Síntesis y solvatofluorocromismo de pigmentos basados en cumarinas conjugadas con pirazolo[1,5-a]pirimidinas y pirazolinas: un enfoque en la quimiodetección de iones
El trabajo de investigación titulado “Síntesis y solvatofluorocromismo de pigmentos basados en cumarinas conjugadas con pirazolo[1,5-a]pirimidinas y pirazolinas: un enfoque en la quimiodetección de iones” y que se desarrolló en el Grupo de Investigación de Compuestos Biorgánicos (GICOBIORG) de la Un...
- Autores:
-
Bravo Piñeros, Néstor Fabian
- Tipo de recurso:
- Doctoral thesis
- Fecha de publicación:
- 2024
- Institución:
- Universidad de los Andes
- Repositorio:
- Séneca: repositorio Uniandes
- Idioma:
- spa
- OAI Identifier:
- oai:repositorio.uniandes.edu.co:1992/75989
- Acceso en línea:
- https://hdl.handle.net/1992/75989
- Palabra clave:
- Sensor molecular
Cumarina
Pirazolo[1,5-a]pirimidinas
Pirazolina
Solvatofluorocromismo
Quimiodetección
Fluorescencia
Cobre
Niquel
Cianuro
Sulfito
Bisulfito
Química
- Rights
- openAccess
- License
- Attribution-NonCommercial-NoDerivatives 4.0 International
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| dc.title.spa.fl_str_mv |
Síntesis y solvatofluorocromismo de pigmentos basados en cumarinas conjugadas con pirazolo[1,5-a]pirimidinas y pirazolinas: un enfoque en la quimiodetección de iones |
| title |
Síntesis y solvatofluorocromismo de pigmentos basados en cumarinas conjugadas con pirazolo[1,5-a]pirimidinas y pirazolinas: un enfoque en la quimiodetección de iones |
| spellingShingle |
Síntesis y solvatofluorocromismo de pigmentos basados en cumarinas conjugadas con pirazolo[1,5-a]pirimidinas y pirazolinas: un enfoque en la quimiodetección de iones Sensor molecular Cumarina Pirazolo[1,5-a]pirimidinas Pirazolina Solvatofluorocromismo Quimiodetección Fluorescencia Cobre Niquel Cianuro Sulfito Bisulfito Química |
| title_short |
Síntesis y solvatofluorocromismo de pigmentos basados en cumarinas conjugadas con pirazolo[1,5-a]pirimidinas y pirazolinas: un enfoque en la quimiodetección de iones |
| title_full |
Síntesis y solvatofluorocromismo de pigmentos basados en cumarinas conjugadas con pirazolo[1,5-a]pirimidinas y pirazolinas: un enfoque en la quimiodetección de iones |
| title_fullStr |
Síntesis y solvatofluorocromismo de pigmentos basados en cumarinas conjugadas con pirazolo[1,5-a]pirimidinas y pirazolinas: un enfoque en la quimiodetección de iones |
| title_full_unstemmed |
Síntesis y solvatofluorocromismo de pigmentos basados en cumarinas conjugadas con pirazolo[1,5-a]pirimidinas y pirazolinas: un enfoque en la quimiodetección de iones |
| title_sort |
Síntesis y solvatofluorocromismo de pigmentos basados en cumarinas conjugadas con pirazolo[1,5-a]pirimidinas y pirazolinas: un enfoque en la quimiodetección de iones |
| dc.creator.fl_str_mv |
Bravo Piñeros, Néstor Fabian |
| dc.contributor.advisor.none.fl_str_mv |
Portilla Salinas, Jaime Antonio |
| dc.contributor.author.none.fl_str_mv |
Bravo Piñeros, Néstor Fabian |
| dc.contributor.jury.none.fl_str_mv |
Marchal Ingrain, Antonio Ortiz Gonzales, Alejandro Rivas Hernández, Ricardo Eusebio |
| dc.contributor.researchgroup.none.fl_str_mv |
Facultad de Ciencias |
| dc.subject.keyword.none.fl_str_mv |
Sensor molecular Cumarina Pirazolo[1,5-a]pirimidinas Pirazolina Solvatofluorocromismo Quimiodetección Fluorescencia Cobre Niquel Cianuro Sulfito Bisulfito |
| topic |
Sensor molecular Cumarina Pirazolo[1,5-a]pirimidinas Pirazolina Solvatofluorocromismo Quimiodetección Fluorescencia Cobre Niquel Cianuro Sulfito Bisulfito Química |
| dc.subject.themes.spa.fl_str_mv |
Química |
| description |
El trabajo de investigación titulado “Síntesis y solvatofluorocromismo de pigmentos basados en cumarinas conjugadas con pirazolo[1,5-a]pirimidinas y pirazolinas: un enfoque en la quimiodetección de iones” y que se desarrolló en el Grupo de Investigación de Compuestos Biorgánicos (GICOBIORG) de la Universidad de Los Andes, bajo la dirección del profesor Dr. Jaime Antonio Portilla Salinas, se centra en el diseño y desarrollo de nuevos compuestos fluorescentes capaces de detectar cationes y aniones. El enfoque de diseño utiliza mecanismos fotofísicos basados en las propiedades electrónicas y de solvatofluorocromismo para los pigmentos sintetizados, los cuales son una serie de compuestos híbridos de cumarina con pirazolo[1,5-a]pirimidina y pirazolina que poseen propiedades fotofísicas modulables según el medio en el que actúan (i.e., disolvente, iones, etc.) y diverso sitio de reconocimiento. El objetivo de investigación principal es explorar cómo los compuestos híbridos obtenidos responden a cambios en el entorno, con especial énfasis en su capacidad para detectar especies químicas como el cobre (Cu²⁺), níquel (Ni²⁺), cianuro (CN⁻), sulfito (SO₃2⁻) y bisulfito (HSO₃⁻). Así, mediante mediciones espectroscópicas, se identificaron las propiedades de absorción, emisión y enlazamiento de los pigmentos, destacando su utilidad como sensores químicos o sondas moleculares. Los experimentos de absorción y emisión revelaron que estos compuestos presentan desplazamientos de Stokes significativos, dependientes de la polaridad y polarizabilidad del solvente, lo que indica una reorganización estructural en sus estados excitados; asimismo, se pudieron establecer los sitios de unión de las sondas con los analitos de interés mediante RMN, algo crucial para los mecanismos de detección. Los resultados obtenidos de la investigación desarrollada en este trabajo de investigación doctoral no solo demuestran la sensibilidad de los pigmentos desarrollados hacia diversos analitos, sino que también amplian las perspectivas en el diseño de sensores fluorescentes más eficientes, con aplicaciones potenciales en campos como el monitoreo ambiental y la industria química. Este trabajo contribuye al desarrollo de herramientas útiles para la detección rápida y precisa de contaminantes, lo que lo convierte en un aporte significativo en la química de materiales y sensores, además que ofrece una formación de amplio alcance e integral al investigador principal, desde la química sintética hasta la analítica. |
| publishDate |
2024 |
| dc.date.issued.none.fl_str_mv |
2024-10-28 |
| dc.date.accessioned.none.fl_str_mv |
2025-02-03T14:32:51Z |
| dc.date.available.none.fl_str_mv |
2025-02-03T14:32:51Z |
| dc.type.none.fl_str_mv |
Trabajo de grado - Doctorado |
| dc.type.driver.none.fl_str_mv |
info:eu-repo/semantics/doctoralThesis |
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info:eu-repo/semantics/acceptedVersion |
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http://purl.org/coar/resource_type/c_db06 |
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https://purl.org/redcol/resource_type/TD |
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instname:Universidad de los Andes |
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reponame:Repositorio Institucional Séneca |
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repourl:https://repositorio.uniandes.edu.co/ |
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instname:Universidad de los Andes reponame:Repositorio Institucional Séneca repourl:https://repositorio.uniandes.edu.co/ |
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spa |
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spa |
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Portilla Salinas, Jaime Antoniovirtual::23122-1Bravo Piñeros, Néstor FabianMarchal Ingrain, AntonioOrtiz Gonzales, AlejandroRivas Hernández, Ricardo EusebioFacultad de Ciencias2025-02-03T14:32:51Z2025-02-03T14:32:51Z2024-10-28https://hdl.handle.net/1992/75989instname:Universidad de los Andesreponame:Repositorio Institucional Sénecarepourl:https://repositorio.uniandes.edu.co/El trabajo de investigación titulado “Síntesis y solvatofluorocromismo de pigmentos basados en cumarinas conjugadas con pirazolo[1,5-a]pirimidinas y pirazolinas: un enfoque en la quimiodetección de iones” y que se desarrolló en el Grupo de Investigación de Compuestos Biorgánicos (GICOBIORG) de la Universidad de Los Andes, bajo la dirección del profesor Dr. Jaime Antonio Portilla Salinas, se centra en el diseño y desarrollo de nuevos compuestos fluorescentes capaces de detectar cationes y aniones. El enfoque de diseño utiliza mecanismos fotofísicos basados en las propiedades electrónicas y de solvatofluorocromismo para los pigmentos sintetizados, los cuales son una serie de compuestos híbridos de cumarina con pirazolo[1,5-a]pirimidina y pirazolina que poseen propiedades fotofísicas modulables según el medio en el que actúan (i.e., disolvente, iones, etc.) y diverso sitio de reconocimiento. El objetivo de investigación principal es explorar cómo los compuestos híbridos obtenidos responden a cambios en el entorno, con especial énfasis en su capacidad para detectar especies químicas como el cobre (Cu²⁺), níquel (Ni²⁺), cianuro (CN⁻), sulfito (SO₃2⁻) y bisulfito (HSO₃⁻). Así, mediante mediciones espectroscópicas, se identificaron las propiedades de absorción, emisión y enlazamiento de los pigmentos, destacando su utilidad como sensores químicos o sondas moleculares. Los experimentos de absorción y emisión revelaron que estos compuestos presentan desplazamientos de Stokes significativos, dependientes de la polaridad y polarizabilidad del solvente, lo que indica una reorganización estructural en sus estados excitados; asimismo, se pudieron establecer los sitios de unión de las sondas con los analitos de interés mediante RMN, algo crucial para los mecanismos de detección. Los resultados obtenidos de la investigación desarrollada en este trabajo de investigación doctoral no solo demuestran la sensibilidad de los pigmentos desarrollados hacia diversos analitos, sino que también amplian las perspectivas en el diseño de sensores fluorescentes más eficientes, con aplicaciones potenciales en campos como el monitoreo ambiental y la industria química. Este trabajo contribuye al desarrollo de herramientas útiles para la detección rápida y precisa de contaminantes, lo que lo convierte en un aporte significativo en la química de materiales y sensores, además que ofrece una formación de amplio alcance e integral al investigador principal, desde la química sintética hasta la analítica.El Ministerio de Ciencias, Tecnología e Innovación (Minciencias), convocatoria No. 1 del Fondo de Ciencia, Tecnología e Innovación (FCTeI) del Sistema General de Regalías (SGR).Universidad de los Andes por medio de Asistencia graduada y crédito condonable.DoctoradoGICOBIORG158 páginasapplication/pdfspaUniversidad de los AndesDoctorado en Ciencias - QuímicaFacultad de CienciasDepartamento de QuímicaAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2Síntesis y solvatofluorocromismo de pigmentos basados en cumarinas conjugadas con pirazolo[1,5-a]pirimidinas y pirazolinas: un enfoque en la quimiodetección de ionesTrabajo de grado - Doctoradoinfo:eu-repo/semantics/doctoralThesisinfo:eu-repo/semantics/acceptedVersionhttp://purl.org/coar/resource_type/c_db06Texthttps://purl.org/redcol/resource_type/TDSensor molecularCumarinaPirazolo[1,5-a]pirimidinasPirazolinaSolvatofluorocromismoQuimiodetecciónFluorescenciaCobreNiquelCianuroSulfitoBisulfitoQuímicaSinhamahapatra, A.; Sutradhar, N.; Pahari, S.; Bajaj, H. 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A Facile Synthesis of Highly Functionalized 4-Arylcoumarins via Kostanecki Reactions Mediated by DBU. Molecules 2011, 16 (8), 6313–6321. https://doi.org/10.3390/molecules16086313.Cao, D.; Liu, Z.; Verwilst, P.; Koo, S.; Jangjili, P.; Kim, J. S.; Lin, W. Coumarin-Based Small-Molecule Fluorescent Chemosensors. Chem Rev 2019, 119 (18), 10403–10519. https://doi.org/10.1021/acs.chemrev.9b00145.Sharma, R. K.; Katiyar, D. Recent Advances in Transition-Metal-Catalyzed Synthesis of Coumarins. Synthesis (Germany). Georg Thieme Verlag August 1, 2016, pp 2303–2322. https://doi.org/10.1055/s-0035-1560450.Dalpozzo, R.; Mancuso, R. Copper-Catalyzed Synthesis of Coumarins. A Mini-Review. Catalysts 2021, 11 (11). https://doi.org/10.3390/catal11111382.Liu, M.; Jiang, Q.; Lu, Z.; Huang, Y.; Tan, Y.; Jiang, Q. A Coumarin-Based Fluorescent Turn-on Probe for Detection of Biothiols in Vitro. Luminescence 2015, 30 (8), 1395–1402. https://doi.org/10.1002/bio.2912.Jung, H. S.; Ko, K. C.; Lee, J. H.; Kim, S. 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