An acid-base switchable [2]rotaxane

被引：130

作者：

Elizarov, AM ^{[1
]}

Chiu, SH ^{[1
]}

Stoddart, JF ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 26期

关键词：

D O I：

10.1021/jo020373d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chemically addressable, bistable [2]rotaxane, which incorporates a dumbbell-shaped component containing both secondary dialkylammonium and 1,2-bis(pyridinium)ethane recognition sites for its ring component, dibenzo[24]crown-8 (DB24C8), has been assembled. H-1 NMR spectroscopy has demonstrated that deprotonation (and reprotonation) of the secondary dialkylammonium (dialkylamine) recognition site induces the DB24C8 ring to move away from this site to the 1,2-bis(pyridinium)ethane one (and back again) in a discrete manner, particularly when the experiment is performed in CDCl3 solution.

引用

页码：9175 / 9181

页数：7

共 56 条

[31] Applying biological principles to the assembly and selection of synthetic superstructures [J].

Greig, LM ;

Philp, D .

CHEMICAL SOCIETY REVIEWS, 2001, 30 (05) :287-302

[32] Cyclodextrin-based molecular machines [J].

Harada, A .

ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (06) :456-464

[33] Single-molecule optomechanical cycle [J].

Hugel, T ;

Holland, NB ;

Cattani, A ;

Moroder, L ;

Seitz, M ;

Gaub, HE .

SCIENCE, 2002, 296 (5570) :1103-1106

[34] Quantitative and spontaneous formation of a doubly interlocking [2]catenane using copper(I) and palladium(II) as templating and assembling centers [J].

Ibukuro, F ;

Fujita, M ;

Yamaguchi, K ;

Sauvage, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (47) :11014-11015

[35]

Jortner J., 1997, MOL ELECT

[36] Organic "magic rings" - The hydrogen bond-directed assembly of catenanes under thermodynamic control [J].

Kidd, TJ ;

Leigh, DA ;

Wilson, AJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (07) :1599-1600

[37] Unusually lowered acidity of ammonium group surrounded by crown ether in a rotaxane system and its acylative neutralization [J].

Kihara, N ;

Tachibana, Y ;

Kawasaki, H ;

Takata, T .

CHEMISTRY LETTERS, 2000, (05) :506-507

[38] GAINING CONTROL OVER MOLECULAR THREADING - BENEFITS OF 2ND COORDINATION SITES AND AQUEOUS-ORGANIC INTERFACES IN ROTAXANE SYNTHESIS [J].

KOLCHINSKI, AG ;

BUSCH, DH ;

ALCOCK, NW .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (12) :1289-1291

[39] [2]rotaxane molecular shuttles employing 1,2-bis(pyridinium)ethane binding sites and dibenzo-24-crown-8 ethers [J].

Loeb, SJ ;

Wisner, JA .

CHEMICAL COMMUNICATIONS, 2000, (19) :1939-1940

[40] 1,2-bis(4,4′-dipyridinium)ethane:: a versatile dication for the formation of [2]rotaxanes with dibenzo-24-crown-8 ether [J].

Loeb, SJ ;

Wisner, JA .

CHEMICAL COMMUNICATIONS, 1998, (24) :2757-2758

← 1 2 3 4 5 6 →