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Encoding stereochemical molecular information on cyclophanes using non-directional interactions and achiral building blocks

Abstract : The stereoselective assembly of achiral constituents through a single spontaneous process into complex covalent architectures bearing multiple stereogenic elements currently seems out of reach to the synthetic chemist. It even seems beyond what nature itself has managed to attain through evolution. Here, we show that such an extreme level of control can be achieved by molecular programming, i.e. by implementing stereo-electronic information on synthetic organic building blocks and exploiting the features of the covalent reactions and interactions, whose interplay acts as a powerful assembling algorithm. Remarkably, we show that non-directional bonds and interactions can reliably transfer this information, delivering in near to physiological conditions, high-molecular weight macrocyclic species carrying up to 8-bits of conformational and configuration information. Beyond the field of supramolecular chemistry, this proof of concept should stimulate the on-demand production of highly structured polyfunctional architectures.
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Preprints, Working Papers, ...
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https://hal.archives-ouvertes.fr/hal-03382026
Contributor : Laurent Vial Connect in order to contact the contributor
Submitted on : Monday, October 18, 2021 - 10:10:02 AM
Last modification on : Tuesday, January 4, 2022 - 5:49:44 AM
Long-term archiving on: : Wednesday, January 19, 2022 - 6:56:11 PM

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Yuan Zhang, Benjamin Ourri, Pierre-Thomas Skowron, Emeric Jeamet, Ana Belenguer, et al.. Encoding stereochemical molecular information on cyclophanes using non-directional interactions and achiral building blocks. 2021. ⟨hal-03382026⟩

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