Design of crystal packings of styrylheterocycles and [2+2] photocycloaddition reactions in their single crystals 6. Synthesis and crystal packings of neutral crown-containing and model styrylheterocyclesстатья

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[1] Design of crystal packings of styrylheterocycles and [2+2] photocycloaddition reactions in their single crystals 6. synthesis and crystal packings of neutral crown-containing and model styrylheterocycles / L. G. Kuz'mina, A. I. Vedernikov, N. A. Lobova et al. // Russian Chemical Bulletin. — 2009. — Vol. 58, no. 6. — P. 1192–1210. Neutral crown-containing and model styrylheterocycles of the 4-pyridine, 4-quinoline, and 9-acridine series were synthesized under acidic catalysis. The influence of the molecular geometry of these compounds, as well as of related styrylheterocycles of the 2-benzothiazole and benzobisthiazole series, on the formation of a particular crystal packing was investigated based on X-ray diffraction data. An extension of the conjugation system in the molecules can result in the sandwich-herringbone packing motif as the only one of the three packing motifs most typical of this class of compounds. This packing provides the preorganization of the structural units for the [2+2] photocycloaddition reaction. The styrylheterocycle containing the bulky 9-acridine moiety is nonplanar due to strong intramolecular steric interactions. The packing motifs formed by nonplanar molecules do not provide the preorganization of the molecules for the [2+2] photocycloaddition. The introduction of the crown ether moiety into the benzene ring of the styrylheterocycle can decrease the predictability of the packing motif as a result of the inclusion of solvent molecules capable of hydrogen bonding with the heteroatoms of the macrocycle in the crystal structure. [ DOI ]

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