20205-30-5

Upstream product

• 100-63-0 phenylhydrazine 
• 563-80-4 3-methyl-butan-2-one 
• 59-88-1 phenylhydrazine hydrochloride 
• 1640-39-7 2,3,3-trimethylindoleniune 
• 629-27-6 1-Iodooctane 
• 542-69-8 1-iodo-butane 

Downstream Products

• 1196490-88-6 C₂₃H₂₉ClNO⁽¹⁺⁾*I^(1-) 
• 132752-00-2 1-butyl-2-((1E,3E)-3-(1-butyl-3,3-dimethylindolin-2-ylidene)prop-1-enyl)-3,3-dimethyl-3H-indolium iodide 
• 1269802-72-3 2-[2-chloro-3-[2-(1,3-dihydro-1-butyl-3,3-dimethyl-2H-indolidine)ethyl-1-cyclohexyl]ethyl-5-(4-diethylamino)benzene]-1-butyl-3,3-dimethylindoline iodide 
• 1047661-13-1 C₂₆H₂₄N₄ 

Relevant academic research and scientific papers

Two different donor subunits substituted unsymmetrical squaraines for solution-processed small molecule organic solar cells

Two unsymmetrical squaraines (USQs) with different donor (D) subunits as photovoltaic materials, namely USQ-11 and USQ-12, were designed and synthesized to investigate the effect of different D subunits on the optoelectronic properties of USQs for the first time. The two USQs compounds were characterized for optical, electrochemical, quantum chemical and optoelectronic properties. By changing the two different D subunits attached to the squaric acid core from 2,3,3-trimethylindolenine to 2-methylbenzothiazole, the HOMO energy levels could be tuned with a stepping of 0.07 eV, and quite different solid state aggregations (H-or J-aggregation) were observed in the thin film by UV-Vis absorption spectra, which were attributed to their distinct steric effects and dipole moments. Solution-processed bulk-heterojunction small molecule organic solar cells fabricated with the USQ-11/PC71BM (1:5, wt%) exhibited extremely higher PCE (4.27%) than that of the USQ-12/PC71BM (2.78%). The much enhanced PCE should be attributed to the simultaneously improved Voc, Jsc and FF.

Spectroscopic study of a novel bis(heptamethine cyanine) dye and its interaction with human serum albumin

A newly synthesized near-infrared (NIR) bis(heptamethine cyanine) dye 7 was evaluated for its utility as a non-covalent label for proteins. This dye forms inter- and intramolecular H-aggregates in polar solvents, even at very low concentrations. The intra

Synthesis of asymmetric monomethine cyanine dyes with red-shifted optical properties

Six novel asymmetrical monomethine cyanine dyes were synthesized via the condensation reaction of 1-butyl-2-(methylthio)benzo[c,d]indol-1-ium iodide and various 1,5-substituted indolenine salts under basic conditions. The dyes were characterized using UV-vis spectroscopy, fluorescence, 1H NMR, 13C NMR, and mass spectrometry; furthermore, the purity of these compounds was observed using LC/ELSD/MS.

“Turn on” fluorescence response of monomethine cyanines caused by noncovalent binding to ct-DNA

Monomethine cyanines have been extensively studied for their use as probes for nucleic acids among other biological systems. Four monomethine cyanine dyes were synthesized with various heterocyclic moieties including quinoline, benzoxazole, benzothiazole, and 3,3-dimethylindolenine adjoining benz[c,d]indol-1-ium, which was found to directly influence their optical and energy profiles. The dyes were characterized by 1H and 13C NMR and HRMS. In this study the twisted conformation unique to monomethine cyanines was exploited in DNA binding studies where the benzoxazole containing sensor displayed up to 700-fold increase in fluorescence when bound to the DNA compared to the unbound form.

Fluorescence properties of indolenine semi-squarylium dyes

3-Butoxy-4-(1-butyl-3,3-dimethyl-3H-indol-2-ylidenemethyl)-3-cyclobut-1, 2-dione exhibited the most intense florescence at fluorescence maxima 536 and 563 nm with fluorescence quantum yield 0.21 among any indolenine semi-squarylium dyes in the crystalline form due to the isolated dimer-type molecular packing and its suitable melting point. This compound showed aggregation-induced emission enhancement.

Symmetrical and asymmetrical cyanine dyes. Synthesis, spectral properties, and bsa association study

New cyanines were prepared by an efficient and practical route with satisfactory overall yield from low-cost starting materials. The photophysical behavior of the cyanines was investigated using UV-vis and steady-state fluorescence in solution, as well as

Acridinium-conjugated aromatic heterocycles as highly potent FtsZ inhibitors: Design, synthesis, and biological evaluation

The epidemic of multidrug resistance (MDR) is a serious threat to public health, and new classes of antibiotics with novel mechanisms of action are in critical need. We rationally designed and efficiently synthesized three series of new chemical entities with potential antibacterial activity targeting filamenting temperature-sensitive mutant Z (FtsZ). Evaluation of these compounds against a panel of Gram-positive bacteria including MDR and vancomycin-resistant Enterococcus?strains indicated that most compounds showed enhanced antibacterial efficacy, comparable or even superior to the reference drugs. The newly synthesized compounds proved to be substrates of the Escherichia coli efflux pump AcrB, thus affecting the activity. Their structure–activity relationships?were summarized in detail. The most potent compound 10f quickly eliminated bacteria in a bactericidal mode, with low susceptibility to induce bacterial resistance. Further mechanistic studies with the BsFtsZ protein revealed that 10f functioned as an effective FtsZ inhibitor through altering the dynamics of FtsZ self-polymerization via a stimulatory mechanism, which leads to inhibition of cell division and cell death. Besides, 10f not only displayed no obvious cytotoxicity to mammalian cells but also had a high efficacy in a murine model of bacteremia in vivo. Regarded as a whole, our findings highlight 10f as a promising new FtsZ-targeting bactericidal agent.

NOVEL SQUARYLIUM COMPOUNDS, AND COMPOSITIONS COMPRISING SAME

The present disclosure is disclosed herein. The present invention relates to a novel squarylium compound and a near infrared absorbing resin composition containing the squarylium compound.

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.

N-alkylated linear heptamethine polyenes as potent non-azole leads against Candida albicans fungal infections

In this study, eighteen heptamethine dyes were synthesised and their antifungal activities were evaluated against three clinically relevant yeast species. The eighteen dyes were placed within classes based on their core subunit i.e. 2,3,3-trimethylindolenine (5a-f), 1,1,2-trimethyl-1H-benzo[e]indole (6a-f), or 2-methylbenzothiazole (7a-f). The results presented herein imply that the three families of cyanine dyes, in particular compounds 5a-f, show high potential as selective scaffolds to treat C. albicans infections. This opens up the opportunity for further optimisation and investigation of this class compounds for potential antifungal treatment.