Triply Threaded [4]Rotaxanes

被引：45

作者：

Danon, Jonathan J. ^{[1
]}

Leigh, David A. ^{[1
,2
]}

McGonigal, Paul R. ^{[2
]}

Ward, John W. ^{[1
]}

Wu, Jhenyi ^{[2
]}

机构：

[1] Univ Manchester, Sch Chem, Oxford Rd, Manchester M13 9PL, Lancs, England

[2] Univ Edinburgh, Sch Chem, Kings Bldg,West Mains Rd, Edinburgh EH9 3JJ, Midlothian, Scotland

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 38期

基金：

英国工程与自然科学研究理事会;

关键词：

ACTIVE-TEMPLATE SYNTHESIS; SWITCHABLE MOLECULAR SHUTTLES; ROTAXANES STABILIZATION; BLOCKING GROUP; RING; MACROCYCLES; CLICK; SIZE; STABILITY; PATHWAY;

D O I：

10.1021/jacs.6b07733

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

[4]Rotaxanes featuring three axles threaded through a single ring have been prepared through active metal template synthesis. Nickel-catalyzed sp(3)-sp(3) hornocouplings of alkyl bromide "half-threads" through 37- and 38-membered 2,2':6',2"-terpyridyl macrocycles generate triply threaded [4]rotaxanes in up to 11% yield. An analogous 39-membered macrocycle produced no rotaxane products under similar conditions. The constitutions of the [4]rotaxanes were determined by NMR spectroscopy and mass spectrometry. Doubly threaded [3]rotaxanes were also obtained from the reactions but no [2]rotaxanes were isolated, suggesting that upon demetalation the axle of a singly threaded rotaxane can slip through a macrocycle that is sufficiently large to accommodate three threads.

引用

页码：12643 / 12647

页数：5