Design and synthesis of fluorenone-based dyes: two-photon excited fluorescent probes for imaging of lysosomes and mitochondria in living cells

Abstract

Three fluorenone-derived two-photon fluorescent probes (TK) targeting the lysosomes (TK-Lyso) and mitochondria (TK-Mito1 and TK-Mito2) were synthesized by introducing different diphenylamine moieties into the fluorenone core. The TK dyes showed high biocompatibility and long-term retention, low cytotoxicity, large Stokes shift and good fluorescence quantum yield. The results of the present work disclose a class of organic dyes with potential wide applications as specific and efficient probes for lysosomes and mitochondria in the study of various biological processes.

Tuning the π-bridge of quadrupolar triarylborane chromophores for one- and two-photon excited fluorescence imaging of lysosomes in live cells

“…Due to its negligible fluorescence in water, they measured its TPEF properties in a dioxane-water mixture and reported a brightness of 116 GM. The fluorenone dye E does not show bright fluorescence in water ( Φ f = 0.07); thus, its TPEF properties were measured in toluene ( σ 2 Φ f = 150 GM) 97. The small size of the molecule might be the reason for its more modest two-photon brightness.…”

Synthesis of Anthraquinones by Iridium-Catalyzed [2 + 2 + 2] Cycloaddition of a 1,2-Bis(propiolyl)benzene Derivative with Alkynes

“…Fluorenones, which have structures similar to those of anthraquinones, are also a fascinating class of compounds due to their wide range of bioactivities [55][56][57][58], and photochemical [59][60][61][62] and electronic natures [63][64][65]. Fortunately, the [2 + 2 + 2] cyclization of benzene-linked ketodyne 4 with alkyne 2j in the presence of [Ir(cod)Cl] 2 (2 mol %), DPPE (4 mol %) in DCM under reflux for 24 h afforded the fluorenone 5j in a 43% yield (entry 1, Table 5).…”

Photophysics, Electrochemistry, Morphology, and Bioimaging Applications of New 1,8‐Naphthalimide Derivatives Containing Different Chromophores

“…Though a chromophore attached to the nitrogen atom has negligible or no influence on the electronic properties that are otherwise dominated by the naphthalimide core, they help to modulate the interchromophoric interactions in the solid state and, consequently, the charge‐transporting properties. Among the pool of aromatic electron‐rich chromophores, carbazoles, triphenylamines, and fluorenes are widely explored because of their easy oxidizability and their ability to transport charges via radical‐cation species. Integration of a hole‐transporting moiety with an electron‐transporting unit is beneficial to balance charge transport in the molecular layer.…”