Solvatomorphs of 25,26,27,28- tetrahydroxycalix[4]arene and 5,11,17,23-tetramino-25,26,27,28-tetrabutoxycalix[4]arene: quenching photoluminescence through switching the guest

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dc.creatorFelipe Terra Martins
dc.creatorLauro June Queiroz Maia
dc.creatorLeonardo da Silva Neto
dc.creatorCleiton Moreira da Silva
dc.creatorAriel Marcelo Sarotti
dc.creatorÂngelo de Fátima
dc.date.accessioned2024-07-25T21:23:46Z
dc.date.accessioned2025-09-09T01:14:46Z
dc.date.available2024-07-25T21:23:46Z
dc.date.issued2017
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico
dc.description.sponsorshipFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas Gerais
dc.description.sponsorshipCAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
dc.description.sponsorshipOutra Agência
dc.identifier.doihttps://doi.org/10.1039/C6CE02649D
dc.identifier.issn1466-8033
dc.identifier.urihttps://hdl.handle.net/1843/71602
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofCrystEngComm
dc.rightsAcesso Restrito
dc.subjectCalixarenos
dc.subjectFotoluminescência
dc.subject.otherSolvatomorphs
dc.subject.otherCalixarenes
dc.titleSolvatomorphs of 25,26,27,28- tetrahydroxycalix[4]arene and 5,11,17,23-tetramino-25,26,27,28-tetrabutoxycalix[4]arene: quenching photoluminescence through switching the guest
dc.typeArtigo de periódico
local.citation.epage1800
local.citation.spage1792
local.citation.volume19
local.description.resumoHere, we have disclosed two solid state forms of 5,11,17,23-tetramino-25,26,27,28-tetrabutoxycalix[4]arene (1) and two solid state forms of the non-functionalized 25,26,27,28-tetrahydroxycalix[4]arene (2). This is the first structural knowledge of a tetra-amino functionalized calixarene derivative, even though this compound is well known and used as a precursor of several other functionalized calix[4]arenes. The two solid forms of 1 differ by the presence of either water or water/dimethylsulfoxide (DMSO) solvent molecules entrapped in the major calixarene cavity, even though the pinched conformation is adopted in both forms as a consequence of the contacts between solvent molecules and phenyl rings. Likewise, the switch from water to DMSO in the cone cavity of 1 has abrogated the photoluminescence (PL) found only in the dihydrate form. Frontier molecular orbital calculations at the B3LYP/6-31G* level of theory support a short-range electron transfer between guest (DMSO) and host (1) molecules quenching the solid state photoluminescence when DMSO is entrapped in the cone. This solvatomorphism approach for PL search in calixarenes opens a perspective on tuning and even increasing the performance of calixarenes through changing the guest solvent molecule. Similarly, the two crystal forms of 2 entrap either methyl alcohol or DMSO in their cones, which, as well as both crystal forms of 1, are packed into sheets through different fashions and contact patterns.
local.identifier.orcidhttps://orcid.org/0000-0002-8151-0306
local.identifier.orcidhttps://orcid.org/0000-0001-9913-8971
local.identifier.orcidhttps://orcid.org/0000-0001-9913-8971
local.identifier.orcidhttps://orcid.org/0000-0003-2344-5590
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://pubs.rsc.org/en/content/articlelanding/2017/ce/c6ce02649d

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