I···N Halogen bonding in 1:1 co-crystals formed between 1,4-diiodotetrafluorobenzene and the isomeric n-pyridinealdazines (n = 2, 3 and 4): Assessment of supramolecular association and influence upon solid-state photoluminescence properties
1:1 Co-crystals formed between 1,4-diiodotetrafluorobenzene and each of the three isomeric npyridinealdazines (n = 2, 3 and 4) have been characterised by X-ray crystallography, a variety of spectroscopic methods, viz. IR, Raman, NMR: solution- and solid-state (13C CP MAS and 13C HPDEC MAS) and fluor...
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| Language: | English |
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Royal Society of Chemistry
2022
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| Online Access: | http://eprints.sunway.edu.my/2125/ http://eprints.sunway.edu.my/2125/1/crystengcomm%202022%2024%207579.pdf |
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| author | Yeo, Chien Ing * Tan, Yee Seng * Kwong, Huey Chong* Lee, Vannajan Sanghiran Tiekink, Edward R. T. * |
| author_facet | Yeo, Chien Ing * Tan, Yee Seng * Kwong, Huey Chong* Lee, Vannajan Sanghiran Tiekink, Edward R. T. * |
| author_sort | Yeo, Chien Ing * |
| building | SU Institutional Repository |
| collection | Online Access |
| description | 1:1 Co-crystals formed between 1,4-diiodotetrafluorobenzene and each of the three isomeric npyridinealdazines (n = 2, 3 and 4) have been characterised by X-ray crystallography, a variety of spectroscopic methods, viz. IR, Raman, NMR: solution- and solid-state (13C CP MAS and 13C HPDEC MAS) and fluorescence as well as by computational chemistry techniques. The primary connection between the respective coformers arises from I···N halogen bonds which give rise to one-dimensional supramolecular chains of varying topology depending on the position of the nitrogen atom in the n-pyridinealdazine isomer. The energies calculated for the I···N contacts are relatively small, varying from -5.4 to -6.3 kcal/mol, with the maximum being in the crystal of the 2 n = 3 isomer. Notable in the molecular packing are C-I···π(pyridine) and C–F···π(arene) interactions in the crystals with the 3- and 4-pyridinealdazine coformers, respectively. The cocrystal formed by 2-pyridinealdazine exhibited fluorescence emission. |
| first_indexed | 2025-11-14T21:19:37Z |
| format | Article |
| id | sunway-2125 |
| institution | Sunway University |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:19:37Z |
| publishDate | 2022 |
| publisher | Royal Society of Chemistry |
| recordtype | eprints |
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| spelling | sunway-21252022-11-14T01:43:27Z http://eprints.sunway.edu.my/2125/ I···N Halogen bonding in 1:1 co-crystals formed between 1,4-diiodotetrafluorobenzene and the isomeric n-pyridinealdazines (n = 2, 3 and 4): Assessment of supramolecular association and influence upon solid-state photoluminescence properties Yeo, Chien Ing * Tan, Yee Seng * Kwong, Huey Chong* Lee, Vannajan Sanghiran Tiekink, Edward R. T. * QD Chemistry 1:1 Co-crystals formed between 1,4-diiodotetrafluorobenzene and each of the three isomeric npyridinealdazines (n = 2, 3 and 4) have been characterised by X-ray crystallography, a variety of spectroscopic methods, viz. IR, Raman, NMR: solution- and solid-state (13C CP MAS and 13C HPDEC MAS) and fluorescence as well as by computational chemistry techniques. The primary connection between the respective coformers arises from I···N halogen bonds which give rise to one-dimensional supramolecular chains of varying topology depending on the position of the nitrogen atom in the n-pyridinealdazine isomer. The energies calculated for the I···N contacts are relatively small, varying from -5.4 to -6.3 kcal/mol, with the maximum being in the crystal of the 2 n = 3 isomer. Notable in the molecular packing are C-I···π(pyridine) and C–F···π(arene) interactions in the crystals with the 3- and 4-pyridinealdazine coformers, respectively. The cocrystal formed by 2-pyridinealdazine exhibited fluorescence emission. Royal Society of Chemistry 2022 Article PeerReviewed text en cc_by_nc http://eprints.sunway.edu.my/2125/1/crystengcomm%202022%2024%207579.pdf Yeo, Chien Ing * and Tan, Yee Seng * and Kwong, Huey Chong* and Lee, Vannajan Sanghiran and Tiekink, Edward R. T. * (2022) I···N Halogen bonding in 1:1 co-crystals formed between 1,4-diiodotetrafluorobenzene and the isomeric n-pyridinealdazines (n = 2, 3 and 4): Assessment of supramolecular association and influence upon solid-state photoluminescence properties. CrystEngComm, 24 (43). pp. 7579-7591. ISSN 1466-8033 https://pubs.rsc.org/en/content/articlelanding/2022/ce/d2ce01165d 10.1039/D2CE01165D |
| spellingShingle | QD Chemistry Yeo, Chien Ing * Tan, Yee Seng * Kwong, Huey Chong* Lee, Vannajan Sanghiran Tiekink, Edward R. T. * I···N Halogen bonding in 1:1 co-crystals formed between 1,4-diiodotetrafluorobenzene and the isomeric n-pyridinealdazines (n = 2, 3 and 4): Assessment of supramolecular association and influence upon solid-state photoluminescence properties |
| title | I···N Halogen bonding in 1:1 co-crystals formed between 1,4-diiodotetrafluorobenzene and the isomeric n-pyridinealdazines (n = 2, 3 and 4): Assessment of supramolecular association and influence upon solid-state photoluminescence properties |
| title_full | I···N Halogen bonding in 1:1 co-crystals formed between 1,4-diiodotetrafluorobenzene and the isomeric n-pyridinealdazines (n = 2, 3 and 4): Assessment of supramolecular association and influence upon solid-state photoluminescence properties |
| title_fullStr | I···N Halogen bonding in 1:1 co-crystals formed between 1,4-diiodotetrafluorobenzene and the isomeric n-pyridinealdazines (n = 2, 3 and 4): Assessment of supramolecular association and influence upon solid-state photoluminescence properties |
| title_full_unstemmed | I···N Halogen bonding in 1:1 co-crystals formed between 1,4-diiodotetrafluorobenzene and the isomeric n-pyridinealdazines (n = 2, 3 and 4): Assessment of supramolecular association and influence upon solid-state photoluminescence properties |
| title_short | I···N Halogen bonding in 1:1 co-crystals formed between 1,4-diiodotetrafluorobenzene and the isomeric n-pyridinealdazines (n = 2, 3 and 4): Assessment of supramolecular association and influence upon solid-state photoluminescence properties |
| title_sort | i···n halogen bonding in 1:1 co-crystals formed between 1,4-diiodotetrafluorobenzene and the isomeric n-pyridinealdazines (n = 2, 3 and 4): assessment of supramolecular association and influence upon solid-state photoluminescence properties |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/2125/ http://eprints.sunway.edu.my/2125/ http://eprints.sunway.edu.my/2125/ http://eprints.sunway.edu.my/2125/1/crystengcomm%202022%2024%207579.pdf |