955950-11-5

Upstream product

• 676348-42-8 5-ethylthiophene-2-carbohydrazide 
• 872-55-9 2-ethylthiophene 
• 955949-97-0 5-ethyl-N’-(1-(2-hydroxy-4-methoxyphenyl)ethylidene)-thiophene-2-carbohydrazide 
• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 

Downstream Products

• 1308305-26-1 C₆₂H₄₈BN₃O₃S₂ 
• 1308305-32-9 C₅₉H₄₃BN₂O₄S₂ 
• 1308305-37-4 C₆₂H₄₄BN₃O₆S₂ 
• 1308305-38-5 C₆₁H₄₈BN₃O₃S₂ 

Relevant academic research and scientific papers

Synthesis and spectral properties of non-symmetrical red and near IR emitter dibenzoBODIPYs

New symmetrical and non-symmetrical benzoBODIPYs have been synthesized from diketones. For the two series the 3 and 5 positions have been substituted by different aromatic rings and onto benzo sub-units different groups have been introduced. The methodology of diketones self-condensation provides symmetrical dyes. By cross-condensation reaction, these positions can be differentiated and specific functions connected to the desired positions. These molecules have been fully characterized and their optical properties analyzed by both experimental and theoretical means. They are red to NIR emitters with a range of emission from 679 to 780 nm in CH2Cl2. They show maxima of absorption between 651 nm and 732 nm, strong ε of around 100,000 M?1 cm?1 and quite good quantum yields from 16% to 75%. The thienyl moiety on α-positions of the nitrogens generates the highest red shifts. Meanwhile dimethylamino groups in the same positions bring, besides chemical properties, proton sensitive dyes. The bromine atom onto the dibenzo sub-units exhibits good reactivity through Sonogashira coupling reactions. This approach provides multifunctional red to NIR dyes with endless possibilities of combination of chemical properties.

RESIN COMPOSITION AND MOLDED ARTICLE

The invention contains a resin and a near infrared fluorescent material which is one type or two or more types of compounds selected from General Formulas (I1) to (I4) and has a maximum fluorescence wavelength of 650 nm or longer. In Formulas, Ra and Rb, Rc and Rd, Rh and Ri, and Rj and Rk form rings together with the nitrogen atom to which Ra, Rc, Rh, and Rj are bonded; Re and Rf represent a halogen atom or an oxygen atom; each of Rl, Rm, Rn, and Ro independently represents a halogen atom, a C1-20 alkyl group, a C1-20 alkoxy group, an aryl group, or a heteroaryl group; Rg, Rr, and Rs represent a hydrogen atom or an electron withdrawing group; and each of Rp and Rq independently represents a hydrogen atom, a halogen atom, a C1-20 alkyl group, a C1-20 alkoxy group, an aryl group, or a heteroaryl group.

Chemistry at boron: Synthesis and properties of red to near-IR fluorescent dyes based on boron-substituted diisoindolomethene frameworks

A general method for the synthesis of difluorobora-diisoindolomethene dyes with phenyl, p-anisole, or ethyl-thiophene substituents has been developed. The nature of the substituents allows modulation of the fluorescence from 650 to 780 nm. Replacement of the fluoro ligands by ethynyl-aryl or ethyl residues is facile using Grignard reagents. Several X-ray molecular structures have been determined, allowing establishment of structure-fluorescence relationships. When the steric crowding around the boron center is severe, the aromatic substituents α to the diisoindolomethene nitrogens are twisted out of coplanarity, and hypsochromic shifts are observed in the absorption and emission spectra. This shift reached 91 nm with ethyl substituents compared to fluoro groups. When ethynyl linkers are used, the core remains flat, and a bathochromic shift is observed. All the fluorophores exhibit relatively high quantum yields for emitters in the 650-800 nm region. When perylene or pyrene residues are connected to the dyes, almost quantitative energy transfer from them to the dye core occurs, providing large virtual Stokes shifts spanning from 8000 to 13 000 cm-1 depending on the nature of the dye. All the dyes are redox active, providing the Bodipy radical cation and anion in a reversible manner. Stepwise reduction or oxidation to the dication and dianion is feasible at higher potentials. We contend that the present work paves the way for the development of a new generation of stable, functionalized luminophores for bioanalytical applications.

Synthesis of novel tetrachromophoric cascade-type Bodipy dyes

Two series of multi-cascade scaffolds bearing a boradiazaindacene (yellow dye) or a boradibenzopyrromethene (green dye) as the final energy acceptor have been synthesized. Each scaffold contains one, two or three alkynylaryl energy donors (such as pyrene D1, perylene D2, and fluorene D3) linked to the boron center. Palladium-catalyzed cross-coupling of dihalogenated Bodipy starting material enabled the step-by-step construction of the different modules. In all cases, selective irradiation in each absorbing subunit resulted in efficient energy transfer over 25 ? to the Bodipy units.

Synthesis of bisisoindolomethene dyes bearing anisole or ethylthiophene residues for red and near-IR fluorescence

New difluorobora-diisoindolomethenes dyes were synthesized from carbohydrazide and o-hydroxy-acetophenone derivatives bearing phenyl, p-anisole or ethylthiophene substituents. The nature of the substituents allows modulating the fluorescence from 650 nm t