29519-77-5

The present invention relates to dye compounds represented by Formulae I and II, which are described in the specification. The dye compounds of the present invention have markedly improved quantum yields and emit strong fluorescence compared to existing cyanine dyes. Due to these advantages, the dye compounds of the present invention can find applications in various fields, for example, as probes for various biological systems where optical imaging is required. Particularly, the dye compounds of the present invention can be used as mitotrackers capable of labeling and tracking mitochondria. Therefore, the dye compounds of the present invention can be used to quantitatively image mitochondria in live tissues and cells. Furthermore, the dye compounds of the present invention can be applied as pH probes for measuring the pH of live cells.

Efficiently organizing molecular nonlinear optical (NLO) chromophores having large first-order hyperpolarizabilities (β) into acentric microstructures for electro-optic (EO) applications represents a significant materials synthesis and processing challenge, in part due to interchromophore dipolar interactions that promote centrosymmetric organization. Here we report the computational modeling, synthesis, and characterization of a series of eight heteroaromatic organic chromophores, designed to self-organize from the vapor phase via directed hydrogen-bond networks, into acentric thin films. Introduction of α,ω-donor-acceptor hydrogen-bonding substituents along the molecular long axes tunes properties such as hyperpolarizability, volatility, thermal stability, film-forming properties, and macroscopic NLO response (χ(2)). DFT-level molecular modeling, INDO/S optical property analysis, and sum-overstates computation indicate that molecular-core fluorination and hydrogen-bond donor incorporation can increase βvec up to 40x versus that of typical fluorine-free chromophores. Furthermore, inclusion of sterically induced biphenyl conjugative decoupling between chromophore π-donor substituents and the hydrogen-bonding donor sites increases β by ～50%. Experimental thin-film second harmonic generation (SHG) spectroscopy confirms these trends in calculated responses, with χ(2) increasing 7.5x upon chromophore core fluorination and 15x with hydrogen-bonding donor substitution, thereby achieving macroscopic responses as high as 302 pm/V at ωo = 1064 nm. In addition to response trends, cluster calculations also reveal linear additivity in βvec with catenation for all benzoic acid-containing chromophores up to longitudinally aligned trimers. Linear scaling of SHG response with film thickness is observed for benzoic acid-containing chromophores up to 1.0 μm film thickness.

Disclosed are analogues of trimethine cyanine dyes which are useful for imparting fluorescent properties to target materials by covalent and non-covalent association. The compounds have the following general formula: optionally substituted by groups R2-R9 wherein groups R6, R7, R8 and R9 are attached to the rings containing X and Y or, optionally are attached to atoms of the Za and Zb ring structures and groups R1-R9 are chosen to provide desired solubility, reactivity and spectral properties to the fluorescent compounds; A is selected from O, S and NR11 where R11 is the substituted amino radical: where R′ is selected from hydrogen, a C1-4 alkyl and aryl and R″ is selected from C1-18 alkyl, aryl, heteroaryl, an acyl radical having from 2-7 carbon atoms, and a thiocarbamoyl radical; Za and Zb each represent a bond or the atoms necessary to complete one, two fused or three fused aromatic rings each ring having five or six atoms, selected from carbon atoms and, optionally, no more than two oxygen, nitrogen and sulphur atoms.

Pyrazol-1-ylphenylacetic acids of the formula STR1 wherein R1, R2 and R3 are the same or different and denote a hydrogen atom or a halogen atom, R4 denotes a hydrogen atom or an alkyl group, A B denotes a carbon-carbon single or double bond, and their salts are pharmacologically active and are useful as medicaments. Medicament compositions are produced therefrom. Their functional carboxylic acid derivatives and other new intermediates are used in their preparation.