Phthalazine-trione as a blue-green light-emitting moiety: crystal structures, photoluminescence and theoretical calculations

Página do item simplificado
dc.creatorFelipe Terra Martins
dc.creatorLauro June Queiroz Maia
dc.creatorGisane Gasparotto
dc.creatorAna Karoline Silva Medanha Valdo
dc.creatorJosé Antônio do Nascimento Neto
dc.creatorLeandro Ribeiro
dc.creatorYuri de Freitas Rego
dc.creatorCleiton Moreira da Silva
dc.creatorAngelo de Fatima
dc.date.accessioned2024-09-26T19:23:09Z
dc.date.accessioned2025-09-08T22:50:14Z
dc.date.available2024-09-26T19:23:09Z
dc.date.issued2018
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/C8NJ02976H
dc.identifier.issn1144-0546
dc.identifier.urihttps://hdl.handle.net/1843/76921
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofNew Journal of Chemistry
dc.rightsAcesso Restrito
dc.subjectFotoluminescência
dc.subjectCompostos heterocíclicos
dc.subjectFuncionais de densidade
dc.subjectOrbitais moleculares
dc.subject.otherPhthalazine
dc.subject.otherPhthalhydrazide
dc.subject.otherHeterocycles compounds
dc.subject.otherDensity functional theory (DFT)
dc.subject.otherFrontier molecular orbitals
dc.titlePhthalazine-trione as a blue-green light-emitting moiety: crystal structures, photoluminescence and theoretical calculations
dc.typeArtigo de periódico
local.citation.epage1321
local.citation.spage1313
local.citation.volume43
local.description.resumoPhthalazine (2,3-diazanaphthalene) and phthalhydrazide (2,3-dihydro-1,4-phthalazinedione) compounds are heterocycles with several biological properties. Most recently, analogous phthalazine-triones also emerged as drug candidates. Herein, we introduced a phthalazine-trione moiety as a promising fluorophore in the blue and green spectral regions. This desired optical property was rationalized based on their crystal structure and time-dependent density functional theory (TD-DFT) calculations. Under ultraviolet (UV) excitation (ca. 360 nm), two light emission maxima at ca. 460 nm and 480 nm were observed for ten phthalazine-triones, regardless of the substitution pattern. This conservation in the light-emitting property was rationalized by our time-dependent DFT calculations for the three phthalazine-triones whose crystal geometries were also determined in this study (4-chlorophenyl, 3-methoxyphenyl and 4-nitrophenyl derivatives) and for those available in literature (4-fluorophenyl and 4-bromophenyl derivatives). Electronic transitions with the largest oscillator strengths were near 360 nm and were in excellent agreement with the experimental excitation energy (UV-visible and photoluminescence spectra). Lifetime values of selected samples could also be determined, which were between 1.59 ns and 3.21 ns. In all compounds, the Frontier molecular orbitals involved in these excitations were distributed over the phthalazine-trione moiety and were not localized on the changeable substituent.
local.identifier.orcidhttps://orcid.org/0000-0002-9913-4716
local.identifier.orcidhttps://orcid.org/0000-0001-9004-0927
local.identifier.orcidhttps://orcid.org/0000-0003-4498-4438
local.identifier.orcidhttps://orcid.org/0000-0002-0967-2300
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/2019/nj/c8nj02976h

Arquivos

Licença do pacote

Agora exibindo 1 - 1 de 1
Imagem de Miniatura
Nome:
License.txt
Tamanho:
1.99 KB
Formato:
Plain Text
Descrição:
Baixar

Coleções

Artigo de Periódico

Logo UFMG