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- Publisher Website: 10.1021/acs.joc.9b02626
- Scopus: eid_2-s2.0-85075781353
- PMID: 31718187
- WOS: WOS:000506089100023
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Article: Dipyrene-Fused Dicyclopenta[a,f]naphthalenes
Title | Dipyrene-Fused Dicyclopenta[a,f]naphthalenes |
---|---|
Authors | |
Keywords | Electron spin resonance spectroscopy Field effect transistors Isomers Pyrene Spectroelectrochemistry |
Issue Date | 2020 |
Publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc |
Citation | The Journal of Organic Chemistry, 2020, v. 85, p. 215-223 How to Cite? |
Abstract | Herein, we demonstrate an efficient synthesis of two antiaromatic constitutional isomers of pyrene-fused dicyclopenta[a,f]naphthalenes (PCPNs) 1a and 1b featuring 44 π-conjugated electrons. Notably, the thermodynamic stability of PCPNs can be tuned by ortho-fusing pyrene moieties to either the a or b bond of dicyclopentanaphthalene (CPN) leading to labile 1,5- (1a) or stable 2,6-naphthoquinodimethane (NQDM) (1b) configurations, respectively. Both isomers 1a and 1b exhibit moderate open-shell biradical characters (y0) of 0.48 and 0.44 and narrow energy gaps of 1.0 and 1.1 eV, respectively. Moreover, the spectroscopic and spin properties of radical cation and anion species of 1a and 1b are elucidated by in situ EPR/UV–vis–NIR spectroelectrochemical investigations. Furthermore, a solution-processed field-effect transistor of 1b was fabricated, manifesting its promising potential in organic electronics. |
Persistent Identifier | http://hdl.handle.net/10722/284789 |
ISSN | 2023 Impact Factor: 3.3 2023 SCImago Journal Rankings: 0.724 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Melidonie, J | - |
dc.contributor.author | Dmitrieva, E | - |
dc.contributor.author | Zhang, K | - |
dc.contributor.author | Fu, Y | - |
dc.contributor.author | Popov, AA | - |
dc.contributor.author | Pisula, W | - |
dc.contributor.author | Berger, R | - |
dc.contributor.author | Liu, J | - |
dc.contributor.author | Feng, X | - |
dc.date.accessioned | 2020-08-07T09:02:39Z | - |
dc.date.available | 2020-08-07T09:02:39Z | - |
dc.date.issued | 2020 | - |
dc.identifier.citation | The Journal of Organic Chemistry, 2020, v. 85, p. 215-223 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | http://hdl.handle.net/10722/284789 | - |
dc.description.abstract | Herein, we demonstrate an efficient synthesis of two antiaromatic constitutional isomers of pyrene-fused dicyclopenta[a,f]naphthalenes (PCPNs) 1a and 1b featuring 44 π-conjugated electrons. Notably, the thermodynamic stability of PCPNs can be tuned by ortho-fusing pyrene moieties to either the a or b bond of dicyclopentanaphthalene (CPN) leading to labile 1,5- (1a) or stable 2,6-naphthoquinodimethane (NQDM) (1b) configurations, respectively. Both isomers 1a and 1b exhibit moderate open-shell biradical characters (y0) of 0.48 and 0.44 and narrow energy gaps of 1.0 and 1.1 eV, respectively. Moreover, the spectroscopic and spin properties of radical cation and anion species of 1a and 1b are elucidated by in situ EPR/UV–vis–NIR spectroelectrochemical investigations. Furthermore, a solution-processed field-effect transistor of 1b was fabricated, manifesting its promising potential in organic electronics. | - |
dc.language | eng | - |
dc.publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/joc | - |
dc.relation.ispartof | The Journal of Organic Chemistry | - |
dc.rights | This document is the Accepted Manuscript version of a Published Work that appeared in final form in [JournalTitle], copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [insert ACS Articles on Request author-directed link to Published Work, see http://pubs.acs.org/page/policy/articlesonrequest/index.html]. | - |
dc.subject | Electron spin resonance spectroscopy | - |
dc.subject | Field effect transistors | - |
dc.subject | Isomers | - |
dc.subject | Pyrene | - |
dc.subject | Spectroelectrochemistry | - |
dc.title | Dipyrene-Fused Dicyclopenta[a,f]naphthalenes | - |
dc.type | Article | - |
dc.identifier.email | Liu, J: juliu@hku.hk | - |
dc.identifier.authority | Liu, J=rp02584 | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/acs.joc.9b02626 | - |
dc.identifier.pmid | 31718187 | - |
dc.identifier.scopus | eid_2-s2.0-85075781353 | - |
dc.identifier.hkuros | 311678 | - |
dc.identifier.volume | 85 | - |
dc.identifier.spage | 215 | - |
dc.identifier.epage | 223 | - |
dc.identifier.isi | WOS:000506089100023 | - |
dc.publisher.place | United States | - |
dc.identifier.issnl | 0022-3263 | - |