93397-90-1

Upstream product

• 575-38-2 1,7-Dihydroxynaphthalene 
• 25953-06-4 4-nitroso-3-hydroxy-N,N-diethylaniline hydrochloride 
• 91-68-9 3-diethylaminophenol 
• 6358-20-9 5-diethylamino-2-nitrosophenol 

Downstream Products

• 99645-27-9 9-diethylamino-3-(p-decyloxybenzoyloxy)benzophenoxazin-5-one 
• 1408335-59-0 C₆₃H₉₆N₂O₆ 

Relevant academic research and scientific papers

Substituted 9-Diethylaminobenzo[ a]phenoxazin-5-ones (Nile Red Analogues): Synthesis and Photophysical Properties

Nile Red is a benzo[a]phenoxazone dye containing a diethylamino substituent at the 9-position. In recent years, it has become a popular histological stain for cellular membranes and lipid droplets due to its unrivaled fluorescent properties in lipophilic environments. This makes it an attractive lead for chemical decoration to tweak its attributes and optimize it for more specialized microscopy techniques, e.g., fluorescence lifetime imaging or two-photon excited fluorescence microscopy, to which Nile Red has never been optimized. Herein, we present synthesis approaches to a series of monosubstituted Nile Red derivatives (9-diethylbenzo[a]phenoxazin-5-ones) starting from 1-naphthols or 1,3-naphthalenediols. The solvatochromic responsiveness of these fluorophores is reported with focus on how the substituents affect the absorption and emission spectra, luminosity, fluorescence lifetimes, and two-photon absorptivity. Several of the analogues emerge as strong candidates for reporting the polarity of their local environment. Specifically, the one- and two-photon excited fluorescence of Nile Red turns out to be very responsive to substitution, and the spectroscopic features can be finely tuned by judiciously introducing substituents of distinct electronic character at specific positions. This new toolkit of 9-diethylbenzo[a]phenoxazine-5-ones constitutes a step toward the next generation of optical molecular probes for advancing the understanding of lipid structures and cellular processes.

Exploring the dark: detecting long-lived Nile Red3ILCT states in Ru(ii) polypyridyl photosensitisers

Two novel Ru(ii) photosensitisers sporting ethynyl-Nile Red chromophores are shown to absorb strongly in the visible region, and to have two distinct but weakly emissive states (1ILCT* and3MLCT*). In addition a long-lived, lower ener

Structural modifications of nile red carbon monoxide fluorescent probe: Sensing mechanism and applications

Carbon monoxide (CO) is a cell-signaling molecule (gasotransmitter) produced endogenously by oxidative catabolism of heme, and the understanding of its spatial and temporal sensing at the cellular level is still an open challenge. Synthesis, optical properties, and study of the sensing mechanism of Nile red Pd-based CO chemosensors, structurally modified by core and bridge substituents, in methanol and aqueous solutions are reported in this work. The sensing fluorescence "off-on" response of palladacycle-based sensors possessing low-background fluorescence arises from their reaction with CO to release the corresponding highly fluorescent Nile red derivatives in the final step. Our mechanistic study showed that electron-withdrawing and electron-donating core substituents affect the rate-determining step of the reaction. More importantly, the substituents were found to have a substantial effect on the Nile red sensor fluorescence quantum yields, hereby defining the sensing detection limit. The highest overall fluorescence and sensing rate enhancements were found for a 2-hydroxy palladacycle derivative, which was used in subsequent biological studies on mouse hepatoma cells as it easily crosses the cell membrane and qualitatively traces the localization of CO within the intracellular compartment with the linear quantitative response to increasing CO concentrations.

NILE RED DERIVATIVES FOR IMPROVED RATIOMETRIC IMAGING FOR NERVE-SPECIFIC CONTRAST

Provided herein are novel Nile Red derivatives with varied electron donating and withdrawing groups to try to influence tissue-specific accumulation and generate a truly adipose specific fluorophore of Formula (I).

Polymerizable liquid crystal composition, polarized light-emitting coating material, novel naphtholactam derivative novel coumarin derivative, novel nile red derivative, and novel anthracene derivative

Provided are a polymerizable liquid crystal composition, a coating material, a medium, and a polarizing device each produced using a polymerizable liquid crystal compound and a colorant and each capable of producing polarized light suitable for polarizing devices, and also a novel naphtholactam derivative, a novel coumarin derivative, a novel Nile Red derivative, and a novel anthracene derivative each suitable for use as the colorant. Specifically provided are a polymerizable liquid crystal composition containing (A) at least one liquid crystal compound having a polymerizable functional group, (B) at least one colorant, and (C) a polymerization initiator, and a novel naphtholactam derivative of formula (IV′), a novel coumarin derivative of formula (VI′), a novel Nile Red derivative of formula (VII′), and a novel anthracene derivative of formula (VIII′) each suitable for use as the colorant (B).

Photoconductive Nile red cyclopalladated metallomesogens

The synthesis and the electrochemical, photophysical and photoconductive properties of two new cyclometallated metallomesogens are described. These two complexes were respectively obtained by covalent metallation of Nile red, or a polyalkylated Nile red derivative, to a palladium(ii) ion and by using a polyalkylated Schiff base as an ancillary ligand to complete the coordination sphere of the metal centre. The introduction of long alkyl chains on either one or both ligands leads to disk-shaped metallomesogens with ordered room temperature columnar organisation induced, in both cases, by the formation of dimeric pairs. As shown by powder X-Ray diffraction studies, both complexes exhibit a columnar rectangular mesophase over a wide temperature range. These complexes show a redox solution behaviour characterised by one reversible single-electron reduction and two consecutive reversible oxidation waves, which give them an electrochemical amphoteric character. Energy levels and distributions of frontier orbitals have been estimated. Photoconductivity of the mesophase at room temperature has been observed from UV-Vis to near IR wavelength. The high thermal, electrochemical and mesophase stabilities of the studied Nile red complexes confirm that cyclometallated Pd(ii) complexes form a new class of photoconductors with features suitable for molecular semiconductor applications. The Royal Society of Chemistry 2012.

Fluorescent compounds for monitoring protein-lipid binding

The invention refers to compounds according to formula I wherein R1 is independently in position 2', 3', or both of the A ring of the compound and is hydroxyl, linear or branched -O-alkyl with 1-12, preferably 3-8, more preferably 4 carbon atoms, -O-carboxylic acid with 1-12, preferably 3-8, more preferably 4 carbon atoms, -O-aromatic compound, linear or branched -O-(CH2)m-CH(NH2)-COOH with m = 1-6, preferably m= 2-4, or any combination thereof, R2 and R3 independently are F, Cl, Br, I, H, CN, -CH=CH-alkyl, -C≡C-alkyl, or an aromatic compound, X is O or S, R4 is in position 8', 10', or 11' of the D ring of the compound and is H or (CH2)n-CH3 with n = 0-6, COOH, CN, or halogen R5 and R6 independently are ethyl-, methyl-, H, or -(CH2)3 connected to position 8 or 10 of the D ring of the fluorescent dye, except compounds according to formula I wherein R1 is 2' or 3' - hydroxyl or 2' -O-(CH2)5-COOH, R2, R3, and R4 are H, X is O, and R5 and R6 are ethyl. The invention further refers to the use of the compounds according to formula I as environmentally sensitive fluorescent dyes. They particularly lend themselves to measure the binding of ligands to lipid binding sites of proteins. They can also be used in an assay for performing this measurement.