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Synthesis of O6‐Corona[3]arene[3]pyridazines and Their Molecular Recognition Property in Organic and Aqueous Media
Abstract:O6‐Corona3]arene3]pyridazines were synthesized from the one‐pot macrocyclic condensation reaction of 3,6‐dichlorotetrazine with 1,4‐dihydroquinone derivatives followed by the inverse electron demand Diels‐Alder reaction of the tetrazine rings with a cyclopentanone‐derived enamine. Conversion of six ester groups within macrocycle into all sodium acetate moieties afforded a water soluble O6‐corona3]arene3]pyridazine. The coronary macrocycle host formed complexes selectively with organic ammoniums and dinitrile guests in a 1: 1 stoichiometric ratio in organic solvents with association constants ranging from (2.96 ± 0.10) × 101 to (2.53 ± 0.33) × 105 L·mol?1. Water soluble O6‐corona3]arene3]pyridazine was also able to complex strongly with organic ammoniums in water to give an association constant up to (2.67 ± 0.21) × 104 L·mol?1. The pseudo‐rotaxane and inclusion structures of the host‐guest complexes were revealed by the X‐ray crystallography.
Keywords:coronarene  O6‐corona[3]arene[3]pyridazine  inverse electron demand Diels‐Alder reaction  molecular recognition  organic ammonium  dinitrile
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