Self-assembly of lattices with high structural complexity from a geometrically simple molecule

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Science  21 Sep 2018:
Vol. 361, Issue 6408, pp. 1242-1246
DOI: 10.1126/science.aat6394

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Robust assembly of aromatic molecules

Organic materials can exhibit high porosity, but the structures often collapse or decompose at high temperatures. Yamagishi et al. synthesized an aromatic molecule that bears a symmetrical outer shell of three dipyridylphenyl wedges and crystallized it from highly dielectric solvents. Porous crystals formed with complex pore-wall structures that resulted from labile C–H⋯N bonds and van der Waals forces. Despite the weakness of these interactions, the porous structure was stable up to 202°C and could be recovered after collapse by exposure to solvent vapor.

Science, this issue p. 1242


Here we report an anomalous porous molecular crystal built of C–H···N-bonded double-layered roof-floor components and wall components of a segregatively interdigitated architecture. This complicated porous structure consists of only one type of fully aromatic multijoint molecule carrying three identical dipyridylphenyl wedges. Despite its high symmetry, this molecule accomplishes difficult tasks by using two of its three wedges for roof-floor formation and using its other wedge for wall formation. Although a C–H···N bond is extremely labile, the porous crystal maintains its porosity until thermal breakdown of the C–H···N bonds at 202°C occurs, affording a nonporous polymorph. Though this nonporous crystal survives even at 325°C, it can retrieve the parent porosity under acetonitrile vapor. These findings show how one can translate simplicity into ultrahigh complexity.

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