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Updated: Feb 19, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Modular synthesis of 4-aminocarbonyl substituted 1,8-naphthalimides and application in single molecule fluorescence
K N Hearn1, T D Nalder, R P Cox
1Centre for Chemistry and Biotechnology, School of Life and Environmental Sciences, Deakin University, Waurn Ponds, 3216, Australia. t.ashton@deakin.edu.au.
Abstract:
Robust methodology to install amide, carbamate, urea and sulfonamide functionality to the 1,8-naphthalimide scaffold has been developed and exemplified. New benzamidonaphthalimide 6, synthesised using this approach, was found to be sensitive to base whereupon fluorescence emission strongly increases (>10-fold) and red-shifts (>4000 cm-1). The optical properties of deprotonated 6 allow for single molecule fluorescence detection, the first example of such behaviour from this class of fluorophore.

