Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science

Synthesis and Fluorescence Properties of New Enaminenaphthalimides

C. John McAdam, Joy L. Morgan, R. Eva Murray , Brian H. Robinson and Jim Simpson

Australian Journal of Chemistry 57(6) 525 - 530
Published: 02 June 2004


The first 4-enamine-N-methyl-1,8-naphthalimides (amine = piperidine, pyrrolidine, morpholine, Prn2NH, Pri2NH) are reported. The X-ray crystal structure of the piperidine derivative confirmed the E-stereochemistry and showed strong Π–Π stacking in the unit cell. The enamines are strongly fluorescent and quantum yields do not vary with the pKb of the amine. The solvent dependence of λ abs and λ flu is consistent with significant charge separation in the excited state.

© CSIRO 2004

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