Abstract
The development of fluorophores emitting in the near-infrared spectral window has gained increased attention given their suitable features for biological imaging. In this work, we have optimised a general and straightforward synthetic approach to prepare a small library of near-infrared-emitting C-bridged nitrobenzodiazoles using commercial precursors. C-bridged benzodiazoles have low molecular weight and neutral character as important features that are not common in most near-infrared dyes. We have investigated their fluorescence response in the presence of a wide array of 60 different biomolecules and identified compound 3i as a potential chemosensor to discriminate between Fe2+ and Fe3+ ions in aqueous media.
Highlights
The development of chemical structures showing enhanced fluorescence emission upon recognition of molecular analytes is an active area of research in analytical chemistry and molecular imaging [1,2,3,4,5]
Building on the recently reported SCOTfluors [41], which feature a benzodiazole core as a fluorogenic scaffold, we designed the synthesis of a small collection of C-bridged benzodiazoles using a two-step protocol with a readily accessible common precursor and commercially available ketone and amine building blocks
We report the synthesis of the first small collection of C-bridged benzodiazoles and their systematic characterization as potential fluorogenic molecules with NIR emission
Summary
The development of chemical structures showing enhanced fluorescence emission upon recognition of molecular analytes is an active area of research in analytical chemistry and molecular imaging [1,2,3,4,5] In addition to their utility as highly sensitive analytical probes for environmental (e.g., metal ion detection) or biological measurements (e.g., quantification of biomarkers in clinical samples) [6,7,8,9,10,11], they have been increasingly used to derivatise bioactive molecules (e.g., peptides, proteins, antibodies) and to prepare complex molecular. C-bridged nitrobenzodiazoles have been recently described as chemical structures with relatively small size ( < 300 Da) and neutral character [41] These properties can facilitate their application for labeling metabolites (e.g., lipids, sugars) as well as their translation to NIR bioimaging. Our results demonstrate the potential utility of the C-bridged nitrobenzodiazole scaffold for the preparation of NIR-emitting activatable probes of smaller size than conventional NIR fluorophores
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