for N-formylation of amines under

1177 Synthesis and Solution Properties of a NovelThermosensitive Poly(benzyl ether) Dendronwith Oligoethyleneoxy Chains at the Periph-ery

OOO

OO

O

O

O

O

O

OO

OOO

O

O

O

O

OO

O

O

O

O

O

O

O

OO

CO2Me

A novel thermosensitive second generation poly(benzyl ether) dendron with oligoethyleneoxy chains at the periphery was synthesized. Its cloud point (CP) decreased with an increasing concentration over a range of concentrations from 9 to 60 wt %. Fluorescent spectroscopy and AFM studies revealed that the dendron self-assembled into the spherical micelles, about 50 nm in diameter, at concentration over its CMC in an aqueous solution. This dendron has a potential as smart thermosensitive materials.

Li Xu, Lidong Shao, Lin Chen, Minqi Hu, andYunmei Bi*doi:10.1246/cl.2010.1177Electronic Supporting Information

1180 Synthesis and Characterization of ArtificialAntigens for Nickel

A novel artificial antigen for Ni2+ was prepared by designed synthetic route, and the obtainedartificial antigen was characterized successfully.

N

O

OH

N

O

O

ON

O

O

O

NaHCO3 N

O

OH

NN

NH

OH

HO

HO

O

O O

O

Protein

N

O

OH

NN

NH

OH

HO

HO

O

O O

O

ProteinNi2+

N N NH

OHO

O

Protein

OHO

N

HO

O

OHONi

+pH 8.5

Protein

Ming Guo,* Xiaoqing Che, Ping Yang, JinyuShen, and Jiayun Yaodoi:10.1246/cl.2010.1180

1182 Selective Synthesis of Secondary Amines viaN-Alkylation of Primary Amines and Am-monia with Alcohols by Supported CopperHydroxide Catalysts R NH2 R' OH+ R

HR'

R' OHNH3 + R'H

R'

Cu(OH)x/Al2O3

Cu(OH)x/Al2O3

N

NJinling He, Kazuya Yamaguchi, and NoritakaMizuno*doi:10.1246/cl.2010.1182Electronic Supporting Information

1184 Preparation of Reduction-sensitive Nanogelswith a Large Swelling Capacity by aSurfactant-free Precipitation Method

Biocompatible and reduction-sensitive nanogels with a large swelling capacity were prepared by the crosslinking reaction of biodegradable polymers without toxic surfactants.

200 nm 10 µm

1 µm

1 µm

Freeze-dried

Dried NPs(270 nm)

Swollen NPs(1.4 µm)

Swelling Reduction

: -SH: -SS-: γ -PGA

Swollen DecomposedAkihiro Nishiguchi, Hiroaki Yoshida, MichiyaMatsusaki, and Mitsuru Akashi*doi:10.1246/cl.2010.1184Electronic Supporting Information

1186 Guest-induced Single-crystal-to-single-crys-tal Transformation in Copper Complexes of1,3,5-Benzenetricarboxylic Acid and 4,4¤-Bipyridine

A 2D noninterpenetrated flexible porous coordination polymer, [Cu(HBTC)(4,4′-bpy)]·C6H11OH·H2O (1), has been synthesized. The cyclohexanol guest molecules in 1 can be removed upon soaking 1 in ethanol. Complex 1 undergoes a single-crystal transformation to form an ethanol solvate, [Cu(HBTC)(4,4′-bpy)(H2O)]·C2H5OH·2H2O (2), and during the process, the octahedral coordination of the copper cation in 1 converts to square-pyramidal coordination in 2.

Jinxi Chen* and Susumu Kitagawadoi:10.1246/cl.2010.1186

Chemistry Letters Vol.39, No.11 (2010)C-128

http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan

Page 7: Chemistry Letters...R N H R N CHO cat. Au:PVP/ base MeOH-H2O/80 C or formalin/EtOH-H2O/27 C under air R' R' Au:PVP is active and selective catalysts for N-formylation of amines under

1188 Nitrogen-15 NMR Spectroscopy of SugarSensor with B­N Interaction as a KeyRegulator of Colorimetric Signals

Yuya Egawa,* Yoshiyuki Tanaka, Ryota Gotoh,Satoshi Niina, Yu Kojima, Naoki Shimomura,Hiroko Nakagawa, Toshinobu Seki, andJun-ichi Anzaidoi:10.1246/cl.2010.1188Electronic Supporting Information

1190 Poly(N-isopropylacrylamide)-grafted Ther-mosensitive Anodized Aluminum OxideMembrane

Thermo-responsive PNIPAM-grafted membrane.

Joo Hee Jang and Insik In*doi:10.1246/cl.2010.1190Electronic Supporting Information

1192 Removal of Perchlorate and Tetrafluorobo-rate Anions from Aqueous Solutions by aSelf-assembled Cu(II) Molecular CapsuleSystem Using Water-insoluble Cu(II) Source

Maiko Yamaguchi, Takeshi Hirakawa, NaokoNishina, Mitsuru Kondo,* Hiromi Aoki, EmiOkuda, and Liang Zhangdoi:10.1246/cl.2010.1192Electronic Supporting Information

1194 A Facile Reprecipitation Method for thePreparation of Polyimide Hollow Sphereswith Controllable Morphologies and Perme-able Shell

We presented our preliminary work on the fabrication of polyimide hollow sphere by reprecipitation method; through fine-tuning the PAA concentration, many intriguing shapes, including deflated capsules, bowl-shaped and dimple-like hollow spheres can be obtained. Adding salt to the PAA solution helps the formation of PI hollow spheres with complete shells. The morphologies can be fixed through imidization, and thus obtained a controllable and reproducible method to prepare high-performance polyimide hollow spheres with various morphologies.

Junzhi Liu, Yuzhi Yan, Zhihua Chen, Yi Gu,and Xikui Liu*doi:10.1246/cl.2010.1194Electronic Supporting Information

1197 Highly Active Supported Nickel Catalysts forPre-reforming of Liquefied Petroleum Gas

375

15000

30000

45000

60000

75000

90000

0

20

40

60

80

SV/m

L g

−1 h

−1

Reaction temperature/°C

Sele

ctiv

ity/

%

CH4

H2

CO2

CO

400 425 450 475 500

Mg–Al mixed oxide supported Ni catalysts can pre-reform liquefied petroleum gas to methane, carbon oxides, and hydrogen under high space velocity with low steam/carbon ratio of 2.0.

Kui Shen, Xueguang Wang,* Xinxing Wang,Xiujing Zou, Xionggang Lu, and WeizhongDingdoi:10.1246/cl.2010.1197Electronic Supporting Information

Chemistry Letters Vol.39, No.11 (2010) C-129

http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan

Page 8: Chemistry Letters...R N H R N CHO cat. Au:PVP/ base MeOH-H2O/80 C or formalin/EtOH-H2O/27 C under air R' R' Au:PVP is active and selective catalysts for N-formylation of amines under

1200 Polystyrene-anchored Palladium(II) Com-plex as an Efficient and Reusable Catalystfor Suzuki Cross-coupling Reaction in WaterMedium

A reusable polystyrene-anchored palladium(II) catalyst has been prepared and characterized. The catalyst was found to be highly effective for the Suzuki cross-coupling reactions of aryl halides with arylboronic acid in water medium under aerobic conditions.

+X

X = Cl, Br, IR1 = H, CH3, OMe, COMe, NO2, CHO

Pd(II) cat.

K2CO3, H2O(HO)2B

R1 R1

R2 R2

R2 = H, CH3, COMe

Manirul Islam,* Paramita Mondal, Kazi Tuhina,Dildar Hossain, and Anupam Singha Roydoi:10.1246/cl.2010.1200Electronic Supporting Information

1203 Label-free Rapid Semiquantitative Detectionof Proteins Down to Sub-monolayer Cover-age by Using Surface-enhanced RamanScattering of Nitrate Ion

A novel heat-induced SERS method was used to selectively enhance a band of NO3

− at 1049 cm−1. A bell shape variation of SERS intensities was observed for the concentration dependency of the lysozyme and insulin.

Zhen Zhou, Genin Gary Huang, and YukihiroOzaki*doi:10.1246/cl.2010.1203Electronic Supporting Information

1206 Acetylated Cyclodextrins as New Organo-gelators

5 µm

O

OOAc

OAc

OAc

6

Toshiyuki Kida, Koichiro Kishimoto, KojiHatano, Masahiro Muraoka, Yohji Nakatsuji,and Mitsuru Akashi*doi:10.1246/cl.2010.1206Electronic Supporting Information

1209 “Substitutable” Polymer Brushes: ReactivePoly(methacrylate) Brushes with Exchange-able Alkoxyamine Units in the Side Chain

Alkoxyamine-containing polymer brushes acting as “substitutable” polymer brushes via dynamic covalent exchange.

Tomoya Sato, Yoshifumi Amamoto, HirokiYamaguchi, Hideyuki Otsuka,* and AtsushiTakahara*doi:10.1246/cl.2010.1209

1212 Aggregation of L-Cysteinato Tricobaltate(III)Anions by Lanthanide(III) Cations intoDimensional Structures That are Controlledby Diastereoisomerism and Ionic Size

Hou Qun Yuan, Asako Igashira-Kamiyama, andTakumi Konno*doi:10.1246/cl.2010.1212Electronic Supporting Information

Chemistry Letters Vol.39, No.11 (2010)C-130

http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan

Page 9: Chemistry Letters...R N H R N CHO cat. Au:PVP/ base MeOH-H2O/80 C or formalin/EtOH-H2O/27 C under air R' R' Au:PVP is active and selective catalysts for N-formylation of amines under

1215 Does Water Liquid Phase Intrude intoHydrophobic Nanospaces of Alkyl-graftedMesoporous Silica Immersed in Water?Detection by 13CCP-MASNMR

Water

Water

Water

Water

Water

n-pentyl-grafted mesoporous silica

n-octyl-grafted mesoporous silica

Kei Inumaru,* Shintaro Kakii, Hiroto Yoshida,and Shoji Yamanakadoi:10.1246/cl.2010.1215

1218 Near-infrared Fluorescence Enhancement byRegularly Arranged Gold Nanoblocks

100 nm

100 nm

Substrate

200 nm 40 nm

Side View

1 mm

1 mm 100 nm

200 nm

200 nm

Top View

Cl

N

N

CH3

CH3CH3

CH3

CH3

CH3

I

3.0

2.5

2.0

1.5

1.0Enh

ance

men

t fac

tor

1000900800700600500

Wavelength / nm

Ext

inct

ion

3.0

2.5

2.0

1.5

1.0

3.0

2.5

2.0

1.5

1.0

(a)

(b)

(c)Fuyuki Ito, Ryuichi Ohta, Yukie Yokota, KoseiUeno, Hiroaki Misawa, and ToshihikoNagamura*doi:10.1246/cl.2010.1218

1220 Trap of Biomolecular Ions in the Gas PhaseProduced by IR-laser Ablation of DropletBeam

Reflectron

Daly detector

Ion-trap/accelerationelectrodes

Skimmers

Dropletnozzle

IR laser

1500 V300 kHz

1 kV

1 kV1.6 kVJun-ya Kohno* and Tamotsu Kondow

doi:10.1246/cl.2010.1220

1222 Novel Phenanthroline Derivatives for Elec-tron Transport in Organic Light-emittingDiodes

N N

Ar Ar

N N

Ar-CHOAc2O

Reflux, 6h

CNCF3

Where Ar =(C-1 to C-4 )

C-1 C-3C-2

SC-4

Voltage/V0

Cu

rren

t D

ensi

ty /

mA

cm

-2

0

50

100

150

200

250

300

350

Lo

g [

L /

cd m

-2]

0

1

2

3

4

5

C-4C-2Alq3

λ/nm

450

Inte

nsi

ty /

Arb

itra

ry U

nit

s

0

2

4

6

8

10

12

14 C2, CIE (x,y),(0.307, 0.652)C 4, CIE (x,y),(0.314, 0.647)Alq3,CIE (x,y),(0.325, 0.623)

2 4 6 8 10 12 14 16 18 20

500 550 600 650

A series of novel arylvinylene-substituted phenanthroline derivatives have been synthesized and their applications as electron-transporting materials in organic light-emitting diodes (OLED’s) have been investigated. One particular derivative, namely, 2,9-bis[2-(thiophen-2-yl)vinyl][1,10]phenanthroline shows significantly lower operating voltage than tris(8-quinolinolato)aluminium(III) (Alq3) and substantially higher lifetime than bathophenanthroline (BPhen).

Poopathy Kathirgamanathan,* SivagnanasundramSurendrakumar, Seenivasagam Ravichandran,Raghava Reddy Vanga, Juan Antipan-Lara,Subramaniam Ganeshamurugan, MuttulinghamKumaravel, Gnanamoly Paramaswara, and VincentArkleydoi:10.1246/cl.2010.1222Electronic Supporting Information

Chemistry Letters Vol.39, No.11 (2010) C-131

http://www.csj.jp/journals/chem-lett/Copyright © 2010 The Chemical Society of Japan