54136-23-1

Upstream product

• 563-80-4 3-methyl-butan-2-one 
• 371-14-2 4-fluorophenylhydrazine 
• 371-40-4 4-fluoroaniline 
• 823-85-8 4-fluorophenyhydrazine hydrochloride 

Downstream Products

• 1261138-49-1 C₂₁H₂₄FN₂⁽¹⁺⁾*I^(1-) 
• 1261138-47-9 C₂₀H₂₁FN₂ 

Relevant academic research and scientific papers

Near-Infrared Heptamethine Cyanine Dyes for Nanoparticle-Based Photoacoustic Imaging and Photothermal Therapy

We have synthesized and characterized a library of near-infrared (NIR) heptamethine cyanine dyes for biomedical application as photoacoustic imaging and photothermal agents. These hydrophobic dyes were incorporated into a polymer-based nanoparticle system to provide aqueous solubility and protection of the photophysical properties of each dye scaffold. Among those heptamethine cyanine dyes analyzed, 13 compounds within the nontoxic polymeric nanoparticles have been selected to exemplify structural relationships in terms of photostability, photoacoustic imaging, and photothermal behavior within the NIR (～650-850 nm) spectral region. The most contributing structural features observed in our dye design include hydrophobicity, rotatable bonds, heavy atom effects, and stability of the central cyclohexene ring within the dye core. The NIR agents developed within this project serve to elicit a structure-function relationship with emphasis on their photoacoustic and photothermal characteristics aiming at producing customizable NIR photoacoustic and photothermal tools for clinical use.

Synthesis and Characterization of Novel Pyrazole Derivatives from 4-Florophenylhydrazine and Study Their Cytotoxicity as Anti-Cancer Agent

Series of new pyrazole derivatives have been successfully synthesized, their purity confirmed by thin-layer chromatography and the chemical structures identified by some spectroscopic techniques like 1H-NMR, APT 13C-NMR and FT-IR. Two synthetic precursors

Ultrabright and Serum-Stable Squaraine Dyes

Highly stable symmetric and asymmetric squaraine fluorophores have been synthesized featuring an internal salt bridge between a quaternary ammonium cation and the central oxycyclobutenolate ring of the chromophore. Some of our newly synthesized symmetric and asymmetric compounds display increased molar absorptivity, quantum yield in serum, and thermal/photochemical stability over previously reported squaraine-based dyes. Consequently, both classes show great promise in resurfacing the normal environment-labile squaraine dyes as novel imaging agents and scaffolds for fluorescence sensing. Furthermore, incorporating a covalent attachment point away from the conjugated system allows for biological tagging applications without disturbing the optimum optical characteristics of the newly designed fluorophore.

Effects of Substituents on Metastable-State Photoacids: Design, Synthesis, and Evaluation of their Photochemical Properties

Recently, metastable-state photoacids have been widely used to control proton transfer in numerous chemical and biological processes as well as applications with visible light. Generally, substituents have a great influence on the photochemical properties of molecules, which will further affect their applications. Yet, the effects of substituents on metastable-state photoacids have not been studied systematically. In this work, 16 metastable-state photoacid derivatives were designed and synthesized on the basis of substituents having a large range of σ–π electron–donor–acceptor capabilities. The effects of substituents on the color display [or maximum absorption band(s)], solubility, pKa values, dark/photoacidity, photosensitivity, and relaxation kinetic(s) were investigated in detail. This study will be helpful for the targeted design and synthesis of promising photoacids and the application of their photocontrolled proton-release processes in functional materials/devices.

Second Generation G-Quadruplex Stabilizing Trimethine Cyanines

G-Quadruplex DNA has been recognized as a highly appealing target for the development of new selective chemotherapeutics, which could result in markedly reduced toxicity toward normal cells. In particular, the cyanine dyes that bind selectively to G-quadruplex structures without targeting duplex DNA have attracted attention due to their high amenability to structural modifications that allows fine-tuning of their biomolecular interactions. We have previously reported pentamethine and symmetric trimethine cyanines designed to effectively bind G-quadruplexes through end stacking interactions. Herein, we are reporting a second generation of drug candidates, the asymmetric trimethine cyanines. These have been synthesized and evaluated for their quadruplex binding properties. Incorporating a benz[c,d]indolenine heterocyclic unit increased overall quadruplex binding, and elongating the alkyl length increases the quadruplex-to-duplex binding specificity.

YELLOW METHINE DYES

The present invention relates to novel methine dyes, methods for the preparation thereof and use thereof for dyeing plastics, especially polyamides, so as to obtain yellow colorings with improved light fastness and improved thermostability.

Croconaines as molecular materials for organic electronics: Synthesis, solid state structure and use in transistor devices

A series of indolenine-based croconaines has been synthesized and their molecular structure has been investigated together with their solid state organization. Ambipolar semiconducting properties have been demonstrated in thin-film transistors, suggesting croconaines as a new class of molecular materials for organic electronics.

Near-Infrared Illumination of Native Tissues for Image-Guided Surgery

Our initial efforts to prepare tissue-specific near-infrared (NIR) fluorescent compounds generated successful correlation between physicochemical properties and global uptake in major organs after systemic circulation and biodistribution. Herein, we focus on the effects on biodistribution based on modulating electronic influencing moieties from donating to withdrawing moieties at both the heterocyclic site and through meso-substitution of pentamethine cyanine fluorophores. These selected modifications harnessed innate biodistribution pathways through the structure-inherent targeting, resulting in effective imaging of the adrenal glands, pituitary gland, lymph nodes, pancreas, and thyroid and salivary glands. These native-tissue contrast agents will arm surgeons with a powerful and versatile arsenal for intraoperative NIR imaging in real time.

OPTICAL FLUORESCENT IMAGING USING CYANINE DYES

no abstract published

FLUORINATED CYANINE COMPOUND AND NEAR-INFRARED CUT FILTER COMPRISING THE COMPOUND

PROBLEM TO BE SOLVED: To provide a fluorinated cyanine compound that is a novel near-infrared absorbing dye having excellent heat resistance, and a thermosetting resin composition prepared with the compound, and a near-infrared cut filter for imaging elements such as CCD and CMOS, prepared therewith and having excellent heat resistance. SOLUTION: The present invention provides a fluorinated cyanine compound represented by formula (1) (R1 independently represent a substituted/unsubstituted C1-C5 alkyl group or a substituted/unsubstituted C1-C5 alkoxyalkyl group; D is a C7 methine chain substituted/unsubstituted by Cl, an acyloxy group and the like or a C10 methine chain including a cyclohexene ring with the substituent; X- is tris(trifluoromethanesulfonyl)methide anion). SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT