A 3 x 14 matrix of substituted N-aryl-1,8-naphthalimides was synthesized for the evaluation and discovery of dual fluorescence. Because of their unique photophysical properties, these dual fluorescent systems represent an exception to the widely studied TICT (Twisted Internal Charge Transfer) fluorescent dyes or tautomeric benzofluorescein class of two-color dyes. The matrix library was designed to investigate the effects of heterocycles, particularly pi-excessive and pi-deficient systems. Of the 42 compounds surveyed, five displayed well-resolved two-color emission in solvents as nonpolar as hexane. Based on the observed trends in fluorescence lambda(max) and quantum yield, a new model is proposed that predicts LW and SW emission for these systems. In addition, this model provides potential design features for the synthesis of new dual fluorescent species.
A convenient and general method was established to append tri-, hexa-, and nonadentate ligands about an aromatic or aliphatic core. This approach allows a variety of commercially available carboxylic acids to be transformed to their N-tris(hydroxymethyl)methylcarboxamides in one step. The selective activation of the acid functionality to form the polyhydroxylated dendritic cores has been achieved using the acyl transfer agent N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline (EEDQ).
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