The modulation effect of electron-rich solvents on the supramolecular networks and photochromic properties of naphthalene diimide molecules

Four naphthalene diimide-based organic molecules comprising donor-acceptor units, 3-DPNDI (1), [3-DPNDI]center dot 2DMF (2), [3-DPNDI]center dot 2NMP (3) and [3-DPNDI]center dot 4DMSO (4) (3-DPNDI = N,N '-di-(3-pyridyl)-1,4,5,8-naphthalene diimide, DMF = dimethyl formamide, NMP = N-methyl-2-pyrrolidone, DMSO = dimethyl sulfoxide), have been synthesized, which exhibit different supramolecular networks through lone pair-pi interactions and discriminative photoinduced electron transfer (ET) accompanying photochromic properties. The combination of different electron-rich solvents with electron-deficient component 3-DPNDI causes the distinct interfacial contacts of electron donors/acceptors, which should be responsible for the different photoresponsive behaviors of 2-4. More importantly, the introduction of DMF and NMP into 3-DPNDI crystal lattices leads to a positive effect on the photoresponsive rate and coloration contrast, while DMSO gives rise to a negative influence on the photochromic properties. This present study illustrates the influence of electron-rich solvents on the resultant supramolecular networks and photochromic behaviors with tunable photoresponsive properties.

Automated summary

Four naphthalene diimide-based organic molecules with different supramolecular networks and photoinduced electron transfer properties have been synthesized, showing distinct photoresponsive behaviors influenced by the introduction of electron-rich solvents. The study illustrates the impact of electron-rich solvents on resultant supramolecular networks and tunable photoresponsive properties.