Two‐Dimensional Supramolecular Polymerization of a Bis‐Urea Macrocycle into a Brick‐Like Hydrogen‐Bonded Network

Author:

Rubert Llorenç1,Islam Md Faizul2,Greytak Andrew B.2,Prakash Rahul2,Smith Mark D.2,Gomila Rosa Maria1,Frontera Antonio1,Shimizu Linda S.2,Soberats Bartolome1ORCID

Affiliation:

1. Department of Chemistry Universitat de les Illes Balears Cra. Valldemossa, Km. 7.5 07122 Palma de Mallorca Spain

2. Department of Chemistry and Biochemistry University of South Carolina Columbia SC-29208 USA

Abstract

AbstractWe report on a dendronized bis‐urea macrocycle 1 self‐assembling via a cooperative mechanism into two‐dimensional (2D) nanosheets formed solely by alternated urea‐urea hydrogen bonding interactions. The pure macrocycle self‐assembles in bulk into one‐dimensional liquid‐crystalline columnar phases. In contrast, its self‐assembly mode drastically changes in CHCl3 or tetrachloroethane, leading to 2D hydrogen‐bonded networks. Theoretical calculations, complemented by previously reported crystalline structures, indicate that the 2D assembly is formed by a brick‐like hydrogen bonding pattern between bis‐urea macrocycles. This assembly is promoted by the swelling of the trisdodecyloxyphenyl groups upon solvation, which frustrates, due to steric effects, the formation of the thermodynamically more stable columnar macrocycle stacks. This work proposes a new design strategy to access 2D supramolecular polymers by means of a single non‐covalent interaction motif, which is of great interest for materials development.

Funder

Ministerio de Ciencia e Innovación

Govern de les Illes Balears

Office of International Science and Engineering

Publisher

Wiley

Subject

General Medicine

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