The synthesis and characterization of some group VII bromo-substituted furyl complexes

ABSTRACT

Furan-based chemistry offers an alternative to thiophene and pyrrole semiconductive materials and has been largely unexplored despite furan's availability from biomass feedstocks. Halogenated furoyl complexes (e.g., 5-bromo) have the potential to be polymerized via coupling reactions. Incorporation of a redox-active transition metal (Mn, Re) allows for “tuning” the electronic properties of the material by changing the metal's oxidation state. The furoyl complexes [Mn(CO)₃{η⁵-1,2-C₅H₃(CO-(5-BrC₄H₂O))₂}] (4a) and [Re(CO)₃{η⁵-1,2-C₅H₃(CO-(5-BrC₄H₂O))₂}] (4b) have been synthesized in relatively high yields and characterized by NMR and IR spectroscopy and Direct Analysis in Real Time MS. Both complexes were synthesized from a convenient route beginning with 5-bromo-2-furoyl chloride, with their results reported herein.

KEYWORDS:

• Redox
• furan
• manganese complexes
• rhenium complexes
• organometallic
• DART-MS

Acknowledgments

The authors would like to thank Dr. Darrin Smith in the Department of Chemistry at Eastern Kentucky University for his support on the DART-MS analysis.