Macrocyclic Amphiphiles with 1,8-Anthrylene Fluorophores: Synthesis and Attempts toward Two-Dimensional Organization

被引：25

作者：

Kissel, Patrick ^{[1
]}

van Heijst, Jeroen ^{[1
]}

Enning, Raoul ^{[2
]}

Stemmer, Andreas ^{[2
]}

Schlueter, A. Dieter ^{[1
]}

Sakamoto, Junji ^{[1
]}

机构：

[1] ETH, Dept Mat, Polymer Chem Lab, CH-8093 Zurich, Switzerland

[2] Nanotechnol Grp, Dept Mech & Proc Engn, CH-8092 Zurich, Switzerland

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 12期

基金：

瑞士国家科学基金会;

关键词：

ANTHRACENE-ACETYLENE OLIGOMERS; MULTIGRAM-SCALE SYNTHESIS; SHAPE-PERSISTENT; PHOTODIMERIZATION; CHEMISTRY; UNITS;

D O I：

10.1021/ol100877g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New macrocyclic amphiphiles with two or three integrated 1,8-anthrylenes have been synthesized by an iterative Sonogashira cross-coupling protocol. The final cyclization has been conducted with 80% yield under cuprous-free dilution conditions. Formation of a monolayer at the air/water interface has also been demonstrated. These results open the intriguing possibility to construct large 2D supramolecular/macromolecular systems for which unique photophysical and -chemical properties are expected.

引用

页码：2778 / 2781

页数：4

共 23 条

[1] Mono- and multilayer formation by diazonium reduction on carbon surfaces monitored with atomic force microscopy "scratching" [J].

Anariba, F ;

DuVall, SH ;

McCreery, RL .

ANALYTICAL CHEMISTRY, 2003, 75 (15) :3837-3844

[2] UNIMOLECULAR PHOTOCHEMISTRY OF ANTHRACENES [J].

BECKER, HD .

CHEMICAL REVIEWS, 1993, 93 (01) :145-172

[3] Photodimerization of anthracenes in fluid solution: structural aspects [J].

Bouas-Laurent, H ;

Castellan, A ;

Desvergne, JP ;

Lapouyade, R .

CHEMICAL SOCIETY REVIEWS, 2000, 29 (01) :43-55

[4] Photodimerization of anthracenes in fluid solutions: (part 2) mechanistic aspects of the photocycloaddition and of the photochemical and thermal cleavage [J].

Bouas-Laurent, H ;

Castellan, A ;

Desvergne, JP ;

Lapouyade, R .

CHEMICAL SOCIETY REVIEWS, 2001, 30 (04) :248-263

[5]

*CCDC, 772825 CCDC

[6] The sonogashira reaction:: A booming methodology in synthetic organic chemistry [J].

Chinchilla, Rafael ;

Najera, Carmen .

CHEMICAL REVIEWS, 2007, 107 (03) :874-922

[7] PALLADIUM CATALYZED SYNTHESIS OF ARYL, HETEROCYCLIC AND VINYLIC ACETYLENE DERIVATIVES [J].

DIECK, HA ;

HECK, FR .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 93 (02) :259-263

[8]

Grave C, 2002, EUR J ORG CHEM, V2002, P3075

[9]

HEGER M, 1993, SURF SCI, V291, P39

[10] An easy and multigram scale synthesis of anthracene-1,8-ditriflate [J].

Kissel, Patrick ;

Weibel, Fabian ;

Federer, Lukas ;

Sakamoto, Junji ;

Schlueter, A. Dieter .

SYNLETT, 2008, (12) :1793-1796

← 1 2 3 →