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
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
收藏
页码:9175 / 9181
页数:7
相关论文
共 56 条
[51]  
2-E
[52]   On the way to rotaxane-based molecular motors:: Studies in molecular mobility and topological chirality [J].
Schalley, CA ;
Beizai, K ;
Vögtle, F .
ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (06) :465-476
[53]   Porphyrin-stoppered [3]- and [5]-rotaxanes [J].
Solladié, N ;
Chambron, JC ;
Sauvage, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (15) :3684-3692
[54]   Catenanes and rotaxanes of the amide type [J].
Vogtle, F ;
Jager, R ;
Handel, M ;
OttensHildebrandt, S .
PURE AND APPLIED CHEMISTRY, 1996, 68 (02) :225-232
[55]   Fabrication and transport properties of single-molecule-thick electrochemical junctions [J].
Wong, EW ;
Collier, CP ;
Behloradsky, M ;
Raymo, FM ;
Stoddart, JF ;
Heath, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (24) :5831-5840
[56]   Enhanced hydrogen bonding induced by optical excitation: Unexpected subnanosecond photoinduced dynamics in a peptide-based [2]rotaxane [J].
Wurpel, GWH ;
Brouwer, AM ;
van Stokkum, IHM ;
Farran, A ;
Leigh, DA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (45) :11327-11328