Real time bioimaging for mitochondria by taking the aggregation process of aggregation-induced emission near-infrared dyes with wash-free staining

Abstract

Triphenylpyrrole derivatives are designed for application in wash-free real-time mitochondrial imaging, which emit NIR signals and feature AIE characteristics.

The Aggregation Regularity Effect of Multiarylpyrroles on Their Near‐Infrared Aggregation‐Enhanced Emission Property

“…[26] Our group is also devoted to designing AIEgens with long wavelength emission and ah igh quantum yield in the aggregated state based on multiarylpyrroles (MAPs) as the backbone. [27][28][29][30] Among them, AIEgens, with triphenylpyrrole as the conjugate skeleton, triphenylamine as the strong donor, 1-ethyl-3,3-dimethyl-3H-indolium as the strong acceptora nd an anchor for the biological target, weres ynthesized, andt he emission wavelength (l em )r eached 724 nm. [30] Moreover,A IEgensc an be used for real-time bioimaging of mitochondria under aw ash-free staining procedure.…”

“…[27][28][29][30] Among them, AIEgens, with triphenylpyrrole as the conjugate skeleton, triphenylamine as the strong donor, 1-ethyl-3,3-dimethyl-3H-indolium as the strong acceptora nd an anchor for the biological target, weres ynthesized, andt he emission wavelength (l em )r eached 724 nm. [30] Moreover,A IEgensc an be used for real-time bioimaging of mitochondria under aw ash-free staining procedure. Recently,( 3cyano-4,5-dimethyl-2,5-dihydrofuran-2-ylidene) propanedinitrile (FE) was introduced into MAPs as as trong acceptor,a nd a series of fused-ring groups,s uch as naphthalene, anthracene, and pyrene, werei ntroduced at the 2,5-position of the pyrrole derivatives to extend the conjugated skeleton, as shown in Scheme 1.…”

“…reported minireviews using a quinoline‐malononitrile core as a building block for diversity‐oriented synthesis of AIE luminogens (AIEgens) [26] . Our group is also devoted to designing AIEgens with long wavelength emission and a high quantum yield in the aggregated state based on multiarylpyrroles (MAPs) as the backbone [27–30] . Among them, AIEgens, with triphenylpyrrole as the conjugate skeleton, triphenylamine as the strong donor, 1‐ethyl‐3,3‐dimethyl‐3 H ‐indolium as the strong acceptor and an anchor for the biological target, were synthesized, and the emission wavelength ( λ em ) reached 724 nm [30] .…”

A diphenylamino-substituted cationic cyclometalated Ir(iii) complex: its aggregation-induced phosphorescent emission and oxygen sensing properties

“…21 Consequently, a number of AIPE-active Ir(III) compounds with different molecular structures were developed in the past few years. [22][23][24][25][26][27][28][29][30][31][32] Cyclometalated Ir(III) complexes are particularly suitable for use as oxygen-sensitive probes (OSPs) in luminescence oxygen sensing, due to their outstanding optical properties. In 1996, Marco and co-workers 33 reported the first use of an Ir(III) complex as the active species in a luminescent oxygen sensor, which attracted much attention and lots of Ir(III) complexes as OSPs have been reported successively thereafter.…”

A novel tetraphenylethylene derivative: 4-methyl-N-[3-(1,2,2-triphenylethenyl)phenyl]benzenesulfonamide with aggregation-induced emission

“…Aggregation-induced emission luminogens (AIEgens) can be dissolved and and are nonradiative in good solvents, while they start to aggregate and radiate, emitting light, when a poor solvent is added to the solution. This is different from aggregation-caused quenching (ACQ) (Ren et al, 2019). Numerous AIEgens were designed and carefully synthesized, and many radiative mechanisms were suggested for their radiation, including conformational planarization, E/Z isomerization, J-aggregate formation, twisted intramolecular charge transfer (TICT), excited-state intramolecular proton transfer (ESIPT) and restriction of intramolecular rotations (RIR).…”