Divergent Reactivity of Diketopyrrolopyrroles: Ring-Opening with Amines We report an unprecedented reaction of a diketopyrrolopyrrole (DPP) with primary and secondary amines that results in the ring-opening of the core with loss of its fluorescence. The various characterization techniques used in this study, such as X-ray diffraction, NMR spectroscopy, mass spectrometry, and UV–vis analysis, warrant accurate identification of the structures of the newly synthesized compounds. DFT studies were also performed in order to understand the mechanism associated with this reaction.

Happy to share my latest publication in Organic Letters @pubs.acs.org 🚀Important and valuable insights on DPP reactivity.
#chemsky #ChemPubs

Three-state molecular switch based on terarylene photo- or redox-induced reversible isomerisation Multi-addressable molecular photoswitches whose isomerisation can be triggered not only by light, but also by other stimuli are appealing for the development of novel smart materials as well as for br...

Just shortly after the 3rd (😱) anniversary of my PhD defense, a work of my thesis got accepted in @chemicalscience.rsc.org 🚀

If you're interested in dual-responsive #photoswitches, check the link out, it's 💎🔓!

#ChemSky #ChemPubs

A new synthetic approach to the 3,4-dihydro-1H-[1,4]oxazino[4,3-a]indole system from ethyl 1H-indole-2-carboxylates and activated glycerol carbonate An efficient synthesis of a small library of potentially bioactive 3,4-dihydro-1H-[1,4]oxazino[4,3-a]indoles is described through the reaction of ethyl 1H-indole-2-carboxylates and activated glycerol ...

Great new article by my labmate et al. 😀 #ChemPubs
doi.org/10.1039/D5RA...

1,3,4-Oxadiazole-Bridged 3,5-Dinitropyrazoles: Powerful Alliance toward High Performance and High Thermal Stability The ever-increasing demand for heat-resistant energetic materials in deep mining and space exploration has led to significant interest in developing new materials with exceptional thermal stability and detonation performance. In this work, a novel heat-resistant energetic compound, 2,5-bis(3,5-dinitro-1H-pyrazol-4-yl)-1,3,4-oxadiazole (3), was achieved through a simple and straightforward method where two 3,5-dinitropyrazole moieties are linked through a 1,3,4-oxadiazole ring. Compound 3, a symmetrical conjugated molecule, demonstrates superior thermal stability (Tdec = 325 °C), good energetic performance (Dv = 8464 m s–1), and improved physical stability (IS = 7.5 J) compared to the industrially used heat-resistant explosive, HNS. The properties of 3 were further optimized by forming energetic salts, 4 and 5. An attempted reaction to synthesize zwitterionic compound 7, having 3,5-dinitropyrazole and 3,5-diamino-1,2,4-triazole ring connected via a C–C bond, resulted in another zwitterionic compound 6. Energetic salts 4 (Tdec = 291 °C) and 5 (Tdec = 275 °C), as well as zwitterionic compound 6 (Tdec = 286 °C), demonstrated excellent decomposition temperatures with good physical stability. The dihydroxylammonium salt (5) (Dv = 8507 m s–1, P = 31.25 GPa) exhibited the best energetic properties, approaching the performance of RDX. The remarkable overall performance of compounds 3-5 makes them suitable candidates for high-performance, heat-resistant explosives.

Today in #JOCasap is a paper describing compounds I’d rather not make - Just Say NO and you can say NO2
Kind of surprised the thermal onset temps are that high
#ChemSky #ChemPubs

This is really cool from @hirohisaohmiya.bsky.social #chemsky #chempubs
Lots of scope with this ingenious methodology

#ChemPubs Very cool selective 3-fluoridation of pyridines via #PyridineAbuse ring opening-ring closing from the Andy McNally lab #CSUchem now out in #JACSasap
Some excellent scope in here
Nice work by all

Helping to clean up #ChemSky I’ll be using #ChemPubs for new and cool papers (new #JACSasap highlight coming in a minute)

Cu-Catalyzed Coupling of Aryl Halides Utilizing Ammonia and Hydroxypicolinamide Ligands The hydroxypicolinamide family of ligands has previously demonstrated utility in Cu-catalyzed C–N couplings and hydroxylation of heteroaryl halides. The application of these ligands has been extended ...

Looking to couple small amines? Even NH3? Super #OPRD from some of my #PfizerChemistry friends with picolinamide ligands for Cu couplings at low %, hi yields/scope-all those hets! So easy I used it to make [REDACTED] inhibitors
This is who I go to for advice – top chemists and friends
#ChemPubs