Sulfonated melanin derivatives: theoretical evaluation of local reactivities and chemical structures
Autor(a) principal: | |
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Data de Publicação: | 2021 |
Outros Autores: | , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNESP |
Texto Completo: | http://dx.doi.org/10.1007/s00894-021-04982-z http://hdl.handle.net/11449/229944 |
Resumo: | Melanins are natural macromolecules present in several organisms responsible for photoprotection, photosensitivity, ion chelation, and thermoregulation. Such materials have attracted attention due to their interesting electronic properties, which suggest their possible application in biocompatible devices. However, the low typical solubility of traditional melanins does not allow the production of good quality thin films. In this sense, soluble compounds obtained via alternative synthetic routes, for instance, via levodopa (L-DOPA) oxidation in sulfonated solvents (S-melanins), can be considered interesting technological materials. Despite this, the structural and electronic features of these compounds are not fully understood. In this context, here we present a theoretical study on the local reactivities of S-melanin building blocks to better understand possible mechanisms involved in its synthesis and propose extended structures of this material. For this purpose, condensed-to-atoms Fukui indices were evaluated in the framework of the density functional theory (DFT). The obtained results show that the different side groups present in S-melanins do not significantly influence the reactivity of the compound in relation to non-functionalized melanins, indicating that both materials can present similar macroscopic structures. Graphical abstract: [Figure not available: see fulltext.]. |
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Repositório Institucional da UNESP |
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Sulfonated melanin derivatives: theoretical evaluation of local reactivities and chemical structuresDensity functional theoryLocal reactivitiesMelanin derivativesMolecular modelingMelanins are natural macromolecules present in several organisms responsible for photoprotection, photosensitivity, ion chelation, and thermoregulation. Such materials have attracted attention due to their interesting electronic properties, which suggest their possible application in biocompatible devices. However, the low typical solubility of traditional melanins does not allow the production of good quality thin films. In this sense, soluble compounds obtained via alternative synthetic routes, for instance, via levodopa (L-DOPA) oxidation in sulfonated solvents (S-melanins), can be considered interesting technological materials. Despite this, the structural and electronic features of these compounds are not fully understood. In this context, here we present a theoretical study on the local reactivities of S-melanin building blocks to better understand possible mechanisms involved in its synthesis and propose extended structures of this material. For this purpose, condensed-to-atoms Fukui indices were evaluated in the framework of the density functional theory (DFT). The obtained results show that the different side groups present in S-melanins do not significantly influence the reactivity of the compound in relation to non-functionalized melanins, indicating that both materials can present similar macroscopic structures. Graphical abstract: [Figure not available: see fulltext.].Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)São Paulo State University (UNESP), Campus of ItapevaSchool of Sciences POSMAT São Paulo State University (UNESP)Brazilian Nanotechnology National Laboratory (LNNano) Brazilian Center for Research in Energy and Materials (CNPEM)São Paulo State University (UNESP), Campus of ItapevaSchool of Sciences POSMAT São Paulo State University (UNESP)CNPq: 420449/2018-3CNPq: 448310/2014-7Universidade Estadual Paulista (UNESP)Brazilian Center for Research in Energy and Materials (CNPEM)Cuba, João P. B. [UNESP]Alves, Gabriel G. B. [UNESP]Galindo, Levy A. [UNESP]Paulin, João V.Batagin-Neto, Augusto [UNESP]2022-04-29T08:36:46Z2022-04-29T08:36:46Z2021-12-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://dx.doi.org/10.1007/s00894-021-04982-zJournal of Molecular Modeling, v. 27, n. 12, 2021.0948-50231610-2940http://hdl.handle.net/11449/22994410.1007/s00894-021-04982-z2-s2.0-85119883746Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengJournal of Molecular Modelinginfo:eu-repo/semantics/openAccess2022-04-29T08:36:46Zoai:repositorio.unesp.br:11449/229944Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T17:12:13.638282Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
dc.title.none.fl_str_mv |
Sulfonated melanin derivatives: theoretical evaluation of local reactivities and chemical structures |
title |
Sulfonated melanin derivatives: theoretical evaluation of local reactivities and chemical structures |
spellingShingle |
Sulfonated melanin derivatives: theoretical evaluation of local reactivities and chemical structures Cuba, João P. B. [UNESP] Density functional theory Local reactivities Melanin derivatives Molecular modeling |
title_short |
Sulfonated melanin derivatives: theoretical evaluation of local reactivities and chemical structures |
title_full |
Sulfonated melanin derivatives: theoretical evaluation of local reactivities and chemical structures |
title_fullStr |
Sulfonated melanin derivatives: theoretical evaluation of local reactivities and chemical structures |
title_full_unstemmed |
Sulfonated melanin derivatives: theoretical evaluation of local reactivities and chemical structures |
title_sort |
Sulfonated melanin derivatives: theoretical evaluation of local reactivities and chemical structures |
author |
Cuba, João P. B. [UNESP] |
author_facet |
Cuba, João P. B. [UNESP] Alves, Gabriel G. B. [UNESP] Galindo, Levy A. [UNESP] Paulin, João V. Batagin-Neto, Augusto [UNESP] |
author_role |
author |
author2 |
Alves, Gabriel G. B. [UNESP] Galindo, Levy A. [UNESP] Paulin, João V. Batagin-Neto, Augusto [UNESP] |
author2_role |
author author author author |
dc.contributor.none.fl_str_mv |
Universidade Estadual Paulista (UNESP) Brazilian Center for Research in Energy and Materials (CNPEM) |
dc.contributor.author.fl_str_mv |
Cuba, João P. B. [UNESP] Alves, Gabriel G. B. [UNESP] Galindo, Levy A. [UNESP] Paulin, João V. Batagin-Neto, Augusto [UNESP] |
dc.subject.por.fl_str_mv |
Density functional theory Local reactivities Melanin derivatives Molecular modeling |
topic |
Density functional theory Local reactivities Melanin derivatives Molecular modeling |
description |
Melanins are natural macromolecules present in several organisms responsible for photoprotection, photosensitivity, ion chelation, and thermoregulation. Such materials have attracted attention due to their interesting electronic properties, which suggest their possible application in biocompatible devices. However, the low typical solubility of traditional melanins does not allow the production of good quality thin films. In this sense, soluble compounds obtained via alternative synthetic routes, for instance, via levodopa (L-DOPA) oxidation in sulfonated solvents (S-melanins), can be considered interesting technological materials. Despite this, the structural and electronic features of these compounds are not fully understood. In this context, here we present a theoretical study on the local reactivities of S-melanin building blocks to better understand possible mechanisms involved in its synthesis and propose extended structures of this material. For this purpose, condensed-to-atoms Fukui indices were evaluated in the framework of the density functional theory (DFT). The obtained results show that the different side groups present in S-melanins do not significantly influence the reactivity of the compound in relation to non-functionalized melanins, indicating that both materials can present similar macroscopic structures. Graphical abstract: [Figure not available: see fulltext.]. |
publishDate |
2021 |
dc.date.none.fl_str_mv |
2021-12-01 2022-04-29T08:36:46Z 2022-04-29T08:36:46Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://dx.doi.org/10.1007/s00894-021-04982-z Journal of Molecular Modeling, v. 27, n. 12, 2021. 0948-5023 1610-2940 http://hdl.handle.net/11449/229944 10.1007/s00894-021-04982-z 2-s2.0-85119883746 |
url |
http://dx.doi.org/10.1007/s00894-021-04982-z http://hdl.handle.net/11449/229944 |
identifier_str_mv |
Journal of Molecular Modeling, v. 27, n. 12, 2021. 0948-5023 1610-2940 10.1007/s00894-021-04982-z 2-s2.0-85119883746 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Journal of Molecular Modeling |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.source.none.fl_str_mv |
Scopus reponame:Repositório Institucional da UNESP instname:Universidade Estadual Paulista (UNESP) instacron:UNESP |
instname_str |
Universidade Estadual Paulista (UNESP) |
instacron_str |
UNESP |
institution |
UNESP |
reponame_str |
Repositório Institucional da UNESP |
collection |
Repositório Institucional da UNESP |
repository.name.fl_str_mv |
Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP) |
repository.mail.fl_str_mv |
|
_version_ |
1808128771238133760 |