Abstract
Two N3O3 macrocyclic compounds with rigid chromogenic 1,8-dihydroxylenanthraquione and flexible diethylenetriamine/dipropenetriamine (L1 and L2), were synthesized and characterized. L1/L2 can interact with alkaline, alkaline-earth, as well as Zn2+, Pb2+, and Al3+ chloride/perchloride evidenced by their DPV change and 1H NMR spectra. Unexpectedly, both L1 and L2 can show chromogenic response to Na+, K+, and TBA+ hydroxide (but not LiOH). Large cavity L2 can show chromic response to Ca(OH)2 and Ba(OH)2, but L1 can only respond to Ca(OH)2 in DMSO. L1 and L2 form 1:1 and 2:1 (Host:Guest) complex respectively with NaCl, NaOH, TBAOH in DMF/DMSO. Both hosts bind smaller Zn2+ and Al3+ in 2:1 in DMSO. L2 can form L2·TBAOH greenish yellow complex that gradually transformed to red L22·TBAOH in two steps in DMSO. Different from other macrocycles, L1 and L2 are ion-pair hosts that recognize cation and OH− via carbonyl groups.
Published Version
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