Solvent-Induced High Fidelity Switching Between Two Discrete Supramolecules

被引:46
作者
Betancourt, Jose E. [1 ]
Martin-Hidalgo, Mariana [1 ]
Gubala, Vladimir [1 ]
Rivera, Jose M. [1 ]
机构
[1] Univ Puerto Rico, Dept Chem, Rio Piedras, PR 00931 USA
关键词
DIRECT NMR DETECTION; 2'-DEOXYGUANOSINE DERIVATIVES; CATION-BINDING; DIFFUSION NMR; INTERCONVERSION; CHEMISTRY; EXCHANGE; INSIGHTS; RELEASE; IONS;
D O I
10.1021/ja809612d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Here we show the reversible high fidelity switching between two discrete self-assembled supramolecules made from a lipophilic 8-phenyl-2'-deoxyguanosine derivative induced by an indirect solvent effect. A hexadecameric supramolecule containing four stacked tetramers, is formed in acetonitrile aided by higher potassium concentrations. When the amount of weakly solvated potassium decreases, due the lower activity of potassium iodide in chloroform, an octamer is formed after the dissociation of the two outer tetramers in the hexadecamer. The switching process results from an unprecedented subtle interplay between the activity of potassium iodide and the steric crowding within the self-assembled structure. Besides the possible applications in nanoconstruction, this phenomenon sheds light into the mechanism of formation of self-assembled supramolecules made from guanosine derivatives.
引用
收藏
页码:3186 / +
页数:5
相关论文
共 33 条
[1]  
Anslyn E. V., 2006, Modern Physical Organic Chemistry
[2]  
Balasubramanian S, 2006, RSC BIOMOL SCI, pV
[3]   Controlled disassembling of self-assembling systems: Toward artificial molecular-level devices and machines [J].
Balzani, V ;
Credi, A ;
Venturi, M .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (08) :4814-4817
[4]  
Balzani V., 2003, Molecular Devices and Machines, a Journey into the Nanoworld
[5]   Hexadecameric self-assembled dendrimers built from 2′-deoxyguanosine derivatives [J].
Betancourt, Jose E. ;
Rivera, Jose M. .
ORGANIC LETTERS, 2008, 10 (11) :2287-2290
[6]   Diffusion NMR spectroscopy in supramolecular and combinatorial chemistry: An old parameter - New insights [J].
Cohen, Y ;
Avram, L ;
Frish, L .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (04) :520-554
[7]   Supramolecular architectures generated by self-assembly of guanosine derivatives [J].
Davis, Jeffery T. ;
Spada, Gian Piero .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (02) :296-313
[8]   G-quartets 40 years later:: From 5′-GMP to molecular biology and supramolecular chemistry [J].
Davis, JT .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (06) :668-698
[9]  
Dill K., 2002, Molecular Driving Forces: Statistical Thermodynamics in Chemistry Biology
[10]   Assessment of cooperativity in self-assembly [J].
Ercolani, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (51) :16097-16103