876400-54-3Relevant academic research and scientific papers
[3]Rotaxanes and [3]pseudorotaxanes with a rigid two-bidentate chelate axle threaded through two coordinating rings
Collin, Jean-Paul,Sauvage, Jean-Pierre,Trolez, Yann,Rissanen, Kari
, p. 2148 - 2154 (2009)
New [3]rotaxanes and [3]pseudorotaxanes have been synthesised using the "gathering and threading" effect of copper(i). By using click chemistry as the "stoppering" reaction, a good yield of the [3]rotaxane was obtained, either as a dicopper complex or as
[2]Rotaxane End-Capping Synthesis by Click Michael-Type Addition to the Vinyl Sulfonyl Group
David, Arthur H. G.,García-Cerezo, Pablo,Campa?a, Araceli G.,Santoyo-González, Francisco,Blanco, Victor
supporting information, p. 6170 - 6179 (2019/04/08)
We report the application of the click Michael-type addition reaction to vinyl sulfone or vinyl sulfonate groups in the synthesis of rotaxanes through the threading-and-capping method. This methodology has proven to be efficient and versatile as it allowed the preparation of rotaxanes using template approaches based on different noncovalent interactions (i.e., donor-acceptor π–π interactions or hydrogen bonding) in yields of generally 60–80 % and up to 91 % aided by the mild conditions required (room temperature or 0 °C and a mild base such as Et3N or 4-(N,N-dimethylamino)pyridine (DMAP)). Furthermore, the use of vinyl sulfonate moieties, which are suitable motifs for coupling-and-decoupling (CAD) chemistry, implies another advantage because it allows the controlled chemical disassembly of the rotaxanes into their components through nucleophilic substitution of the sulfonates resulting from the capping step with a thiol under mild conditions (Cs2CO3 and room temperature).
A dual-response [2]rotaxane based on a 1,2,3-triazole ring as a novel recognition station
Zheng, Haiyan,Zhou, Weidong,Lv, Jing,Yin, Xiaodong,Li, Yongjun,Liu, Huibiao,Li, Yuliang
experimental part, p. 13253 - 13262 (2010/06/19)
Two novel multilevel switchable [2]rotaxanes containing an ammonium and a triazole station have been constructed by a CuI-catalyzed azide-alkyne cycloaddition reaction. The macrocycle of [2]rotaxane containing a C6-chain bridge between the two
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
