Naphthalenediimide derivates are a class of π-conjugated molecules largely investigated in the literature and used as building blocks for metal-organic frameworks or coformers for hydrogen-bond-based cocrystals. However, their tendency to establish halogen-bond interactions remains unexplored. By using a crystalline engineering approach, we report here four new cocrystals with N,N′-di(4-pyrydyl)-naphthalene-1,4,5,8-tetracarboxidiimide and diiodo-substituted coformers, easily obtained via a mechanochemical protocol. Cocrystals were characterized via NMR, electron ionization mass spectrometry, thermogravimetric analysis, powder X-ray diffraction, and single-crystal X-ray diffraction. Crystallographic structures were then finely examined and correlated with energy framework calculations to understand the relative contribution of halogen-bond and π-πinteractions toward framework stabilization.

Mechanochemical Preparation of Dipyridyl-Naphthalenediimide Cocrystals: Relative Role of Halogen-Bond and π-πInteractions / Mazzeo, P. P.; Pioli, M.; Montisci, F.; Bacchi, A.; Pelagatti, P.. - In: CRYSTAL GROWTH & DESIGN. - ISSN 1528-7483. - 21:10(2021), pp. 5687-5696. [10.1021/acs.cgd.1c00531]

Mechanochemical Preparation of Dipyridyl-Naphthalenediimide Cocrystals: Relative Role of Halogen-Bond and π-πInteractions

Mazzeo P. P.;Pioli M.;Montisci F.;Bacchi A.
;
Pelagatti P.
2021

Abstract

Naphthalenediimide derivates are a class of π-conjugated molecules largely investigated in the literature and used as building blocks for metal-organic frameworks or coformers for hydrogen-bond-based cocrystals. However, their tendency to establish halogen-bond interactions remains unexplored. By using a crystalline engineering approach, we report here four new cocrystals with N,N′-di(4-pyrydyl)-naphthalene-1,4,5,8-tetracarboxidiimide and diiodo-substituted coformers, easily obtained via a mechanochemical protocol. Cocrystals were characterized via NMR, electron ionization mass spectrometry, thermogravimetric analysis, powder X-ray diffraction, and single-crystal X-ray diffraction. Crystallographic structures were then finely examined and correlated with energy framework calculations to understand the relative contribution of halogen-bond and π-πinteractions toward framework stabilization.
Mechanochemical Preparation of Dipyridyl-Naphthalenediimide Cocrystals: Relative Role of Halogen-Bond and π-πInteractions / Mazzeo, P. P.; Pioli, M.; Montisci, F.; Bacchi, A.; Pelagatti, P.. - In: CRYSTAL GROWTH & DESIGN. - ISSN 1528-7483. - 21:10(2021), pp. 5687-5696. [10.1021/acs.cgd.1c00531]
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11381/2898537
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