180397-92-6Relevant academic research and scientific papers
Chemical On/Off Switching of Mechanically Planar Chirality and Chiral Anion Recognition in a [2]Rotaxane Molecular Shuttle
Corra, Stefano,De Vet, Christiaan,Groppi, Jessica,La Rosa, Marcello,Silvi, Serena,Baroncini, Massimo,Credi, Alberto
, p. 9129 - 9133 (2019/06/17)
We exploit a reversible acid-base triggered molecular shuttling process to switch an appropriately designed rotaxane between prochiral and mechanically planar chiral forms. The mechanically planar enantiomers and their interconversion, arising from ring shuttling, have been characterized by NMR spectroscopy. We also show that the supramolecular interaction of the positively charged rotaxane with optically active anions causes an imbalance in the population of the two enantiomeric coconformations. This result represents an unprecedented example of chiral molecular recognition and can disclose innovative approaches to enantioselective sensing and catalysis.
Synthesis of a novel secondary dialkylammonium salt with three stations and its threading through the cavity of two crown ethers
Shen, Jianfen,Luo, Yan,Chen, Rener,Han, Deman,Jiang, Huajiang,Zhou, Qizhong
, p. 100 - 104 (2013/07/26)
In this paper, a novel secondary dialkylammonium salt with three stations (G1) was synthesized in 5 steps. 1H NMR was used to study the threading of G1 through the cavity of dibenzo-24-crown-8 (DB24C8) and benzo-21-crown-7
Positive cooperativity in the template-directed synthesis of monodisperse macromolecules
Belowich, Matthew E.,Valente, Cory,Smaldone, Ronald A.,Friedman, Douglas C.,Thiel, Johannes,Cronin, Leroy,Stoddart, J. Fraser
, p. 5243 - 5261 (2012/05/20)
Two series of oligorotaxanes R and R′ that contain -CH 2NH2+CH2- recognition sites in their dumbbell components have been synthesized employing template-directed protocols. [24]Crown-8 rings self-assemble by a c
Self-Assembling - and Rotaxanes from Secondary Dialkylammonium Salts and Crown Ethers
Ashton, Peter R.,Glink, Peter T.,Stoddart, J. Fraser,Tasker, Peter A.,White, Andrew J. P.,Williams, David J.
, p. 729 - 736 (2007/10/03)
The self-assembly of three new rotaxanes - two rotaxanes and a rotaxane - formed by a "threading followed by stoppering" approach is described.These template-directed syntheses rely on the formation of pseudorotaxane intermediates, which self-assemble in solution from functionalized secondary dialkylammonium hexafluorophosphate threads and macrocyclic polyether rings (either dibenzocrown-8 or its asymmetric constitutional isomer).The stoppers - substituted 1,2,3-triazoles - were created by thermally allowed 1,3-dipolar cycloaddition between azido groups, which terminate the threads, and di-tert-butyl acetylenedicarboxylate. - Keywords: interlocking molecules; molecular recognition; pseudorotaxanes; rotaxanes; template syntheses
