Cyclobutane Scaffold in Bolaamphiphiles: Effect of Diastereoisomerism and Regiochemistry on Their Surface Activity Aggregate Structure

Langmuir : the ACS Journal of Surfaces and Colloids
Bernat Pi-BoledaRosa M Ortuño

Abstract

Cationic bolaamphiphiles have been synthesized starting from meso cis- or chiral trans-1,2-difunctionalized cyclobutane derivatives. They include cis/trans pairs of diastereoisomers, of N- or C-centered bisamides. The goal of this work was to investigate the influence of stereochemistry and regiochemistry on their abilities as surfactants and self-assembly. Very large differences in surface coverage (2-fold), critical micellar concentration (cmc, up to 2 orders of magnitude), and aggregate structure (from lamellae to fibers) for the four molecules are remarkable due to regio- and stereochemistry differences. Computational calculations were carried out to rationalize the experimental findings and a new methodology has been developed to calculate the structure of these bolaamphiphiles at the surface. Although the four surfactants adopt a wicket-like conformation, for N-centered trans, the distance between polar heads is much larger than that for the other three molecules, as suggested by calculations. We have shown that the interplay between the regiochemistry and stereoisomerism, enhanced by rigidity of the cyclobutane ring, affects different physicochemical properties quite differently. That is, the cmc value is mainly governed...Continue Reading

References

Jun 6, 2002·Journal of the American Chemical Society·Satoshi KobayashiKenji Hanabusa
Jun 10, 2004·Chemical Reviews·Jürgen-Hinrich Fuhrhop, Tianyu Wang
Oct 8, 2005·Journal of Computational Chemistry·Jay L BanksRonald M Levy
Jul 10, 2009·Journal of the American Chemical Society·Fredric M MengerSyed A A Rizvi
Oct 18, 2012·Chemical Society Reviews·Nicholas D Petkovich, Andreas Stein
Jul 26, 2013·Chemical Society Reviews·A SorrentiR M Ortuño
May 24, 2014·Langmuir : the ACS Journal of Surfaces and Colloids·Pei Xun LiJeffrey Penfold
Aug 20, 2015·Langmuir : the ACS Journal of Surfaces and Colloids·Alessandro SorrentiRosa M Ortuño
Jun 22, 2016·Langmuir : the ACS Journal of Surfaces and Colloids·Alessandro SorrentiRamon Pons

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Citations

Jul 14, 2021·Bioconjugate Chemistry·Maria J GómaraIsabel Haro
Aug 28, 2021·International Journal of Molecular Sciences·Amalia Mezei, Ramon Pons
Dec 31, 2021·Langmuir : the ACS Journal of Surfaces and Colloids·Tsukasa MoritaTomokazu Yoshimura

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