Molecular Organization in Crystals of Bis(diaminotriazinyl)-Substituted Derivatives of Benzene, Pyridine, and Pyrazine

Abstract

The bis(diaminotriazinyl)-substituted derivatives of benzene, pyridine, and pyrazine 1−6 were made to test the ability of the 4,6-diamino-1,3,5-triazinyl group (DAT) to direct molecular organization by hydrogen bonding. Analysis of the structures of compounds 1−6 by X-ray crystallography revealed that the DAT groups control association by forming hydrogen bonds according to the well-established motifs I−III. The resulting association normally produces complex networks consisting of tapes, rings, and sheets. 1,2-Disubstituted compounds 1−3 have structures in which the DAT groups do not lie close to the plane of the aryl or heteroaryl core, whereas 1,3-disubstituted compounds 4−6 adopt flattened conformations. The observed structures of compounds 1−6, which include novel embraces and rings held together by hydrogen bonds, highlight the special ability of motifs based on DAT groups to direct molecular association.

Hydrogen Bond Patterns of Dipyridone and Bis(Hydroxypyridinium) Cations

“…It is noteworthy that here again, all C–N, C–O, and C–C bonds are normal (average bond lengths d C–N = 1.174 Å, d C–O = 1.302 Å, and d C–C = 1.400 Å). 8 , 13 …”

“…Dicationic (4H 2 ) 2+ species are interconnected involving bridging of trifluoroacetate anions according to unitary graph sets (50) within a layered structure (Figure 3a). 22 8,13 Hirshfeld Surface Analysis. The intermolecular interactions in 2−4 have been further examined and visualized by HSA using CrystalExplorer21 software.…”

“…Therefore, hydrogen bonds are important for the development of fundamental and applied fields. They are the most commonly used intermolecular interactions to design ordered bulk materials. , Single-crystal X-ray diffraction (SCXRD) is one of the main characterization techniques that have been extensively used to elucidate the hydrogen bonding patterns of various compounds which incorporate one or multiples sticky sites such as hydroxy (−OH), carboxylic (−COOH), diaminotriazinyl (DAT), pyridonyl groups, etc. − In chemistry, the strategy that uses non-covalent interactions to direct the molecular organization is the concept of crystal engineering …”

Mimicking 2,2′:6′,2′′:6′′,2′′′-quaterpyridine complexes for the light-driven hydrogen evolution reaction: synthesis, structural, thermal and physicochemical characterizations

“…Complexes based on coordination of both unsubstituted and functionalized bipyridine (bpy), terpyridine (tpy) and quaterpyridine (qtpy) with transition metals have been widely studied in particular for the formation of various metallosupramolecular architectures. [1][2][3][4][5][6][7][8] There is very extensive literature concerning polypyridine ligands and their complexes, but a relatively few investigations have been done on functionalized systems, particularly on qtpy. Many interests were focused on qtpy, a tetradentate ligand that can form metal complexes of different geometries.…”

“…In crystal engineering these molecules are known as tectoligands because of their dual ability to bind metal ions and simultaneously engage in predictable intermolecular interactions such as hydrogen bonds according to reliable patterns (Chart 1b). 5,10,11 In supramolecular chemistry, the self-assembly of tectoligands with metal ions forms metallotectons. [12][13][14][15][16][17][18] Creation of metallosupramolecules 19,20 using 4-6 has several advantages: (i) the synthesis is easy and the yield is high, (ii) the coordination chemistry is similar to 1-3, (iii) in solid-state, reliable hydrogen bond networks with predened structures are expected, (iv) the presence of amino groups and triazinyl rings may lead to ne tuning of activities of the metal complexes for catalysis.…”