Carboxylated Pillar[6]arene Emulates Pillar[5]arene in the Host–Guest Crystal Complexes and Shows Conformational Flexibility in the Solution/Gas Phase

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dc.contributor.authorButkiewicz, Helena
dc.contributor.authorKosiorek, Sandra
dc.contributor.authorSashuk, Volodymyr
dc.contributor.authorZimnicka, Magdalena M.
dc.contributor.authorDanylyuk, Oksana
dc.contributor.organizationInstitute of Physical Chemistry, Polish Academy of Sciencesen
dc.contributor.organizationInstitute of Organic Chemistry, Polish Academy of Sciencesen
dc.date.accessioned2024-01-08T12:13:11Z
dc.date.available2024-01-08T12:13:11Z
dc.date.issued2023
dc.description.abstractDespite the thriving interest in the aqueous complexation properties of carboxylated pillar[6]arene, its solid state supramolecular chemistry has remained a mystery. Here, overcoming challenging crystallogenesis, we report the first crystallographic authentication of carboxylated pillar[6]arene in the form of two host–guest inclusion complexes with methyl viologen and pentamidine. The key to the successful crystallization of carboxylated pillar[6]arene is the mixed ionization state of its 12 carboxylic substituents. The deprotonation of several but not all substituents enables intermolecular hydrogen bonding and, as a result, “gluing” and crystallization of pillar[6]arene complexes with the aid of carboxylic-carboxylate, carboxylic-carboxylic, and amidinium-carboxylate supramolecular synthons. Single crystal X-ray diffraction analysis revealed that upon guest inclusion pillar[6]arene adopts a quasi-pentagonal shape rather than the expected hexagonal shape. The squeezed quasi-pentagonal conformation of the six-membered macrocycle is stabilized by two intramolecular hydrogen bonds between pillar[6]arene substituents. Moreover, the distinctive deviation of the macrocycle from hexagonal shape stays operative in the solution/gas phase as concluded from ion mobility mass spectrometry (IM-MS) studies and theoretical calculations. These results provide the first insight into how to gain control over the conformation of flexible pillar[6]arene with a view of solid state design of more advanced supramolecular host–guest structures.en
dc.description.sponsorshipNational Science Centre of Poland (PRELUDIUM 14 No. 2017/27/N/ST5/01931)
dc.identifier.citationCryst. Growth Des. 2023, 23, 1, 11–18 ; https://doi.org/10.1021/acs.cgd.2c01135en
dc.identifier.doi10.1021/acs.cgd.2c01135
dc.identifier.issn1528-7483
dc.identifier.issn1528-7505
dc.identifier.urihttps://open.icm.edu.pl/handle/123456789/23512
dc.language.isoen
dc.publisherAmerican Chemical Societyen
dc.rightsUznanie autorstwa 4.0 Międzynarodowe*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.titleCarboxylated Pillar[6]arene Emulates Pillar[5]arene in the Host–Guest Crystal Complexes and Shows Conformational Flexibility in the Solution/Gas Phaseen
dc.typearticleen
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