Rational Monomer Design towards 2D Polymers: Synthesis of a Macrocycle with Three 1,8-Anthrylene Units

被引：30

作者：

Kissel, Patrick ^{[1
]}

Schlueter, A. Dieter ^{[1
]}

Sakamoto, Junji ^{[1
]}

机构：

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

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 36期

关键词：

anthracenes; cross-coupling; photodimerization; macrocycles; topochemical polymerization; ANTHRACENE-ACETYLENE OLIGOMERS; MULTIGRAM-SCALE SYNTHESIS; BUILDING-BLOCKS; PHOTODIMERIZATION; POLYMERIZATION; MONOLAYERS; CHEMISTRY; PHOTOCHEMISTRY; CONSTRUCTION; GRAPHENE;

D O I：

10.1002/chem.200900781

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A study was conducted to demonstrate the synthesis of a macrocycle with three 1,8-anthrylene units. Anthracene units were selected as connection sites to conduct the investigations. The 1,8-anthrylene building blocks were prepared starting from 1-(triisopropylsilyl)ethynyl-8-(trimrthylsilyl)e-thynyl-anthracene and 1,8-di[(trimethylsilyl)ethynyl]anthracene. The set of building blocks were iteratively assembled into the target compound on the basis of the Sonogashira cross-coupling protocol. Feasibility of the synthesis of the macrocycle was successfully demonstrated by iterative use of palladium-catalyzed cross-coupling protocols. Milligram-scale synthesis of the macrocycle and a similar structure that carried OH groups were investigated.

引用

页码：8955 / 8960

页数：6

共 59 条

[1]

[Anonymous], 2009, ANGEW CHEM INT EDIT

[2]

[Anonymous], 1968, CLAY MINER

[3] TEMPLATE SYNTHESIS OF 2-DIMENSIONAL NETWORK OF CROSS-LINKED ACRYLATE POLYMER IN A CAST MULTIBILAYER FILM [J].

ASAKUMA, S ;

OKADA, H ;

KUNITAKE, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (05) :1749-1755

[4] UNIMOLECULAR PHOTOCHEMISTRY OF ANTHRACENES [J].

BECKER, HD .

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

[5] POLYMERIZATION OF MONOLAYERS OF VINYL AND DIVINYL MONOMERS [J].

BEREDJICK, N ;

BURLANT, WJ .

JOURNAL OF POLYMER SCIENCE PART A-1-POLYMER CHEMISTRY, 1970, 8 (10) :2807-+

[6] Expanding the registry of aromatic amide foldamers: Folding, photochemistry and assembly using diaza-anthracene units [J].

Berni, Ernanuela ;

Dolain, Christel ;

Kauffmann, Brice ;

Leger, Jean-Michel ;

Zhan, Chuanlang ;

Huc, Ivan .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (07) :2687-2694

[7] POLYMERIZATION OF ADSORBED MONOLAYERS .I. PREPARATION OF CLAY-POLYMER COMPLEX [J].

BLUMSTEIN, A .

JOURNAL OF POLYMER SCIENCE PART A-GENERAL PAPERS, 1965, 3 (7PA) :2653-+

[8] 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

[9] 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

[10] INTERFACIAL CROSS-LINKING POLYMERIZATION PROCESS IN OIL-WATER EMULSIONS [J].

BREDIMAS, M ;

VEYSSIE, M ;

STRZELECKI, L ;

LIEBERT, L .

COLLOID AND POLYMER SCIENCE, 1977, 255 (10) :975-979

← 1 2 3 4 5 6 →