Regioselective Ru-Catalyzed Direct 2,5,8,11-Alkylation of Perylene Bisimides

被引：119

作者：

Nakazono, Satomi ^{[1
]}

Imazaki, Yusuke ^{[1
]}

Yoo, Hyejin ^{[3
]}

Yang, Jaesung ^{[3
]}

Sasamori, Takahiro ^{[4
]}

Tokitoh, Norihiro ^{[4
]}

Cedric, Tassel ^{[1
]}

Kageyama, Hiroshi ^{[1
]}

Kim, Dongho ^{[3
]}

Shinokubo, Hiroshi ^{[2
]}

Osuka, Atsuhiro ^{[1
]}

机构：

[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan

[2] Nagoya Univ, Dept Appl Chem, Grad Sch Engn, Chikusa Ku, Nagoya, Aichi 4648603, Japan

[3] Yonsei Univ, Dept Chem, Seoul 120749, South Korea

[4] Kyoto Univ, Inst Chem Res, Kyoto 6110011, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 31期

关键词：

alkylation; fluorescence; perylenes; ruthenium; single-molecule studies; CARBON-HYDROGEN BONDS; FLUORESCENCE; STABILITY; ENERGY; CHARGE; DYES;

D O I：

10.1002/chem.200901318

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A study was conducted to demonstrate the first selective synthesis of 2,5,8,11-substituted perlylene tetracarboxylic acid bisimides (PBI). A mixture of bis(N-ethylpropyl)PBI and trimethylvinylsilane was heated in mesitylene at 165°C for 60 hours in the presence of of 6 mol% of [RuH2(CO) (PPh3)3]. Tetraalkylated PBI was obtained in 94% yield after silica-gel separation. It was found that the alkylation of N-(2,6-diisopropyl)phenylPBI needed longer reaction times due to its lower solubility, but afforded the desired product in quantitative yield. It was observed that solubility in organic solvents was significantly enhanced after tetraalkylation. It was also found that the alkylation was unable to change the absorption and emission properties in the solution state significantly, but lowered molar extinction coefficients of the lowest energy absorption band.

引用

页码：7530 / 7533

页数：4

共 24 条

[1] Cyanated perylene-3,4-dicarboximides and perylene-3,4:9,10-bis(dicarboximide):: Facile chromophoric oxidants for organic photonics and electronics [J].

Ahrens, MJ ;

Fuller, MJ ;

Wasielewski, MR .

CHEMISTRY OF MATERIALS, 2003, 15 (14) :2684-2686

[2]

ASAMI T, 1998, Patent No. 10306216

[3] Novel core-expanded rylenebis(dicarboximide) dyes bearing pentacene units:: Facile synthesis and photophysical properties [J].

Avlasevich, Yuri ;

Mueller, Sibylle ;

Erk, Peter ;

Muellen, Klaus .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (23) :6555-6561

[4] Energy dissipation in multichromophoric single dendrimers [J].

De Schryver, FC ;

Vosch, T ;

Cotlet, M ;

Van der Auweraer, M ;

Müllen, K ;

Hofkens, J .

ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (07) :514-522

[5] From industrial colorants to single photon sources and biolabels:: The fascination and function of rylene dyes [J].

Herrmann, Andreas ;

Muellen, Klaus .

CHEMISTRY LETTERS, 2006, 35 (09) :978-985

[6] Tuning orbital energetics in arylene diimide semiconductors. Materials design for ambient stability of n-type charge transport [J].

Jones, Brooks A. ;

Facchetti, Antonio ;

Wasielewski, Michael R. ;

Marks, Tobin J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (49) :15259-15278

[7] Catalytic C-H/olefin coupling [J].

Kakiuchi, F ;

Murai, S .

ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (10) :826-834

[8] CATALYTIC ADDITION OF AROMATIC CARBON-HYDROGEN BONDS TO OLEFINS WITH THE AID OF RUTHENIUM COMPLEXES [J].

KAKIUCHI, F ;

SEKINE, S ;

TANAKA, Y ;

KAMATANI, A ;

SONODA, M ;

CHATANI, N ;

MURAI, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1995, 68 (01) :62-83

[9] A novel fluorescent dye with strong, anisotropic solid-state fluorescence, small stokes shift, and high photostability [J].

Langhals, H ;

Krotz, O ;

Polborn, K ;

Mayer, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (16) :2427-2428

[10] CYCLIC CARBOXYLIC IMIDE STRUCTURES AS STRUCTURE ELEMENTS OF HIGH-STABILITY - NOVEL DEVELOPMENTS IN PERYLENE DYE CHEMISTRY [J].

LANGHALS, H .

HETEROCYCLES, 1995, 40 (01) :477-500

← 1 2 3 →