876400-52-1Relevant academic research and scientific papers
Efficient synthesis of a labile copper(I)-rotaxane complex using click chemistry
Mobian, Pierre,Collin, Jean-Paul,Sauvage, Jean-Pierre
, p. 4907 - 4909 (2006)
Copper(I)-induced threading of 5,5′-diazidomethyl-2,2′-bipyridine through a coordinating ring followed by reaction of a propargyl ether attached to a stopper group leads to the desired rotaxane in 62% yield. The reaction is carried out under the 'click ch
Formation of a hydrogen-bonded barbiturate [2]-rotaxane
Tron, Arnaud,Thornton, Peter J.,Rocher, Mathias,Jacquot De Rouville, Henri-Pierre,Desvergne, Jean-Pierre,Kauffmann, Brice,Buffeteau, Thierry,Cavagnat, Dominique,Tucker, James H. R.,McClenaghan, Nathan D.
supporting information, p. 1358 - 1361 (2014/04/03)
Interlocked structures containing the classic Hamilton barbiturate binding motif comprising two 2,6-diamidopyridine units are reported for the first time. Stable [2]-rotaxanes can be accessed either through hydrogen-bonded preorganization by a barbiturate
Adjustable receptor based on a [3]rotaxane whose two threaded rings are rigidly attached to two porphyrinic plates: Synthesis and complexation studies
Collin, Jean-Paul,Frey, Julien,Heitz, Valerie,Sauvage, Jean-Pierre,Tock, Christian,Allouche, Lionel
scheme or table, p. 5609 - 5620 (2009/09/24)
The design and synthesis of a new type of receptor based on a [3]rotaxane, consisting of one thread and two threaded rings, is reported, as wellas some of its complexing properties toward given guests. Two rings rig idly attached to porphyrins are threaded by a stiff rod incorporating two 2,2′-bipyridine- like chelates, the threading process being driven by two Cu(I) atoms acting as templates. A double-stoppering reaction based on click chemistry leads to the copper-complexed [3]rotaxane in which the rings are located close to the central part of the thread and the distance between the two porphyrin plates is short. Removal of the twoCu(I) cations releases the two rings which are now free to move along a nd around the thread. In these two states of the [3]rotaxane, free and complexed with copper, the two zinc(II) porphyrins attached to the rings can bind different ditopic guests bearing pyridyl groups or amines as terminal functions. UV-visible and NMR DOSY experiments were realized withguests of different sizes, and the association constants were determine d. The free [3]rotaxane is both a strong and highly adaptable receptor with high stability constants for the host/guest complexes, log K being in the range of 6.3-7.5 for guests with a length varying between 2.8 and 18 ?. The copper-complexed [3]rotaxane is still a good receptor for small guests due to an entropic gain for this preorganized molecule compared to the free [3]rotaxane, but it is a less strong receptor for guests which do not fit the short distance between the two porphyrins.
Synthesis of new copper(I)-complexed rotaxanes via click chemistry
Durot, Stéphanie,Mobian, Pierre,Collin, Jean-Paul,Sauvage, Jean-Pierre
, p. 8496 - 8503 (2008/12/21)
The Cu(I)-catalyzed dipolar cycloaddition of azides and terminal alkynes ('click' chemistry) has been used as a mild and efficient stoppering reaction for the preparation of new copper(I)-complexed rotaxanes.
Catalytic "click" rotaxanes: A substoichiometric metal-template pathway to mechanically interlocked architectures
Aucagne, Vincent,Haenni, Kevin D.,Leigh, David A.,Lusby, Paul J.,Walker, D. Barney
, p. 2186 - 2187 (2007/10/03)
A route to mechanically interlocked architectures that requires only a catalytic quantity of template is described. The strategy utilizes the Cu(I)-catalyzed 1,3-cycloaddition of azides with terminal alkynes. Chelating the Cu(I) to an endotopic-binding macrocycle means that the metal atom binds to the alkyne and azide in such a way that the metal-mediated bond-forming reaction occurs through the cavity of the macrocycle, forming a rotaxane. Addition of pyridine to the reaction mixture enables the Cu(I) to turn over during the reaction, permitting substoichiometric amounts of the metal to be used. The yields are very high for a rotaxane-forming reaction (up to 94% with stoichiometric Cu(I); 82% with 20 mol % of Cu(I)), and the procedure is practically simple to do (no requirement for an inert atmosphere nor dried or distilled solvents). Copyright
