10
Chemistry Letters http://www.csj.jp/journals/chem-lett/ Vol.39 No.9 CMLTAG September, 2010 ISSN 0366-7022 Copyright © 2010 The Chemical Society of Japan Highlight Review 908 Bifunctional Organometallic Catalysis and Reactivity Using Heterocyclic Phosphines and Metallated Heterocycles C C R H Ph2P Ru C Cp PPh 2 CH N N R t -Bu t -Bu H2O Ph2P Ru C Cp PPh2 CH2 HN N O R t -Bu t -Bu C CH2 O R H catalyst Douglas B. Grotjahn doi:10.1246/cl.2010.908 Pyridyl- and imidazolylphosphines accelerate anti-Markovnikov alkyne hydration and alkene isomerization and deuteration by factors of 1000 to more than 10000. Evidence for proton transfer and hydrogen bonding in catalytic intermediates comes from computational, mechanistic, and structural studies. Related concepts are being applied to a novel class of protic N-heterocyclic carbene complexes which feature an unusual NH group. Letter 915 Photocatalytic Styrene Polymerization by Novel Bichromophoric Pd Catalyst Having Long Excited-state Lifetime Kei Murata, Masaharu Ito, Akiko Inagaki,* and Munetaka Akita* doi:10.1246/cl.2010.915 Electronic Supporting Information http://www.csj.jp/journals/chem-lett/ Copyright © 2010 The Chemical Society of Japan

Chemistry Lettersincrease was 40.2 mass %, which was consistent with the theoretical value calculated from the following reaction. Li 2CuO 2(s) + CO 2(g) CuO(s) + Li 2CO 3(s) Yusuke

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Page 1: Chemistry Lettersincrease was 40.2 mass %, which was consistent with the theoretical value calculated from the following reaction. Li 2CuO 2(s) + CO 2(g) CuO(s) + Li 2CO 3(s) Yusuke

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

Vol.39 No.9 CMLTAGSeptember, 2010 ISSN 0366-7022

Copyright © 2010 The Chemical Society of Japan

Highlight Review

908 Bifunctional Organometallic Catalysis andReactivity Using Heterocyclic Phosphinesand Metallated Heterocycles

C

C

R

H

Ph2P Ru

C

Cp

PPh2

CHNN

Rt -But -Bu

H2O Ph2P Ru

C

Cp

PPh2

CH2 HNN O

R t -But -Bu

C

CH2 O

R

Hcatalyst

Douglas B. Grotjahndoi:10.1246/cl.2010.908

Pyridyl- and imidazolylphosphines accelerate anti-Markovnikov alkyne hydration and alkene isomerization and deuteration byfactors of 1000 to more than 10000. Evidence for proton transfer and hydrogen bonding in catalytic intermediates comes fromcomputational, mechanistic, and structural studies. Related concepts are being applied to a novel class of protic N-heterocycliccarbene complexes which feature an unusual NH group.

Letter

915 Photocatalytic Styrene Polymerization byNovel Bichromophoric Pd Catalyst HavingLong Excited-state Lifetime

Kei Murata, Masaharu Ito, Akiko Inagaki,* andMunetaka Akita*doi:10.1246/cl.2010.915Electronic Supporting Information

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

Page 2: Chemistry Lettersincrease was 40.2 mass %, which was consistent with the theoretical value calculated from the following reaction. Li 2CuO 2(s) + CO 2(g) CuO(s) + Li 2CO 3(s) Yusuke

918 Highly Active Cs2O/Ru/Pr6O11 as a Catalystfor Ammonia Decomposition

0

20

40

60

80

100

473 523 573 623 673 723 773

Cs2ORb2OK2ONa2O

Li2ONon-

Ru/Pr6O11

Ru/La2O3Cs2ONon-

NH

3co

nver

sion

/%

Temperature/K

equilibrium

Katsutoshi Nagaoka,* Kyoko Honda, MegumiIbuki, Katsutoshi Sato, and Yusaku Takitadoi:10.1246/cl.2010.918Electronic Supporting Information

920 Synthesis of Dichlorobis(1,4-dimesityl-1H-1,2,3-triazol-5-ylidene)palladium [PdCl2-(TMes)2] and Its Application to Suzuki­Miyaura Coupling Reaction

Tatsuhito Nakamura, Kenichi Ogata, andShin-ichi Fukuzawa*doi:10.1246/cl.2010.920Electronic Supporting Information

923 Peculiar Wettability Based on OrientationalChange of Self-assembled HemisphericalPAMAM Dendrimer Layer

Tomohiro Fukuda, Erino Matsumoto, NobuhikoYui, and Yoshiko Miura*doi:10.1246/cl.2010.923Electronic Supporting Information

926 Turn-on Detection of Targeted BiochemicalReactions by Triple Resonance NMR Anal-ysis Using Isotope-labeled Probe

Keigo Mizusawa, Ryuji Igarashi, Kosei Uehira,Yoshimasa Takafuji, Yasuhiko Tabata, HidehitoTochio, Masahiro Shirakawa,* ShinsukeSando,* and Yasuhiro Aoyama*doi:10.1246/cl.2010.926Electronic Supporting Information

929 Redox Catalysis of Halide Ion for FormalCross-dehydrogenative Coupling: BromideIon-catalyzed Direct Oxidative ¡-Acetoxyla-tion of Ketones

O

RR'

H

H

Br− catO

RR'

OAc

Bromide ion-catalyzed oxidative coupling

AcO

[O]

Takashi Nagano,* Zhenhua Jia, Xingshu Li,Ming Yan, Gui Lu, Albert S. C. Chan,* andTamio Hayashi*doi:10.1246/cl.2010.929Electronic Supporting Information

Chemistry Letters Vol.39, No.9 (2010)C-102

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

Page 3: Chemistry Lettersincrease was 40.2 mass %, which was consistent with the theoretical value calculated from the following reaction. Li 2CuO 2(s) + CO 2(g) CuO(s) + Li 2CO 3(s) Yusuke

932 Sub-picosecond UV-pump and IR-probeSpectroscopy of 9-Fluorenone in DeuteratedAcetonitrile and Methanol

UV Pump Pulse Transient IR absorption spectra

IR Probe Pulse

5

4

3

2

1

0

Del

ta A

bs. /

mO

D

15801560154015201500

Wavenumber / cm−1

2 ps8 ps20 ps50 ps

Satori Hirai, Motohiro Banno, Kaoru Ohta,*Dipak K. Palit, and Keisuke Tominaga*doi:10.1246/cl.2010.932

935 Preparation of Dispersible Chitosan Par-ticles with Borate Crosslinking for Anti-microbial and Antifungal Application

NH3+

O

HO

O

NH3+

OH

HO

O

O

NH3+

O

HO

O

NH3+

OH

HO

O

O

O

B-

HO

HO O

OH

HO

O

O

NH3+ n

+B

HO OH

HO OH-

Chitosan-boric acid complex

Shoji Nagaoka,* Kanako Saita, SeitaroKobayashi, Maki Horikawa, TomohiroShirosaki, Makoto Takafuji, and HirotakaIhara*doi:10.1246/cl.2010.935Electronic Supporting Information

938 Synthesis of Siloxene Derivatives with Or-ganic Groups

Si

Si

Si

Si

Si

Si

Si Si Si

H H HSiSiSi

H O H

H HH HO H

HCl

R : OMe

O

ROH

(CH2)11

Si

Si

Si

Si

Si

Si

Si Si Si

SiSiSi

Ca Ca Ca

Si

Si

Si

Si

Si

Si

Si Si Si

SiSiSi

Ca Ca Ca

Si

Si

Si

Si

Si

Si

Si Si Si

SiSiSi

Ca Ca CaCa Ca Ca

Si

Si

Si

Si

Si

Si

Si Si Si

H O HSiSiSi

H H H

O HH HH HR

Si

Si

Si

Si

Si

Si

Si Si Si

H HSiSiSi

H O H

H OH HH H

R

-CaCl2

CaSi2

Organosiloxene

R

R

R

n

n

H

R

Yusuke Sugiyama,* Hirotaka Okamoto, andHideyuki Nakano*doi:10.1246/cl.2010.938Electronic Supporting Information

940 NO Insertion Reaction of Ethyl(nitrosyl)-ruthenium Complex Having Hydrotris(pyr-azolyl)borate and Conversion to Acetaldox-ime and Acetonitrile Complexes

2

O

BNN

NN

H

Ru

NN

NCl

benzene,reflux

PPh3

3

BNN

NN

H

Ru

NN

NCl

PPh3O

4

BNN

NN

H

Ru

NN

NCl

PPh3OH

5

BNN

NN

H

Ru

NN

NCl

PPh3

B

NN

NNHRu NN

Cl

NB

N N

NH RuN

Cl

O

N O

6

benzene,reflux

N

N

Yasuhiro Arikawa,* Shin-ya Tashita, SosekiYamaguchi, Hitomi Miyahara, Taiki Asayama,Keisuke Umakoshi, and Masayoshi Onishidoi:10.1246/cl.2010.940Electronic Supporting Information

942 Aqueous Synthesis of Highly LuminescentAmorphous CdSe Quantum Dots at LowTemperature

PL spectra of CdSe QDs obtained at different temperatures by water bath. Images underirradiation of a handheld ultraviolet lamp, excitation wavelength is 365 nm.

Lianxiang Song, Junling Duan, and JinhuaZhan*doi:10.1246/cl.2010.942Electronic Supporting Information

Chemistry Letters Vol.39, No.9 (2010) C-103

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

Page 4: Chemistry Lettersincrease was 40.2 mass %, which was consistent with the theoretical value calculated from the following reaction. Li 2CuO 2(s) + CO 2(g) CuO(s) + Li 2CO 3(s) Yusuke

944 Fabrication of 3D Co3O4 Homoarchitecturesvia a Novel Template-assisted Coprecipita-tion Process

The 3D Co3O4 hierarchical structures are

and electronics. We have developed

secondary Co3O4 nanowire arrays on

attractive for potential applications aslithium batteries, gas sensor, catalyst,

an effective method to synthesize

primary homogeneous fiber substrates.Chao Pan,* Yonggang Wang, Jieshan Qiu,*Bing Qu, and Jing Wangdoi:10.1246/cl.2010.944Electronic Supporting Information

946 Self-coordinated Phthalocyanine Nanoaggre-gates

Mutsumi Kimura,* Tatsuya Hatanaka, YokoTatewaki, Tadashi Fukawa, and Hirofusa Shiraidoi:10.1246/cl.2010.946

948 Synthesis of Boron-containing CDS-1 Zeoliteby Topotactic Dehydration­Condensation of[B]-PLS-1 Prepared from Layered SilicateH-LDS

H-LDS [B]-PLS-1 [B]-CDS-1B

calcinationDry Gel

Conversion

(010) (100)(100)

Kenichi Komura,* Tomoyuki Murase,Yoshihiro Sugi, and Mamoru Koketsudoi:10.1246/cl.2010.948Electronic Supporting Information

950 Indigo Dye as a Positive-electrode Materialfor Rechargeable Lithium Batteries

Masaru Yao,* Miho Araki, Hiroshi Senoh,Shin-ichi Yamazaki, Tetsuo Sakai, and KazuakiYasudadoi:10.1246/cl.2010.950Electronic Supporting Information

953 Intramolecular Excitation Energy Transferfrom Visible-light Absorbing ChlorophyllDerivatives to a Near-infrared-light EmittingBoron Dipyrromethene Moiety

NH N

HNN

O

N

N

N

O

O

BF

F

OO

O

O

Visiblelight

Near-infrared

light

Energy transfer

Yumiko Kataoka, Yutaka Shibata, and HitoshiTamiaki*doi:10.1246/cl.2010.953Electronic Supporting Information

Chemistry Letters Vol.39, No.9 (2010)C-104

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

Page 5: Chemistry Lettersincrease was 40.2 mass %, which was consistent with the theoretical value calculated from the following reaction. Li 2CuO 2(s) + CO 2(g) CuO(s) + Li 2CO 3(s) Yusuke

956 Photochromic Nucleobase Photoisomerizedby Visible Light

Shinzi Ogasawara,* Syoji Ito, HiroshiMiyasaka, and Mizuo Maedadoi:10.1246/cl.2010.956Electronic Supporting Information

958 Liquid­Liquid Relaxation in the Super-cooled Liquid State of Ethylbenzene: Ther-mal Studies Using a Prototype DTA Sensorfor the Study of Vapor-deposited Samples A DTA sensor was fabricated for the in situ study

deposited in a high vacuum. Using this, the optical

of ethylbenzene was confirmed to accompany a

of structural relaxation of molecular glass vapor-

anomaly observed for the supercooled liquid state

liquid-to-liquid relaxation phenomenon.

Kikujiro Ishii,* Yuki Yokoyama, RyoMoriyama, and Hideyuki Nakayamadoi:10.1246/cl.2010.958

961 Supercritical Hydrothermal Synthesis ofCarboxylic Acid-surface-functionalized TiO2

Nanocrystals: pH Sensitive Dispersion andHybridization with Organic Compounds

Highly surface functionalized TiO2 (anatase) nanocrystals were synthesized by supercriticalhydrothermal method. The surface modifier layer of the TiO2 nanocrystal revealedextraordinarily high thermal and chemical stability. Because of the functional modification,the TiO2 nanocrystals showed sharp pH sensitivie dispersion.

Toshihiko Arita,* Ken-ichi Moriya, KimitakaMinami, Takashi Naka, and TadafumiAdschiri*doi:10.1246/cl.2010.961Electronic Supporting Information

964 Epitaxial Growth of Faceted Co Nanopar-ticles on Sapphire Surfaces

Yui Ogawa, Hiroki Ago,* and Masaharu Tsujidoi:10.1246/cl.2010.964

966 Synthesis and CO2 Absorption Properties ofSingle-phase Li2CuO2 as a CO2 Absorbent

Mass change of the single-phase Li2CuO2

synthesized with quenching rate of 24.5°C s−1 was measured under 100 vol %CO2 atmosphere from room temperatureto 1000 °C at 5 °C min−1 of the heatingrate. The measured maximum massincrease was 40.2 mass %, which wasconsistent with the theoretical valuecalculated from the following reaction.

Li2CuO2(s) + CO2(g) CuO(s) + Li2CO3(s)

Yusuke Matsukura, Takeshi Okumura, RyotaKobayashi, and Katsuyoshi Oh-ishi*doi:10.1246/cl.2010.966

Chemistry Letters Vol.39, No.9 (2010) C-105

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

Page 6: Chemistry Lettersincrease was 40.2 mass %, which was consistent with the theoretical value calculated from the following reaction. Li 2CuO 2(s) + CO 2(g) CuO(s) + Li 2CO 3(s) Yusuke

968 Resolution of 1,2,3,3a,4,8b-Hexahydrocyclo-penta[b]indole via Diastereomeric Salt For-mation with N-Tosyl-(R)-phenylglycine

rac-1

NH

COOH

HN Ts

NH

NH

(R )-2

(3aS,8bS )-1

(3aR,8bR )-1EtOH

+

+

seeding

seeding

(3aR,8bR )-1 / (R )-2 salt

(3aS,8bS )-1 / (R )-2 salt

Shinji Higashijima,* Yukiko Inoue, TakayaMaehashi, Hidetoshi Miura, Yasuhiro Kubota,Kazumasa Funabiki, and Masaki Matsuidoi:10.1246/cl.2010.968Electronic Supporting Information

970 Control of Ag+ Permeation by Na+ Concen-tration on the Basis of Volume Change inPoly(acrylic acid) Gel

Kazutake Takada,* Atsushi Shibata, and AkioYuchidoi:10.1246/cl.2010.970Electronic Supporting Information

972 Selective Methanation of CO in ReformateGas over Ni/TiO2 Catalyst

Selective methanation of CO was performed over Ni/TiO2. CO in reformate gas was completelyremoved at 150–300 °C. The CH4 concentration in the outlet gas could be maintained below 1%in the whole temperature region because Ni/TiO2 suppressed the CO2 methanation. It can beconsidered that the formation of CO by the reverse water-gas-shift reaction is blocked by theapplication of TiO2 to the support of Ni catalyst and that it results in the high CO/CO2

selectivity of Ni/TiO2.

10wt%Ni/TiO2

10wt%Ni/Al2O3

10wt%Co/TiO2

0.5wt%Ru/Al2O3

0

0.05

0.1

0.15

0.2

0.25

150 200 250 300Temperature / °C

CO

con

cent

ratio

n / %

0

0.5

1

1.5

2

2.5

3

150 200 250 300Temperature / °C

CH

4 c

once

ntra

tion

/ %

Kohei Urasaki, Yuta Tanpo, Tomoki Takahiro,Jayaraj Christopher, Ryuji Kikuchi, ToshinoriKojima, and Shigeo Satokawa*doi:10.1246/cl.2010.972

974 Morphology of Rare-earth (Y, Sm) Nano-structures Synthesized by the Surfactant-assembled Method

Katsura Nishiyama,* Takashi Hanamoto,Hirotake Shigematsu, Keitaro Kitada, KaiIketaki, Toshihiko Kaji, and Masahiro Hiramotodoi:10.1246/cl.2010.974

976 Effect of Surface-oxidized Structure of Sin-gle-walled Carbon Nanotubes on Hetero-geneous Direct Electron-transfer Reactionof Cytochrome c

No redox wave of cytochrome c was

redox wave of cytochrome c with

observed at UV−ozone-treated SWCNT-

observed at Au electrode modified withas-grown SWCNTs. Well-defined

diffusion-controlled process was

modified Au electrode. Masato Tominaga,* Hiroyuki Yamaguchi,Shingo Sakamoto, and Isao Taniguchidoi:10.1246/cl.2010.976

Chemistry Letters Vol.39, No.9 (2010)C-106

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

Page 7: Chemistry Lettersincrease was 40.2 mass %, which was consistent with the theoretical value calculated from the following reaction. Li 2CuO 2(s) + CO 2(g) CuO(s) + Li 2CO 3(s) Yusuke

978 Thermally Two-stepped Spin TransitionsInduced by Intramolecular Electron Trans-fers in a Cyanide-bridged Molecular Square

Masayuki Nihei, Yoshihiro Sekine, NaokiSuganami, and Hiroki Oshio*doi:10.1246/cl.2010.978Electronic Supporting Information

980 Facile Synthesis of Hierarchical AluminaMonoliths with Tubular Macropores andOrdered Mesoporous Walls

Nonwoven fabric was employed as themacropore template, leading to the formationof alumina monolith with hierarchicallymacro/mesoporous structure. The incorporation

ordered mesoporous alumina, and the obtainedmonolith shows high thermal stability up to900 °C.

of macropores does not disturb the regularity of

Kuibao Zhang, Zhengyi Fu,* Jinyong Zhang,Tadachika Nakayama, Koichi Niihara, andSooWohn Leedoi:10.1246/cl.2010.980

983 Study on a Novel Two-dimensional HPLCand Wide-bore Electrophoresis System

By precisely fixing the inner cooling capillary to the center of a quartz tube and introducing asolitary injection capillary, a new and better wide-bore electrophoresis (WBE) system wasbuilt and has shown great potential. Further, a novel high-performance two-dimensional hybridof HPLC and WBE (HPLC–WBE) was developed with a injection valve as the interface.High-resolution separations were observed in both the improved WBE system and the2D HPLC–WBE system.

Youxin Li, Xin Fang, Shibin Zhao, TingtingZhai, Xiaochun Sun, and James Jianmin Bao*doi:10.1246/cl.2010.983Electronic Supporting Information

986 Seven-coordinate Rhenium(III) Complexeswith a Labile Coordination Site Assembledon Indium-doped Tin Oxide (ITO) Elec-trodes: Catalytic Reduction of Dioxygen toHydrogen Peroxide

Hideki Sugimoto,* Hiroyuki Tano, HiroyukiMiyake, and Shinobu Itoh*doi:10.1246/cl.2010.986Electronic Supporting Information

989 Synthesis and Properties of 1,3-Dithiole-[5]dendralenes with Two Thiophene Spacers

S S

S SS S S S

SS SS

S S

SS SSS S

SS SS+

+

+

+

S S

S SS S S S

SS SS+

+

+

+

S S

S SS S S

SS SS+

• •

+

+

+

32+ 34+

36+

S S

S SS SS S

SS SS+

+

+

++

35+•

−2e

+2e

−2e

+2e

−e

+e

−e

+e

3

Hiroaki Horiuchi and Yohji Misaki*doi:10.1246/cl.2010.989Electronic Supporting Information

Chemistry Letters Vol.39, No.9 (2010) C-107

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

Page 8: Chemistry Lettersincrease was 40.2 mass %, which was consistent with the theoretical value calculated from the following reaction. Li 2CuO 2(s) + CO 2(g) CuO(s) + Li 2CO 3(s) Yusuke

992 Label-free Biosensor Using Polyion-modifiedGold Nanorods Adsorbed on a Glass Sub-strate

Antigen−antibody binding resulted in the peak shifts (44 nm) of the SP band shift of polyion-modified gold nanorods on a glass substrate.

Kanako Honda,* Hirofumi Kawazumi,Naotoshi Nakashima, and Yasuro Niidome*doi:10.1246/cl.2010.992

994 Fabrication and Enhanced Rectifying Per-formance of Zn1¹xCoxO Nanowall VerticallyGrowing on Si Wafer

ZnO and Co-doped ZnO mesocrystalline nanowall/p-Si heterojunctions are prepared bya chemical precursor route, which exhibits a rectifying behavior with a lower turn-onvoltage tuned by Co2+ dopant concentration.

-2 -1 0 1 2

0.0

0.6

1.2

1.8

2.4

3.0

Bias Voltage/V

ZnOZn

0.993Co

0.007O

Zn0.986

Co0.014

O

Cu

rren

t/m

A

Guoxing Zhu, Yuanjun Liu, Chi Zhang,Zonglong Zhu, and Zheng Xu*doi:10.1246/cl.2010.994Electronic Supporting Information

996 Gel-phase Extraction for the Removal ofHeavy-metal Ions

Heavy-metal ions permeate across anion-exchange membrane and are fixedin the gel phase containing precipitating

are co-ions of the ion-exchangemembrane.

reagents or chelating reagents, which

Manabu Igawa,* Hirohito Kanamori, and BenNanzaidoi:10.1246/cl.2010.996

998 A Novel Method to Discriminate betweenPlant- and Petroleum-derived Plastics byStable Carbon Isotope Analysis

C3 plants

-35

-30

-25

-20

-15

-10

-5

C

arbo

n is

otop

ic c

ompo

sitio

n (‰

, vs.

PD

B)

Corn(C4 plant)

Rice(C3 plant)

Plastic(Rice)

Plastic(Corn)

Plastic(Petroleum)

Sugarcane(C4 plant)

Potato(C3 plant)

Wheat(C3 plant)

Corn-derivedplastic

Petroleum-derivedplastic

Rice-derivedplastic

C4 plants

Yaeko Suzuki,* Fumikazu Akamatsu, RumikoNakashita, and Takashi Korenagadoi:10.1246/cl.2010.998

1000 Covalent Attachment of Organic Groupsonto Single-walled Carbon Nanotubes viaCopper(I)-promoted Radical Addition

R-Cl

CuCl, bPy, CuR

n

Yongsheng Li,* Chunhua Xu, and Yaomin Xudoi:10.1246/cl.2010.1000Electronic Supporting Information

Chemistry Letters Vol.39, No.9 (2010)C-108

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

Page 9: Chemistry Lettersincrease was 40.2 mass %, which was consistent with the theoretical value calculated from the following reaction. Li 2CuO 2(s) + CO 2(g) CuO(s) + Li 2CO 3(s) Yusuke

1002 Synthetic Studies on the Natural MultidrugResistance Modulator, Irciniasulfonic Acid B

Synthetic studies on the natural MDR modulator irciniasulfonic acid (ISA)-B utilizing crossmetathesis and the Horner−Wadsworth−Emmons olefination.

O

OH

OH

O

OH

NH

O

OH

SO3H

Chisato Emura, Ryuichi Higuchi, andTomofumi Miyamoto*doi:10.1246/cl.2010.1002

1004 Reversible Aggregation and Deaggregationof Helicene-grafted Chiral Silica Nanopar-ticles Induced by Aromatic Solvents

Silica nanoparticles of 210 and 440-nm sizes were grafted with (P)- and (Mn)-1,12-

trimethoxysilane. The chiral nanoparticles deaggregated and aggregated in soft and hardaromatic solvents. When sonicated in iodobenzene, a soft solvent, the nanoparticles weredispersed at a concentration of 0.2nmgnmL-1. In hard benzotrifluoride, aggregation occurred,forming blocks of 5600nnm size. In bromobenzene, chlorobenzene, and toluene, aggregates

dimethylbenzo[c]phenanthrenes by silane coupling with helicenamidated (3-aminopropyl)-

of intermediate sizes were formed. The process was reversible, and when blocks formed inbenzotrifluoride were sonicated in iodobenzene, bromobenzene, chlorobenzene, and toluene,smaller aggregates formed. The CD spectra of the aggregates exhibited larger Cotton effects.

Zengjian An, Yoshizumi Yasui, TakanariTogashi, Tadafumi Adschiri, Shunpei Hitosugi,Hiroyuki Isobe, Takeshi Higuchi, MasatsuguShimomura, and Masahiko Yamaguchi*doi:10.1246/cl.2010.1004Electronic Supporting Information

1006 Trialkyl(pentafluorocyclotriphosphazenyl)-ammonium Bis(trifluoromethylsulfonyl)-imide Acting as Nonflammable Room-tem-perature Ionic Liquids

N

N

PN

P

NP

F

F

F

F

F

R1

R2

R2

ClN

PN

P

NP

ClF

F

F

F

F

N

O

O

CF3S

O

O3C

Et2O CHCl3

NR1R22 Li+TFSI-

[Nmnn Cpz][Cl]Cpz-Cl

N444Cpz; m = n = 4

TFSI- = F

N888Cpz; m = n = 8

N411Cpz; m = 4, n = 1

N611Cpz; m = 6, n = 1

[Nmnn Cpz][TFSI]

R1 = -(CH2)m-H

R2 = -(CH2)n-H

S

Tsutomu Shiragami,* Yoko Nakamura, JinMatsumoto, Masashi Otsuki, and MasahideYasudadoi:10.1246/cl.2010.1006Electronic Supporting Information

1008 PEGylated Polymer Micelle-based NitricOxide (NO) Photodonor with NO-mediatedAntitumor Activity

Naoki Kanayama, Kazuhiro Yamaguchi, andYukio Nagasaki*doi:10.1246/cl.2010.1008Electronic Supporting Information

1010 A Facile Approach for Preparing Poly-methylphenylsilsesquioxane with Well-de-fined Ladder Structure via NonhydrolyticCondensation Well-ordered ladder-like poly-

methylphenylsilsesquioxane wassynthesized by a nonhydrolyticcondensation approach for the firsttime, which is easy to carry out withreadily available starting materials.Xiu Wei Jia, Min Zhi Rong,* Ming Qiu

Zhang,* and Xiao Ji Yedoi:10.1246/cl.2010.1010Electronic Supporting Information

Chemistry Letters Vol.39, No.9 (2010) C-109

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

Page 10: Chemistry Lettersincrease was 40.2 mass %, which was consistent with the theoretical value calculated from the following reaction. Li 2CuO 2(s) + CO 2(g) CuO(s) + Li 2CO 3(s) Yusuke

1013 Asymmetric Allylation of Aldehydes Cata-lyzed by Simple Dual Small Organic Mole-cules: L-Proline and L-Prolinol

A novel and simple methodology for the asymmetric allylation of aldehydes was reported.Double small organic molecules such as L-proline and L-prolinol were first employed forproviding chiral environment so as to afford the chiral homoallylic alcohols in high yieldsand moderate enantioselectivities in our protocol.

+R-CHO4ÅMS, CH2Cl2

Ph

OH

**SnBr

2.0 equiv L-proline

–78 °C, 10 h

1.1 equiv L-prolinol

3

Yield 64-90%ee 32-64%

Guo-hong Chen, Ling-yan Liu,* Xiao-ningWei, Wei-xing Chang, and Jing Li*doi:10.1246/cl.2010.1013

1016 Trifluoromethanesulfonate Anion-linkedSupramolecular Frameworks of Cucurbit-[5]uril and Cucurbit[7]uril

Two crystals based on cucurbit[5]uril

acid and structurally determined bysingle-crystal X-ray diffraction analyses.These two crystal structuresdemonstrated that the highly orderedtrifluoromethanesulfonate anions playessential roles in the formation ofthree-dimensionalframeworks with 1D channels.

and cucurbit[7]uril have beensynthesized in trifluoromethanesulfonic

supramolecularJie Zhang, Huifang Ren, and Li Liu*doi:10.1246/cl.2010.1016Electronic Supporting Information

1018 Preparation of Well-defined Nanometer-sized Layered Double Hydroxides by NovelpH Adjustment Method Using Ion-exchangeResin

Konomi Nitoh, Andre Ayral, and MakotoOgawa*doi:10.1246/cl.2010.1018

Chemistry Letters Vol.39, No.9 (2010)C-110

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