(30,31) Here we then demonstrate that halogen-bond cocrystals derived from the combination of the poorly soluble π-donor 1 with four different iodine-containing coformers can be synthesized in high purity through a simple mechanochemical approach. It is well-known that mechanochemical synthesis is often able to overcome the problems derived from the use of insoluble reagents, and its successful application in the preparation of cocrystals includes a large number of literature reported examples.
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To overcome this problem, the synthesis of the target cocrystals was attempted by manual grinding of 1 with the corresponding halogenated coformers, in the presence of substoichiometric amounts of DMF (LAG = liquid-assisted grinding).
Owing to the low solubility of 1, cocrystallization reactions conducted in solution led to the isolation of X-ray quality single crystals of the target compounds in poor yields. 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.
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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. N, N′-di(4-pyridyl)-naphthalene-1,4,5,8-tetracarboxydiimide ( 1) belongs to the class of naphthalenediimides (NDI), rigid π-conjugated molecules characterized by an electron-poor naphthalene core ( Scheme 1) largely investigated in the past decade.
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