Please use this identifier to cite or link to this item:
https://doi.org/10.1039/c4sc03866e
DC Field | Value | |
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dc.title | Phenalenyl-fused porphyrins with different ground states | |
dc.contributor.author | Zeng W. | |
dc.contributor.author | Lee S. | |
dc.contributor.author | Son M. | |
dc.contributor.author | Ishida M. | |
dc.contributor.author | Furukawa K. | |
dc.contributor.author | Hu P. | |
dc.contributor.author | Sun Z. | |
dc.contributor.author | Kim D. | |
dc.contributor.author | Wu J. | |
dc.date.accessioned | 2020-09-10T01:57:23Z | |
dc.date.available | 2020-09-10T01:57:23Z | |
dc.date.issued | 2015 | |
dc.identifier.citation | Zeng W., Lee S., Son M., Ishida M., Furukawa K., Hu P., Sun Z., Kim D., Wu J. (2015). Phenalenyl-fused porphyrins with different ground states. Chemical Science 6 (4) : 2427-2433. ScholarBank@NUS Repository. https://doi.org/10.1039/c4sc03866e | |
dc.identifier.issn | 20416520 | |
dc.identifier.uri | https://scholarbank.nus.edu.sg/handle/10635/175512 | |
dc.description.abstract | Materials based on biradicals/biradicaloids have potential applications for organic electronics, photonics and spintronics. In this work, we demonstrated that hybridization of porphyrin and polycyclic aromatic hydrocarbon could lead to a new type of stable biradicals/biradicaloids with tunable ground state and physical property. Mono- and bis-phenalenyl fused porphyrins 1 and 2 were synthesized via an intramolecular Friedel-Crafts alkylation-followed-by oxidative dehydrogenation strategy. Our detailed experimental and theoretical studies revealed that 1 has a closed-shell structure with a small biradical character (y = 0.06 by DFT calculation) in the ground state, while 2 exists as a persistent triplet biradical at room temperature under inert atmosphere. Compound 1 underwent hydrogen abstraction from solvent during the crystal growing process while compound 2 was easily oxidized in air to give two dioxo-porphyrin isomers 11a/11b, which can be correlated to their unique biradical character and spin distribution. The physical properties of 1 and 2, their dihydro/tetrahydro-precursors 7/10, and the dioxo-compounds 11a/11b were investigated and compared. © 2015 The Royal Society of Chemistry. | |
dc.publisher | Royal Society of Chemistry | |
dc.source | Unpaywall 20200831 | |
dc.subject | Aromatic hydrocarbons | |
dc.subject | Dehydrogenation | |
dc.subject | Isomers | |
dc.subject | Physical properties | |
dc.subject | Polycyclic aromatic hydrocarbons | |
dc.subject | Porphyrins | |
dc.subject | Hydrogen abstraction | |
dc.subject | Inert atmospheres | |
dc.subject | Intramolecular friedel-crafts | |
dc.subject | Organic electronics | |
dc.subject | Oxidative dehydrogenations | |
dc.subject | Porphyrin isomers | |
dc.subject | Spin distribution | |
dc.subject | Theoretical study | |
dc.subject | Ground state | |
dc.type | Article | |
dc.contributor.department | DEPT OF CHEMISTRY | |
dc.description.doi | 10.1039/c4sc03866e | |
dc.description.sourcetitle | Chemical Science | |
dc.description.volume | 6 | |
dc.description.issue | 4 | |
dc.description.page | 2427-2433 | |
Appears in Collections: | Staff Publications Elements |
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10_1039_c4sc03866e.pdf | 1.88 MB | Adobe PDF | OPEN | None | View/Download |
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