Unique phenanthrenequinone imidazole-based fluorescent materials with aggregation-induced or two-photon emission

Abstract

In this work, we developed a single fluorophore core with different substituents that can exhibit either outstanding AIE or two-photon properties.

Zincke’s Salt-Substituted Tetraphenylethylenes for Fluorometric Turn-On Detection of Glutathione and Fluorescence Imaging of Cancer Cells

“…Fluorogens with aggregation-induced emission (AIE) characteristics have received increasing attentions in recent years. − A number of AIE fluorogens have been reported. Among them, tetraphenylethylene (TPE) and its derivatives have been extensively investigated because TPE compounds can be easily synthesized and functionalized. ,, TPE molecules with either charged or reactive moieties have been successfully utilized for constructing chemo-/biosensors. − The sensing mechanism is based on the manipulation of aggregation and deaggregation of AIE molecules, which is achieved with the specific chemical and enzyme-catalyzed reactions.…”

“…Among them, tetraphenylethylene (TPE) and its derivatives have been extensively investigated because TPE compounds can be easily synthesized and functionalized. ,, TPE molecules with either charged or reactive moieties have been successfully utilized for constructing chemo-/biosensors. − The sensing mechanism is based on the manipulation of aggregation and deaggregation of AIE molecules, which is achieved with the specific chemical and enzyme-catalyzed reactions. Moreover, TPE molecules with targeting groups have been used for cell imaging, which possesses a low signal-to-noise ratio and can be performed without washing steps. − …”

Aryl-Phenanthro[9,10-d]imidazole: A Versatile Scaffold for the Design of Optical-Based Sensors

“…Liu et al have reported phenanthro­[9,10- d ]­imidazole P19 bearing an indolium moiety (Figure a) . This compound exhibited two main absorption bands at 387 and 550 nm and strong fluorescence emission at 462–550 nm with a large two-photon excitation action cross-section between 760–860 nm, owing to the ICT process caused by the indolium moiety.…”

“…(c) Two-photon fluorescence images of the mouse liver tissues incubated with P19 (10 μM) for 1 h. (1) Mitochondrial pH 3D fluorescence images (λ exc = 800 nm, λ em = 425–475 nm); (2) mitochondrial pH 3D fluorescence images (λ exc = 800 nm, λ em = 500–550 nm); mean fluorescence intensities of the (3) blue and (4) green channels at different depths. Adapted with permission from ref . Copyright 2017 The Royal Society of Chemistry.…”

“…Liu et al described the synthesis of P38 bearing a tertiary amine group as a fluorescent sensor prone to AIE (Figure a) . Compound P38 exhibited absorption at 360 and 420 nm with emission at 402–420 nm, depending on the solvent.…”