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Methyl Scanning for Mechanochemical Chalcogen‐Bonding Cascade Switches

Publié dansChemistryOpen, vol. 9, no. 1, p. 18-22
Date de publication2020
Résumé

Chalcogen‐bonding cascade switching was introduced recently to produce the chemistry tools needed to image physical forces in biological systems. In the original flipper probe, one methyl group appeared to possibly interfere with the cascade switch. In this report, this questionable methyl group is replaced by a hydrogen. The deletion of this methyl group in planarizable push‐pull probes was not trivial because it required the synthesis of dithienothiophenes with four different substituents on the four available carbons. The mechanosensitivity of the resulting demethylated flipper probe was nearly identical to that of the original. Thus methyl groups in the switching region are irrelevant for function, whereas those in the twisting region are essential. This result supports the chalcogen‐bonding cascade switching concept and, most importantly, removes significant synthetic demands from future probe development.

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Citation (format ISO)
ZHANG, Xiang, SAKAI, Naomi, MATILE, Stefan. Methyl Scanning for Mechanochemical Chalcogen‐Bonding Cascade Switches. In: ChemistryOpen, 2020, vol. 9, n° 1, p. 18–22. doi: 10.1002/open.201900288
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Article (Published version)
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ISSN du journal2191-1363
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Informations techniques

Création08/01/2020 17:29:00
Première validation08/01/2020 17:29:00
Heure de mise à jour15/03/2023 18:41:34
Changement de statut15/03/2023 18:41:34
Dernière indexation12/02/2024 13:09:01
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