Aromatic pi-complexation of 1,5-diisocyanonaphthalene with benzene derivatives
Abstract Aromatic π-complexes play a significant role in various chemical and biological systems, significantly influencing their physico-chemical and spectroscopic properties. The identification of new compounds capable of π-complex formation is therefore of great interest. The paper investigates t...
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Nature Portfolio
2025-01-01
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| Series: | Scientific Reports |
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| Online Access: | https://doi.org/10.1038/s41598-024-84769-3 |
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| author | Erika Kopcsik Zoltán Mucsi Rajmond Schiwert László Vanyorek Béla Viskolcz Miklós Nagy |
| author_facet | Erika Kopcsik Zoltán Mucsi Rajmond Schiwert László Vanyorek Béla Viskolcz Miklós Nagy |
| author_sort | Erika Kopcsik |
| collection | DOAJ |
| description | Abstract Aromatic π-complexes play a significant role in various chemical and biological systems, significantly influencing their physico-chemical and spectroscopic properties. The identification of new compounds capable of π-complex formation is therefore of great interest. The paper investigates the fluorescent properties of 1,5-diisocyanonaphthalene (1,5-DIN) in different aromatic solvents, demonstrating its potential for distinguishing between aromatics based on emission spectra. The resulting spectra can be classified as benzene-, toluene-, and xylene-like types and may be used for the fingerprint identification of benzenes with different electron donating/withdrawing substituents. Comparative studies with related compounds revealed that lower electron density in the naphthalene core favors π-complex formation. The study also found that electron-donating groups in solvents caused more significant redshifts, while electron-withdrawing groups had minimal impact. High-level DFT calculations supported these observations, showing that stronger π-π interactions lead to greater redshifts, particularly in solvents, such as toluene and xylenes. The research suggests that 1,5-DIN’s distinct emission behaviors can be leveraged for compositional analysis of benzene-toluene-xylene (BTX) mixtures, with specific emphasis on the influence of electron density and solvent interactions on the emission properties. |
| format | Article |
| id | doaj-art-738a150185cf4a058748cd7eb34bcfbd |
| institution | Kabale University |
| issn | 2045-2322 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Scientific Reports |
| spelling | doaj-art-738a150185cf4a058748cd7eb34bcfbd2025-01-05T12:16:00ZengNature PortfolioScientific Reports2045-23222025-01-0115111010.1038/s41598-024-84769-3Aromatic pi-complexation of 1,5-diisocyanonaphthalene with benzene derivativesErika Kopcsik0Zoltán Mucsi1Rajmond Schiwert2László Vanyorek3Béla Viskolcz4Miklós Nagy5Institute of Chemistry, University of MiskolcInstitute of Chemistry, University of MiskolcInstitute of Chemistry, University of MiskolcInstitute of Chemistry, University of MiskolcInstitute of Chemistry, University of MiskolcInstitute of Chemistry, University of MiskolcAbstract Aromatic π-complexes play a significant role in various chemical and biological systems, significantly influencing their physico-chemical and spectroscopic properties. The identification of new compounds capable of π-complex formation is therefore of great interest. The paper investigates the fluorescent properties of 1,5-diisocyanonaphthalene (1,5-DIN) in different aromatic solvents, demonstrating its potential for distinguishing between aromatics based on emission spectra. The resulting spectra can be classified as benzene-, toluene-, and xylene-like types and may be used for the fingerprint identification of benzenes with different electron donating/withdrawing substituents. Comparative studies with related compounds revealed that lower electron density in the naphthalene core favors π-complex formation. The study also found that electron-donating groups in solvents caused more significant redshifts, while electron-withdrawing groups had minimal impact. High-level DFT calculations supported these observations, showing that stronger π-π interactions lead to greater redshifts, particularly in solvents, such as toluene and xylenes. The research suggests that 1,5-DIN’s distinct emission behaviors can be leveraged for compositional analysis of benzene-toluene-xylene (BTX) mixtures, with specific emphasis on the influence of electron density and solvent interactions on the emission properties.https://doi.org/10.1038/s41598-024-84769-3Aromatic pi-complexFluorescenceSolvatochromic effectIsonitrileDFTPi-stacking |
| spellingShingle | Erika Kopcsik Zoltán Mucsi Rajmond Schiwert László Vanyorek Béla Viskolcz Miklós Nagy Aromatic pi-complexation of 1,5-diisocyanonaphthalene with benzene derivatives Scientific Reports Aromatic pi-complex Fluorescence Solvatochromic effect Isonitrile DFT Pi-stacking |
| title | Aromatic pi-complexation of 1,5-diisocyanonaphthalene with benzene derivatives |
| title_full | Aromatic pi-complexation of 1,5-diisocyanonaphthalene with benzene derivatives |
| title_fullStr | Aromatic pi-complexation of 1,5-diisocyanonaphthalene with benzene derivatives |
| title_full_unstemmed | Aromatic pi-complexation of 1,5-diisocyanonaphthalene with benzene derivatives |
| title_short | Aromatic pi-complexation of 1,5-diisocyanonaphthalene with benzene derivatives |
| title_sort | aromatic pi complexation of 1 5 diisocyanonaphthalene with benzene derivatives |
| topic | Aromatic pi-complex Fluorescence Solvatochromic effect Isonitrile DFT Pi-stacking |
| url | https://doi.org/10.1038/s41598-024-84769-3 |
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