Thinking Outside the Blue Box: Induced Fit within a Unique Self-Assembled Polycationic Cyclophane
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Thinking Outside the Blue Box: Induced Fit within a Unique Self-Assembled Polycationic CyclophaneAutor(es)
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2019-02-07Cita bibliográfica
Blanco-Gómez, A.; Fernández-Blanco, Á.; Blanco, V.; Rodríguez, J.; Peinador, C.; García, M. D. Thinking Outside the “Blue Box”: Induced Fit within a Unique Self-Assembled Polycationic Cyclophane. J. Am. Chem. Soc. 2019, 141 (9), 3959–3964. https://doi.org/10.1021/jacs.8b12599
Resumo
[Abstract] We present herein the development of a new polycationic molecular receptor, inspired by the ubiquitous cyclobis(paraquat-p-phenylene)cyclophane (“blue box”). Our analogue, the “white box”, has been easily self-assembled on a preparative scale in water, using a template-assisted process by acyl hydrazone bonding of complementary bis(pyridinium)xylylene tweezers, followed by kinetic trapping of the empty receptor. The obtained macrocycle was found to display a marked pH responsiveness in water, because of an abnormal acidity of the amide protons within its structure. Consequently, and because of the concurrence of rotational isomerism under acidic conditions (fixed at higher pH values), the compound was found to display a dual behavior as a conformationally locked/flexible molecular host, being able to recognize appropriate aromatic substrates, in a lock and key or induced fit fashion, by a conjunction of π–π, C–H···π, and, crucially, the hydrophobic effect.
Palabras chave
Aromatic compound
Macrocycles
Mixtures
Molecular structure
Receptors
Macrocycles
Mixtures
Molecular structure
Receptors
Descrición
This document is the Accepted Manuscript version of a Published Work that appeared
in final form in Journal of the American Chemical Society.
Versión do editor
Dereitos
© 2019 American Chemical Society after peer review and technical editing by the publisher.
ISSN
1520-5126