Cove‐Edged Nanographenes with Localized Double Bonds
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http://hdl.handle.net/10045/106788
Title: | Cove‐Edged Nanographenes with Localized Double Bonds |
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Authors: | Gu, Yanwei | Muñoz‐Mármol, Rafael | Wu, Shaofei | Han, Yi | Ni, Yong | Díaz-García, María A. | Casado, Juan | Wu, Jishan |
Research Group/s: | Física de la Materia Condensada |
Center, Department or Service: | Universidad de Alicante. Departamento de Física Aplicada | Universidad de Alicante. Instituto Universitario de Materiales |
Keywords: | Aromaticity | Contorted aromatics | Cove edge | Nanographenes | Optoelectronics |
Knowledge Area: | Física de la Materia Condensada |
Issue Date: | 18-May-2020 |
Publisher: | Wiley-VCH Verlag GmbH & Co. KGaA |
Citation: | Angewandte Chemie International Edition. 2020, 59(21): 8113-8117. doi:10.1002/anie.202000326 |
Abstract: | The efficient synthesis and electronic properties of two large‐size cove‐edged nanographenes (NGs), CN1 and CN2, are presented. X‐ray crystallographic analysis reveals a contorted backbone for both molecules owing to the steric repulsion at the inner cove position. Noticeably, the dominant structures of these molecules contain four (for CN1) or six (for CN2) localized C=C double bonds embedded in nine (for CN1) or twelve (for CN2) aromatic sextet rings according to Clar's formula, which is supported by bond length analysis and theoretical (NICS, ACID) calculations. Furthermore, Raman spectra exhibit a band associated with the longitudinal CC stretching mode of olefinic double bonds. Owing to the existence of the additional olefinic bonds, both compounds show a small band gap (1.84 eV for CN1 and 1.37 eV for CN2). They also display moderate fluorescence quantum yield (35 % for CN1 and 50 % for CN2) owing to the contorted geometry, which can suppress aggregation in solution. |
Sponsor: | J.W. acknowleges financial support from the MOE Tier 3 programme (MOE2014-T3-1-004) and NRF Investigatorship (NRF-NRFI05-2019-0005). J.C. acknowledges MINECO and Junta de Andalucía of Spain projects (PGC2018-098533-BI00 and UMA18FEDERJA057). M.A.D.-G. and R.M.-M. thank support from MINECO through the research project MAT2015-66586-R and the FPI fellowship (no. BES-2016-077681), respectively. |
URI: | http://hdl.handle.net/10045/106788 |
ISSN: | 1433-7851 (Print) | 1521-3773 (Online) |
DOI: | 10.1002/anie.202000326 |
Language: | eng |
Type: | info:eu-repo/semantics/article |
Rights: | © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim |
Peer Review: | si |
Publisher version: | https://doi.org/10.1002/anie.202000326 |
Appears in Collections: | INV - Física de la Materia Condensada - Artículos de Revistas |
Files in This Item:
File | Description | Size | Format | |
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Wu_etal_2020_AngewChemIntEd_final.pdf | Versión final (acceso restringido) | 2,23 MB | Adobe PDF | Open Request a copy |
Wu_etal_2020_AngewChemIntEd_accepted.pdf | Accepted Manuscript (acceso abierto) | 3,01 MB | Adobe PDF | Open Preview |
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