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Upstream product

• 37774-61-1 N-(3-phenyl-2H-isoindol-1-yl)-N-(3-phenyl-1H-isoindol-1-ylidene)amine 
• 37774-61-1 N-(3-phenyl-2H-isoindol-1-yl)-N-(3-phenyl-1H-isoindol-1-ylidene)amine 
• 100-58-3 phenylmagnesium bromide 
• 91-15-6 phthalonitrile 
• 109-63-7 boron trifluoride diethyl etherate 
• 108-86-1 bromobenzene 

Relevant academic research and scientific papers

Chiral benzo-fused Aza-BODIPYs with optical activity extending into the NIR range

Chiral benzo-fused aza-BODIPYs, namely N,N-difluoroboryl-[(dinaphtho[1,2-e:1′,2′-g]-1,4-dioxocine)-1-[N-(3-phenyl-2H-isoindole-1-yl)methylene]-3-phenyl-1H-isoindol-1-ylidene)amine] (1) and N,N-difluoroboryl-[(dinaphtho[1,2-e:1′,2′-g]-1,4-dioxocine)-1-[(di

Aza-BODIPY Derivatives Containing BF(CN) and B(CN)2 Moieties

Two novel aza-BODIPY derivatives are synthesized, with the fluorine atoms in the BF2 moiety replaced by cyano groups. The introduction of cyano groups changes the phenyl substituents on the 3,5 positions from parallel to antiparallel. The HOMO/

Ultrafast Photoinduced Electron Transfer and Charge Stabilization in Donor-Acceptor Dyads Capable of Harvesting Near-Infrared Light

To harvest energy from the near-infrared (near-IR) and infrared (IR) regions of the electromagnetic spectrum, which constitutes nearly 70'% of the solar radiation, there is a great demand for near-IR and IR light-absorbing sensitizers that are capable of

Synthesis and spectroscopic properties of fused-ring-expanded aza-boradiazaindacenes

A series of fused-ring-expanded aza-boradiazaindacene (aza-BODIPY) dyes have been synthesized by reacting arylmagnesium bromides with phthalonitriles or naphthalenedicarbonitriles. An analysis of the structure-property relationships has been carried out based on X-ray crystallography, optical spectroscopy, and theoretical calculations. Benzo and 1,2-naphtho-fused 3,5-diaryl aza-BODIPY dyes display markedly red shifted absorption and emission bands in the near-IR region (>700a nm) due to changes in the energies of the frontier MOs relative to those of 1,3,5,7-tetraaryl aza-BODIPYs. Only one 1,2-naphtho-fused aza-BODIPY of the three possible isomers is formed due to steric effects, and 2,3-naphtho-fused compounds could not be characterized because the final BF 2 complexes are unstable in solution. The incorporation of a i￡N(CH3)2 group at the para-positions of a benzo-fused 3,5-diaryl aza-BODIPY quenches the fluorescence in polar solvents and results in a ratiometric pH response, which could be used in future practical applications as an NIR "turn-on" fluorescence sensor.

Synthesis, properties and reactivity of BCl2 aza-BODIPY complexes and salts of the aza-dipyrrinato scaffold

The synthesis and characterisation of the BCl2-chelated complexes of both archetypal aza-dipyrrin sub-Types are presented. A stepwise halogen exchange, leading to a mixed-halide Cl-B-F intermediate, is implicated in the conversion of F-Aza-BODIPYs to Cl-Aza-BODIPYs upon treatment with BCl3. The utility of the Cl-Aza-BODIPY scaffold to facilitate substitutions at boron is demonstrated under mild conditions through treatment with aryl Grignard reagents. Additionally, the lability of the B-Cl bond enables facile removal of the BCl2 group, i.e. deprotection of F-Aza-BODIPYs, under aqueous conditions. Three aza-dipyrrin HX salts were also synthesised and characterised. The pKa of the protonated aza-dipyrrin was determined to be 4, thereby providing insight regarding the storage and stability of such species.

Synthesis and charge-transfer dynamics in a ferrocene-containing organoboryl aza-bodipy donor-acceptor triad with boron as the hub

A N,N′-bis(ferroceneacetylene)boryl complex of 3,3′-diphenylazadiisoindolylmethene was synthesized by the reaction of an N,N′-difluoroboryl complex of 3,3′-diphenylazadiisoindolylmethene and ferroceneacetylene magnesium bromide. The novel diiron complex w

Synthesis and characterization of near-infrared absorbing benzannulated aza-BODIPY dyes

A series of novel aza-diisoindolmethine dyes 9 with six different aryl and heteroaryl groups at the indole moiety have been synthesized by the addition of aryl Grignard compounds to phthalodinitrile and subsequent reaction with formamide. A plausible reaction mechanism, through a Leuckart-Wallach-type reduction has been confirmed by means of DFT calculations of the related transition and intermediate states. The corresponding boron difluoride complexes (10) of 9 were prepared in a subsequent reaction step and the spectroscopic and electrochemical properties of 9 and 10 have been investigated both experimentally and theoretically. The aza-diisoindolmethines 9 exhibit an absorption maximum in the range from 615 to 720 nm, whereas the complexes 10 show a bathochromically shifted absorption maximum between 681 and 793 nm. Measurements of 9 and 10 by cyclic voltammetry display fully reversible redox waves for the reduction and oxidation with higher potentials for 10. From the measured redox potentials, the HOMO and LUMO energy levels were calculated for 9 and 10. The frontier orbital energies, the energies of the absorption bands, as well as the orbitals involved in the absorption process were calculated with DFT and compared to the measured results of 9 and 10. The absorption maximum can be related to an intense HOMO-LUMO transition and the more-pronounced stabilization of the LUMO upon complexation is the origin of the bathochromic shift of the absorption. Additionally, single-crystal structures for two species, 10d and 10f, are reported.

Synthesis of N,N-difluoroboryl complexes of 3,3′-diarylazadiisoindolylmethenes

N,N-Difluoroboryl complexes of 3,3′-diarylazadiisoindolylmethenes were synthesized by the reaction of BF3·OEt2 and 3,3′-diarylazadiisoindolylmethenes, which were easily prepared from a reaction between phthalonitrile and aryl Grignard reagents. These novel dyes exhibit strong absorption in the visible region and intense fluorescence in the vis/NIR region. Their synthesis, characterization, and optical properties are reported in this Letter.