Described herein is an efficient strategy for assembling a new library of functionalized polycyclic purinium salts with a wide range of anions through Rh-catalyzed C-H activation/annulation of 6-arylpurine nucleosides with alkynes under mild reaction conditions. The resulting products displayed tunable photoluminescence covering most of the visible spectrum. Mechanistic insights delineated the rhodium catalyst's mode of action. A purinoisoquinolinium-coordinated rhodium(I) sandwich complex was well characterized and identified as the key intermediate.
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- - The study uses femtosecond transient absorption spectroscopy to observe a redshift in the stimulated emission signal of a specific purinium salt molecule when dissolved in DMSO, with a significant shift occurring in just 4.8 picoseconds.
- - When the solvent is mixed with glycerol, the emission redshift delays increase to 6.9 picoseconds for 25% glycerol and 68 picoseconds for 50% glycerol, showing that viscosity affects the emission properties.
- - The research suggests that the molecule undergoes a twisted intramolecular charge transfer process, where the rotation of certain parts is slowed down in more viscous environments, leading to a prolonged emission lifetime and a shift in the emission spectrum
Hydrogen evolution-enabled rhodaelectro-catalyzed [4+2] annulations of purines and 7-deazapurines with alkynes.
Chem Commun (Camb)
August 2022
College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. China.
A rhodium-catalyzed electrochemical regioselective annulation of 6-phenylpurines and 6-phenyl-7-deazapurines with alkynes has been developed. Electricity is used to recycle the active rhodium-based catalyst, promote the evolution of H and help in reducing the reaction temperature. This mild and green method enables a broad substrate scope and wide functional group tolerance, providing a new series of polycyclic purinium and 7-deazapurinium salts in high yields.
View Article and Find Full Text PDFRhodium(III)-Catalyzed Synthesis of Diverse Fluorescent Polycyclic Purinium Salts from 6-Arylpurine Nucleosides and Alkynes.
Org Lett
June 2022
Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.
Described herein is an efficient strategy for assembling a new library of functionalized polycyclic purinium salts with a wide range of anions through Rh-catalyzed C-H activation/annulation of 6-arylpurine nucleosides with alkynes under mild reaction conditions. The resulting products displayed tunable photoluminescence covering most of the visible spectrum. Mechanistic insights delineated the rhodium catalyst's mode of action.
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