Anion Recognition by a Pincer-Type Host Constructed from Two Polyamide Macrocyclic Frameworks Jointed by a Photo-Addressable Azobenzene Switch

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dc.contributor.authorNiedbała, Patryk
dc.contributor.authorCeborska, Magdalena
dc.contributor.authorMart, Mehmet
dc.contributor.authorIgnacak, Wiktor
dc.contributor.authorJurczak, Janusz
dc.contributor.authorDąbrowa, Kajetan
dc.contributor.editorPawelec, Barbara
dc.contributor.organizationInstitute of Organic Chemistry, Polish Academy of Sciencesen
dc.contributor.organizationInstitute of Physical Chemistry, Polish Academy of Sciencesen
dc.date.accessioned2022-07-19T12:50:11Z
dc.date.available2022-07-19T12:50:11Z
dc.date.issued2022
dc.description.abstractA sterically crowded light-responsive host 1 was synthetized with a 93% yield by applying a post-functionalization protocol utilizing the double amidation of 4,4′-azodibenzoyl dichloride with a readily available 26-membered macrocyclic amine. X-ray structures of two hydrates of trans-1 demonstrate a very different alignment of the azobenzene linkage, which is involved in T-shape or parallel-displaced π⋯π stacking interactions with the pyridine-2,6-dicarboxamide moieties from the macrocyclic backbone. Despite the rigidity of the macrocyclic framework, which generates a large steric hindrance around the azobenzene chromophore, the host 1 retains the ability to undergo a reversible cis⟷trans isomerization upon irradiation with UVA (368 nm) and blue (410 nm) light. Moreover, thermal cis→trans back-isomerization (ΔG0 = 106.5 kJ∙mol−1, t½ = 141 h) is markedly slowed down as compared to the non-macrocyclic analog. 1H NMR titration experiments in DMSO-d6/0.5% water solution reveal that trans-1 exhibits a strong preference for dihydrogenphosphate (H2PO4−) over other anions (Cl−, MeCO2−, and PhCO2−), whereas the photogenerated metastable cis-1 shows lower affinity for the H2PO4− anion.en
dc.description.sponsorshipNational Science Centre (grant 2018/29/B/ST5/01366; grant UMO-2016/23/D/ST5/03301)
dc.identifier.citationNiedbała, P.; Ceborska, M.; Mehmet, M.; Ignacak, W.; Jurczak, J.; Dąbrowa, K. Anion Recognition by a Pincer-Type Host Constructed from Two Polyamide Macrocyclic Frameworks Jointed by a Photo-Addressable Azobenzene Switch. Materials 2022, 15, 692. https://doi.org/10.3390/ma15020692en
dc.identifier.doi10.3390/ma15020692
dc.identifier.issn1996-1944
dc.identifier.urihttps://open.icm.edu.pl/handle/123456789/21498
dc.language.isoen
dc.publisherMDPIen
dc.rightsUznanie autorstwa 4.0 Międzynarodowe*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.subjectanion recognitionen
dc.subjectmacrocycleen
dc.subjectazobenzeneen
dc.subjectpincer hosten
dc.subjectphotoisomerizationen
dc.titleAnion Recognition by a Pincer-Type Host Constructed from Two Polyamide Macrocyclic Frameworks Jointed by a Photo-Addressable Azobenzene Switchen
dc.typearticleen
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