14238-53-0

Usage

Uses

Used in Pharmaceutical Applications:
(4E)-3-hydroxy-2-[(Z)-(1,3,3-trimethylindol-2-ylidene)methyl]-4-[(1,3,3-trimethylindol-2-yl)methylidene]cyclobut-2-en-1-one is used as a pharmaceutical compound for its unique structural features and potential therapeutic properties. Its hydroxy and methylidene groups, along with the trimethylindol-2-ylidene moiety, may contribute to its biological activity and interactions with biological targets.
Used in Chemical Research:
(4E)-3-hydroxy-2-[(Z)-(1,3,3-trimethylindol-2-ylidene)methyl]-4-[(1,3,3-trimethylindol-2-yl)methylidene]cyclobut-2-en-1-one is used as a research compound in the field of organic chemistry. Its unique structure and functional groups make it an interesting subject for studying chemical reactions, synthesis, and properties of complex organic molecules.
Used in Material Science:
(4E)-3-hydroxy-2-[(Z)-(1,3,3-trimethylindol-2-ylidene)methyl]-4-[(1,3,3-trimethylindol-2-yl)methylidene]cyclobut-2-en-1-one is used as a component in the development of new materials with specific properties. Its structural features and functional groups may contribute to the creation of materials with unique characteristics, such as optical, electronic, or mechanical properties, for various applications in material science.

InChI:InChI=1/C28H28N2O2/c1-27(2)19-11-7-9-13-21(19)29(5)23(27)15-17-25(31)18(26(17)32)16-24-28(3,4)20-12-8-10-14-22(20)30(24)6/h7-16H,1-6H3/p+1

Upstream product

• 1224096-80-3 Br^(1-)*C₁₄H₁₈NO₂⁽¹⁺⁾ 
• 2892-51-5 squaric acid 
• 5418-63-3 1,2,3,3-tetramethyl-3H-indolium iodide 
• 5231-87-8 3,4-diethoxy-3-cyclobuten-1,2-dione 
• 118-12-7 1,3,3-Trimethyl-2-methyleneindoline 
• 1640-39-7 2,3,3-trimethylindoleniune 

Relevant academic research and scientific papers

A novel fast green method for the preparation of the squaraine dye 3-oxo-4[(1,3,3-trimethyl-3H-indol-1-ium-2-yl)methylene]-2-[(1,3,3-trimethylindolin-2-ylidene)methyl]cyclobut-1-enolate, inner salt

A novel green method was developed for the preparation of a squaraine dye, on an 8-mmol scale, by microwave irradiation of two equivalents of 1,3,3-trimethyl-2-methyleneindoline with one equivalent squaric acid in the green solvent, ethyl l-lactate. The time required for this green synthesis is only 4?min. The target squaraine dye was isolated in excellent yield (81%) and with high purity.

Synthesis of squaraine dyes under mild conditions: Applications for labelling and sensing of biomolecules

We report the synthesis of squaraine dyes under mild conditions by carbodiimide activation of squaric acid or semi-squaraine dyes. Despite low yields when the reaction was carried out in solution, these conditions were successfully applied to efficient pe

Molecular structure and spectral properties of indolenine based norsquaraines versus squaraines

Novel indolenine based norsquaraine dyes, wherein the oxygen of the squaric acid bridge was substituted with a barbituric or a dicyanomethylene group, were synthesized and their molecular structure, spectral and luminescent properties were compared to those of analogous squaraine dyes. The molecular structure was investigated using X-ray analysis, NMR spectroscopy and ab initio DFT B3LYP/6-311G (d, p) simulations. The calculated populations of possible conformers and the barriers of internal rotations were found to be in good agreement with the experimental data. Norsquaraines absorb and emitt light within the same long-wavelength spectral range as the corresponding squaraines but due to intramolecular H-bonds and increased conformational rigidity they were less sensitive to solvent polarity and the presence of protein (BSA).

Solid-state fluorescence of squarylium dyes

An N-butyl indolenine squarylium dye could include toluene and p-xylene and exhibited the solid-state fluorescence in near-infrared region (F max=761 nm) in crystalline form due to inhibition of π/π-interactions between the fluorophores.

Design and Synthesis of Near-Infrared Mechanically Interlocked Molecules for Specific Targeting of Mitochondria

The entrapment of squaraine (SQ) within a molecular container to form rotaxane has been shown to improve the dye stability and the fluorescence proficiency inside the mitochondria. The macrocycle provides shelter and protects the near-infrared (NIR) SQ chromophore from nucleophilic attacks made by the exposed thiol of Cys-containing mitochondrial proteins and mitochondrial glutathione. Herein a microwave-assisted template-directed clipping reaction on low-loading 2-chlorotrityl chloride resin is used to develop an NIR unsymmetrical squaraine rotaxane in high quantum yield.

MACROPHAGE IDENTIFICATION AGENT, AND IDENTIFICATION METHOD, SORTING METHOD, EVALUATION METHOD, SCREENING METHOD AND KIT USING THE MACROPHAGE IDENTIFIER AGENT

An object of the present invention is to provide an identification method for a macrophage subtype using an organic compound. Another object of the present invention is to provide a macrophage identification agent containing an organic compound in which a spectral characteristic obtained when the organic compound is added is different depending on a macrophage subtype. Still another object of the present invention is to provide an evaluation method for a macrophage subtype using a macrophage identification agent, an analysis method for correlation between a macrophage subtype and a test substance, a screening method for correlation between a macrophage subtype and a test substance, and a kit. An identification method for a macrophage subtype utilizing that a spectral characteristic obtained with an organic compound added is different depending on a macrophage subtype is provided.

Regioselective synthesis of 1,2- vs 1,3-squaraines

Squaraines have been known for many decades as very stable and versatile vis-NIR absorbing dyes. They have found applications for example as sensitizers in organic photovoltaics and photodetectors. The most common squaraine structure is the 1,3-regioisomer. Their 1,2-regioisomers are seldom mentioned and unanimously regarded as side products. A facile direct synthesis of 1,2-squaraines, highlighting the role played by reaction conditions and electronic factors, is described. The first electrochemical characterization of these dyes is also shown.

1-(Carbamoylmethyl)-3H-indolium squaraine dyes: Synthesis, spectra, photo-stability and association with BSA

Novel, squarylium dyes containing 1-(alkylcarbamoylmethyl)-2,3,3-trimethyl- 3H-indolium groups were synthesized and their UV/Vis and fluorescence spectra, aggregation, photo-stability and association with bovine serum albumin were studied. The absorption and emission max wavelengths of the dyes in different solvents were in the range 619-653?nm. Compared to a typical ethyl squarylium dye, the introduction of alkylcarbamoylmethyl groups reduced aggregation and improved molar extinction coefficient, fluorescence quantum yield and photo-stability in water. Moreover, the fluorescence intensity of the dyes increased upon the addition of BSA in pH 7.0 phosphate buffer solution. An excellent linear relationship (r2?=?0.9982) was obtained between fluorescence intensity and bovine serum albumin concentration.

Luminescent compounds

The invention provides reporter compounds based on squaric, croconic, and/or rhodizonic acid, among others, reactive intermediates used to synthesize the reporter compounds, and methods of synthesizing and using the reporter compounds, among others. The reporter compounds relate generally to the following structure: Here, Z is a four, five, or six-member aromatic ring, and A, B, C, D, E, and F are substituents of Z, where F is absent when Z is a five-member ring, and where E and F are absent when Z is a four-member ring. A, B, C, D, E, and F are selected from a variety of elements and groups, including but not necessarily limited to O, S, Se, Te, C(Ra)(Rb), N—Rc, N(Rd)(Re), W1, and W2.

Luminescent compounds

Luminescent compounds, reactive intermediates used to synthesize luminescent compounds, and methods of synthesizing and using luminescent compounds. These compounds may be based on squaric, croconic, and rhodizonic acid, and their analogs, among others, and relate generally to the structure: where Z is a four, five, or six-member aromatic ring, and A, B, C, D, E, and F are substituents of Z, in any order, that may include O, S, Se, Te, C(Ra)(Rb), N-Rc, N(Rd)(Re), W1, and W2. Generally, each compound includes at least one of W1 or W2, where W1 and W2 have the structures: respectively. The compounds may include a reactive group and/or a carrier. The luminescent compounds may be useful in both free and conjugated forms as probes, labels, and/or indicators.