Photophysical and Photochemical Properties and Aggregation Behavior of Phthalocyanine and Naphthalocyanine Derivatives
Autor(a) principal: | |
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Data de Publicação: | 2018 |
Outros Autores: | , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Journal of the Brazilian Chemical Society (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018000601199 |
Resumo: | The photophysical and photochemical properties of phthalocyanine and naphthalocyanine with similar structures were studied in solution and with density-functional theory (DFT) computational method. The extended π-conjugated system in naphthalocyanines causes a bathochromic shift in UV-Vis, emission and excitation bands, and promotes lesser generation of singlet oxygen in solution when compared to phthalocyanines. Time dependent DFT (TD-DFT) calculations point out the molecular orbitals involved in Q-band transition, corresponding to highest occupied molecular orbital (HOMO) to lowest unoccupied molecular orbital (LUMO) transition with a concentration of charge along x-axis, while the transition to LUMO+1 is in y-axis direction. The presence of tert-butyl substituents does not affect the molecular orbitals shape, but affect their energies. Aggregation studies in dimethyl sulfoxide (DMSO):water solutions showed that naphthalocyanines studied have more aggregation tendency than the phthalocyanines. DFT studies indicated that stacked-dimers are preferred to rotated-stacked conformation due the interaction between ZnII and nitrogen atom from different monomers. |
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Photophysical and Photochemical Properties and Aggregation Behavior of Phthalocyanine and Naphthalocyanine Derivativesphthalocyaninenaphthalocyanineaggregationphotophysicalcomputational studiesThe photophysical and photochemical properties of phthalocyanine and naphthalocyanine with similar structures were studied in solution and with density-functional theory (DFT) computational method. The extended π-conjugated system in naphthalocyanines causes a bathochromic shift in UV-Vis, emission and excitation bands, and promotes lesser generation of singlet oxygen in solution when compared to phthalocyanines. Time dependent DFT (TD-DFT) calculations point out the molecular orbitals involved in Q-band transition, corresponding to highest occupied molecular orbital (HOMO) to lowest unoccupied molecular orbital (LUMO) transition with a concentration of charge along x-axis, while the transition to LUMO+1 is in y-axis direction. The presence of tert-butyl substituents does not affect the molecular orbitals shape, but affect their energies. Aggregation studies in dimethyl sulfoxide (DMSO):water solutions showed that naphthalocyanines studied have more aggregation tendency than the phthalocyanines. DFT studies indicated that stacked-dimers are preferred to rotated-stacked conformation due the interaction between ZnII and nitrogen atom from different monomers.Sociedade Brasileira de Química2018-06-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018000601199Journal of the Brazilian Chemical Society v.29 n.6 2018reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20170215info:eu-repo/semantics/openAccessSouza,Thalita F. M. deAntonio,Felipe C. T.Zanotto,MateusHomem-de-Mello,PaulaRibeiro,Anderson O.eng2018-05-18T00:00:00Zoai:scielo:S0103-50532018000601199Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2018-05-18T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Photophysical and Photochemical Properties and Aggregation Behavior of Phthalocyanine and Naphthalocyanine Derivatives |
title |
Photophysical and Photochemical Properties and Aggregation Behavior of Phthalocyanine and Naphthalocyanine Derivatives |
spellingShingle |
Photophysical and Photochemical Properties and Aggregation Behavior of Phthalocyanine and Naphthalocyanine Derivatives Souza,Thalita F. M. de phthalocyanine naphthalocyanine aggregation photophysical computational studies |
title_short |
Photophysical and Photochemical Properties and Aggregation Behavior of Phthalocyanine and Naphthalocyanine Derivatives |
title_full |
Photophysical and Photochemical Properties and Aggregation Behavior of Phthalocyanine and Naphthalocyanine Derivatives |
title_fullStr |
Photophysical and Photochemical Properties and Aggregation Behavior of Phthalocyanine and Naphthalocyanine Derivatives |
title_full_unstemmed |
Photophysical and Photochemical Properties and Aggregation Behavior of Phthalocyanine and Naphthalocyanine Derivatives |
title_sort |
Photophysical and Photochemical Properties and Aggregation Behavior of Phthalocyanine and Naphthalocyanine Derivatives |
author |
Souza,Thalita F. M. de |
author_facet |
Souza,Thalita F. M. de Antonio,Felipe C. T. Zanotto,Mateus Homem-de-Mello,Paula Ribeiro,Anderson O. |
author_role |
author |
author2 |
Antonio,Felipe C. T. Zanotto,Mateus Homem-de-Mello,Paula Ribeiro,Anderson O. |
author2_role |
author author author author |
dc.contributor.author.fl_str_mv |
Souza,Thalita F. M. de Antonio,Felipe C. T. Zanotto,Mateus Homem-de-Mello,Paula Ribeiro,Anderson O. |
dc.subject.por.fl_str_mv |
phthalocyanine naphthalocyanine aggregation photophysical computational studies |
topic |
phthalocyanine naphthalocyanine aggregation photophysical computational studies |
description |
The photophysical and photochemical properties of phthalocyanine and naphthalocyanine with similar structures were studied in solution and with density-functional theory (DFT) computational method. The extended π-conjugated system in naphthalocyanines causes a bathochromic shift in UV-Vis, emission and excitation bands, and promotes lesser generation of singlet oxygen in solution when compared to phthalocyanines. Time dependent DFT (TD-DFT) calculations point out the molecular orbitals involved in Q-band transition, corresponding to highest occupied molecular orbital (HOMO) to lowest unoccupied molecular orbital (LUMO) transition with a concentration of charge along x-axis, while the transition to LUMO+1 is in y-axis direction. The presence of tert-butyl substituents does not affect the molecular orbitals shape, but affect their energies. Aggregation studies in dimethyl sulfoxide (DMSO):water solutions showed that naphthalocyanines studied have more aggregation tendency than the phthalocyanines. DFT studies indicated that stacked-dimers are preferred to rotated-stacked conformation due the interaction between ZnII and nitrogen atom from different monomers. |
publishDate |
2018 |
dc.date.none.fl_str_mv |
2018-06-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018000601199 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532018000601199 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.21577/0103-5053.20170215 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
Journal of the Brazilian Chemical Society v.29 n.6 2018 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Journal of the Brazilian Chemical Society (Online) |
collection |
Journal of the Brazilian Chemical Society (Online) |
repository.name.fl_str_mv |
Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
||office@jbcs.sbq.org.br |
_version_ |
1750318180801183744 |