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Article: Wave-shaped polycyclic hydrocarbons with controlled aromaticity

TitleWave-shaped polycyclic hydrocarbons with controlled aromaticity
Authors
Issue Date2019
Citation
Chemical Science, 2019, v. 10, n. 14, p. 4025-4031 How to Cite?
Abstract© The Royal Society of Chemistry. Controlling the aromaticity and electronic properties of curved π-conjugated systems has been increasingly attractive for the development of novel functional materials for organic electronics. Herein, we demonstrate an efficient synthesis of two novel wave-shaped polycyclic hydrocarbons (PHs) 1 and 2 with 64 π-electrons. Among them, the wave-shaped π-conjugated carbon skeleton of 2 is unambiguously revealed by single-crystal X-ray crystallography analysis. The wave-shaped geometry is induced by steric congestion in the cove and fjord regions. Remarkably, the aromaticity of these two structural isomers can be tailored by the annulated direction of cyclopenta[b]fluorene units. Isomer 1 (Eoptg = 1.13 eV) behaves as a closed-shell compound with weakly antiaromatic feature, whereas its structural isomer 2 displays a highly stable tetraradical character (y0 = 0.23; y1 = 0.22; t1/2 = 91 days) with a narrow optical energy gap of 0.96 eV. Moreover, the curved PH 2 exhibits remarkable ambipolar charge transport in solution-processed organic thin-film transistors. Our research provides a new insight into the design and synthesis of stable functional curved aromatics with multiradical characters.
Persistent Identifierhttp://hdl.handle.net/10722/276642
ISSN
2023 Impact Factor: 7.6
2023 SCImago Journal Rankings: 2.333
PubMed Central ID
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorMa, Ji-
dc.contributor.authorZhang, Ke-
dc.contributor.authorSchellhammer, Karl Sebastian-
dc.contributor.authorFu, Yubin-
dc.contributor.authorKomber, Hartmut-
dc.contributor.authorXu, Chi-
dc.contributor.authorPopov, Alexey A.-
dc.contributor.authorHennersdorf, Felix-
dc.contributor.authorWeigand, Jan J.-
dc.contributor.authorZhou, Shengqiang-
dc.contributor.authorPisula, Wojciech-
dc.contributor.authorOrtmann, Frank-
dc.contributor.authorBerger, Reinhard-
dc.contributor.authorLiu, Junzhi-
dc.contributor.authorFeng, Xinliang-
dc.date.accessioned2019-09-18T08:34:13Z-
dc.date.available2019-09-18T08:34:13Z-
dc.date.issued2019-
dc.identifier.citationChemical Science, 2019, v. 10, n. 14, p. 4025-4031-
dc.identifier.issn2041-6520-
dc.identifier.urihttp://hdl.handle.net/10722/276642-
dc.description.abstract© The Royal Society of Chemistry. Controlling the aromaticity and electronic properties of curved π-conjugated systems has been increasingly attractive for the development of novel functional materials for organic electronics. Herein, we demonstrate an efficient synthesis of two novel wave-shaped polycyclic hydrocarbons (PHs) 1 and 2 with 64 π-electrons. Among them, the wave-shaped π-conjugated carbon skeleton of 2 is unambiguously revealed by single-crystal X-ray crystallography analysis. The wave-shaped geometry is induced by steric congestion in the cove and fjord regions. Remarkably, the aromaticity of these two structural isomers can be tailored by the annulated direction of cyclopenta[b]fluorene units. Isomer 1 (Eoptg = 1.13 eV) behaves as a closed-shell compound with weakly antiaromatic feature, whereas its structural isomer 2 displays a highly stable tetraradical character (y0 = 0.23; y1 = 0.22; t1/2 = 91 days) with a narrow optical energy gap of 0.96 eV. Moreover, the curved PH 2 exhibits remarkable ambipolar charge transport in solution-processed organic thin-film transistors. Our research provides a new insight into the design and synthesis of stable functional curved aromatics with multiradical characters.-
dc.languageeng-
dc.relation.ispartofChemical Science-
dc.rightsThis work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.-
dc.titleWave-shaped polycyclic hydrocarbons with controlled aromaticity-
dc.typeArticle-
dc.description.naturepublished_or_final_version-
dc.identifier.doi10.1039/C8SC05416A-
dc.identifier.pmid31105925-
dc.identifier.pmcidPMC6499110-
dc.identifier.scopuseid_2-s2.0-85064043051-
dc.identifier.volume10-
dc.identifier.issue14-
dc.identifier.spage4025-
dc.identifier.epage4031-
dc.identifier.eissn2041-6539-
dc.identifier.isiWOS:000467988600010-
dc.identifier.issnl2041-6520-

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