Piperonal chalcone derivative incorporating the pyrazolo[3,4-b]pyridine moiety; crystal structure, spectroscopic characterization and quantum chemical investigations

A single crystal of a piperonal chalcone derivative was obtained, fully characterized, and crystallized by a slow evaporation technique. The synthesized compound was characterized by UV-Visible, FT-IR, HRMS, 1H NMR, and 13C NMR spectroscopic studies and X-ray crystallography, revealing that the crys...

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Autores:: Polo-Cuadrado, Efraín
Ferrer, Karoll
Osorio, Edison
Brito, Iván
Cisterna, Jonathan
Espinoza, Luis
Alderete, Joel B.
Gutiérrez, Margarita

Tipo de recurso:: Article of investigation

Fecha de publicación:: 2023

Institución:: Universidad de Ibagué

Repositorio:: Repositorio Universidad de Ibagué

Idioma:: eng

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network_name_str	Repositorio Universidad de Ibagué
repository_id_str
dc.title.eng.fl_str_mv	Piperonal chalcone derivative incorporating the pyrazolo[3,4-b]pyridine moiety; crystal structure, spectroscopic characterization and quantum chemical investigations
title	Piperonal chalcone derivative incorporating the pyrazolo[3,4-b]pyridine moiety; crystal structure, spectroscopic characterization and quantum chemical investigations
spellingShingle	Piperonal chalcone derivative incorporating the pyrazolo[3,4-b]pyridine moiety; crystal structure, spectroscopic characterization and quantum chemical investigations Enlaces químicos Estructura cristalina Orbitales moleculares Piridina; Monocristales Análisis espectroscópico Chemical bonds Crystal structure Molecular orbitals Pyridine; Single crystals Spectroscopic analysis X ray crystallography Chalcone derivatives Chalcones Crystals structures Hirshfeld surfaces N.L.O. properties NLO properties Quantum chemical investigation Slow evaporation techniques Spectroscopic characterization Synthesised
title_short	Piperonal chalcone derivative incorporating the pyrazolo[3,4-b]pyridine moiety; crystal structure, spectroscopic characterization and quantum chemical investigations
title_full	Piperonal chalcone derivative incorporating the pyrazolo[3,4-b]pyridine moiety; crystal structure, spectroscopic characterization and quantum chemical investigations
title_fullStr	Piperonal chalcone derivative incorporating the pyrazolo[3,4-b]pyridine moiety; crystal structure, spectroscopic characterization and quantum chemical investigations
title_full_unstemmed	Piperonal chalcone derivative incorporating the pyrazolo[3,4-b]pyridine moiety; crystal structure, spectroscopic characterization and quantum chemical investigations
title_sort	Piperonal chalcone derivative incorporating the pyrazolo[3,4-b]pyridine moiety; crystal structure, spectroscopic characterization and quantum chemical investigations
dc.creator.fl_str_mv	Polo-Cuadrado, Efraín Ferrer, Karoll Osorio, Edison Brito, Iván Cisterna, Jonathan Espinoza, Luis Alderete, Joel B. Gutiérrez, Margarita
dc.contributor.author.none.fl_str_mv	Polo-Cuadrado, Efraín Ferrer, Karoll Osorio, Edison Brito, Iván Cisterna, Jonathan Espinoza, Luis Alderete, Joel B. Gutiérrez, Margarita
dc.subject.armarc.none.fl_str_mv	Enlaces químicos Estructura cristalina Orbitales moleculares Piridina; Monocristales Análisis espectroscópico
topic	Enlaces químicos Estructura cristalina Orbitales moleculares Piridina; Monocristales Análisis espectroscópico Chemical bonds Crystal structure Molecular orbitals Pyridine; Single crystals Spectroscopic analysis X ray crystallography Chalcone derivatives Chalcones Crystals structures Hirshfeld surfaces N.L.O. properties NLO properties Quantum chemical investigation Slow evaporation techniques Spectroscopic characterization Synthesised
dc.subject.proposal.eng.fl_str_mv	Chemical bonds Crystal structure Molecular orbitals Pyridine; Single crystals Spectroscopic analysis X ray crystallography Chalcone derivatives Chalcones Crystals structures Hirshfeld surfaces N.L.O. properties NLO properties Quantum chemical investigation Slow evaporation techniques Spectroscopic characterization Synthesised
description	A single crystal of a piperonal chalcone derivative was obtained, fully characterized, and crystallized by a slow evaporation technique. The synthesized compound was characterized by UV-Visible, FT-IR, HRMS, 1H NMR, and 13C NMR spectroscopic studies and X-ray crystallography, revealing that the crystal belongs to a triclinic crystal system with a P1̄ space group, Z = 2. In the present work, we focus on molecular modeling studies such as Hirshfeld surface analysis, energy framework calculations, frontier molecular orbital analysis, natural bond orbital analysis, and NLO properties of a π-conjugate system combining the chalcone and the pyrazole[3,4-b]pyridine scaffolds to describe the in-depth structural analysis thereof. Good agreement was found between the calculated results and experimental data. In addition, Hirshfeld surface analysis of the crystal structure showed that the intermolecular stabilization in the crystal packing comes mainly from H⋯H bond interactions. The chalcone crystal exhibits significant NLO properties suggesting that it could be considered a potential candidate for application in nonlinear optical devices.
publishDate	2023
dc.date.issued.none.fl_str_mv	2023-02-09
dc.date.accessioned.none.fl_str_mv	2025-08-25T15:10:49Z
dc.date.available.none.fl_str_mv	2025-08-25T15:10:49Z
dc.type.none.fl_str_mv	Artículo de revista
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dc.type.coarversion.none.fl_str_mv	http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.content.none.fl_str_mv	Text
dc.type.driver.none.fl_str_mv	info:eu-repo/semantics/article
dc.type.version.none.fl_str_mv	info:eu-repo/semantics/publishedVersion
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dc.identifier.citation.none.fl_str_mv	Polo-Cuadrado, E., Ferrer, K., Osorio, E., Brito, I., Cisterna, J., Espinoza, L., Alderete, J. y Gutiérrez, M. (2023). Piperonal chalcone derivative incorporating the pyrazolo[3,4-b]pyridine moiety; crystal structure, spectroscopic characterization and quantum chemical investigations. RSC Advances, 13(8), 5197 - 5207. DOI: 10.1039/d2ra08101f
dc.identifier.doi.none.fl_str_mv	10.1039/d2ra08101f
dc.identifier.issn.none.fl_str_mv	20462069
dc.identifier.uri.none.fl_str_mv	https://hdl.handle.net/20.500.12313/5532
dc.identifier.url.none.fl_str_mv	https://pubs.rsc.org/en/content/articlelanding/2023/ra/d2ra08101f
identifier_str_mv	Polo-Cuadrado, E., Ferrer, K., Osorio, E., Brito, I., Cisterna, J., Espinoza, L., Alderete, J. y Gutiérrez, M. (2023). Piperonal chalcone derivative incorporating the pyrazolo[3,4-b]pyridine moiety; crystal structure, spectroscopic characterization and quantum chemical investigations. RSC Advances, 13(8), 5197 - 5207. DOI: 10.1039/d2ra08101f 10.1039/d2ra08101f 20462069
url	https://hdl.handle.net/20.500.12313/5532 https://pubs.rsc.org/en/content/articlelanding/2023/ra/d2ra08101f
dc.language.iso.none.fl_str_mv	eng
language	eng
dc.relation.citationendpage.none.fl_str_mv	5207
dc.relation.citationissue.none.fl_str_mv	8
dc.relation.citationstartpage.none.fl_str_mv	5197
dc.relation.citationvolume.none.fl_str_mv	13
dc.relation.ispartofjournal.none.fl_str_mv	RSC Advances
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Opt., 2010, 39 , 143 —148 M. Makowska-Janusik , E. Gondek , I. V. Kityk , J. Wisła , J. Sanetra and A. Danel , Chem. Phys., 2004, 306 , 265 —271 J. Chen , Q. Ren , X. Wang , T. Li , H. Yang , J. Zhang and G. Li , Opt., 2012, 123 , 1761 —1764 J. P. Abraham , D. Sajan , V. Shettigar , S. M. Dharmaprakash , I. Němec , I. Hubert Joe and V. S. Jayakumar , J. Mol. Struct., 2009, 917 , 27 —36 K. Ozga , E. Gondek , A. Danel and K. Chaczatrian , Opt. Commun., 2004, 231 , 437 —446 L. Shen , Z. Li , X. Wu , W. Zhou , J. Yang and Y. Song , RSC Adv., 2020, 10 , 15199 —15205 E. D. Dsilva , D. Narayan Rao , R. Philip , R. J. Butcher , Rajnikant and S. M. Dharmaprakash , J. Phys. Chem. Solids, 2011, 72 , 824 —830 S. R. Marder , W. E. Torruellas , M. Blanchard-Desce , V. Ricci , G. I. Stegeman , S. Gilmour , J. L. Brédas , J. Li , G. U. Bublitz and S. G. Boxer , Science, 1997, 276 , 1233 —1236 V. Shettigar , P. S. Patil , S. Naveen , S. M. Dharmaprakash , M. A. Sridhar and J. Shashidhara Prasad , J. Cryst. Growth, 2006, 295 , 44 —49 B. Gu , W. Ji , X.-Q. Huang , P. S. Patil and S. M. Dharmaprakash , Opt. Express, 2009, 17 , 1126 H. J. Ravindra , A. J. Kiran , S. M. Dharmaprakash , N. Satheesh Rai , K. Chandrasekharan , B. Kalluraya and F. Rotermund , J. Cryst. Growth, 2008, 310 , 4169 —4176 P. Poornesh , K. Ravi , G. Umesh , P. K. Hegde , M. G. Manjunatha , K. B. Manjunatha and A. V. Adhikari , Opt. Commun., 2010, 283 , 1519 —1527 B. Gu , W. Ji , P. S. Patil , S. M. Dharmaprakash and H. T. Wang , Appl. Phys. Lett., 2008, 92 , 091118 S. Y. Priya , R. K. Rao , V. P. Chalapathi and C. Author , J. Clin. Med. Images Short Reports, 2018, 1 , 1 —9 R. Kumar , T. Karthick , P. Tandon , P. Agarwal , A. P. Menezes and A. Jayarama , J. Mol. Struct., 2018, 1164 , 180 —190 A. P. Menezes and A. Jayarama , J. Mol. Struct., 2014, 1075 , 246 —253 A. J. Kiran , H. W. Lee , H. J. Ravindra , S. M. Dharmaprakash , K. Kim , H. Lim and F. Rotermund , Curr. Appl. Phys., 2010, 10 , 1290 —1296 E. Polo , K. 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dc.rights.eng.fl_str_mv	© 2023 The Royal Society of Chemistry.
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spelling	Polo-Cuadrado, Efraínf8016ac0-3f43-4599-89b2-3d8e129cb357-1Ferrer, Karoll0741e87e-5d05-4ee5-b0a0-8cd6831569ae-1Osorio, Edisone6d834e4-46ca-40f0-ab7c-630a35856901-1Brito, Iván26ac473f-3c45-4d5a-9701-4e0cf4753fa9-1Cisterna, Jonathanfe7a5916-839c-42da-8e1c-d8ed97240a9b-1Espinoza, Luis22f7ebbc-329d-4ab6-9c2b-2e7eed3adcae-1Alderete, Joel B.1e551baa-cc16-4cf8-a340-1bd35189146a-1Gutiérrez, Margarita3d6c891b-b6e6-4157-b398-c6ef08538087-12025-08-25T15:10:49Z2025-08-25T15:10:49Z2023-02-09A single crystal of a piperonal chalcone derivative was obtained, fully characterized, and crystallized by a slow evaporation technique. The synthesized compound was characterized by UV-Visible, FT-IR, HRMS, 1H NMR, and 13C NMR spectroscopic studies and X-ray crystallography, revealing that the crystal belongs to a triclinic crystal system with a P1̄ space group, Z = 2. In the present work, we focus on molecular modeling studies such as Hirshfeld surface analysis, energy framework calculations, frontier molecular orbital analysis, natural bond orbital analysis, and NLO properties of a π-conjugate system combining the chalcone and the pyrazole[3,4-b]pyridine scaffolds to describe the in-depth structural analysis thereof. Good agreement was found between the calculated results and experimental data. In addition, Hirshfeld surface analysis of the crystal structure showed that the intermolecular stabilization in the crystal packing comes mainly from H⋯H bond interactions. The chalcone crystal exhibits significant NLO properties suggesting that it could be considered a potential candidate for application in nonlinear optical devices.application/pdfPolo-Cuadrado, E., Ferrer, K., Osorio, E., Brito, I., Cisterna, J., Espinoza, L., Alderete, J. y Gutiérrez, M. (2023). Piperonal chalcone derivative incorporating the pyrazolo[3,4-b]pyridine moiety; crystal structure, spectroscopic characterization and quantum chemical investigations. RSC Advances, 13(8), 5197 - 5207. DOI: 10.1039/d2ra08101f10.1039/d2ra08101f20462069https://hdl.handle.net/20.500.12313/5532https://pubs.rsc.org/en/content/articlelanding/2023/ra/d2ra08101fengRoyal Society of ChemistryReino Unido52078519713RSC AdvancesS. Basu Ind. Eng. Chem. Prod. Res. Dev., 1984, 23 , 183 —186A. Abudurusuli , J. Li and S. Pan , Dalton Trans., 2021, 50 , 3155 —3160S. Tao , T. Miyagoe , A. Maeda , H. Matsuzaki , H. Ohtsu , M. Hasegawa , S. Takaishi , M. Yamashita and H. Okamoto , Adv. Mater., 2007, 19 , 2707 —2710I. D. Borges , J. A. V. Danielli , V. E. G. Silva , L. O. Sallum , J. E. Queiroz , L. D. Dias , I. Iermak , G. L. B. Aquino , A. J. Camargo , C. Valverde , C. Valverde , F. A. P. Osório , F. A. P. Osório , B. Baseia , B. Baseia , H. B. Napolitano and H. B. 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Commun., 2019, 75 , 1620 —1626© 2023 The Royal Society of Chemistry.info:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2Atribución-NoComercial 4.0 Internacional (CC BY-NC 4.0)https://creativecommons.org/licenses/by-nc/4.0/https://pubs.rsc.org/en/content/articlelanding/2023/ra/d2ra08101fEnlaces químicosEstructura cristalinaOrbitales molecularesPiridina; MonocristalesAnálisis espectroscópicoChemical bondsCrystal structureMolecular orbitalsPyridine; Single crystalsSpectroscopic analysisX ray crystallographyChalcone derivativesChalconesCrystals structuresHirshfeld surfacesN.L.O. propertiesNLO propertiesQuantum chemical investigationSlow evaporation techniquesSpectroscopic characterizationSynthesisedPiperonal chalcone derivative incorporating the pyrazolo[3,4-b]pyridine moiety; crystal structure, spectroscopic characterization and quantum chemical investigationsArtículo de revistahttp://purl.org/coar/resource_type/c_2df8fbb1http://purl.org/coar/version/c_970fb48d4fbd8a85Textinfo:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionPublicationORIGINALArtículo.pdfArtículo.pdfapplication/pdf232832https://repositorio.unibague.edu.co/bitstreams/93692291-28a3-4e22-a988-399ee20af5e1/download9f56475de339284daaa81c86c017ebbcMD52TEXTArtículo.pdf.txtArtículo.pdf.txtExtracted texttext/plain3402https://repositorio.unibague.edu.co/bitstreams/3fc89b54-e214-4f36-942a-ac58bebc0a3e/download72003f468148b61c12a390730016df6fMD53THUMBNAILArtículo.pdf.jpgArtículo.pdf.jpgIM Thumbnailimage/jpeg21476https://repositorio.unibague.edu.co/bitstreams/9f515dd0-4e31-4433-b840-97f7fcad432a/download59157ea9feb44eb80d8260051b7a0883MD54LICENSElicense.txtlicense.txttext/plain; charset=utf-8134https://repositorio.unibague.edu.co/bitstreams/c18203d9-ab0b-40db-be60-76e22ae331a5/download2fa3e590786b9c0f3ceba1b9656b7ac3MD5120.500.12313/5532oai:repositorio.unibague.edu.co:20.500.12313/55322025-09-12 11:47:54.086https://creativecommons.org/licenses/by-nc/4.0/© 2023 The Royal Society of Chemistry.https://repositorio.unibague.edu.coRepositorio Institucional Universidad de Ibaguébdigital@metabiblioteca.comQ3JlYXRpdmUgQ29tbW9ucyBBdHRyaWJ1dGlvbi1Ob25Db21tZXJjaWFsLU5vRGVyaXZhdGl2ZXMgNC4wIEludGVybmF0aW9uYWwgTGljZW5zZQ0KaHR0cHM6Ly9jcmVhdGl2ZWNvbW1vbnMub3JnL2xpY2Vuc2VzL2J5LW5jLW5kLzQuMC8=

Piperonal chalcone derivative incorporating the pyrazolo[3,4-b]pyridine moiety; crystal structure, spectroscopic characterization and quantum chemical investigations

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