The First Pretzel-Shaped Molecules - via Catenane Precursors

Light‐Harvesting in Multichromophoric Rotaxanes

“…The macrocycles W and W-Py were synthesized according to literature procedures. [8,19] CH 2 Cl 2 , MeOH, EtOAc, and toluene were dried and distilled prior to use by usual laboratory methods, whereas all other solvents were used from commercial sources. Thin-layer chromatography (TLC) was performed www.chemeurj.org on pre-coated silica gel 60/F 254 plates (Merck KGaA).…”

An Introduction to the Mechanical Bond

“…248 (iii) Kuroda's macrotricyclic homo [2]catenane of quadruply interlocked cages, 249 (iv) a macrobicyclic [3]catenane, also known as a bis [2]catenane, 250 (v) a branched [6]catenane, 135 (vi) a side-chain poly [2]catenane, 251 (vii) a main-chain poly [2]catenane, which was originally introduced by Geerts,252 (viii) a macrotricyclic hetero [2]catenane, introduced by Becher 253 (ix) a macrobicyclic hetero [4]catenane resulting from a collaboration between Vögtle and Sauvage, 254 (x) covalently bridged [2]catenanes, which originated 106 as precatena nes in Schill's directed syntheses, but later became known [255][256][257] as pretzelanes or [2]pseudocatenanes (xi) a doubly threaded macrobicyclic [2]catenane introduced by Becher 258 under the title of a [3]pseudocatenane, a topology also known [259][260][261] as a 'handcuff' catenane, (xii) a [4]pseudocatenane introduced by Chen,262 (xiii) a macrotricyclic hetero [7]catenane arising from a Nitschke-Sanders collaboration, 263 (xiv) Vögtle's cyclic bis [2]catenane, 264 and (xv) Chiu's cyclic tetrakis [2]catenane. 265 The structures of many beautiful MIMs have also been elucidated in the solid state by X-ray crystallography.…”

Hydrogen-Bond-Mediated Template Synthesis of Rotaxanes, Catenanes, and Knotanes

“…The "magic rod" experiment for preparation of rotaxanes from intact axles and wheels through a reversible olefin metathesis reaction introduction of a covalent bridge between the two components leads to new topologies, i.e., pretzelanes [170,171] and [1]rotaxanes [172]. This was accomplished through replacement of one or more of the amide groups incorporated in the axle and wheel by sulfonamide groups [173], which can be deprotonated more readily and thus permit selective alkylation.Alternatively, substitution of the catenane macrocycles with OH groups at the isophthalic acid derivatives permits the reaction with an alkyl diiodide to yield the pretzelane.…”