Aqueous Assembly of Zwitterionic Daisy Chains

被引：9

作者：

Aeschi, Yves ^{[1
,2
]}

Drayss-Orth, Sylvie ^{[1
]}

Valasek, Michal ^{[3
]}

Haussinger, Daniel ^{[1
]}

Mayor, Marcel ^{[1
,2
,3
,4
]}

机构：

[1] Univ Basel, Dept Chem, St Johanns Ring 19, CH-4056 Basel, Switzerland

[2] Univ Basel, Swiss Nanosci Inst, Klingelbergstr 82, CH-4056 Basel, Switzerland

[3] Karlsruhe Inst Technol, Inst Nanotechnol INT, POB 3640, D-76021 Karlsruhe, Germany

[4] Sun Yat Sen Univ, Sch Chem, LIFM, Guangzhou 510275, Guangdong, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2019年 / 25卷 / 01期

基金：

瑞士国家科学基金会;

关键词：

click-chemistry; cyclophane; daisy chain; hydrophobic complexation; rotaxane; DONOR-ACCEPTOR; CYCLOPHANE; EXCHANGE; COMPLEXATION; MOLECULES; ROTAXANES; BINDING;

D O I：

10.1002/chem.201803944

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis and characterization of zwitterionic molecular [c2]- and [a2]-daisy chains are described, relying on recognition of a positively charged cyclophane and a negatively charged oligo(phenylene-ethynylene) (OPE) rod in aqueous medium. For this purpose, syntheses of an acetylene-functionalized macrocyclic receptor and a water-soluble OPE-rod as the guest component are presented, from which a heteroditopic daisy chain monomer was prepared. This monomer aggregated strongly in water/methanol 4:1 and formed molecular daisy chains, which were isolated as interlocked species from a stoppering reaction at 1 mm concentration. The cyclic dimer [c2] was the main product with an isolated yield of 30 % and consisted of a mixture of diastereomers, as evidenced by H-1 NMR spectroscopy.

引用

页码：285 / 295

页数：11

共 67 条

[1] Assembly of [2]Rotaxanes in Water [J].

Aeschi, Yves ;

Drayss-Orth, Sylvie ;

Valasek, Michal ;

Raps, Felix ;

Haussinger, Daniel ;

Mayor, Marcel .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (28) :4091-4103

[2] Azo-dye rotaxanes [J].

Anderson, S ;

Claridge, TDW ;

Anderson, HL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (12) :1310-1313

[3] An approach to insulated molecular wires: synthesis of water-soluble conjugated rotaxanes [J].

Anderson, S ;

Aplin, RT ;

Claridge, TDW ;

Goodson, T ;

Maciel, AC ;

Rumbles, G ;

Ryan, JF ;

Anderson, HL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (15) :2383-2397

[4]

ANDERSON S, 1997, ANGEW CHEM, V109, P1367

[5]

[Anonymous], ANGEW CHEM

[6]

[Anonymous], ANGEW CHEM

[7]

[Anonymous], 2004, KnochelAngew. Chem., DOI DOI 10.1002/ANGE.200454084

[8]

Ashton PR, 1998, ANGEW CHEM INT EDIT, V37, P1294, DOI 10.1002/(SICI)1521-3773(19980518)37:9<1294::AID-ANIE1294>3.0.CO

[9]

2-F

[10] CATALYTIC CYCLOPHANES .5. CATALYTIC CYCLOPHANES - A PORPHYRIN-BRIDGED CYCLOPHANE AS A MODEL FOR CYTOCHROME-P-450 ENZYMES [J].

BENSON, DR ;

VALENTEKOVICH, R ;

DIEDERICH, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (02) :191-193

← 1 2 3 4 5 6 7 →