ZHONG, Yulong; SOBIECH, Thomas; KAUFFMANN, Brice; SONG, Bo; LI, Xiaopeng; FERRAND, Yann; HUC, Ivan; GONG, Bing

doi:10.1039/d3sc00524k

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ZHONG, Yulong

SOBIECH, Thomas

KAUFFMANN, Brice
Soutien à la Recherche de l'Institut Européen de Chimie Biologique

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Chemical Science. 2023-05-10, vol. 14, n° 18, p. 4759-4768

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Two aromatic oligoamides, the 8-residue H8 and 16-residue H16, that adopt stable, cavity-containing helical conformations were examined for their complexation of rodlike dicationic guest, octyl viologen (OV 2+) and parabis(trimethylammonium)benzene (TB 2+). Studies based on 1D and 2D 1 H NMR, isothermal titration calorimetry (ITC), and Xray crystallography demonstrated that H8 and H16 wraps around two OV 2+ ions as a double helix and a single helix, respectively, resulting in 2:2 and 1:2 complexes. Compared to H8, the longer H16 binds the OV 2+ ions in much higher binding affinity and with extraordinary negative cooperativity. In contrast to its 1:2 binding with OV 2+ , the binding of helix H16 with the bulkier guest TB 2+ shows the same affinity but with a 1:1 ratio. This novel host-guest system is featured by the pairwise placement of otherwise strongly repulsive OV 2+ ions in the same cavity, strong negative cooperativity, and mutual adaptability of hosts and guests. The resultant 2:2, 1:2, and 1:1 complexes are highly stable pseudofoldaxanes with few known precedents. a.< Leer menos

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Hollow helices as high-affinity hosts: Single and double helical pseudofoldaxanes

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