The [2 + 2] condensation between 1,8-dihydroxyanthraquinone diester and 1,3-diamino-2-propanol in ethanol affords pseudocalixarene macrocyclic L2 in high yield. Heating L2 to 200 °C in DMSO can generate much smaller [1 + 1] macrocycle L1 . Crystal structure of L1 shows that all non-hydrogen atoms are coplanar except one carbon from 1,3-diamino-2-propanol. L1 is quite inert, but L2 can interact with alkaline, alkaline-earth, as well as Zn 2+ , Cu 2+ , Fe 3+ and Al 3+ cation (chloride) evidenced by their CV and 1 H NMR. With a L2 :M (1:2), there are discernable UV–vis spectrum/ 1 H NMR changes in the presence Cu 2+ , Fe 3+ , Al 3+ . Anion plays a key role in the cation binding process as the chromogenic response to Li + , Na + , K + , Ba 2+ and TBA + hydroxide. L2 forms 1:1 complex with TBAOH and 2:3 complex with NaOH, KOH, Ba(OH) 2 in DMSO. L2 reacts with LiOH in 1:4 stoichiometric and is one of the highest lithium loading ligand. The reaction is second-order with t 1/2 ~ 30 min for 0.25 mM L2 in the presence of 4.0 eq. LiOH. Besides hydroxide, L2 can interact with TBAF to form 1:1 host–guest complexes evidenced by their color and NMR change. With bulky cation, TBAOH shifts E p(II) more negative, while other cations shift E p(II) to positive. L2 is an ion pair acceptor that binds hydroxide and fluoride salt chromogenic.
Two N 3 O 3 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 Zn 2+ , Pb 2+ , and Al 3+ chloride/perchloride evidenced by their DPV change and 1 H 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 Zn 2+ and Al 3+ in 2:1 in DMSO. L2 can form L2·TBAOH greenish yellow complex that gradually transformed to red L2 2 ·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.
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