Interactive Twin Intramolecular Hydrogen Bonds Enable Bright, S‐Blue Emissive, Environment‐Insensitive Single‐Benzene Fluorophores

Abstract

Small‐molecule dyes that emit blue fluorescence, particularly those that emit in the S‐blue region, are limited in number. Functionalization of benzene with electron‐donating and ‐accepting groups generates single‐benzene fluorophores (SBFs) with tunable emission properties. By exploring the unprecedented, interactive twin intramolecular H‐bonds, a novel type of SBFs that exhibits several notable features for bioimaging applications is developed. Specifically, aniline derivatives bearing two carbonyl/carboxyl groups at ortho‐positions have interactive H‐bonds, which lead to conformational restriction, suppressed solvation, and increased HOMO‐LUMO energy gaps from those of the conventional SBFs that have non‐interactive H‐bonds. The interactive H‐bonds are manifested by notable photophysical properties among the new SBFs, such as S‐blue emissive, bright, photo‐ and chemo‐stable, solid‐state‐emissive, and environment (pH, polarity, and viscosity)‐insensitive. The use of the highly faceted dye system to develop a reliable fluorescent probe, organelle‐staining dyes, and a fluorescence‐resonance‐energy‐transfer probe for hydrogen sulfide demonstrates its potential in bioimaging applications.

Does the active hydrogen atom in the hydantoin anion affect the physical properties, CO2 capture and conversion of ionic liquids?

“…When CO 2 is absorbed, the original chain-like intermolecular hydrogen bonds are converted into cyclic quasi-intramolecular hydrogen bonds, resulting in a decrease in η . 31–33 As the original N–H and CO groups of [Hy] − are involved in the formation of the cyclic hydrogen bonds of [Hy–CO 2 ] − , their infrared absorption intensity is weakened and the chemical shift is shifted to higher fields.…”

A General Strategy Toward pH‐Resistant Phenolic Fluorophores for High‐Fidelity Sensing and Bioimaging Applications

“…Remarkably, Pyr _ Mor in pH 7.4 universal buffer displayed little change in its fluorescence intensity when irradiated with 365 nm UV light for 30 min, whereas that of Pyr decreased dramatically (Figure S16). The reason for the enhanced photostability is not certain, but we suspect that introducing the H‐bonding acceptor may reduce solvent‐mediated photodegradation processes involving the free hydroxyl group [20,4d] …”

Monophenyl luminescent material with dual-state emission and pH sensitivity for cell imaging

“…Small molecule fluorescent probes are highly valued for their ability to easily penetrate cellular membranes of living organisms, allowing for cell imaging without requiring complex preparation techniques. 28 However, fluorescent probes with a single benzene ring structure exhibit low luminescence efficiency, poor colour modulation of luminescence, and require excitation light at energy levels 29 that may be harmful to cells and tissues. There is an urgent need to improve both the brightness and the efficiency of the luminescence in materials that are based on monobenzene rings for bio-imaging purposes.…”