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A greener tetraphenylporphyrin synthesis and metallation: an undergraduate teaching experiment

A greener tetraphenylporphyrin synthesis and metallation: an undergraduate teaching experiment
Contributors
Edward Zovinka
Professor of Chemistry | Saint Francis University
Matthew Cranswick
Oregon State University
John De Backere
Assistant Professor, Teaching Stream | University of Toronto, St. George Campus
Beyond Benign
Beyond Benign, Inc.
Learning Objets
Summary
In this experiment, 5,10,15,20-tetraphenyl-21H,23H-porphyrin (H2TPP) is synthesized on the microscale using an optimized procedure with a research-grade microwave apparatus (CEM Discover). This experiment can also be extended to the para-substituted phenyl derivatives.

Metalloporphyrins, with an array of metals, can then be synthesized using greener routes including mechanochemical methods (with a Mixer Mill), microwave, or reflux in conjunction with the synthesized porphyrin ligand and a metal salt, such as a zinc or copper acetate. The ligand and products are analyzed using UV-Vis spectroscopy the results of which can be related to electronic structure.

This experiment was developed with students Matthew A. Nitka, Katarina E. Zerbee, and Julianne M. Dee.
Keyword Tags
Bioorganic
Coordination Chemistry
Spectroscopy
Link to external
https://doi.org/10.1080/17518253.2022.2164700
Learning Goals/Student Objectives
In performing this experiment, a student will:

1. Use microwave-assisted and mechanochemical synthesis techniques.
2. Evaluate “green metrics” for conventional versus alternative synthesis approaches.
3. Explain electronic structure of H2TPP based on theory and spectroscopy.
4. Analyze changes in UV-spectra and discuss in terms of electronic structure.
Object Type
Laboratory experiment
Audience
Upper/Advanced Undergraduate
Common pedagogies covered
Collaborative/cooperative learning
Hands-on learning
Green Chemistry Principles
Waste Prevention
Safer Solvents and Auxiliaries
Design for Energy Efficiency
Use of Renewable Feedstocks
Safety Precautions, Hazards, and Risk Assessment
Propionic acid is corrosive. Metal salts are inherently toxic. Ethanol is highly flammable.

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Submitted by

John De Backere
Reviewed by
Ryan Trovitch
Published on
Moderation state
Published
Collection
Greener Inorganic Labs
Time required (if applicable)
4 hours (and up)
Other notes/information
Iterations of this experiment have been run at both the University of Toronto and Saint Francis University.
Creative Commons License
Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.