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Reaction-Based, Fluorescent Film Deposition from Dopamine and a Diamine-Tethered, Bis–Resorcinol Coupler

The reaction-based deposition on various surfaces of an all-organic fluorescent coating is reported here, involving autoxidation of 2 mM dopamine in carbonate buffer at pH 9.0, in the presence of a 1 mM diamine–resorcinol coupler (Bis–Res) prepared from 2,4-dihydroxybenzaldehyde and hexamethylenedia...

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Detalles Bibliográficos
Autores principales: Alfieri, Maria Laura, Iacomino, Mariagrazia, Napolitano, Alessandra, d’Ischia, Marco
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6769982/
https://www.ncbi.nlm.nih.gov/pubmed/31540228
http://dx.doi.org/10.3390/ijms20184532
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author Alfieri, Maria Laura
Iacomino, Mariagrazia
Napolitano, Alessandra
d’Ischia, Marco
author_facet Alfieri, Maria Laura
Iacomino, Mariagrazia
Napolitano, Alessandra
d’Ischia, Marco
author_sort Alfieri, Maria Laura
collection PubMed
description The reaction-based deposition on various surfaces of an all-organic fluorescent coating is reported here, involving autoxidation of 2 mM dopamine in carbonate buffer at pH 9.0, in the presence of a 1 mM diamine–resorcinol coupler (Bis–Res) prepared from 2,4-dihydroxybenzaldehyde and hexamethylenediamine (HMDA). Spectral analysis of the films coupled with an LC-MS investigation of the yellow fluorescent mixture was compatible with the formation and deposition of HMDA-linked methanobenzofuroazocinone fluorophores. Both the emission properties and hydrophobicity of the film were abated in a reversible manner following exposure to acid vapors. These results provide an entry to efficient and practical fluorescent coating methodologies based on in situ generation and the deposition of wet adhesive, as well as fluorescent materials combining a strongly emitting fluorophore with the film-forming properties of long chain diamines.
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spelling pubmed-67699822019-10-30 Reaction-Based, Fluorescent Film Deposition from Dopamine and a Diamine-Tethered, Bis–Resorcinol Coupler Alfieri, Maria Laura Iacomino, Mariagrazia Napolitano, Alessandra d’Ischia, Marco Int J Mol Sci Article The reaction-based deposition on various surfaces of an all-organic fluorescent coating is reported here, involving autoxidation of 2 mM dopamine in carbonate buffer at pH 9.0, in the presence of a 1 mM diamine–resorcinol coupler (Bis–Res) prepared from 2,4-dihydroxybenzaldehyde and hexamethylenediamine (HMDA). Spectral analysis of the films coupled with an LC-MS investigation of the yellow fluorescent mixture was compatible with the formation and deposition of HMDA-linked methanobenzofuroazocinone fluorophores. Both the emission properties and hydrophobicity of the film were abated in a reversible manner following exposure to acid vapors. These results provide an entry to efficient and practical fluorescent coating methodologies based on in situ generation and the deposition of wet adhesive, as well as fluorescent materials combining a strongly emitting fluorophore with the film-forming properties of long chain diamines. MDPI 2019-09-13 /pmc/articles/PMC6769982/ /pubmed/31540228 http://dx.doi.org/10.3390/ijms20184532 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Alfieri, Maria Laura
Iacomino, Mariagrazia
Napolitano, Alessandra
d’Ischia, Marco
Reaction-Based, Fluorescent Film Deposition from Dopamine and a Diamine-Tethered, Bis–Resorcinol Coupler
title Reaction-Based, Fluorescent Film Deposition from Dopamine and a Diamine-Tethered, Bis–Resorcinol Coupler
title_full Reaction-Based, Fluorescent Film Deposition from Dopamine and a Diamine-Tethered, Bis–Resorcinol Coupler
title_fullStr Reaction-Based, Fluorescent Film Deposition from Dopamine and a Diamine-Tethered, Bis–Resorcinol Coupler
title_full_unstemmed Reaction-Based, Fluorescent Film Deposition from Dopamine and a Diamine-Tethered, Bis–Resorcinol Coupler
title_short Reaction-Based, Fluorescent Film Deposition from Dopamine and a Diamine-Tethered, Bis–Resorcinol Coupler
title_sort reaction-based, fluorescent film deposition from dopamine and a diamine-tethered, bis–resorcinol coupler
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6769982/
https://www.ncbi.nlm.nih.gov/pubmed/31540228
http://dx.doi.org/10.3390/ijms20184532
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