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...
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| Format: | Article |
| Language: | English |
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Universidad Nacional de Colombia
2018-01-01
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| Series: | Revista Colombiana de Química |
| Subjects: | |
| Online Access: | https://revistas.unal.edu.co/index.php/rcolquim/article/view/66281 |
| _version_ | 1818528229024071680 |
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| author | Cesar Sierra Brian Castro Agudelo Cristian Ochoa-Puentes William Rodriguez-Cordoba Andreas Reiber |
| author_facet | Cesar Sierra Brian Castro Agudelo Cristian Ochoa-Puentes William Rodriguez-Cordoba Andreas Reiber |
| author_sort | Cesar Sierra |
| collection | DOAJ |
| 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 are
linked 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 an
intraligand 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. |
| first_indexed | 2024-12-11T06:47:03Z |
| format | Article |
| id | doaj.art-302becce81bc4dce9503379e30d8fac3 |
| institution | Directory Open Access Journal |
| issn | 0120-2804 2357-3791 |
| language | English |
| last_indexed | 2024-12-11T06:47:03Z |
| publishDate | 2018-01-01 |
| publisher | Universidad Nacional de Colombia |
| record_format | Article |
| series | Revista Colombiana de Química |
| spelling | doaj.art-302becce81bc4dce9503379e30d8fac32022-12-22T01:17:03ZengUniversidad Nacional de ColombiaRevista Colombiana de Química0120-28042357-37912018-01-01471778510.15446/rev.colomb.quim.v47n1.6628146744Synthesis, characterization, X-ray crystal structure and DFT calculations of 4-([2,2':6',2''-terpyridin]- 4'-yl)phenolCesar Sierra0Brian Castro Agudelo1Cristian Ochoa-Puentes2William Rodriguez-Cordoba3Andreas Reiber4Universidad Nacional de ColombiaUniversidad de la AmazoniaUniversidad Nacional de ColombiaUniversidad Nacional de ColombiaUniversidad de los AndesThe 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 are linked 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 an intraligand 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.https://revistas.unal.edu.co/index.php/rcolquim/article/view/66281TerpyridineKrönhke reactionCrystal structureTD-DFT |
| spellingShingle | Cesar Sierra Brian Castro Agudelo Cristian Ochoa-Puentes William Rodriguez-Cordoba Andreas Reiber Synthesis, characterization, X-ray crystal structure and DFT calculations of 4-([2,2':6',2''-terpyridin]- 4'-yl)phenol Revista Colombiana de Química Terpyridine Krönhke reaction Crystal structure TD-DFT |
| title | 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_short | 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 |
| topic | Terpyridine Krönhke reaction Crystal structure TD-DFT |
| url | https://revistas.unal.edu.co/index.php/rcolquim/article/view/66281 |
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