Relies on the supramolecular-templatically synthetic strategy discovered by Sauvage, the topology inspired synthesis of the mechanically interlocked molecules (MIMs) such as rotaxanes and catenanes has made significant development in different supramolecular complex. Comparing with the MIMs in which two or more covalently linked components are held together by mechanical bonds, the mechanically selflocked molecules (MSMs), such as molecular knots, [1]rotaxanes, [1]catenanes, pretzelanes and Molecular Figures-of-Eight are the molecules which have the threading or tangling topology in only one covalently linked component. Herein, we wish to report an efficient synthesis of [1]catenanes and topological new molecules [c1]daisy chains as diastereomers via HOBT catalyzed macrolactamization of A1/A2-dicarboxylato pillar[5]arenes with the alkyldiamines. The erythro- and threo- [c1]daisy chains which are the mesomers and racemates aroused by the planar chirality of pillar[5]arenes are characterized by NMR spectroscopy, mass spectrometry and chiral HPLC. This one-pot reaction is relevant to the self-assembly of the pillar[5]arenes and the alkyldiamines, in which HOBT remembered this assemblies and promoted them to convert to the MSMs. We anticipate that the so-called dual template effect strategies used here can be applied to the rational synthesis of other interlocked and selflocked molecular architectures. Figure.  1 The rational formation of the [1]catenanes and [c1]daisy chains  Hydrogens have been omitted for clarity. Carbons of (pS)-pillararene component are green except the purple oxacetyl group, carbons of (pR)-pillararene are red, carbons of alkyl chain are black, oxygens are yellow, and nitrogens are blue. The ruby H is HOBT.We thank 973 Program (2011CB932502) and NNSFC (91227107) for financial support.References 1. Forgan, R. S.; Sauvage, J.-P.; Stoddart, J. F. Chem. Rev. 2011  , 111, 5434�5464.2. Xue, M. Yang, Y. Chi, X. Zhang, Z.; Huang, F. Acc. Chem. Res. 2012  ,  45, 1294�1308.3. Ogoshi, T.; Akutsu, T.; Yamafuji, D.; Aoki, T.; Yamagishi T. Angew. Chem. Int. Ed. 2013  , 52, 8111�8115.

Efficient synthesis of mechanically selflocked molecules based on pillararenes

248th National Meeting (2014)

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