Synthesis and Fluorescence Properties of 4-aminobenzo[f]Isoindole Derivatives

Abstract

We report a new route to benzo[f ]isoindole derivatives that possess strong fluorescence. The structure of the newly synthesised compounds was confirmed by NMR, IR and mass spectra, along with X-ray crystallographic studies. Absorption and fluorescence spectra of the new compounds were recorded. It was established that tautomerism of 4-aminobenzo[f ]isoindoles defines the properties of these compounds. Also, the influence of substituents at the N-2 position on the luminescence properties was studied; the fluorescence intensity is dependent on the water content in organic solvents, and can be used to indicate their moisture content.

Synthesis, Autoorganization and Reactivity of Amphiphilic Derivatives of 1‐Aminoisoindole in Water and Formamide

“…For product B we can observe the presence of one ABX spin system. 1 H-NMR spectrum of this compound is fully identical to the spectra described in our article [25]. Mono-Michael adduct has the characteristic ABMX spin system.…”

“…The data were integrated with SAINT, and an empirical absorption correction with SADABS was applied. [22][23][24] The structure was solved by direct methods, using SHELXS-97 and refined using the least-squares method on F 2 [25].…”

“…The conditions for this procedure were the same as in the previous reaction. Besides the same Because of the complexity of the product separation, low yields and susceptibility to products degradation, we analyzed the final fractions from flash-chromatography and studied the structure of the products by the characteristic signals in the 1 H-NMR spectra and compared them with the previously synthesized substances [16,25] (Fig. 7).…”

“…We proposed a mechanism for these reactions according to our previous studies [16,25] (Scheme 4). First, a molecule of N-phenylmaleimide reacts with 2-alkyl-1-aminoisoindole hydrobromide with the formation of the mono-Michael adduct C. There are two possible ways of interaction: (1) simple Michael addition; (2) Diels-Alder reaction (due to the Curtin-Hammet principle) with the further rearrangement.…”