Synthesis, characterization, X-ray crystal structure and DFT calculations of 4-([2,2':6',2''-terpyridin]- 4'-yl)phenol
The synthesis of new terpyridine (Tpy) derivatives has been subject of extensive research due to its potential as functional materials for solar energy conversion, among other applications. In this contribution, the 4-([2,2':6',2''-terpyridin]-4'-yl)phenol (TpyOH) has been s...
- Autores:
-
Sierra, Cesar
Castro Agudelo, Brian
Ochoa-Puentes, Cristian
Rodriguez-Cordoba, William
Reiber, Andreas
- Tipo de recurso:
- Article of journal
- Fecha de publicación:
- 2018
- Institución:
- Universidad Nacional de Colombia
- Repositorio:
- Universidad Nacional de Colombia
- Idioma:
- spa
- OAI Identifier:
- oai:repositorio.unal.edu.co:unal/66258
- Acceso en línea:
- https://repositorio.unal.edu.co/handle/unal/66258
http://bdigital.unal.edu.co/67282/
- Palabra clave:
- 54 Química y ciencias afines / Chemistry
Terpiridine
reação de Krönhke
estrutura de cristal
TD-DFT
Terpiuridina
reacción de Krönhke
estructura cristalina
TD-DFT
Terpyridine
Krönhke reaction
Crystal structure
TD-DFT
- Rights
- openAccess
- License
- Atribución-NoComercial 4.0 Internacional
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Synthesis, characterization, X-ray crystal structure and DFT calculations of 4-([2,2':6',2''-terpyridin]- 4'-yl)phenol |
| title |
Synthesis, characterization, X-ray crystal structure and DFT calculations of 4-([2,2':6',2''-terpyridin]- 4'-yl)phenol |
| spellingShingle |
Synthesis, characterization, X-ray crystal structure and DFT calculations of 4-([2,2':6',2''-terpyridin]- 4'-yl)phenol 54 Química y ciencias afines / Chemistry Terpiridine reação de Krönhke estrutura de cristal TD-DFT Terpiuridina reacción de Krönhke estructura cristalina TD-DFT Terpyridine Krönhke reaction Crystal structure TD-DFT |
| title_short |
Synthesis, characterization, X-ray crystal structure and DFT calculations of 4-([2,2':6',2''-terpyridin]- 4'-yl)phenol |
| title_full |
Synthesis, characterization, X-ray crystal structure and DFT calculations of 4-([2,2':6',2''-terpyridin]- 4'-yl)phenol |
| title_fullStr |
Synthesis, characterization, X-ray crystal structure and DFT calculations of 4-([2,2':6',2''-terpyridin]- 4'-yl)phenol |
| title_full_unstemmed |
Synthesis, characterization, X-ray crystal structure and DFT calculations of 4-([2,2':6',2''-terpyridin]- 4'-yl)phenol |
| title_sort |
Synthesis, characterization, X-ray crystal structure and DFT calculations of 4-([2,2':6',2''-terpyridin]- 4'-yl)phenol |
| dc.creator.fl_str_mv |
Sierra, Cesar Castro Agudelo, Brian Ochoa-Puentes, Cristian Rodriguez-Cordoba, William Reiber, Andreas |
| dc.contributor.author.spa.fl_str_mv |
Sierra, Cesar Castro Agudelo, Brian Ochoa-Puentes, Cristian Rodriguez-Cordoba, William Reiber, Andreas |
| dc.subject.ddc.spa.fl_str_mv |
54 Química y ciencias afines / Chemistry |
| topic |
54 Química y ciencias afines / Chemistry Terpiridine reação de Krönhke estrutura de cristal TD-DFT Terpiuridina reacción de Krönhke estructura cristalina TD-DFT Terpyridine Krönhke reaction Crystal structure TD-DFT |
| dc.subject.proposal.spa.fl_str_mv |
Terpiridine reação de Krönhke estrutura de cristal TD-DFT Terpiuridina reacción de Krönhke estructura cristalina TD-DFT Terpyridine Krönhke reaction Crystal structure TD-DFT |
| description |
The synthesis of new terpyridine (Tpy) derivatives has been subject of extensive research due to its potential as functional materials for solar energy conversion, among other applications. In this contribution, the 4-([2,2':6',2''-terpyridin]-4'-yl)phenol (TpyOH) has been synthesized, characterized and studied through several methods, including X-ray crystallography and computational approaches. Single crystal X-ray structure analysis shows that TpyOH is essentially planar, with dihedral angles of about 5.03° between the central pyridinyl and the phenolic ring, and also 6.05 and 12.2° in the terpyridine moiety. In the crystal, molecules arelinked by intermolecular hydrogen bonds and through π-π stacking interactions. Using a time-dependent density functional theory approach and taking into account bulk solvent effects, the absorption and fluorescence spectra of TpyOH were investigated and compared. The TD-DFT S0→Sn and S1→S0 transition energies are in good agreement with experimental results. The frontier molecular orbitals analysis showed that the low-energy absorption band has anintraligand charge transfer character (ICT), while the high-energy band is a common feature of π-π* transitions of the Tpy moiety. The S1→S0 emission transition also has an ICT character, with a 90% contribution from the HOMO→LUMO transitions. |
| publishDate |
2018 |
| dc.date.issued.spa.fl_str_mv |
2018-01-01 |
| dc.date.accessioned.spa.fl_str_mv |
2019-07-03T01:47:04Z |
| dc.date.available.spa.fl_str_mv |
2019-07-03T01:47:04Z |
| dc.type.spa.fl_str_mv |
Artículo de revista |
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http://purl.org/coar/resource_type/c_2df8fbb1 |
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info:eu-repo/semantics/article |
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info:eu-repo/semantics/publishedVersion |
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http://purl.org/coar/resource_type/c_6501 |
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http://purl.org/coar/version/c_970fb48d4fbd8a85 |
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Text |
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http://purl.org/redcol/resource_type/ART |
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http://purl.org/coar/resource_type/c_6501 |
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publishedVersion |
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ISSN: 2357-3791 |
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https://repositorio.unal.edu.co/handle/unal/66258 |
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http://bdigital.unal.edu.co/67282/ |
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ISSN: 2357-3791 |
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https://repositorio.unal.edu.co/handle/unal/66258 http://bdigital.unal.edu.co/67282/ |
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spa |
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spa |
| dc.relation.spa.fl_str_mv |
https://revistas.unal.edu.co/index.php/rcolquim/article/view/66281 |
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Universidad Nacional de Colombia Revistas electrónicas UN Revista Colombiana de Química Revista Colombiana de Química |
| dc.relation.references.spa.fl_str_mv |
Sierra, Cesar and Castro Agudelo, Brian and Ochoa-Puentes, Cristian and Rodriguez-Cordoba, William and Reiber, Andreas (2018) Synthesis, characterization, X-ray crystal structure and DFT calculations of 4-([2,2':6',2''-terpyridin]- 4'-yl)phenol. Revista Colombiana de Química, 47 (1). pp. 77-85. ISSN 2357-3791 |
| dc.rights.spa.fl_str_mv |
Derechos reservados - Universidad Nacional de Colombia |
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http://purl.org/coar/access_right/c_abf2 |
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Atribución-NoComercial 4.0 Internacional |
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http://creativecommons.org/licenses/by-nc/4.0/ |
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info:eu-repo/semantics/openAccess |
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Atribución-NoComercial 4.0 Internacional Derechos reservados - Universidad Nacional de Colombia http://creativecommons.org/licenses/by-nc/4.0/ http://purl.org/coar/access_right/c_abf2 |
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openAccess |
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application/pdf |
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Universidad Nacional de Colombia - Sede Bogotá - Facultad de Ciencias - Departamento de Química |
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Universidad Nacional de Colombia |
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Atribución-NoComercial 4.0 InternacionalDerechos reservados - Universidad Nacional de Colombiahttp://creativecommons.org/licenses/by-nc/4.0/info:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2Sierra, Cesar5e240691-46c0-4aa9-ac71-6e12f3aaa871300Castro Agudelo, Brian1461b28e-07c1-4b4b-8abf-49ae76333535300Ochoa-Puentes, Cristianc0d63173-235a-4347-b3db-65001ad22faa300Rodriguez-Cordoba, Williamad295672-a277-469f-a4da-3168bdeb147b300Reiber, Andreasf766fdd1-14ff-4676-83e2-d51c926324703002019-07-03T01:47:04Z2019-07-03T01:47:04Z2018-01-01ISSN: 2357-3791https://repositorio.unal.edu.co/handle/unal/66258http://bdigital.unal.edu.co/67282/The synthesis of new terpyridine (Tpy) derivatives has been subject of extensive research due to its potential as functional materials for solar energy conversion, among other applications. In this contribution, the 4-([2,2':6',2''-terpyridin]-4'-yl)phenol (TpyOH) has been synthesized, characterized and studied through several methods, including X-ray crystallography and computational approaches. Single crystal X-ray structure analysis shows that TpyOH is essentially planar, with dihedral angles of about 5.03° between the central pyridinyl and the phenolic ring, and also 6.05 and 12.2° in the terpyridine moiety. In the crystal, molecules arelinked by intermolecular hydrogen bonds and through π-π stacking interactions. Using a time-dependent density functional theory approach and taking into account bulk solvent effects, the absorption and fluorescence spectra of TpyOH were investigated and compared. The TD-DFT S0→Sn and S1→S0 transition energies are in good agreement with experimental results. The frontier molecular orbitals analysis showed that the low-energy absorption band has anintraligand charge transfer character (ICT), while the high-energy band is a common feature of π-π* transitions of the Tpy moiety. The S1→S0 emission transition also has an ICT character, with a 90% contribution from the HOMO→LUMO transitions.A síntese de derivados de terpiridina (Tpy) tem sido estudada devido ao seu potencial para a conversão de energia solar. Nesta contribuição, o 4-([2,2':6',2''- terpiridina]-4'-il) fenol (TpyOH) foi sintetizado, caracterizado e estudado por vários métodos. A análise de estrutura de raios X de cristal único mostra que o TpyOH é plano, com ângulos diedros de 5,03 ° entre o piridinilo central e o anel fenólico, e também 6,05 e 12,2 ° na porção de terpiridina. No cristal, as moléculas são ligadas por ligações intermoleculares de hidrogênio e através de interações de empilhamento π-π. Usando uma abordagem da teoria funcional da densidade dependente do tempo e levando em consideração os efeitos do solvente em massa, foram investigados e comparados os espectros de absorção e fluorescência do TpyOH. As energias de transição TD-DFT S0→Sn e S1→S0 estão de acordo com os resultados experimentais. A análise de orbitários moleculares de fronteira mostrou que a banda de absorção de baixa energia possui um caráter de transferência de carga intraligando (TIC), enquanto a banda de alta energia é uma característica comum das transições π-π* da fração Tpy. A transição de emissão S1→S0 também tem um caráter TIC, com uma contribuição de 90% das transições HOMO→LUMO.La síntesis de derivados terpiridinicos (Tpy) se ha investigado ampliamente debido a su potencial para la conversión de energía solar. En este artículo se sintetizó y caracterizó el 4-([2,2':6',2'' terpiridin]-4'-il)fenol (TpyOH), a través de varias metodologías como la cristalografía de rayos X y herramientas computacionales. El análisis de rayos X de monocristal mostró que el TpyOH es plano, con ángulos diedros de 5,03° entre el piridinilo central y el anillo fenólico, con presencia de ángulos de 6,05 y 12,2º en la porción terpiridínica. En el cristal, las moléculas están unidas por enlaces de hidrógeno intermoleculares y mediante interacciones de apilamiento π-π. Utilizando cálculos DFT dependientes del tiempo (TD-DFT) y teniendo en cuenta el efecto de los disolventes, se investigaron y compararon los espectros de absorción y fluorescencia de TpyOH. Las energías de transición TD-DFT de S0→Sn y S1→S0 concuerdan con los resultados experimentales. El análisis de orbitales moleculares de frontera mostró que la banda de absorción de baja energía corresponde a transferencia de carga intraligando (ICT); mientras que la banda de alta energía es común en las transiciones π-π* del resto Tpy. La emisión debido a la transición S1→S0 corresponde a ICT, con una contribución del 90% proveniente de transiciones HOMO→LUMO.application/pdfspaUniversidad Nacional de Colombia - Sede Bogotá - Facultad de Ciencias - Departamento de Químicahttps://revistas.unal.edu.co/index.php/rcolquim/article/view/66281Universidad Nacional de Colombia Revistas electrónicas UN Revista Colombiana de QuímicaRevista Colombiana de QuímicaSierra, Cesar and Castro Agudelo, Brian and Ochoa-Puentes, Cristian and Rodriguez-Cordoba, William and Reiber, Andreas (2018) Synthesis, characterization, X-ray crystal structure and DFT calculations of 4-([2,2':6',2''-terpyridin]- 4'-yl)phenol. Revista Colombiana de Química, 47 (1). pp. 77-85. ISSN 2357-379154 Química y ciencias afines / ChemistryTerpiridinereação de Krönhkeestrutura de cristalTD-DFTTerpiuridinareacción de Krönhkeestructura cristalinaTD-DFTTerpyridineKrönhke reactionCrystal structureTD-DFTSynthesis, characterization, X-ray crystal structure and DFT calculations of 4-([2,2':6',2''-terpyridin]- 4'-yl)phenolArtículo de revistainfo:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501http://purl.org/coar/resource_type/c_2df8fbb1http://purl.org/coar/version/c_970fb48d4fbd8a85Texthttp://purl.org/redcol/resource_type/ARTORIGINAL66281-359240-1-PB.pdfapplication/pdf3319684https://repositorio.unal.edu.co/bitstream/unal/66258/1/66281-359240-1-PB.pdf4ac382b0c0c3ba920dab8b67d022d007MD51THUMBNAIL66281-359240-1-PB.pdf.jpg66281-359240-1-PB.pdf.jpgGenerated Thumbnailimage/jpeg8538https://repositorio.unal.edu.co/bitstream/unal/66258/2/66281-359240-1-PB.pdf.jpg46cdc6b64d2e815153fc53601a2f1232MD52unal/66258oai:repositorio.unal.edu.co:unal/662582024-05-15 23:09:09.641Repositorio Institucional Universidad Nacional de Colombiarepositorio_nal@unal.edu.co |