1031443-55-6

Basic information

• Product Name: 5,5-difluoro-2,8-diiodo-1,3,7,9,10-pentamethyl-5H-4λ⁴,5λ⁴-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine
• Synonyms: 5,5-difluoro-2,8-diiodo-1,3,7,9,10-pentamethyl-5H-4λ⁴,5λ⁴-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine
• CAS NO: 1031443-55-6
• Molecular Weight: 513.903
• Mol File: 1031443-55-6.mol

Chemical Properties

• CAS DataBase Reference: 5,5-difluoro-2,8-diiodo-1,3,7,9,10-pentamethyl-5H-4λ⁴,5λ⁴-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5-difluoro-2,8-diiodo-1,3,7,9,10-pentamethyl-5H-4λ⁴,5λ⁴-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine(1031443-55-6)
• EPA Substance Registry System: 5,5-difluoro-2,8-diiodo-1,3,7,9,10-pentamethyl-5H-4λ⁴,5λ⁴-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine(1031443-55-6)

Safety Data

• Hazardous Substances Data: 1031443-55-6(Hazardous Substances Data)

Upstream product

• 121207-31-6 4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene 
• 7782-68-5 iodic acid 
• 516-12-1 N-iodo-succinimide 
• 7553-56-2 iodine 
• 625-82-1 2,4-dimethyl-1H-pyrrole 

Downstream Products

• 1031443-60-3 C₄₆H₅₉BF₂N₄ 
• 1031443-59-0 4,4-difluoro-1,3,5,7,8-pentamethyl-2,6-bis(p-tolylethynyl)-4-bora-3a,4a-diaza-s-indacene 
• 1031443-62-5 4,4-bis(p-tolylethynyl)-1,3,5,7,8-pentamethyl-2,6-diiodo-4-bora-3a,4a-diaza-s-indacene 
• 1325234-16-9 C₃₂H₂₇BF₂N₂O₂ 
• 1325234-19-2 C₃₅H₂₇BF₂N₄O 
• 1325234-13-6 C₂₃H₂₂BF₂IN₂O 
• 1325234-31-8 C₃₂H₂₉BF₂N₂O₂ 

Relevant articles and documents

Two fluorescent 2,6-substituted pyridyl boron-dipyrromethene dyes for selective sensing of cuprous ions

Two new pyridine-substituted boron-dipyrromethene (BODIPY) dyes have been synthesized via the Suzuki coupling reactions of 2,6-diiodo-1,3,5,7-tetramethyl- 8-methyl-4,4-difluoroboradiazaindacene and respective pyridinylboronic acid. The molecular structures of the two title compounds have been determined by single-crystal X-ray diffraction analyses. The absorption and steady-state fluorescent properties in different solvents were investigated, which showed that the two compounds are highly fluorescent with a relatively small Stokes shift, high fluorescent quantum yields and little solvent dependence, similar to other BODIPY chromophores. The fluorescence of two compounds were highly sensitive towards Cu+, owing to significant interactions between Cu+ and the nitrogen atoms on the pyridine rings.

Reactive Oxygen Species Mediated Activation of a Dormant Singlet Oxygen Photosensitizer: From Autocatalytic Singlet Oxygen Amplification to Chemicontrolled Photodynamic Therapy

Here we show the design, preparation, and characterization of a dormant singlet oxygen (1O2) photosensitizer that is activated upon its reaction with reactive oxygen species (ROS), including 1O2 itself, in what constitutes an autocatalytic process. The compound is based on a two segment photosensitizer-trap molecule where the photosensitizer segment consists of a Br-substituted boron-dipyrromethene (BODIPY) dye. The trap segment consists of the chromanol ring of α-tocopherol, the most potent naturally occurring lipid soluble antioxidant. Time-resolved absorption, fluorescence, and 1O2 phosphorescence studies together with fluorescence and 1O2 phosphorescence emission quantum yields collected on Br2B-PMHC and related bromo and iodo-substituted BODIPY dyes show that the trap segment provides a total of three layers of intramolecular suppression of 1O2 production. Oxidation of the trap segment with ROS restores the sensitizing properties of the photosensitizer segment resulting in ～40-fold enhancement in 1O2 production. The juxtaposed antioxidant (chromanol) and prooxidant (Br-BODIPY) antagonistic chemical activities of the two-segment compound enable the autocatalytic, and in general ROS-mediated, activation of 1O2 sensitization providing a chemical cue for the spatiotemporal control of 1O2.The usefulness of this approach to selectively photoactivate the production of singlet oxygen in ROS stressed vs regular cells was successfully tested via the photodynamic inactivation of a ROS stressed Gram negative Escherichia coli strain.

Monofluorination and Trifluoromethylation of BODIPY Dyes for Prolonged Single-Molecule Detection

Electrophilic monofluorination with Selectfluor and nucleophilic trifluoromethylation with the Ruppert-Prakesh reagent of dimethyl-, tetramethyl- and pentamethyl-substituted boron dipyrromethenes (BODIPY) are investigated. Monofluorinated dyes are synthesized with low yields (a hypsochromic shift by up to 17 nm in both absorption and emission, slightly enhanced intersystem crossing, and higher photostability. Further development of soft fluorination and trifluoromethylation methods is therefore highly desired.

Nanoscale Fluorescent Metal–Organic Framework@Microporous Organic Polymer Composites for Enhanced Intracellular Uptake and Bioimaging

Polymer-modified metal–organic frameworks combine the advantages of both soft polymers and crystalline metal–organic frameworks (MOFs). It is a big challenge to develop simple methods for surface modification of MOFs. In this work, MOF@microporous organic polymer (MOP) hybrid nanoparticles (UNP) have been synthesized by epitaxial growth of luminescent boron-dipyrromethene (BODIPYs)–imine MOPs on the surface of UiO-MOF seeds, which exhibit low cytotoxicity, smaller size distribution, well-retained pore integrity, and available functional sites. After folic acid grafting, the enhanced intracellular uptake and bioimaging was validated.

BODIPY dyes with β-conjugation and their applications for high-efficiency inverted small molecule solar cells

Small molecule BODIPY dyes incorporating conjugated substituents at the β sites have been synthesized. Solution processed inverted bulk heterojunction cells were fabricated from the blends of the dyes and PC 71BM. The cells exhibited very high open-circuit voltages (>0.9 V) and a high conversion efficiency of 3.22% has been achieved.

Quantitative Profiling of the Heavy-Atom Effect in BODIPY Dyes: Correlating Initial Rates, Atomic Numbers, and 1O2 Quantum Yields

Direct oxidation using molecular oxygen is both attractive and atom-efficient. However, this process first requires the catalyst-based activation or electronic reconfiguration of inert O2. The most expedient strategy relies on the generation of singlet oxygen (1O2; a1Δg) from the triplet state (3O2; X3Σg–) by a photosensitizer. In the current arsenal of photosensitizers, boron-dipyrromethene (BODIPY) cores are considered privileged on account of their unique photophysical characteristics and the ability to tune their behavior through facile structural modifications such as halogen (X) incorporation. Thus, the scaffold has become synonymous with the renowned heavy-atom effect (HAE), a phenomenon that correlates the increasing atomic number (ZX) of pendant halogen atoms with an enhanced probability of intersystem crossing (S1→T1). Herein, a facile GC-based method to assess catalyst performance has been developed and validated with a focused set of halogenated BODIPY scaffolds. An initial-rate approximation was applied to a model transformation and follows the HAE trend (v0,H 0,Cl 0,Br 0,I). This operationally simple approach was corroborated by complementary determinations of absolute singlet oxygen and photoluminescence quantum yields and time-resolved luminescence decays to evaluate lifetimes. For double logarithmic plots, linear correlations between relative intersystem-crossing rates kXisc/kYisc and relative atomic numbers ZX/ZY for the respective substituents with corresponding slopes of approximately 4 were obtained, that is, kisc ~ Z4, which also was shown to hold for the fluorescence-lifetime-corrected singlet-oxygen quantum yields as independent measurements. This substantiates theoretical predictions pertaining to the heavy-atom effect.

Fine-Tuning Plasmon-Molecule Interactions in Gold-BODIPY Nanocomposites: The Role of Chemical Structure and Noncovalent Interactions

Strong coupling between localized surface plasmons and molecular absorptions leads to remarkable changes in the photophysical properties of dye-loaded metal nanoparticles. Here, we report supramolecular nanocomposites consisting of BODIPY, tryptophan, and gold nanoparticles, and investigate the effect of structural variations on their photophysical properties. Our results indicate that the photostability and photosensitization properties of the nanocomposites depend on the chemical composition of the BODIPY molecules. The singlet oxygen quantum yield of the nanocomposites NC1 (BODIPY, B1 bearing a single methyl group) and NC3 (BODIPY, B3 with 5 methyl and 2 iodo groups) were 0.46 and 0.42, respectively, which were significantly higher compared to their individual components. Ultrafast spectroscopy studies revealed that the migration of photoexcited BODIPY electrons to the plasmonic photoexcitation allowed electron transfer into the singlet oxygen states, thereby leading to efficient generation of singlet oxygen.

Effect of Substituents on the Photophysical Properties and Bioimaging Application of BODIPY Derivatives with Triphenylamine Substituents

We investigated the intramolecular charge transfer characteristics in the S1 state of boron-dipyrromethene (BODIPY) derivatives with triphenylamine (TPA) substituents, depending on the substituted position and the number of substituents. Based on the spectroscopic and theoretical results, the β-substitution of TPA on BODIPY hybridizes locally excited and intramolecular charge transfer characteristics in the S1 state because of strong coupling between the highest occupied molecular orbitals of BODIPY and TPA moieties, and consequently, the BODIPY derivatives with β-substituted TPAs exhibit strong red-color fluorescence around 640 nm in nonpolar and moderately polar solvents. The TPA substituent with propeller-like nonplanar geometry could prevent H-type aggregation between neighboring BODIPY derivative units and induce aggregation-induced emission enhancement (AIEE) characteristics of the BODIPY derivatives with TPA substituents, which are helpful to maintain their emission efficiencies under highly concentrated and condensed conditions. Since the red-color emission and AIEE property of the BODIPY derivatives with β-substituted TPAs are promising characteristics for a bioimaging application, we applied these derivatives to L-929 fibroblast cells for cellular imaging. The BODIPY derivative with a single β-substituted TPA (compound 2) was effectively loaded into porous silica nanoparticles (SNPs). Consequently, we achieved good cellular uptake of 2-SNPs and good cellular imaging, which further confirmed the bioimaging ability of 2-SNPs.

Synthesis, photophysical and concentration-dependent tunable lasing behavior of 2,6-diacetylenyl-functionalized BODIPY dyes

2,6-Diacetylenyl- and 2,6-bis(arylacetylenyl)-functionalized pentamethyl-difluoroborondipyrromethene (BODIPY) derivatives, namely, PBDP1 and PBDP2-4 (aryl = phenyl, 4-methoxyphenyl, or 4-cyanophenyl), respectively, which exhibit extended π-conjugation, were synthesized and characterized by various spectroscopic methods. Significant bathochromic shifts in both absorption and emission were observed upon modifying the structure of the BODIPY core via the strategy of extending its π-conjugation. The derivatives displayed efficient emission in the yellow-to-red spectral region, with a high fluorescence quantum yield and a relatively large Stokes shift. Under conditions of transverse pumping in a cuvette, PBDP1 and PBDP2 exhibited highly efficient and stable laser activity for up to 180 and 110 minutes of continuous irradiation, respectively. Amplified spontaneous emission (FWHM of ca. 2.5 nm) with an efficiency of 41% and 36% was achieved for PBDP1 and PBDP2, respectively, in toluene, which had tunable ranges of 561 to 580 nm and 602 to 617 nm, respectively, on irradiation with a Q-switched Nd:YAG laser at 532 nm. The lasing properties of PBDP3 and PBDP4, which contain electron-donating (-OMe) and electron-withdrawing (-CN) arylacetylenyl moieties, respectively, were also investigated. A corresponding digold(i) diacetylide organometallic complex, namely, (PPh3)Au-C≡C-BODIPY-C≡C-Au(PPh3) (PBDP5) was also synthesized and characterized to study the effect of Au(i). PBDP5 exhibited phosphorescence in the vis-NIR region centered at 751 nm at 77 K owing to heavy-atom-induced intersystem crossing.

PHOTODYNAMIC THERAPY PHOTOSENSITIZERS

A compound of formula (I) useful as a photosensitizer in photodynamic therapy is provided. There is also provided a photosensitizing composition for use in photodynamic therapy comprising this compound. Finally, there are provided a method of killing cells under oxidative stress conditions and a method for the selective delivery of singlet oxygen (1O2) to cells having an increased reactive oxygen species (ROS) concentration, these methods comprising the steps of contacting such cells with a compound of formula (I), and exposing the cells to light.