The halogen-bond interaction should lead to the formation of 1D chains supported by halogen-bond intermolecular interactions, where the pyridine nitrogen atoms act as halogen-bond acceptors, while the iodine atoms play the role of the halogen-bond donors.
To explore the ability of 1 as an XB acceptor in cocrystals, we performed a series of cocrystallization experiments between 1 and several diiodo-substituted organic molecules, such as 1,4-diiodobenzene ( DIB), 1,4-diiodotetrafluorobenzene ( DITFB), 4,4′-diiodobiphenylene ( DIBPH), and molecular iodine ( I 2), as depicted in Scheme 1. (28) Although pyridine-based systems have been extensively used for halogen-bond (XB)-based cocrystals, (29) to the best of our knowledge 1 has never been embedded in a cocrystal matrix through a halogen bond connecting the pyridine moieties with XB donors. (19) NDIs have also been largely investigated as coformers for hydrogen-bond (HB)-based cocrystals. (27) Exploiting their affinity with aromatic guest molecules that ultimately influence their emission profile, it is possible to reveal the guest uptake even at very low concentrations. (11−15) The robustness of the aromatic core has pushed forward the use of NDIs as rigid linkers for chemoresponsive luminescent metal–organic frameworks (MOFs), (16−22) metallacycles, (23−26) or supramolecular assemblies. Their electron affinity, ability to behave as charge carriers, and excellent thermal and oxidative stability make them promising candidates for organic electronic applications, photovoltaic devices, and flexible displays.
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