26559-67-1

Upstream product

• 81-86-7 4-bromo-1,8-naphthalenedicarboxylic anhydride 
• 95-54-5 1,2-diamino-benzene 
• 7267-05-2 4-bromo-naphthalene-1,8-dicarboxylic acid 
• 2051-98-1 5-bromoacenaphthene 
• 140-29-4 phenylacetonitrile 
• 83-32-9 acenaphthene 
• 81-84-5 1,8-Naphthalic anhydride 
• 21563-29-1 4-bromo-1,8-naphthalene anhydride 

Downstream Products

• 1469991-87-4 3-(4-fluorophenylamino)-benzo[de]benzo[4,5]imidazo[2,1-a]isoquinolin-7-one 
• 1469991-89-6 3-(2,6-difluorophenylamino)-benzo[de]benzo[4,5]imidazo[2,1-a]isoquinolin-7-one 
• 1469991-91-0 3-cyclohexylamino-benzo[de]benzo[4,5]imidazo[2,1-a]isoquinolin-7-one 
• 1448254-60-1 C₂₅H₁₆N₂O₂ 
• 203114-08-3 C₂₅H₁₇N₃O 

Relevant academic research and scientific papers

Fructose recognition using new “Off-On” fluorescent chemical probes based on boronate-tagged 1,8-naphthalimide

It has recently been found that hereditary fructose intolerance (HFI) alongside the blood glucose level can be an important indicator in diabetes or some metabolic disorders. Over time, fluorescent organic molecules have grown in popularity for selective recognitions of a wide range of analytes. This work introduces new synthesized molecules based on boronate-tagged 1,8-naphthalimide with a planar structure and high fusion loops for rapid optical detection of fructose. Boronic acids which form five-membered boronate esters with diols have become increasingly popular in the synthesis of small chemical receptors. Two new water-soluble fluorescent selectophores have been successfully synthesized and their selectivity has been studied in sensing saccharides. The synthesized selectophores indicated selectivity toward fructose compared to other tested saccharides within the range of 0.16 to 50 mM at the physiological pH 7.4. The designed fluorescent probes were used to measure the percentage of fructose in fructose corn syrup. The results revealed that the (2-(((2-((7-oxo-7H-benzo[d,e]benzo[4,5]imidazo[2,1-a]isoquinolin-3-yl)amino)ethyl)amino)methyl)phenyl)boronic acid (NONB) probe was able to determine the concentration of fructose satisfactorily, suggesting that this probe can potentially be applied for quantitative detection of fructose in real samples.

FRET-based ratiometric detection of Hg2+ and biothiols using naphthalimide-rhodamine dyads

A new naphthalimide-rhodamine-based dyad 1 in CH3CN-HEPES (1:1) buffer solution exhibits fluorescence resonance energy transfer (FRET) from naphthalimide to the rhodamine moiety on addition of only Hg2+ ions and allows ratiometric absorption and fluorimetric estimation of Hg2+ ions between 50 nM (10 ppb) to 2 μM (0.4 ppm). FRET-induced fluorescence changes were recovered again by the subsequent addition of thiol amino acids via reverse FRET. The interconversion of probe 1 and 1·Hg2+via the complexation/decomplexation by the modulation of Hg2+/Cys exhibited a selective probe for biothiols in real samples.

Positional isomeric chemosensors: Fluorescent and colorimetric cyanide detection based on Si-O cleavage

Highly selective and sensitive fluorescent and colorimetric cis/trans isomers 3 were rationally designed and investigated for the fast detection and visualization of cyanide ions (TBACN and NaCN) via CN-promoted Si-O cleavage in aqueous solution and in the solid state. The CN-promoted desilylation induced significant variations of the optical signals of cis- and trans-3, which mainly depend upon the steric arrangement of the Si-O group in relation to the π-extended system.

Solid-State Fluorophore Based on π-Extended Heteroaromatic Acceptor: Polymorphism, Mechanochromic Luminescence, and Electroluminescence

A novel light-emitting material 4-(4-diphenylaminophenyl)-benzo[d,e]benzo[4,5]imidazo[2,1-a]isoquinolin-7-one (4-TPA-BBI) is synthesized and characterized. 4-TPA-BBI exhibits excellent polymorphism, mechanochromic luminescence (MCL), and electroluminescence properties. It can form three different aggregate species: yellow rod-like crystal (Y-crystal), orange needle-like crystal (O-crystal), and red solid (R-solid). It is observed that the Y-crystal can be reversibly changed to R-solid upon external stimuli, while O-crystal can be irreversibly transformed to R-solid via sublimation under a vacuum. Crystallographic and photophysical studies indicate that the Y-crystal featuring loose molecular packing demonstrates a high photoluminescence quantum yield (φPL ≈ 1) and obvious MCL property, while the compactly packed O-crystal shows a lower φPL of 0.646 with negligible MCL. A nondoped light-emitting device based on 4-TPA-BBI as an emitter exhibits bright orange emission with a peak at 588 nm, a high external quantum efficiency of 4.4%, and a maximum luminance of 22470 cd m-2

The synthesis and study of fluorescent PAMAM-based dendritic molecules

New water soluble and fluorescent PAMAM-based dendritic molecules based on the naphthalimide derivative 7H-benz[de]benzimidazo[2,1-a]isoquinoline-7-one as the fluorescent unit, have been prepared and their photophysical properties studied in aqueous solution over a wide pH range. The dendrons are all strongly fluorescent through an intramolecular charge transfer (ICT) excited state, but this can be modulated by photoinduced electron transfer (PeT) processes, which increases with higher PAMAM dendron generation.

Synthesis and fluorescence quenching mechanism of novel naphthalimide derivative by nanographene oxide

Novel naphthalimide derivative with amine functional group was prepared, and its FTIR and 1H and 13C NMR spectral characteristics were reported. The fluorescence quenching of synthesized dye by nanographene oxide was studied using absorption and fluorescence measurements. From the stern-Volmer analysis, we observed that the quenching was mainly due to the dynamic mechanism. The CV plots indicate that the quenching also went through an electron transfer process. The binding constant (K) and the number of binding sites (n) were calculated based on the fluorescence quenching data. In addition, the free energy change (ΔG) for the electron transfer process was calculated.

Naphthalene Benzimidazole Based Neutral Ir(III) Emitters for Deep Red Organic Light-Emitting Diodes

Rigid naphthalene benzimidazole (NBI) based ligands (L1 and L2) are synthesized and utilized to make deep red phosphorescent cyclometalated iridium(III) complexes ([Ir(NBI)2(PyPzCF3)] (1) and [Ir(DPANBI)2(PyPzCF3)] (2)). Complexes 1 and 2 are prepared from the reaction of L1/L2 with the aid of ancillary ligands (PyPzCF3, 2-(3-(trifluoromethyl)-1H-pyrazol-5-yl)pyridine) in a two step method. The complexes are characterized by analytical and spectroscopic methods, as well as X-ray diffraction for 1. These complexes show a strong emission in the range of 635-700 nm that extends up to the near-infrared region (800 nm). The introduction of the diphenylamino (DPA) donor group on the naphthalene unit leads to a further red-shift in the emission. The complexes exhibit radiative quantum efficiency (φPL) of 0.27-0.29 in poly(methylmethacrylate) film and relatively short phosphorescence decay lifetimes (τ = 1.1-3.5 μs). The structural, electronic, and optical properties are investigated with the support of density functional theory (DFT) and time-dependent-DFT calculations. The calculation results indicate that the lowest-lying triplet (T1) excited state of 1 has a mixed metal-to-ligand charge transfer (3MLCT) and ligand-centered (3LC) character, while 2 shows a dominant 3LC character. Deep red-emitting organic light-emitting diodes fabricated using 1 as a dopant display a maximum external quantum efficiency of 10.9% with the CIE color coordinates of (0.690, 0.294), with an emission centered at 644 and 700 nm. Similarly, the emitter 2 also shows a maximum external quantum efficiency of 6.9% with emissions at 657 and 722 nm.

Naphthalimide-based optical turn-on sensor for monosaccharide recognition using boronic acid receptor

A highly selective and sensitive fluorescent sensor for the determination of fructose is developed. The fluorescent sensor was prepared by incorporating a new naphthalimide dye with a planar structure as a selectophore and graphene oxide (GO) nanoplatelets as a quencher for rapid optical detection of fructose. The designed probe, made with the high fusion loop-containing dye, along with the GO nanoplatelets, detected fructose over the other monosaccharides very well. The proposed sensor displays a linear response range of 7 × 10-5 to 3 × 10-2 M with a low limit of detection of 23 × 10-6 M in solution at pH 7.4. This sensor shows a good selectivity towards fructose with respect to other saccharides. The proposed sensor was then applied to the determination of fructose in human plasma with satisfactory results.

NOVEL COLOR CONVERTER

Color converter comprising at least one polymer and at least one organic fluorescent dye comprising at least one structural unit of the formula (I) where the structural unit may be mono- or polysubstituted by identical or different substituents and where one or more CH groups of the six-membered ring of the benzimidazole structure shown may be replaced by nitrogen.

TWO-PHOTON FLUORESCENT PROBE USING NAPHTHALENE AS MATRIX AND PREPARATION METHOD AND USE THEREOF

The present invention provides a novel category of naphthalene-based two-photon fluorescent probes having a general formula I, wherein: X is selected from the X1, X2, X3 and X4; The mentioned two-photon fluorescent probes have a low fluorescence background in the non-tumor cells and tissues, and have a strong and specific fluorescent signal in the tumor cells and tissues. These probes have a certain level of water-solubility, while having good membrane permeability. In addition, they have a bigger effective two-photon absorption cross section. The compounds of the present invention also have a lower biotoxicity, phototoxicity and photobleaching. There is sufficient difference between the spectral range thereof and that of a biological sample.