Abstract
Chiral photoresponsive host 1 was prepared by a high-yield Cs2CO3-templated macrocyclization. Trans-1 transforms into long-lived cis-1 (25 days) upon irradiation with green light, and the backward transformation is triggered by blue light. Both isomers prefer potassium among alkali metal cations, and cis-1 binds cations stronger than trans-1 (Kcis/Ktrans ≤ 4.1). 1H NMR titration experiments as well as density functional theory studies reveal that sucrose ring oxygen residues and azobenzene nitrogen atoms in 1 contribute to cation coordination.
Highlights
Chiral photoresponsive host 1 was prepared by a high-yield Cs2CO3-templated macrocyclization
Preparation of host 1 was accomplished in six steps starting from sucrose (Scheme 1 and Table 1)
The remaining free hydroxyl groups were protected as benzyl ethers under standard conditions to afford fully protected sucrose 4 in very good yield (80%)
Summary
Chiral photoresponsive host 1 was prepared by a high-yield Cs2CO3-templated macrocyclization. Hosts 1 (cis or trans, Scheme 3b−d) as well as complexes of 1 with alkali metal triflates (Scheme 3b,c,e and Figures S2−S7) showed no signs of photodegradation after several cycles of alternate irradiation with green and blue light.
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