Hierarchic Supramolecular Interactions within Assemblies in Solution and in the Crystal of 2,3,6,7‐Tetrasubstituted 5,5′‐(Anthracene‐9,10‐diyl)bis[pyrimidin‐2‐amines]

堆积 超分子化学 化学 结晶学 胺气处理 晶体结构 Crystal(编程语言) 分子 吸收(声学) 光化学 材料科学 有机化学 计算机科学 复合材料 程序设计语言
作者
Teodor Silviu Balaban,Andreas Eichhöfer,Michael J. Krische,Jean‐Marie Lehn
出处
期刊:Helvetica Chimica Acta [Wiley]
卷期号:89 (2): 333-351 被引量:13
标识
DOI:10.1002/hlca.200690037
摘要

Abstract The title compounds 6 and 7 were synthesized in good yield ( Schemes 1 and 2 ), and their mode of assembly was studied both in solution, for the tetrakis(decyloxy) derivative 6 , and in the crystal, for the tetramethoxy analogue 7 . The pyrimidin‐2‐amine moieties of 6 and 7 can engage in three different supramolecular interactions: i ) metal ligation via one of the pyrimidine N‐atoms, ii ) cooperative double H‐bonding via the NH 2 group, and iii ) π–π ‐stacking interactions. In solution, coordination of the central Zn‐atom within the soluble porphyrinatozinc complex 19 leads to significant changes in the NMR and absorption spectra of 6 . In the absence of metal ligation, the next strongest interaction is H‐bonding which can operate in nonpolar or moderately polar solvents. In these cases, however, no stacking interaction or inclusion compounds could be put into evidence in the case of 6 by absorption, fluorescence, or NMR spectroscopies. The π ‐stacking interactions were only observed in the crystal of 7 in conjunction with double H‐bonding. Slightly disordered DMSO molecules are also H‐bonded to the NH 2 groups of 7 , perturbing the expected packing. The present study illustrates some of the challenges inherent to directing hierarchical assembly processes in the solid state.

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