Cyanuric acid-melamine lattice

The cyclic hexamer 9 (named rosette ) presents 18 hydrogen bonds48,49 9 is the first step in the formation of the cyanuric acid/melamine lattice formed by a sheet of non-covalent aggregates50. 

Zerkowski, J. A., Seto, C. T. and Whitesides, G. M. (1992). Solid-state structures of rosette and crinkled tape motifs derived from the cyanuric acid-melamine lattice. J. Am. Chem. Soc. 114, 5473. 

Early work of Whitesides demonstrated the formation of heteromeric cyclic assemblies of barbital and ArW,-bis(4-tert-butylphenyl)-melamine that formed a 2D hydrogen-bonded rosette , of composition 3(barbital) 3(melamine), in the solid state.24 The components assembled via 18 hydrogen bonds based on alternating ADA and DAD sequences of a cyanuric acid-melamine lattice. Covalent... 

Two self-assembling systems — SAMs (self-assembled monolayers) and aggregates based on CA M (cyanuric acid melamine lattice) — are not unique in non-covalent synthesis, but they illustrate many of the ideas of non-covalent synthesis, and suggest the ways in which this area differs in its philosophy and objectives from covalent synthesis. 

This approach mimics familiar biological self-assembly phenomena such as protein folding [ 192], protein aggregation [ 192] and nucleotide pairing [ 188]. It incorporates features described in each of the above strategies (i.e., I—III), to give specialized nanoscopic structures, that can be precisely designed, usually with excellent control over CMDPs. Recent examples include so called structure directed synthesis by Stoddart [3a] (see Chapter 1 of this book) to produce toroidal bis-bipyridinium cyclophanes that are reminiscent of a molecular abacus , melamine-cyanuric acid lattices by Whitesides [193] and unique helical structures based on coordination of bipyridyl units to copper (II) ions by Lehn [194],... 

Figure 2 The structure of the hydrogen-bonded CA M lattice. Three classes of aggregates that we have observed in solution and the solid state are highlighted the rosette, crinkled tape, and linear tape motifs. The molecular strucmres of melamine and cyanuric acid and their abbreviated representation as dark and light disks are shown...

J.A. Zerkowski, C.T. Seto, G.M. Whitesides, Solid State Structure of Rosette and Crinkled Tape Motifs Derived from the Cyanuric Acid and Melamine Lattice , J. Am. Chem. Soc., 114,5473 (1992)... 

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