Please use this identifier to cite or link to this item:
https://doi.org/10.1021/acs.joc.9b02796
DC Field | Value | |
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dc.title | Sulfur-Doped (Dibenzo)heptazethrene and (Dibenzo)octazethrene Diradicaloids | |
dc.contributor.author | C. H. E. Chow | |
dc.contributor.author | PHAN VAN HOA | |
dc.contributor.author | ZHANG XIAOJIE | |
dc.contributor.author | Wu Jishan | |
dc.date.accessioned | 2020-05-08T08:36:34Z | |
dc.date.available | 2020-05-08T08:36:34Z | |
dc.date.issued | 2019-11-12 | |
dc.identifier.citation | C. H. E. Chow, PHAN VAN HOA, ZHANG XIAOJIE, Wu Jishan (2019-11-12). Sulfur-Doped (Dibenzo)heptazethrene and (Dibenzo)octazethrene Diradicaloids. Journal of Organic Chemistry 85 : 234-240. ScholarBank@NUS Repository. https://doi.org/10.1021/acs.joc.9b02796 | |
dc.identifier.issn | 0022-3263 | |
dc.identifier.issn | 1520-6904 | |
dc.identifier.uri | https://scholarbank.nus.edu.sg/handle/10635/167849 | |
dc.description.abstract | We report the synthesis and characterization of sulfur-doped dibenzoheptazethrene (DBHZ-2S) and dibenzooctazethrene (DBOZ-2S) dications. Their neutral precursors 9a/9b were synthesized by acid-mediated intramolecular cyclization reaction of sulfoxides and the dications were prepared by treating 9a/9b with NOSbF6 or AgSbF6, respectively. Both dications displayed open-shell singlet ground state with a moderate diradical character (y0 = 0.44 for DBHZ-2S and 0.66 for DBOZ-2S) and a small singlet−triplet energy gap (ΔES‑T = −3.9 kcal/mol for DBHZ-2S and −3.2 kcal/mol for DBOZ-2S). The open-shell singlet diradical nature of DBHZ-2S and DBOZ-2S were supported by electronic absorption spectroscopy, electron spin resonance spectroscopy, variable-temperature NMR studies, together with spin-unrestricted density functional theory calculations. However, synthesis and isolation of the sulfur-doped heptazethrene (HZ-2S) and octazethrene (OZ-2S) dications upon chemical oxidation of their corresponding neutral precursors 5a/5b were not successful owing to their high reactivity. | |
dc.publisher | ACS | |
dc.type | Article | |
dc.contributor.department | DEPT OF CHEMISTRY | |
dc.description.doi | 10.1021/acs.joc.9b02796 | |
dc.description.sourcetitle | Journal of Organic Chemistry | |
dc.description.volume | 85 | |
dc.description.page | 234-240 | |
dc.published.state | Published | |
dc.grant.id | NRF-NRFI05-2019-0005 | |
dc.grant.fundingagency | NRF | |
Appears in Collections: | Staff Publications Elements |
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