101730-27-2

Upstream product

• 75-52-5 nitromethane 
• 6552-66-5 3-(4-methoxyphenyl)-1-p-tolylprop-2-en-1-one 
• 3594-36-3 1,3-bis(p-methylphenyl)-1,3-propanedione 
• 3179-10-0 1-methoxy-4-(2-nitro-vinyl)-benzene 

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• 85658-03-3 4-(4-methoxyphenyl)-2-(4-tolyl)furan 

Relevant academic research and scientific papers

Synthesis and photophysical properties of nitrated aza-BODIPYs

A series of ten electron deficient aza-BODIPYs were prepared through a facile nitration strategy where either one, two, or four nitro groups can be regioselectively attached which represents a novel synthetic transformation of the core structure. Installation of the highly withdrawing nitro group on the 2- and 6-positions was found to greatly impact the absorption and emission profiles of the aza-BODIPY core in comparison to their non-nitrated precursors as seen through unusually large negative solvatochromic effects and Stokes shifts, resulting in exceptional photophysical tunability. TD-DFT calculations also revealed that nitration on the 2- and 6-positions greatly stabilized both HOMO and LUMO energy levels by an average of 0.61 eV, resulting in average HOMO and LUMO energies of -4.46 eV and -6.44 eV, respectively. Moreover, preliminary studies suggested that nitrated aza-BODIPYs possess moderate to superior photostabilities when compared to their non-nitrated analogues. Combined, these data demonstrate that nitration of the 2- and 6-positions is a viable strategy in designing effective push-pull aza-BODIPYs with near-IR absorption and emission profiles. This journal is

Sequential Michael addition/retro-Claisen condensation of 1,3-diarylpropan-1,3-diones with nitrostyrenes: one-step synthesis of 4-nitro-1,3-diarylbutan-1-ones

Abstract : The sequential Michael addition/retro-Claisen condensation of 1,3-diarylpropan-1,3-diones with nitrostyrenes is described. 4-Nitro-1,3-diarylbutan-1-ones were efficiently synthesized in good to high yield under mild, transition-metal-free condition. This one-step method involving sequential carbon-carbon bond formation and cleavage provides a good alternative to the synthesis of various γ-nitro ketones. Graphical abstract: The sequential Michael addition/retro-Claisen condensation of 1,3-diarylpropan-1,3-diones with nitrostyrenes is described. 4-Nitro-1,3-diarylbutan-1-ones were efficiently synthesized in good to high yield under mild and transition-metal-free condition. [Figure not available: see fulltext.].