Design and synthesis of chemosensors based on 7-ferrocenylpyrazolo[1,5-a]pyrimidines for the detection of H+ and CN-
En este trabajo de grado se realiza la investigación de la síntesis y aplicaciones de moléculas híbridas inorgánica/orgánica de 7-ferrocenilpirazolo[1,5-a]pirimidina. Las aplicaciones se centran en la detección óptica de protón en medio orgánico y en la detección óptica y electroquímica de cianuro....
- Autores:
-
Peña Bernal, Carlos Arturo
- Tipo de recurso:
- Fecha de publicación:
- 2021
- Institución:
- Universidad de los Andes
- Repositorio:
- Séneca: repositorio Uniandes
- Idioma:
- eng
- OAI Identifier:
- oai:repositorio.uniandes.edu.co:1992/56303
- Acceso en línea:
- http://hdl.handle.net/1992/56303
- Palabra clave:
- Pyrazolo[1,5-a]pyrimidine
Colvatochromism
Chemosensor
Cyanide
Quimiosensores
Pirazolopirimidinas
Química
- Rights
- openAccess
- License
- http://creativecommons.org/licenses/by-nc-nd/4.0/
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UNIANDES2_1112fda8f3487b8cc809ce11e40e17b9 |
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oai:repositorio.uniandes.edu.co:1992/56303 |
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UNIANDES2 |
| network_name_str |
Séneca: repositorio Uniandes |
| repository_id_str |
|
| dc.title.none.fl_str_mv |
Design and synthesis of chemosensors based on 7-ferrocenylpyrazolo[1,5-a]pyrimidines for the detection of H+ and CN- |
| title |
Design and synthesis of chemosensors based on 7-ferrocenylpyrazolo[1,5-a]pyrimidines for the detection of H+ and CN- |
| spellingShingle |
Design and synthesis of chemosensors based on 7-ferrocenylpyrazolo[1,5-a]pyrimidines for the detection of H+ and CN- Pyrazolo[1,5-a]pyrimidine Colvatochromism Chemosensor Cyanide Quimiosensores Pirazolopirimidinas Química |
| title_short |
Design and synthesis of chemosensors based on 7-ferrocenylpyrazolo[1,5-a]pyrimidines for the detection of H+ and CN- |
| title_full |
Design and synthesis of chemosensors based on 7-ferrocenylpyrazolo[1,5-a]pyrimidines for the detection of H+ and CN- |
| title_fullStr |
Design and synthesis of chemosensors based on 7-ferrocenylpyrazolo[1,5-a]pyrimidines for the detection of H+ and CN- |
| title_full_unstemmed |
Design and synthesis of chemosensors based on 7-ferrocenylpyrazolo[1,5-a]pyrimidines for the detection of H+ and CN- |
| title_sort |
Design and synthesis of chemosensors based on 7-ferrocenylpyrazolo[1,5-a]pyrimidines for the detection of H+ and CN- |
| dc.creator.fl_str_mv |
Peña Bernal, Carlos Arturo |
| dc.contributor.advisor.none.fl_str_mv |
Portilla Salinas, Jaime Antonio Tigreros Ortíz, Alexis |
| dc.contributor.author.none.fl_str_mv |
Peña Bernal, Carlos Arturo |
| dc.contributor.jury.none.fl_str_mv |
Gamba Sánchez, Diego Alexander Chaur Valencia, Manuel Noe |
| dc.contributor.researchgroup.es_CO.fl_str_mv |
Grupo de Investigación en Compuestos Bio-orgánicos (GICOBIORG) |
| dc.subject.keyword.none.fl_str_mv |
Pyrazolo[1,5-a]pyrimidine Colvatochromism Chemosensor Cyanide |
| topic |
Pyrazolo[1,5-a]pyrimidine Colvatochromism Chemosensor Cyanide Quimiosensores Pirazolopirimidinas Química |
| dc.subject.armarc.none.fl_str_mv |
Quimiosensores Pirazolopirimidinas |
| dc.subject.themes.es_CO.fl_str_mv |
Química |
| description |
En este trabajo de grado se realiza la investigación de la síntesis y aplicaciones de moléculas híbridas inorgánica/orgánica de 7-ferrocenilpirazolo[1,5-a]pirimidina. Las aplicaciones se centran en la detección óptica de protón en medio orgánico y en la detección óptica y electroquímica de cianuro. |
| publishDate |
2021 |
| dc.date.issued.none.fl_str_mv |
2021-12 |
| dc.date.accessioned.none.fl_str_mv |
2022-03-10T19:58:08Z |
| dc.date.available.none.fl_str_mv |
2022-03-10T19:58:08Z |
| dc.type.spa.fl_str_mv |
Trabajo de grado - Maestría |
| dc.type.coarversion.fl_str_mv |
http://purl.org/coar/version/c_970fb48d4fbd8a85 |
| dc.type.driver.spa.fl_str_mv |
info:eu-repo/semantics/masterThesis |
| dc.type.content.spa.fl_str_mv |
Text |
| dc.type.redcol.spa.fl_str_mv |
http://purl.org/redcol/resource_type/TM |
| dc.identifier.uri.none.fl_str_mv |
http://hdl.handle.net/1992/56303 |
| dc.identifier.instname.spa.fl_str_mv |
instname:Universidad de los Andes |
| dc.identifier.reponame.spa.fl_str_mv |
reponame:Repositorio Institucional Séneca |
| dc.identifier.repourl.spa.fl_str_mv |
repourl:https://repositorio.uniandes.edu.co/ |
| url |
http://hdl.handle.net/1992/56303 |
| identifier_str_mv |
instname:Universidad de los Andes reponame:Repositorio Institucional Séneca repourl:https://repositorio.uniandes.edu.co/ |
| dc.language.iso.es_CO.fl_str_mv |
eng |
| language |
eng |
| dc.relation.references.es_CO.fl_str_mv |
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A Turn-on Fluorescent Sensor for Imaging Labile Fe3+ in Live Neuronal Cells at Subcellular Resolution. ChemBioChem 2012, 13 (11), 1569-1573. https://doi.org/10.1002/cbic.201200202. Samanta, S.; Manna, U.; Ray, T.; Das, G. An Aggregation-Induced Emission (AIE) Active Probe for Multiple Targets: A Fluorescent Sensor for Zn2+ and Al3+ & a Colorimetric Sensor for Cu2+ and F. Dalton Trans. 2015, 44 (43), 18902-18910. https://doi.org/10.1039/C5DT03186A. Cho, H.; Chae, J. B.; Kim, C. A Thiophene-Based Blue-Fluorescent Emitting Chemosensor for Detecting Indium (III) Ion. Inorg. Chem. Commun. 2018, 97, 171-175. https://doi.org/10.1016/j.inoche.2018.09.037. Bakker, E.; Telting-Diaz, M. Electrochemical Sensors. Anal. Chem. 2002, 74 (12), 2781-2800. https://doi.org/10.1021/ac0202278. Gale, P. A.; Caltagirone, C. Fluorescent and Colorimetric Sensors for Anionic Species. Coord. Chem. Rev. 2018, 354, 2-27. https://doi.org/10.1016/j.ccr.2017.05.003. McNaughton, D. A.; Fares, M.; Picci, G.; Gale, P. A.; Caltagirone, C. Advances in Fluorescent and Colorimetric Sensors for Anionic Species. Coord. Chem. Rev. 2021, 427, 213573. https://doi.org/10.1016/j.ccr.2020.213573. Ataman, D.; Akkaya, E. U. Selective Chromogenic Response via Regioselective Binding of Cations: A Novel Approach in Chemosensor Design. Tetrahedron Lett. 2002, 43 (22), 3981-3983. https://doi.org/10.1016/S0040-4039(02)00725-6. Liu, Z.; Zhang, C.; Wang, X.; He, W.; Guo, Z. Design and Synthesis of a Ratiometric Fluorescent Chemosensor for Cu(II) with a Fluorophore Hybridization Approach. Org. Lett. 2012, 14 (17), 4378-4381. https://doi.org/10.1021/ol301849z. Qin, J.; Yang, Z.; Fan, L.; Cheng, X.; Li, T.; Wang, B. Design and Synthesis of a Chemosensor for the Detection of Al3+ Based on ESIPT. Anal. Methods 2014, 6 (18), 7343-7348. https://doi.org/10.1039/C4AY01330A. DiScenza, D. J.; Culton, E.; Verderame, M.; Lynch, J.; Serio, N.; Levine, M. 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Dyes Pigments 2013, 98 (2), 273-279. https://doi.org/10.1016/j.dyepig.2013.01.028. Huang, H.; Xin, Z.; Yuan, L.; Wang, B.-Y.; Cao, Q.-Y. New Ferrocene-Pyrene Dyads Bearing Amide/Thiourea Hybrid Donors for Anion Recognition. Inorganica Chim. Acta 2018, 483, 425-430. https://doi.org/10.1016/j.ica.2018.08.055. Vidal, M.; Pastenes, C.; Rezende, M. C.; Aliaga, C.; Domínguez, M. The Inverted Solvatochromism of Protonated Ferrocenylethenyl-Pyrimidines: The First Example of the Solvatochromic Reversal of a Hybrid Organic/Inorganic Dye. Org. Chem. Front. 2019, 6 (23), 3896-3901. https://doi.org/10.1039/C9QO01043B. Kaping, S.; Sunn, M.; Singha, L. I.; Vishwakarma, J. N. Ultrasound Assisted Synthesis of Pyrazolo[1,5-a]Pyrimidine-Antipyrine Hybrids and Their Anti-Inflammatory and Anti-Cancer Activities. Eur. J. Chem. 2020, 11 (1), 68-79. https://doi.org/10.5155/eurjchem.11.1.68-79.1942. Kaping, S.; Boiss, I.; Singha, L. I.; Helissey, P.; Vishwakarma, J. N. A Facile, Regioselective Synthesis of Novel 3-(N-Phenylcarboxamide)Pyrazolo[1,5-a]Pyrimidine Analogs in the Presence of KHSO$$_{4}$$in Aqueous Media Assisted by Ultrasound and Their Antibacterial Activities. Mol. Divers. 2016, 20 (2), 379-390. https://doi.org/10.1007/s11030-015-9639-6. Jayasudha, P.; Manivannan, R.; Elango, K. P. Simple Colorimetric Chemodosimeters for Selective Sensing of Cyanide Ion in Aqueous Solution via Termination of ICT Transition by Michael Addition. Sens. Actuators B Chem. 2015, 221, 1441-1448. https://doi.org/10.1016/j.snb.2015.08.017. Nam, N. L.; Grandberg, I. I.; Sorokin, V. I. Pyrazolopyrimidines Based on 5-Aminopyrazoles Unsubstituted at the Position 1. Chem. Heterocycl. Compd. 2002, 38 (11), 1371-1374. https://doi.org/10.1023/A:1022186627777. Kong, F.; Liu, R.; Chu, R.; Wang, X.; Xu, K.; Tang, B. A Highly Sensitive Near-Infrared Fluorescent Probe for Cysteine and Homocysteine in Living Cells. Chem. 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Visible and Near-Infrared Chemosensor for Colorimetric and Ratiometric Detection of Cyanide. J. Mater. Chem. 2009, 19 (4), 522-530. https://doi.org/10.1039/B813478B. Babu, B.; Mack, J.; Nyokong, T. Naked Eye and Colorimetric Detection of Cyanide with a 1,3-Diethyl-2-Thiobarbituric Acid Substituted Ferrocene Chemosensor. ChemistrySelect 2021, 6 (7), 1448-1452. https://doi.org/10.1002/slct.202100163. WHO. Guidelines for Drinking-Water Quality, Fourth Edition. 564. |
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Al consultar y hacer uso de este recurso, está aceptando las condiciones de uso establecidas por los autores.http://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2Portilla Salinas, Jaime Antoniovirtual::3240-1Tigreros Ortíz, Alexisvirtual::3241-1Peña Bernal, Carlos Arturob6d5bc29-bd00-4cf5-975a-8a6d9e1d7b59600Gamba Sánchez, Diego AlexanderChaur Valencia, Manuel NoeGrupo de Investigación en Compuestos Bio-orgánicos (GICOBIORG)2022-03-10T19:58:08Z2022-03-10T19:58:08Z2021-12http://hdl.handle.net/1992/56303instname:Universidad de los Andesreponame:Repositorio Institucional Sénecarepourl:https://repositorio.uniandes.edu.co/En este trabajo de grado se realiza la investigación de la síntesis y aplicaciones de moléculas híbridas inorgánica/orgánica de 7-ferrocenilpirazolo[1,5-a]pirimidina. Las aplicaciones se centran en la detección óptica de protón en medio orgánico y en la detección óptica y electroquímica de cianuro.This work investigates the rational design of novel chemosensors based on hybrid inorganic/organic structures for detecting H+ and CN-. The synthesis of chemosensors that integrate ferrocene and pyrazolo[1,5-a]pyrimidine molecules is due to the D-A behavior this hybrid system exhibits. A solvatochromic study of 7-ferrocenyl-2-methylpyrazolo[1,5-a]pyrimidine, along with a multiparametric analysis from Catalán's coefficients, is made to understand better how the probe molecule interacts with different solvents in the determination and quantification of H+, with calculated LoD of 0.63 µmol L-1. The integration of an indolium moiety was used for the colorimetric sensing of CN-. The chemosensor showed an intense red coloration losing upon the nucleophilic addition of CN- to the chemosensor molecule with calculated LoD of 0.11 µmol L-1, well below the WHO requirements (1.9 µmol L-1).Magíster en QuímicaMaestría65 hojasengUniversidad de los AndesMaestría en QuímicaFacultad de CienciasDepartamento de QuímicaDesign and synthesis of chemosensors based on 7-ferrocenylpyrazolo[1,5-a]pyrimidines for the detection of H+ and CN-Trabajo de grado - Maestríainfo:eu-repo/semantics/masterThesishttp://purl.org/coar/version/c_970fb48d4fbd8a85Texthttp://purl.org/redcol/resource_type/TMPyrazolo[1,5-a]pyrimidineColvatochromismChemosensorCyanideQuimiosensoresPirazolopirimidinasQuímicaWang, B.; Anslyn, E. V. Chemosensors: Principles, Strategies, and Applications; John Wiley & Sons, 2011.Khalil, G.; Brückner, C.; Ghandehari, M. Molecular Probes. 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Rev. 2020, 42, 100340. https://doi.org/10.1016/j.jphotochemrev.2020.100340.Upadhyay, S.; Singh, A.; Sinha, R.; Omer, S.; Negi, K. Colorimetric Chemosensors for D-Metal Ions: A Review in the Past, Present and Future Prospect. J. Mol. Struct. 2019, 1193, 89-102. https://doi.org/10.1016/j.molstruc.2019.05.007.Wu, D.; C. Sedgwick, A.; Gunnlaugsson, T.; U. Akkaya, E.; Yoon, J.; D. James, T. Fluorescent Chemosensors: The Past, Present and Future. Chem. Soc. Rev. 2017, 46 (23), 7105-7123. https://doi.org/10.1039/C7CS00240H.Kaur, K.; Saini, R.; Kumar, A.; Luxami, V.; Kaur, N.; Singh, P.; Kumar, S. Chemodosimeters: An Approach for Detection and Estimation of Biologically and Medically Relevant Metal Ions, Anions and Thiols. Coord. Chem. Rev. 2012, 256 (17), 1992-2028. https://doi.org/10.1016/j.ccr.2012.04.013.Pati, P. B. Organic Chemodosimeter for Cyanide: A Nucleophilic Approach. Sens. Actuators B Chem. 2016, 222, 374-390. https://doi.org/10.1016/j.snb.2015.08.044.Lee, S. Y.; Lee, J. J.; Bok, K. H.; Kim, J. A.; So, Y. K.; Kim, C. A Colorimetric Chemosensor for the Sequential Recognition of Mercury (II) and Iodide in Aqueous Media. Inorg. Chem. Commun. 2016, 70, 147-152. https://doi.org/10.1016/j.inoche.2016.06.004.Zhong, Z.; Zhang, D.; Li, D.; Zheng, G.; Tian, Z. Turn-on Fluorescence Sensor Based on Naphthalene Anhydride for Hg2+. Tetrahedron 2016, 72 (49), 8050-8054. https://doi.org/10.1016/j.tet.2016.10.033.Xu, W.-J.; Qi, D.-Q.; You, J.-Z.; Hu, F.-F.; Bian, J.-Y.; Yang, C.-X.; Huang, J. Coumarin-Based "Turn-off" Fluorescent Chemosensor with High Selectivity for Cu2+ in Aqueous Solution. J. Mol. Struct. 2015, 1091, 133-137. https://doi.org/10.1016/j.molstruc.2015.02.083.Wei, Y.; Aydin, Z.; Zhang, Y.; Liu, Z.; Guo, M. A Turn-on Fluorescent Sensor for Imaging Labile Fe3+ in Live Neuronal Cells at Subcellular Resolution. ChemBioChem 2012, 13 (11), 1569-1573. https://doi.org/10.1002/cbic.201200202.Samanta, S.; Manna, U.; Ray, T.; Das, G. 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Fluorescent Chemosensors Containing Redox-Active Ferrocene: A Review. Dalton Trans. 2021, 50 (34), 11681-11700. https://doi.org/10.1039/D1DT02077C.Fu, Y.; S. Finney, N. Small-Molecule Fluorescent Probes and Their Design. RSC Adv. 2018, 8 (51), 29051-29061. https://doi.org/10.1039/C8RA02297F.Geddes, C. D.; Lakowicz, J. R. Advanced Concepts in Fluorescence Sensing: Part A: Small Molecule Sensing; Springer Science & Business Media, 2007.Fang, Y.; Dehaen, W. Small-Molecule-Based Fluorescent Probes for f-Block Metal Ions: A New Frontier in Chemosensors. Coord. Chem. Rev. 2021, 427, 213524. https://doi.org/10.1016/j.ccr.2020.213524.Pal, A.; Ranjan Bhatta, S.; Thakur, A. Recent Advances in the Development of Ferrocene Based Electroactive Small Molecules for Cation Recognition: A Comprehensive Review of the Years 2010-2020. Coord. Chem. Rev. 2021, 431, 213685. https://doi.org/10.1016/j.ccr.2020.213685.Yin, J.; Huang, L.; Wu, L.; Li, J.; James, T. D.; Lin, W. 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