Estudio termodinámico y de acomplejamiento de C-etilresorcin [4] areno con fluorenona y Cu (II)

El desarrollo de sensores supramoleculares fluorescentes ha sido de interés debido a su bajo costo, respuesta rápida y alta sensibilidad. Se han desarrollado sensores supramoleculares con MOF de resorcinarenos y algunos basados en polímeros de coordinación pero su síntesis tiene una gran complejidad...

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Autores:
Mongua Niño, Santiago José
Tipo de recurso:
Trabajo de grado de pregrado
Fecha de publicación:
2023
Institución:
Universidad de los Andes
Repositorio:
Séneca: repositorio Uniandes
Idioma:
spa
OAI Identifier:
oai:repositorio.uniandes.edu.co:1992/73354
Acceso en línea:
https://hdl.handle.net/1992/73354
Palabra clave:
C-etilresorcin[4]arenos
Fluorenona
Química
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openAccess
License
https://repositorio.uniandes.edu.co/static/pdf/aceptacion_uso_es.pdf
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network_acronym_str UNIANDES2
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repository_id_str
dc.title.none.fl_str_mv Estudio termodinámico y de acomplejamiento de C-etilresorcin [4] areno con fluorenona y Cu (II)
title Estudio termodinámico y de acomplejamiento de C-etilresorcin [4] areno con fluorenona y Cu (II)
spellingShingle Estudio termodinámico y de acomplejamiento de C-etilresorcin [4] areno con fluorenona y Cu (II)
C-etilresorcin[4]arenos
Fluorenona
Química
title_short Estudio termodinámico y de acomplejamiento de C-etilresorcin [4] areno con fluorenona y Cu (II)
title_full Estudio termodinámico y de acomplejamiento de C-etilresorcin [4] areno con fluorenona y Cu (II)
title_fullStr Estudio termodinámico y de acomplejamiento de C-etilresorcin [4] areno con fluorenona y Cu (II)
title_full_unstemmed Estudio termodinámico y de acomplejamiento de C-etilresorcin [4] areno con fluorenona y Cu (II)
title_sort Estudio termodinámico y de acomplejamiento de C-etilresorcin [4] areno con fluorenona y Cu (II)
dc.creator.fl_str_mv Mongua Niño, Santiago José
dc.contributor.advisor.none.fl_str_mv Vargas Escamilla, Edgar Francisco
dc.contributor.author.none.fl_str_mv Mongua Niño, Santiago José
dc.contributor.jury.none.fl_str_mv Moreno Piraján, Juan Carlos
Reiber, Andreas
Hurtado Belalcazar, John Jady
dc.contributor.researchgroup.none.fl_str_mv Facultad de Ciencias::Termodinámica de Soluciones
dc.subject.keyword.none.fl_str_mv C-etilresorcin[4]arenos
Fluorenona
topic C-etilresorcin[4]arenos
Fluorenona
Química
dc.subject.themes.spa.fl_str_mv Química
description El desarrollo de sensores supramoleculares fluorescentes ha sido de interés debido a su bajo costo, respuesta rápida y alta sensibilidad. Se han desarrollado sensores supramoleculares con MOF de resorcinarenos y algunos basados en polímeros de coordinación pero su síntesis tiene una gran complejidad y costo. Dado lo anterior, en este trabajo se desarrolló un estudio de las propiedades de acomplejamiento en solución de la fluorenona y el Cu (II) con el C-etilresorcin[4]areno mediante técnicas espectrofotométricas. Adicionalmente, se desarrolló un estudio volumétrico y sonométrico de la fluorenona en acetonitrilo para relacionarlo con el acomplejamiento observado con el C-etilresorcin[4]areno en solución.
publishDate 2023
dc.date.issued.none.fl_str_mv 2023-12-07
dc.date.accessioned.none.fl_str_mv 2024-01-19T15:10:15Z
dc.date.available.none.fl_str_mv 2024-01-19T15:10:15Z
dc.type.none.fl_str_mv Trabajo de grado - Pregrado
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dc.relation.references.none.fl_str_mv Guo, C.; Sedgwick, A. C.; Hirao, T.; Sessler, J. L. Supramolecular Fluorescent Sensors: An Historical Overview and Update. Coord Chem Rev 2021, 427, 213560. https://doi.org/https://doi.org/10.1016/j.ccr.2020.213560.
You, L.; Zha, D.; Anslyn, E. V. Recent Advances in Supramolecular Analytical Chemistry Using Optical Sensing. Chem Rev 2015, 115 (15), 7840–7892. https://doi.org/10.1021/cr5005524. 

Mako, T. L.; Racicot, J. M.; Levine, M. Supramolecular Luminescent Sensors. Chem Rev 2019, 119 (1), 322–477. https://doi.org/10.1021/acs.chemrev.8b00260. 

Eddaif, L.; Shaban, A.; Szendro, I. Calix[4]Resorcinarene Macrocycles Interactions with Cd2+, Hg2+, Pb2+, and Cu2+ Cations: A QCM-I and Langmuir Ultra-Thin Monolayers Study. Electroanalysis 2020, 32 (4), 755–766. https://doi.org/https://doi.org/10.1002/elan.201900651.
Formica, M.; Fusi, V.; Giorgi, L.; Micheloni, M. New Fluorescent Chemosensors for Metal Ions in Solution. Coord Chem Rev 2012, 256 (1), 170–192. https://doi.org/https://doi.org/10.1016/j.ccr.2011.09.010. 

Vural Gürsel, I.; Noël, T.; Wang, Q.; Hessel, V. Separation/Recycling Methods for Homogeneous Transition Metal Catalysts in Continuous Flow. Green Chemistry 2015, 17 (4), 2012–2026. https://doi.org/10.1039/C4GC02160F. 

Panchal, U.; Modi, K.; Dey, S.; Prajapati, U.; Patel, C.; Jain, V. K. A Resorcinarene- Based “Turn-off” Fluorescence Sensor for 4-Nitrotoluene: Insights from Fluorescence and 1H NMR Titration with Computational Approach. J Lumin 2017, 184, 74–82. https://doi.org/https://doi.org/10.1016/j.jlumin.2016.11.066. 

Jain, V. K.; Pillai, S. G.; Pandya, R. A.; Agrawal, Y. K.; Shrivastav, P. S. Molecular Octopus: Octa Functionalized Calix[4]Resorcinarene-Hydroxamic Acid [C4RAHA] for Selective Extraction, Separation and Preconcentration of U(VI). Talanta 2005, 65 (2), 466–475. https://doi.org/https://doi.org/10.1016/j.talanta.2004.06.033. 

Riveros, D. Estudio de La Solvatación de C-Alquilresorcin[4]Arenos, Universidad de los Andes, Bogotá, 2016. 

Bhatt, K. D.; Gupte, H. S.; Makwana, B. A.; Vyas, D. J.; Maity, D.; Jain, V. K. Calix Receptor Edifice; Scrupulous Turn Off Fluorescent Sensor for Fe(III), Co(II) and Cu(II). J Fluoresc 2012, 22 (6), 1493–1500. https://doi.org/10.1007/s10895-012- 1086-5. 

Li, Y.; Csók, Z.; Szuroczki, P.; Kollár, L.; Kiss, L.; Kunsági-Máté, S. Fluorescence Quenching Studies on the Interaction of a Novel Deepened Cavitand towards Some Transition Metal Ions. Anal Chim Acta 2013, 799, 51–56. https://doi.org/https://doi.org/10.1016/j.aca.2013.09.013. 

Secenji, G.; Matisz, G.; Csók, Z.; Kollár, L.; Kunsági-Máté, S. Temperature- Dependent Fluorescence Quenching of a Cavitand Derivative by Copper Ions. Chem Phys Lett 2016, 657, 60–64. https://doi.org/https://doi.org/10.1016/j.cplett.2016.05.045.
Boxhall Philip C Bulman; Elsegood Mark R J; Chan Yohan; Heaney Harry; Holmes Kathryn E; McGrath Matthew J, J. Y. P. The Synthesis of Axially Chiral Resorcinarenes from Resorcinol Monoalkyl Ethers and Aldehyde Dimet hylacetals. Synlett 2003, 2003 (07), 1002–1006. https://doi.org/10.1055/s-2003-39294.
Botta, B.; Iacomacci, P.; Di Giovanni, C.; Delle Monache, G.; Gacs-Baitz, E.; Botta, M.; Tafi, A.; Corelli, F.; Misiti, D. The Tetramerization of 2,4-Dimethoxycinnamates. A Novel Route to Calixarenes. J Org Chem 1992, 57 (12), 3259–3261. https://doi.org/10.1021/jo00038a001. 

Hoegberg, A. G. S. Two Stereoisomeric Macrocyclic Resorcinol-Acetaldehyde Condensation Products. J Org Chem 1980, 45 (22), 4498–4500. https://doi.org/10.1021/jo01310a046. 

Galindres Jiménez, D. M. Estudio Fisicoquímico de Resorcin[4]Arenos Sulfonatos y Su Interacción Con Albúmina de Suero Bovino. Uniandes 2019. http://hdl.handle.net/1992/41300 (accessed 2023-12-01).
Weinelt, F.; Schneider, H. J. Host-Guest Chemistry. 27. Mechanisms of Macrocycle Genesis. The Condensation of Resorcinol with Aldehydes. J Org Chem 1991, 56 (19), 5527–5535. https://doi.org/10.1021/jo00019a011. 

Abis, L.; Dalcanale, E.; Du vosel, A.; Spera, S. Nuclear Magnetic Resonance Elucidation of Ring-Inversion Processes in Macrocyclic Octaols. Journal of the Chemical Society, Perkin Transactions 2 1990, No. 12, 2075–2080. https://doi.org/10.1039/P29900002075.
Sahoo, S. K.; Sharma, D.; Bera, R. K.; Crisponi, G.; Callan, J. F. Iron(Iii) Selective Molecular and Supramolecular Fluorescent Probes. Chem Soc Rev 2012, 41 (21), 7195–7227. https://doi.org/10.1039/C2CS35152H. 

Brewster, M. E.; Loftsson, T. Cyclodextrins as Pharmaceutical Solubilizers. Adv Drug Deliv Rev 2007, 59 (7), 645–666. https://doi.org/https://doi.org/10.1016/j.addr.2007.05.012. 

Renny, J. S.; Tomasevich, L. L.; Tallmadge, E. H.; Collum, D. B. Method of Continuous Variations: Applications of Job Plots to the Study of Molecular Associations in Organometallic Chemistry. Angewandte Chemie International Edition 2013, 52 (46), 11998–12013. https://doi.org/https://doi.org/10.1002/anie.201304157. 

Thordarson, P. Determining Association Constants from Titration Experiments in Supramolecular Chemistry. Chem. Soc. Rev. 2011, 40 (3), 1305–1323. https://doi.org/10.1039/C0CS00062K. 

Roy, M. N.; Saha, S.; Barman, S.; Ekka, D. Host–Guest Inclusion Complexes of RNA Nucleosides inside Aqueous Cyclodextrins Explored by Physicochemical and Spectroscopic Methods. RSC Adv 2016, 6 (11), 8881–8891. https://doi.org/10.1039/C5RA24102B.
Wang, Z.; Cao, J.; Meng, F. Interactions between Protein-like and Humic-like Components in Dissolved Organic Matter Revealed by Fluorescence Quenching. Water Res 2015, 68, 404–413. https://doi.org/https://doi.org/10.1016/j.watres.2014.10.024. 

Ryan, D. K.; Weber, J. H. Fluorescence Quenching Titration for Determination of Complexing Capacities and Stability Constants of Fulvic Acid. Anal Chem 1982, 54 (6), 986–990. https://doi.org/10.1021/ac00243a033. 

Behera, P. K.; Mukherjee, T.; Mishra, A. K. Simultaneous Presence of Static and Dynamic Component in the Fluorescence Quenching for Substituted Naphthalene— 
CCl4 System. J Lumin 1995, 65 (3), 131–136. https://doi.org/https://doi.org/10.1016/0022-2313(95)00067-Z.
Moreno-Gómez, N.; Buchner, R.; Vargas, E. F. Temperature Effect on the Solvation of Two Ionic Resorcin[4]Arenes from Volumetric and Acoustic Properties in Polar Media. J Mol Liq 2019, 291, 111233. https://doi.org/10.1016/j.molliq.2019.111233.
Taylor, B. N.; Kuyatt, C. E. Guidelines for Evaluating and Expressing the Uncertainty of NIST Measurement Results. NIST Technical Note 1994, 1297. https://doi.org/10.6028/NIST.TN.1900.
Burakowski, A.; Gliński, J. Hydration Numbers of Nonelectrolytes from Acoustic Methods. Chem Rev 2012, 112 (4), 2059–2081. https://doi.org/10.1021/cr2000948. 

Iloukhani, H.; Almasi, M. Densities, Viscosities, Excess Molar Volumes, and Refractive Indices of Acetonitrile and 2-Alkanols Binary Mixtures at Different Temperatures: Experimental Results and Application of the Prigogine–Flory– Patterson Theory. Thermochim Acta 2009, 495 (1), 139–148. https://doi.org/https://doi.org/10.1016/j.tca.2009.06.015.
Krakowiak, J.; Grzybkowski, W. Apparent Molar Volume and Compressibility of Tetrabutylphosphonium Bromide in Various Solvents. J Chem Eng Data 2010, 55 (7), 2624–2629. https://doi.org/10.1021/je900888e. 

Basílio, N.; Garcia-Rio, L.; Martín-Pastor, M. Calixarene-Based Surfactants: Evidence of Structural Reorganization upon Micellization. Langmuir 2012, 28 (5), 2404–2414. https://doi.org/10.1021/la204004h.
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spelling Vargas Escamilla, Edgar Franciscovirtual::109-1Mongua Niño, Santiago JoséMoreno Piraján, Juan Carlosvirtual::110-1Reiber, Andreasvirtual::111-1Hurtado Belalcazar, John Jadyvirtual::112-1Facultad de Ciencias::Termodinámica de Soluciones2024-01-19T15:10:15Z2024-01-19T15:10:15Z2023-12-07https://hdl.handle.net/1992/73354instname:Universidad de los Andesreponame:Repositorio Institucional Sénecarepourl:https://repositorio.uniandes.edu.co/El desarrollo de sensores supramoleculares fluorescentes ha sido de interés debido a su bajo costo, respuesta rápida y alta sensibilidad. Se han desarrollado sensores supramoleculares con MOF de resorcinarenos y algunos basados en polímeros de coordinación pero su síntesis tiene una gran complejidad y costo. Dado lo anterior, en este trabajo se desarrolló un estudio de las propiedades de acomplejamiento en solución de la fluorenona y el Cu (II) con el C-etilresorcin[4]areno mediante técnicas espectrofotométricas. Adicionalmente, se desarrolló un estudio volumétrico y sonométrico de la fluorenona en acetonitrilo para relacionarlo con el acomplejamiento observado con el C-etilresorcin[4]areno en solución.Universidad de los AndesQuímicoPregradoQuímica Supramolecular27 páginasapplication/pdfspaUniversidad de los AndesQuímicaFacultad de CienciasDepartamento de Químicahttps://repositorio.uniandes.edu.co/static/pdf/aceptacion_uso_es.pdfinfo:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2Estudio termodinámico y de acomplejamiento de C-etilresorcin [4] areno con fluorenona y Cu (II)Trabajo de grado - Pregradoinfo:eu-repo/semantics/bachelorThesisinfo:eu-repo/semantics/acceptedVersionhttp://purl.org/coar/resource_type/c_7a1fAudiovisualhttp://purl.org/redcol/resource_type/TPC-etilresorcin[4]arenosFluorenonaQuímicaGuo, C.; Sedgwick, A. C.; Hirao, T.; Sessler, J. L. Supramolecular Fluorescent Sensors: An Historical Overview and Update. Coord Chem Rev 2021, 427, 213560. https://doi.org/https://doi.org/10.1016/j.ccr.2020.213560.You, L.; Zha, D.; Anslyn, E. V. Recent Advances in Supramolecular Analytical Chemistry Using Optical Sensing. Chem Rev 2015, 115 (15), 7840–7892. https://doi.org/10.1021/cr5005524. 
Mako, T. L.; Racicot, J. M.; Levine, M. Supramolecular Luminescent Sensors. Chem Rev 2019, 119 (1), 322–477. https://doi.org/10.1021/acs.chemrev.8b00260. 
Eddaif, L.; Shaban, A.; Szendro, I. Calix[4]Resorcinarene Macrocycles Interactions with Cd2+, Hg2+, Pb2+, and Cu2+ Cations: A QCM-I and Langmuir Ultra-Thin Monolayers Study. Electroanalysis 2020, 32 (4), 755–766. https://doi.org/https://doi.org/10.1002/elan.201900651.Formica, M.; Fusi, V.; Giorgi, L.; Micheloni, M. New Fluorescent Chemosensors for Metal Ions in Solution. Coord Chem Rev 2012, 256 (1), 170–192. https://doi.org/https://doi.org/10.1016/j.ccr.2011.09.010. 
Vural Gürsel, I.; Noël, T.; Wang, Q.; Hessel, V. Separation/Recycling Methods for Homogeneous Transition Metal Catalysts in Continuous Flow. Green Chemistry 2015, 17 (4), 2012–2026. https://doi.org/10.1039/C4GC02160F. 
Panchal, U.; Modi, K.; Dey, S.; Prajapati, U.; Patel, C.; Jain, V. K. A Resorcinarene- Based “Turn-off” Fluorescence Sensor for 4-Nitrotoluene: Insights from Fluorescence and 1H NMR Titration with Computational Approach. J Lumin 2017, 184, 74–82. https://doi.org/https://doi.org/10.1016/j.jlumin.2016.11.066. 
Jain, V. K.; Pillai, S. G.; Pandya, R. A.; Agrawal, Y. K.; Shrivastav, P. S. Molecular Octopus: Octa Functionalized Calix[4]Resorcinarene-Hydroxamic Acid [C4RAHA] for Selective Extraction, Separation and Preconcentration of U(VI). Talanta 2005, 65 (2), 466–475. https://doi.org/https://doi.org/10.1016/j.talanta.2004.06.033. 
Riveros, D. Estudio de La Solvatación de C-Alquilresorcin[4]Arenos, Universidad de los Andes, Bogotá, 2016. 
Bhatt, K. D.; Gupte, H. S.; Makwana, B. A.; Vyas, D. J.; Maity, D.; Jain, V. K. Calix Receptor Edifice; Scrupulous Turn Off Fluorescent Sensor for Fe(III), Co(II) and Cu(II). J Fluoresc 2012, 22 (6), 1493–1500. https://doi.org/10.1007/s10895-012- 1086-5. 
Li, Y.; Csók, Z.; Szuroczki, P.; Kollár, L.; Kiss, L.; Kunsági-Máté, S. Fluorescence Quenching Studies on the Interaction of a Novel Deepened Cavitand towards Some Transition Metal Ions. Anal Chim Acta 2013, 799, 51–56. https://doi.org/https://doi.org/10.1016/j.aca.2013.09.013. 
Secenji, G.; Matisz, G.; Csók, Z.; Kollár, L.; Kunsági-Máté, S. Temperature- Dependent Fluorescence Quenching of a Cavitand Derivative by Copper Ions. Chem Phys Lett 2016, 657, 60–64. https://doi.org/https://doi.org/10.1016/j.cplett.2016.05.045.Boxhall Philip C Bulman; Elsegood Mark R J; Chan Yohan; Heaney Harry; Holmes Kathryn E; McGrath Matthew J, J. Y. P. The Synthesis of Axially Chiral Resorcinarenes from Resorcinol Monoalkyl Ethers and Aldehyde Dimet hylacetals. Synlett 2003, 2003 (07), 1002–1006. https://doi.org/10.1055/s-2003-39294.Botta, B.; Iacomacci, P.; Di Giovanni, C.; Delle Monache, G.; Gacs-Baitz, E.; Botta, M.; Tafi, A.; Corelli, F.; Misiti, D. The Tetramerization of 2,4-Dimethoxycinnamates. A Novel Route to Calixarenes. J Org Chem 1992, 57 (12), 3259–3261. https://doi.org/10.1021/jo00038a001. 
Hoegberg, A. G. S. Two Stereoisomeric Macrocyclic Resorcinol-Acetaldehyde Condensation Products. J Org Chem 1980, 45 (22), 4498–4500. https://doi.org/10.1021/jo01310a046. 
Galindres Jiménez, D. M. Estudio Fisicoquímico de Resorcin[4]Arenos Sulfonatos y Su Interacción Con Albúmina de Suero Bovino. Uniandes 2019. http://hdl.handle.net/1992/41300 (accessed 2023-12-01).Weinelt, F.; Schneider, H. J. Host-Guest Chemistry. 27. Mechanisms of Macrocycle Genesis. The Condensation of Resorcinol with Aldehydes. J Org Chem 1991, 56 (19), 5527–5535. https://doi.org/10.1021/jo00019a011. 
Abis, L.; Dalcanale, E.; Du vosel, A.; Spera, S. Nuclear Magnetic Resonance Elucidation of Ring-Inversion Processes in Macrocyclic Octaols. Journal of the Chemical Society, Perkin Transactions 2 1990, No. 12, 2075–2080. https://doi.org/10.1039/P29900002075.Sahoo, S. K.; Sharma, D.; Bera, R. K.; Crisponi, G.; Callan, J. F. Iron(Iii) Selective Molecular and Supramolecular Fluorescent Probes. Chem Soc Rev 2012, 41 (21), 7195–7227. https://doi.org/10.1039/C2CS35152H. 
Brewster, M. E.; Loftsson, T. Cyclodextrins as Pharmaceutical Solubilizers. Adv Drug Deliv Rev 2007, 59 (7), 645–666. https://doi.org/https://doi.org/10.1016/j.addr.2007.05.012. 
Renny, J. S.; Tomasevich, L. L.; Tallmadge, E. H.; Collum, D. B. Method of Continuous Variations: Applications of Job Plots to the Study of Molecular Associations in Organometallic Chemistry. Angewandte Chemie International Edition 2013, 52 (46), 11998–12013. https://doi.org/https://doi.org/10.1002/anie.201304157. 
Thordarson, P. Determining Association Constants from Titration Experiments in Supramolecular Chemistry. Chem. Soc. Rev. 2011, 40 (3), 1305–1323. https://doi.org/10.1039/C0CS00062K. 
Roy, M. N.; Saha, S.; Barman, S.; Ekka, D. Host–Guest Inclusion Complexes of RNA Nucleosides inside Aqueous Cyclodextrins Explored by Physicochemical and Spectroscopic Methods. RSC Adv 2016, 6 (11), 8881–8891. https://doi.org/10.1039/C5RA24102B.Wang, Z.; Cao, J.; Meng, F. Interactions between Protein-like and Humic-like Components in Dissolved Organic Matter Revealed by Fluorescence Quenching. Water Res 2015, 68, 404–413. https://doi.org/https://doi.org/10.1016/j.watres.2014.10.024. 
Ryan, D. K.; Weber, J. H. Fluorescence Quenching Titration for Determination of Complexing Capacities and Stability Constants of Fulvic Acid. Anal Chem 1982, 54 (6), 986–990. https://doi.org/10.1021/ac00243a033. 
Behera, P. K.; Mukherjee, T.; Mishra, A. K. Simultaneous Presence of Static and Dynamic Component in the Fluorescence Quenching for Substituted Naphthalene— 
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