Stimuli-controlled self-assembly of diverse tubular aggregates from one single small monomer

Qixun Shi, Tomas Javorskis, Karl-Erik Bergquist, Artūras Ulčinas, Gediminas Niaura, Ieva Matulaitienė, Edvinas Orentas () and Kenneth Wärnmark ()
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Qixun Shi: Center for Analysis and Synthesis, Lund University
Tomas Javorskis: Vilnius University
Karl-Erik Bergquist: Center for Analysis and Synthesis, Lund University
Artūras Ulčinas: Center for Physical Sciences and Technology
Gediminas Niaura: Center for Physical Sciences and Technology
Ieva Matulaitienė: Center for Physical Sciences and Technology
Edvinas Orentas: Vilnius University
Kenneth Wärnmark: Center for Analysis and Synthesis, Lund University

Nature Communications, 2017, vol. 8, issue 1, 1-9

Abstract: Abstract The design and synthesis of new stimuli-responsive hydrogen-bonding monomers that display a diversity of self-assembly pathways is of central importance in supramolecular chemistry. Here we describe the aggregation properties of a simple, intrinsically C2-symmetric enantiopure bicyclic cavity compound bearing a terminally unsubstituted ureidopyrimidinone fragment fused with a pyrrole moiety in different solvents and in the absence and presence of C60 and C70 guests. The tetrameric cyclic aggregate is selectively obtained in chlorinated solvents, where only part of the available hydrogen bonding sites are utilized, whereas in toluene or upon addition of C70 guests, further aggregation into tubular supramolecular polymers is achieved. The open-end cyclic assemblies rearrange into a closed-shell capsule upon introduction of C60 with an accompanied symmetry breaking of the monomer. Our study demonstrates that a C60 switch can be used to simultaneously control the topology and occupancy of tubular assemblies resulting from the aggregation of small monomers.

Date: 2017
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DOI: 10.1038/ncomms14943

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