Anthracene adamantylbisurea receptors: switching of anion binding by photocyclization (CROSBI ID 221763)
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Blažek Bregović, Vesna ; Halasz, Ivan ; Basarić, Nikola ; Mlinarić-Majerski, Kata
engleski
Anthracene adamantylbisurea receptors: switching of anion binding by photocyclization
Anion binding of adamantane bisurea receptors 1e4 bearing anthracene chromophores was investigated in DMSO solution by UVevis and fluorescence titrations. All derivatives form stable complexes with F¯ (K1:2z105e106 M¯ 2), AcO¯ (K1:1z103 M¯ 1), and H2PO4¯ (K1:1z103e104 M¯ 1, K1:2z105e106 M¯2). Photochemical reactivity of 1e4 in the [4pţ4p] photocyclizations was also investigated. Anthracene 1 is photochemically stable, 3 and 4 undergo reaction giving mixture of products, but 2 reacts selectively yielding only cyclic product 5. Product 5 was isolated and characterized by X-ray analysis. Cyclic receptor 5 also binds anions but forms complexes with different stability constants than its opened analogue 2. Anthracene 2 forms more stable complex with H2PO4¯, whereas cyclic receptor 5 forms the most stable complex with AcO¯ (K1:1 >106 M¯ 1).
Anion receptors; Anthracenes; Ureas; Photocycloaddition
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