850454-08-9

Upstream product

• 625-82-1 2,4-dimethyl-1H-pyrrole 
• 1122-91-4 4-bromo-benzaldehyde 

Downstream Products

• 850534-67-7 1,3,5,7-tetramethyl-8-(4'-aminophenyl-N-(2''-amino)-phenyl)-difluoroboradiaza-s-indacene 
• 1340481-37-9 C₂₁H₂₄BBrN₂O₂ 

Relevant academic research and scientific papers

An analysis of the photophysical and optical limiting properties of a novel 1,3,5-TristyrylBODIPY dye

The synthesis and characterization of a novel dibrominated 1,3,5-TristyrylBODIPY dye is reported, and its potential utility as a singlet oxygen photosensitizer and optical limiting material is assessed. The main spectral band lies in the therapeutic window, and there is a moderately high singlet oxygen quantum yield making the dye potentially suitable for use in biomedical applications and as an optical limiting dye at 532 nm. The optical limiting parameters are comparable to those reported previously for 3,5-distyrylBODIPYs, which suggests that mixtures of 3,5-distyryl and 1,3,5-Tristyryl compounds that are formed in Knoevenagel condensation reactions could be used for this application. Theoretical calculations are used to assess the effect of 1,3,5-Tristyryl substitution. A smaller red shift of the main spectral band is observed upon styrylation at the 1-position than is the case with the 3,5-positions due to there being smaller MO coefficients at this position, limiting the utility of this structural modification method for shifting the main BODIPY spectral band further into the therapeutic window.

A bodipy based dual functional probe for the detection of hydrogen sulfide and H2S induced apoptosis in cellular systems

A bodipy based dual functional probe 1 has been designed and synthesized, which selectively detects H2S as well as monitors H2S induced apoptosis in cells.

Modulating absorption and charge transfer in bodipy-carbazole donor-acceptor dyads through molecular design

Three bodipy-based (BDP = 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) donor-acceptor dyads were designed and synthesized, and their ground-state and photophysical properties were systematically characterized. The electronic coupling between the BDP chromophore and an electron-donating carbazole (Carb) moiety was tuned by attachment via the meso and the beta positions on the BDP core, and through the use of various chemical linkers (phenyl and alkynyl) to afford mesoBDP-Carb, mesoBDP-phen-Carb, and betaBDP-alk-Carb. meso-Substituted dyads were found to retain ground-state absorption features of the unsubstituted BDP. However, variation of the linkage between the donor and acceptor moieties modulated the photophysical behavior of excited-state deactivation by controlling the rate of photoinduced internal charge transfer (ICT). The beta-substituted dyad dramatically tuned (red shifted) the absorption spectrum, while retaining desired features of the BDP, specifically stability and high extinction coefficients, however the ICT kinetics were accelerated compared to the meso-substituted dyads. Density functional theory (DFT) and time-dependent DFT (TDDFT) were carried out on the six potential dyads formed between BDP and Carb (attachment using the beta and meso positions for all three connections: direct, phenyl and alkynyl) to support the experimental observations. DFT and TDDFT showed molecular orbital density spread across the HOMO level only when attachment occurred through the beta position of BDP. In the meso-substituted BDP-Carb dyads, the molecular orbitals resembled those of the unsubstituted BDP. This work reveals several possible synthetic paradigms to tune photophysical properties with directed synthetic modifications and provides a mechanistic understanding of the ground- and excited- state behavior in these small-molecule donor-acceptor dyads.

Syntheses of 2-aryl benzothiazoles via photocatalyzed oxidative condensation of amines with 2-aminothiophenol in the presence of bodipy derivatives

A simple, convenient, and efficient new method for synthesis of 2-aryl benzothiazoles under mild conditions with nonmetal catalyst has been developed. Boron-dipyrromethene (BODIPY) dyes were used as photocatalysts for aerobic oxidative reactions of amine with 2-aminothiophenol. The approach will be very useful for the synthesis of benzothiazole derivatives and the development of photocatalytic reactions.

Spectroscopic, computational modeling and cytotoxicity of a series of meso-phenyl and meso-thienyl-BODIPYs

A series of twenty-two BODIPY compounds were synthesized, containing various meso-phenyl and meso-thienyl groups, and their spectroscopic and structural properties were investigated using both experimental and computational methods. Further functionalizat

Convenient one-pot procedure for synthesizing 4,4′-dimethoxy- boradiaza-s-indacene dyes and their application to cell labeling

We succeeded in developing a convenient one-pot pathway for synthesizing 4,4′-dimethoxy-boradiaza-s-indacene dyes 4a-d. The structures feature two methoxy groups in place of the fluorine atoms in 4,4′-difluoro-4- boradiaza-s-indacene. These novel dyes emi

Design, synthesis and characterization of a novel fluorescent probe for nitric oxide based on difluoroboradiaza-s-indacene fluorophore

Nitric oxide (NO) is a gaseous, free radical, which plays a role as an intracellular second messenger and a diffusible intercellular messenger. To obtain evidence for NO function in vivo, 1,3,5,7-tetramethyl-8-(4′-aminophenyl-N-(2′′-amino)-phenzyl) -difluoroboradiaza-s-indacene (TMAPABODIPY) was designed and synthesized as a fluorescent probe for nitric oxide, which features high photostability and no pH dependency over a wide pH range. The fluorescence of TMAPABODIPY itself is very strong. When TMAPABODIPY traps NO in the presence of dioxygen, the weak fluorescent triazole form is obtained, which offers the advantages of specificity, and sensitivity for direct detection of NO. The relationship was obtained between the quenching fluorescence intensity and NO concentration in the range 0.02-4.0 μmol l-1. The detection limit is 5 nmol l -1 (S/N = 3). The proposed method has been used to monitor the release of NO from S-nitrosocysteine, a NO-releasing agent.