Anion Modulated Expression of Chirality in Hydrogen Bond Templated Mechanically Chiral [2]Rotaxanes

被引：7

作者：

Spicer, Rebecca L. ^{[1
]}

Shearman, Curtis C. ^{[1
]}

Evans, Nicholas H. ^{[1
]}

机构：

[1] Univ Lancaster, Dept Chem, Lancaster LA1 4YB, England

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2023年 / 29卷 / 21期

关键词：

anion recognition; chirality; molecular shuttle; rotaxanes; supramolecular chemistry; INTERLOCKED MOLECULES; SQUARAINE ROTAXANE; SHUTTLE; RECOGNITION; SQUARAMIDE; CATENANES; SWITCHES; RING;

D O I：

10.1002/chem.202203502

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The syntheses of two novel mechanically chiral rotaxanes containing urea and squaramide motifs (in yields of 33 % and 22 %, respectively) are presented. H-1 NMR spectroscopic titrations reveal shuttling of the macrocycle - detectable by modulation of the expression of mechanical chirality in the NMR spectrum - is possible through the addition of achiral chloride anions, a process which is reversed by the addition of sodium cations.

引用

页数：8

共 63 条

[1] The Squaramide versus Urea Contest for Anion Recognition [J].

Amendola, Valeria ;

Bergamaschi, Greta ;

Boiocchi, Massimo ;

Fabbrizzi, Luigi ;

Milani, Michele .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (14) :4368-4380

[2]

[Anonymous], 2007, ANGEW CHE

[3]

[Anonymous], SUPPORTING INFORM, pS5

[4]

[Anonymous], 2014, Angew. Chem., Int. Ed., DOI DOI 10.1002/ANGE.201407580

[5]

Barendt, 2016, ANGEW CHE, V128, P11235

[6] Anion-Mediated Photophysical Behavior in a C60 Fullerene [3]Rotaxane Shuttle [J].

Barendt, Timothy A. ;

Rasovic, Ilija ;

Lebedeva, Maria A. ;

Farrow, George A. ;

Auty, Alexander ;

Chekulaev, Dimitri ;

Sazanovich, Igor V. ;

Weinstein, Julia A. ;

Porfyrakis, Kyriakos ;

Beer, Paul D. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (05) :1924-1936

[7] Selective Nitrate Recognition by a Halogen-Bonding Four-Station [3]Rotaxane Molecular Shuttle [J].

Barendt, Timothy A. ;

Docker, Andrew ;

Marques, Igor ;

Felix, Vitor ;

Beer, Paul D. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (37) :11069-11076

[8]

Barrell M. J., 2008, ANGEW CHEM, V120, P8156

[9] An Ion-Pair Template for Rotaxane Formation and its Exploitation in an Orthogonal Interaction Anion-Switchahle Molecular Shuttle [J].

Barrell, Michael J. ;

Leigh, David A. ;

Lusby, Paul J. ;

Slawin, Alexandra M. Z. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (42) :8036-8039

[10] Selecting reactions and reactants using a switchable rotaxane organocatalyst with two different active sites [J].

Beswick, Jack ;

Blanco, Victor ;

De Bo, Guillaume ;

Leigh, David A. ;

Lewandowska, Urszula ;

Lewandowski, Bartosz ;

Mishiro, Kenji .

CHEMICAL SCIENCE, 2015, 6 (01) :140-143

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