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 * 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

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Abstract

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.

Item Type: Article
Subjects: Q Science > QD Chemistry
Divisions: Others > Non Sunway Academics
Sunway University > School of Medical and Life Sciences [formerly School of Healthcare and Medical Sciences until 2020] > Sunway Biofunctional Molecules Discovery Centre [formerly Research Centre for Crystalline Materials until 2023]
Depositing User: Ms Yong Yee Chan
Related URLs:
Date Deposited: 14 Nov 2022 01:43
Last Modified: 14 Nov 2022 01:43
URI: http://eprints.sunway.edu.my/id/eprint/2125

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