ORGN 605 |
| Here we report the first successful synthesis of the diastereomeric [3]rotaxane containing two achiral wheels, where the two wheels are covalently linked and are mechanically bonded onto an achiral axle leading to topologically chiral “Bonnane”, which is a simplest member of a new chiral family based on architectural features of Rotaxanes. By applying our new efficient trapping synthesis (chemical threading) for amide based rotaxanes, which relies on hydrogen-bond-templated threading of various dicarboxylic acid chlorides through the cyclic tetramides (wheels) under mild reaction conditions, we allowed the Axel, 4,4'-Stilbenedicaroboxylic acid dichloride, to react with a Stopper (4-aminophenylene)-p-tritylanilide in presence of a sulfonamide Wheel to get diastereomeric [3]rotaxane. This is further reacted with a linker (1,10-diioddodecane or bis(4-bromomethylphenyl)methane) to yield corresponding Bonnanes. The structure of Bonnanes were proved by means of MALDI-TOF mass spectrometry and 1H-NMR spectroscopy. The interlinkage of two achiral wheels on a symmetrical axle of Bonnanes, resulted in topological chirality (nanochirality) of the molecule: a pair of enantiomers and meso form. The successful synthesis of amide based cyclodiastereomeric Bonnanes leads to novel highly topologically chiral nanoarchitectures which might be useful on the long way to molecular devices/motors/machines.
|
|
Heterocycles, Aromatics, Metal-Mediated Reactions and Syntheses, Materials, Devices, and Switches
8:00 PM-10:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster
Sci-Mix
Division of Organic Chemistry |
