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Article: Extension of Non-alternant Nanographenes Containing Nitrogen-Doped Stone-Thrower-Wales Defects
Title | Extension of Non-alternant Nanographenes Containing Nitrogen-Doped Stone-Thrower-Wales Defects |
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Authors | |
Keywords | Antiaromaticity. Azupyrene N-Doping Nanographenes Non-Alternant Topologies |
Issue Date | 20-Jul-2023 |
Publisher | Wiley |
Citation | Angewandte Chemie International Edition, 2023, v. 62, n. 35 How to Cite? |
Abstract | Non-alternant topologies have attracted considerable attention due to their unique physiochemical characteristics in recent years. Here, three novel topological nanographenes molecular models of nitrogen-doped Stone-Thrower-Wales (S-T-W) defects were achieved through intramolecular direct arylation. Their chemical structures were unambiguously elucidated by single-crystal analysis. Among them, threefold intramolecular direct arylation compound (C42H21N) is the largest nanographene bearing a N-doped non-alternant topology to date, in which the non-benzenoid rings account for 83 % of the total molecular skeleton. The absorption maxima of this compound was located in the near-infrared region with a long tail up to 900 nm, which was much longer than those reported for similarly sized N-doped nanographene with six-membered rings (C40H15N). In addition, the electronic energy gaps of these series compounds clearly decreased with the introduction of non-alternant topologies (from 2.27 eV to 1.50 eV). It is noteworthy that C42H21N possesses such a low energy gap (E-g(opt)=1.40 eV; E-g(cv)=1.50 eV), yet is highly stable under ambient conditions. Our work reported herein demonstrates that the non-alternant topology could significantly influence the electronic configurations of nanocarbons, where the introduction of a non-alternanting topology may be an effective way to narrow the energy gap without extending the molecular & pi;-conjugation. |
Persistent Identifier | http://hdl.handle.net/10722/331335 |
ISSN | 2023 Impact Factor: 16.1 2023 SCImago Journal Rankings: 5.300 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Wang, C | - |
dc.contributor.author | Deng, ZQ | - |
dc.contributor.author | Phillips, DL | - |
dc.contributor.author | Liu, JZ | - |
dc.date.accessioned | 2023-09-21T06:54:49Z | - |
dc.date.available | 2023-09-21T06:54:49Z | - |
dc.date.issued | 2023-07-20 | - |
dc.identifier.citation | Angewandte Chemie International Edition, 2023, v. 62, n. 35 | - |
dc.identifier.issn | 1433-7851 | - |
dc.identifier.uri | http://hdl.handle.net/10722/331335 | - |
dc.description.abstract | Non-alternant topologies have attracted considerable attention due to their unique physiochemical characteristics in recent years. Here, three novel topological nanographenes molecular models of nitrogen-doped Stone-Thrower-Wales (S-T-W) defects were achieved through intramolecular direct arylation. Their chemical structures were unambiguously elucidated by single-crystal analysis. Among them, threefold intramolecular direct arylation compound (C42H21N) is the largest nanographene bearing a N-doped non-alternant topology to date, in which the non-benzenoid rings account for 83 % of the total molecular skeleton. The absorption maxima of this compound was located in the near-infrared region with a long tail up to 900 nm, which was much longer than those reported for similarly sized N-doped nanographene with six-membered rings (C40H15N). In addition, the electronic energy gaps of these series compounds clearly decreased with the introduction of non-alternant topologies (from 2.27 eV to 1.50 eV). It is noteworthy that C42H21N possesses such a low energy gap (E-g(opt)=1.40 eV; E-g(cv)=1.50 eV), yet is highly stable under ambient conditions. Our work reported herein demonstrates that the non-alternant topology could significantly influence the electronic configurations of nanocarbons, where the introduction of a non-alternanting topology may be an effective way to narrow the energy gap without extending the molecular & pi;-conjugation. | - |
dc.language | eng | - |
dc.publisher | Wiley | - |
dc.relation.ispartof | Angewandte Chemie International Edition | - |
dc.rights | This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. | - |
dc.subject | Antiaromaticity. | - |
dc.subject | Azupyrene | - |
dc.subject | N-Doping | - |
dc.subject | Nanographenes | - |
dc.subject | Non-Alternant Topologies | - |
dc.title | Extension of Non-alternant Nanographenes Containing Nitrogen-Doped Stone-Thrower-Wales Defects | - |
dc.type | Article | - |
dc.description.nature | published_or_final_version | - |
dc.identifier.doi | 10.1002/anie.202306890 | - |
dc.identifier.pmid | 37421410 | - |
dc.identifier.scopus | eid_2-s2.0-85165282151 | - |
dc.identifier.volume | 62 | - |
dc.identifier.issue | 35 | - |
dc.identifier.eissn | 1521-3773 | - |
dc.identifier.isi | WOS:001032240100001 | - |
dc.publisher.place | WEINHEIM | - |
dc.identifier.issnl | 1433-7851 | - |