Synthesis, photophysical properties and solvatochromic analysis of some naphthalene-1,8-dicarboxylic acid derivatives

Synthesis and Solvent Dependent Fluorescence of Some Piperidine-Substituted Naphthalimide Derivatives and Consequences for Water Sensing

“…Consequently, by the coupling reactions of 2-hydroxy-6-amino-1,8-naphthalimide intermediates 4 and 5 with 5-bromo-3-methyl-5H-furan-2-one 6, we accessed new potentially fluorescent derivatives 7 and 8, respectively. The reaction was car-strigolactone mimics [47]. Consequently, by the coupling reactions of 2-hydroxy-6-amino-1,8-naphthalimide intermediates 4 and 5 with 5-bromo-3-methyl-5H-furan-2-one 6, we accessed new potentially fluorescent derivatives 7 and 8, respectively.…”

“…Therefore, by the reactions of 4-chloro-1,8-naphthalic anhydride 1 with some cyclic secondary amines such as 4-methylpiperidine and 4-benzylpiperidine, respectively, 4-amino-1,8-naphthalic anhydride derivatives 2 and 3 were obtained. In the next step, the resulting 4-amino-1,8-naphthalic anhydride compounds 2 and 3 reacted with hydroxylamine hydrochloride in dioxane, under basic conditions, at reflux temperature, to give 2-hydroxy-6-amino-1,8-naphthalimide intermediates 4 and 5 , respectively [ 47 ]. These intermediates presented interesting photophysical properties that convinced us that they are useful fluorophores for the syntheses of potentially fluorescent naphthalimide-based strigolactone mimics [ 47 ].…”

“…In the next step, the resulting 4-amino-1,8-naphthalic anhydride compounds 2 and 3 reacted with hydroxylamine hydrochloride in dioxane, under basic conditions, at reflux temperature, to give 2-hydroxy-6-amino-1,8-naphthalimide intermediates 4 and 5 , respectively [ 47 ]. These intermediates presented interesting photophysical properties that convinced us that they are useful fluorophores for the syntheses of potentially fluorescent naphthalimide-based strigolactone mimics [ 47 ]. Consequently, by the coupling reactions of 2-hydroxy-6-amino-1,8-naphthalimide intermediates 4 and 5 with 5-bromo-3-methyl-5 H -furan-2-one 6 , we accessed new potentially fluorescent derivatives 7 and 8 , respectively.…”

“…The electronic absorption spectra of naphthalimide derivatives show a broad absorption band in the visible range, located at 402 nm for 7 , in dioxane ( Figure 2 a). This absorption band can be assignable to a π-π* transition due to the naphthalimide moiety [ 10 , 47 , 48 ]. A shift to longer wavelength of visible absorption band was observed as the solvent polarity increased ( Table 1 ).…”

“…The intermediate compounds, 6-amino-benzo[ de ]isochromene-1,3-diones 2 and 3 , and 2-hydroxy-6-amino-benzo[ de ]isoquinoline-1,3-diones 4 and 5 , were obtained according to the reported procedures [ 47 ]. The common intermediate, 5-bromo-3-methyl-5 H -furan-2-one 6 , was prepared in good yield by the bromination of 3-methyl-5 H -furan-2-one with N -bromosuccinimide in carbon tetrachloride by a previously described method [ 74 ].…”