Synthesis, optical and electrochemical properties of isomeric dibenzophenanthroline derivatives
Acid catalysed Friedländer cyclization of 2-aminobenzophenones with 1,2-, 1,3-, and 1,4-cyclohexadiones, followed by aromatization, has been used to prepare dibenzophenanthrolines (DBPs) containing 1,10-, 1,7- and 4,7-phenanthroline units, whose optoelectronic properties have been compared. The LUMO...
| Main Authors: | , , , , , , , , , , |
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| Format: | Journal Article |
| Language: | English |
| Published: |
2021
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| Online Access: | https://hdl.handle.net/10356/153444 |
| _version_ | 1824453732034674688 |
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| author | Ghosh, Animesh Li, Tianjiao Ni, Wenjun Wu, Tong Liang, Caihong Budanovic, Maja Morris, Samuel Alexander Klein, Maciej Webster, Richard David Gurzadyan, Gagik G. Grimsdale, Andrew C. |
| author2 | School of Materials Science and Engineering |
| author_facet | School of Materials Science and Engineering Ghosh, Animesh Li, Tianjiao Ni, Wenjun Wu, Tong Liang, Caihong Budanovic, Maja Morris, Samuel Alexander Klein, Maciej Webster, Richard David Gurzadyan, Gagik G. Grimsdale, Andrew C. |
| author_sort | Ghosh, Animesh |
| collection | NTU |
| description | Acid catalysed Friedländer cyclization of 2-aminobenzophenones with 1,2-, 1,3-, and 1,4-cyclohexadiones, followed by aromatization, has been used to prepare dibenzophenanthrolines (DBPs) containing 1,10-, 1,7- and 4,7-phenanthroline units, whose optoelectronic properties have been compared. The LUMO energies for all isomers were similar but the 4,7-isomers possessed significantly higher HOMOs than the other isomers, resulting in them having smaller HOMO-LUMO energy gaps. Compared with 1,10-DBP isomers, the emission of 1,7-DBPs is strongly quenched due to efficient charge transfer. The 4,7-DBP isomers show strongly enhanced photoluminescence due to excimer formation but appear to be less photostable due to their higher HOMO levels. Bis(phenylethynyl)-substituted derivatives demonstrated improved solubility and stronger luminescence properties than their unsubstituted analogues. |
| first_indexed | 2025-02-19T03:11:05Z |
| format | Journal Article |
| id | ntu-10356/153444 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2025-02-19T03:11:05Z |
| publishDate | 2021 |
| record_format | dspace |
| spelling | ntu-10356/1534442023-02-28T19:53:11Z Synthesis, optical and electrochemical properties of isomeric dibenzophenanthroline derivatives Ghosh, Animesh Li, Tianjiao Ni, Wenjun Wu, Tong Liang, Caihong Budanovic, Maja Morris, Samuel Alexander Klein, Maciej Webster, Richard David Gurzadyan, Gagik G. Grimsdale, Andrew C. School of Materials Science and Engineering School of Physical and Mathematical Sciences Science::Chemistry::Organic chemistry Cyclic Voltammetry Friedlander Condensation Heteroacenes Organic Semiconductor Photoluminescence Acid catalysed Friedländer cyclization of 2-aminobenzophenones with 1,2-, 1,3-, and 1,4-cyclohexadiones, followed by aromatization, has been used to prepare dibenzophenanthrolines (DBPs) containing 1,10-, 1,7- and 4,7-phenanthroline units, whose optoelectronic properties have been compared. The LUMO energies for all isomers were similar but the 4,7-isomers possessed significantly higher HOMOs than the other isomers, resulting in them having smaller HOMO-LUMO energy gaps. Compared with 1,10-DBP isomers, the emission of 1,7-DBPs is strongly quenched due to efficient charge transfer. The 4,7-DBP isomers show strongly enhanced photoluminescence due to excimer formation but appear to be less photostable due to their higher HOMO levels. Bis(phenylethynyl)-substituted derivatives demonstrated improved solubility and stronger luminescence properties than their unsubstituted analogues. Ministry of Education (MOE) Accepted version We acknowledge funding from the Singapore Ministry of Education through the Academic Research Fund Tier 1 grant RG117/15 and Tier 2 grant MOE2019-T2-1-085. 2021-12-12T08:02:10Z 2021-12-12T08:02:10Z 2021 Journal Article Ghosh, A., Li, T., Ni, W., Wu, T., Liang, C., Budanovic, M., Morris, S. A., Klein, M., Webster, R. D., Gurzadyan, G. G. & Grimsdale, A. C. (2021). Synthesis, optical and electrochemical properties of isomeric dibenzophenanthroline derivatives. Asian Journal of Organic Chemistry. https://dx.doi.org/10.1021/acs.jcpb.1c07045 2193-5807 https://hdl.handle.net/10356/153444 10.1021/acs.jcpb.1c07045 en RG117/15 MOE2019-T2-1-085 Asian Journal of Organic Chemistry This is the peer reviewed version of the following article: Ghosh, A., Li, T., Ni, W., Wu, T., Liang, C., Budanovic, M., Morris, S. A., Klein, M., Webster, R. D., Gurzadyan, G. G. & Grimsdale, A. C. (2021). Synthesis, optical and electrochemical properties of isomeric dibenzophenanthroline derivatives. Asian Journal of Organic Chemistry, which has been published in final form at https://doi.org.remotexs.ntu.edu.sg/10.1002/ajoc.202100670. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. application/pdf application/pdf |
| spellingShingle | Science::Chemistry::Organic chemistry Cyclic Voltammetry Friedlander Condensation Heteroacenes Organic Semiconductor Photoluminescence Ghosh, Animesh Li, Tianjiao Ni, Wenjun Wu, Tong Liang, Caihong Budanovic, Maja Morris, Samuel Alexander Klein, Maciej Webster, Richard David Gurzadyan, Gagik G. Grimsdale, Andrew C. Synthesis, optical and electrochemical properties of isomeric dibenzophenanthroline derivatives |
| title | Synthesis, optical and electrochemical properties of isomeric dibenzophenanthroline derivatives |
| title_full | Synthesis, optical and electrochemical properties of isomeric dibenzophenanthroline derivatives |
| title_fullStr | Synthesis, optical and electrochemical properties of isomeric dibenzophenanthroline derivatives |
| title_full_unstemmed | Synthesis, optical and electrochemical properties of isomeric dibenzophenanthroline derivatives |
| title_short | Synthesis, optical and electrochemical properties of isomeric dibenzophenanthroline derivatives |
| title_sort | synthesis optical and electrochemical properties of isomeric dibenzophenanthroline derivatives |
| topic | Science::Chemistry::Organic chemistry Cyclic Voltammetry Friedlander Condensation Heteroacenes Organic Semiconductor Photoluminescence |
| url | https://hdl.handle.net/10356/153444 |
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