American Chemical Society
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Synthesis of Naphthalimide Derivatives and Their Luminescence upon Complexation with Cucurbit[n]uril Hosts

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journal contribution
posted on 2023-08-23, 14:04 authored by Yong Wu, Dongdong Sun, Xie Han, Zhiyong Zhao, Feng Liang, Simin Liu
A series of naphthalimide derivatives are synthesized and their binding behavior upon complexation with cucurbit[n]urils (CB[n]s) has been investigated. With a heavy atom (bromine) on the naphthalimide core, 4-bromo-1,8-naphthalimide derivatives 14 show short room-temperature phosphorescence (RTP) lifetimes with low quantum yields. Their RTP properties are significantly enhanced in the presence of CB[8] or CB[10] both in aqueous solution and solid state owing to the efficient suppression of nonradiative decay and isolation of quenching factors by the rigid cavity of CB[n]. Without the bromine atom, 1,8-naphthalimide derivatives 5 and 6 show strong excimer emission upon complexation with CB[10] accompanied by fluorescence transition from blue to cyan. The fluorescence colors of 4-(dimethylamino)-1,8-naphthalimide derivatives 7 and 8 change from blue to white to yellow with the addition of CB[n]. This host–guest complexation strategy to modulate the luminescence of the luminophore would further broaden the application of luminescent materials.