Nickel Porphyrin Synthesis by Microwave Irradiation
University
Shawnee State University
Major
Chemistry: General
Student Type
Undergraduate Student
Presentation Types
Oral Group Presentation (Live)
Keywords:
Synthesis, Nickel porphyrin, Microwave reaction, metal complexing
Abstract
Tetraphenylporphyrin (TPP) was synthesized through a one‑pot, microwave‑assisted condensation of pyrrole and benzaldehyde using DBU as the solvent. The reaction mixture was subsequently treated with nickel(II) chloride in an effort to achieve simultaneous metalation of the porphyrin macrocycle. Reaction progress was monitored by TLC using a 7:1 hexane:ethyl acetate solvent system, and the crude product was purified by column chromatography under the same conditions. Structural characterization by ¹H NMR confirmed successful formation of tetraphenylporphyrin. However, additional investigation is required to optimize and verify the nickel insertion step, as current data does not conclusively demonstrate formation of the nickel–porphyrin complex. This work establishes an efficient route to TPP and identifies key parameters for further refinement of the metalation process.
Human and Animal Subjects
no
IRB or IACUC Approval
yes
Faculty Mentor Name
Wendi Fleeman
Faculty Mentor Title
Professor
Faculty Mentor Department
Natural Sciences
Recommended Citation
Sarver, Isabelle and Skeenes, Ian, "Nickel Porphyrin Synthesis by Microwave Irradiation" (2026). Celebration of Scholarship. 2.
https://digitalcommons.shawnee.edu/cos/2026/daytwo/2
Nickel Porphyrin Synthesis by Microwave Irradiation
Tetraphenylporphyrin (TPP) was synthesized through a one‑pot, microwave‑assisted condensation of pyrrole and benzaldehyde using DBU as the solvent. The reaction mixture was subsequently treated with nickel(II) chloride in an effort to achieve simultaneous metalation of the porphyrin macrocycle. Reaction progress was monitored by TLC using a 7:1 hexane:ethyl acetate solvent system, and the crude product was purified by column chromatography under the same conditions. Structural characterization by ¹H NMR confirmed successful formation of tetraphenylporphyrin. However, additional investigation is required to optimize and verify the nickel insertion step, as current data does not conclusively demonstrate formation of the nickel–porphyrin complex. This work establishes an efficient route to TPP and identifies key parameters for further refinement of the metalation process.