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Article: Pyrene-Fused s-Indacene

TitlePyrene-Fused s-Indacene
Authors
Issue Date2018
Citation
Journal of Organic Chemistry, 2018, v. 83, n. 12, p. 6633-6639 How to Cite?
Abstract© 2018 American Chemical Society. One antiaromatic polycyclic hydrocarbon (PH) with and without solubilizing tert-butyl substituents, namely s-indaceno[2,1-a:6,5-a′]dipyrene (IDPs), has been synthesized by a four-step protocol. The IDPs represent the longitudinal, peri-extension of the indeno[1,2-b]fluorene skeleton towards a planar 40 π-electron system. Their structures were unambiguously confirmed by X-ray crystallographic analysis. The optoelectronic properties were studied by UV/vis absorption spectroscopy and cyclic voltammetry. These studies revealed that peri-fusion renders the IDP derivatives with a narrow optical energy gap of 1.8 eV. The maximum absorption of IDPs is shifted by 160 nm compared to the parent indenofluorene. Two quasi-reversible oxidation as well as reduction steps indicate an excellent redox behavior attributed to the antiaromatic core. Formation of the radical cation and the dication was monitored by UV/vis absorption spectroscopy during titration experiments. Notably, the fusion of s-indacene with two pyrene moieties lead to IDPs with absorption maxima approaching the near infrared (NIR) regime.
Persistent Identifierhttp://hdl.handle.net/10722/276594
ISSN
2023 Impact Factor: 3.3
2023 SCImago Journal Rankings: 0.724
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorMelidonie, Jason-
dc.contributor.authorLiu, Junzhi-
dc.contributor.authorFu, Yubin-
dc.contributor.authorWeigand, Jan J.-
dc.contributor.authorBerger, Reinhard-
dc.contributor.authorFeng, Xinliang-
dc.date.accessioned2019-09-18T08:34:05Z-
dc.date.available2019-09-18T08:34:05Z-
dc.date.issued2018-
dc.identifier.citationJournal of Organic Chemistry, 2018, v. 83, n. 12, p. 6633-6639-
dc.identifier.issn0022-3263-
dc.identifier.urihttp://hdl.handle.net/10722/276594-
dc.description.abstract© 2018 American Chemical Society. One antiaromatic polycyclic hydrocarbon (PH) with and without solubilizing tert-butyl substituents, namely s-indaceno[2,1-a:6,5-a′]dipyrene (IDPs), has been synthesized by a four-step protocol. The IDPs represent the longitudinal, peri-extension of the indeno[1,2-b]fluorene skeleton towards a planar 40 π-electron system. Their structures were unambiguously confirmed by X-ray crystallographic analysis. The optoelectronic properties were studied by UV/vis absorption spectroscopy and cyclic voltammetry. These studies revealed that peri-fusion renders the IDP derivatives with a narrow optical energy gap of 1.8 eV. The maximum absorption of IDPs is shifted by 160 nm compared to the parent indenofluorene. Two quasi-reversible oxidation as well as reduction steps indicate an excellent redox behavior attributed to the antiaromatic core. Formation of the radical cation and the dication was monitored by UV/vis absorption spectroscopy during titration experiments. Notably, the fusion of s-indacene with two pyrene moieties lead to IDPs with absorption maxima approaching the near infrared (NIR) regime.-
dc.languageeng-
dc.relation.ispartofJournal of Organic Chemistry-
dc.titlePyrene-Fused s-Indacene-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/acs.joc.8b00925-
dc.identifier.pmid29772900-
dc.identifier.scopuseid_2-s2.0-85047418636-
dc.identifier.volume83-
dc.identifier.issue12-
dc.identifier.spage6633-
dc.identifier.epage6639-
dc.identifier.eissn1520-6904-
dc.identifier.isiWOS:000445712900036-
dc.identifier.issnl0022-3263-

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