A novel ﬂuorescent molecule based on 1,8-
naphthalimide: synthesis, spectral properties,
and application in cell imaging
Received: 28 June 2010 / Accepted: 14 October 2010 / Published online: 23 November 2010
Ó The Author(s) 2010. This article is published with open access at Springerlink.com
Abstract A novel naphthalimide molecule, 4-(2-methoxyethoxy)-N-butyl-1,8-
naphthalimide (MEBN), has been synthesized and characterized. The UV–visible
absorption and ﬂuorescence emission spectral properties in n-hexane, toluene,
, and CH
OH were studied. Its optical properties depend on solvent polarity.
The application of MEBN in cell imaging was investigated.
Keywords 1,8-Naphthalimide Á Fluorescence Á Synthesis Á Cell imaging
Derivatives of 1,8-naphthalimide usually exhibit strong ﬂuorescence. They have
been widely used as colorants in the polymer industry, ﬂuorescent probes for
medical and biological purposes, and as n-type materials in organic light-emitting
diodes ; they are potential anti-HIV drugs, ﬂuorescent cell markers, DNA-
cleaving agents, liquid-crystal additives, and laser dyes .
The excellent ﬂuorescent properties of commercial 1,8-naphthalimide com-
pounds depend largely on the presence of strong electron-donating groups, typically
such groups as alkoxy and alkylamine, at the C-4 position . It is known that
4-alkoxy-1,8-naphthalimides have been widely used as ﬂuorescent brightening agents.
In this paper, a novel 4-alkoxy-1,8-naphthalimide compound, 4-(2-methoxyethoxy)-
N-butyl-1,8-naphthalimide (MEBN) was prepared by a simple method. The
UV–visible absorption and ﬂuorescence emission spectral properties were studied.
Application in cell imaging was investigated.
H. Xiao (&) Á M. Chen Á G. Shi Á L. Wang Á H. Yin Á C. Mei
Department of Chemistry, Shanghai Normal University, 200234 Shanghai,
People’s Republic of China
Res Chem Intermed (2010) 36:1021–1026