A greener tetraphenylporphyrin synthesis and metallation: an undergraduate teaching experiment

IF 5.8 3区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY Green Chemistry Letters and Reviews Pub Date : 2023-01-02 DOI:10.1080/17518253.2022.2164700
Matthew A. Nitka, Katarina E. Zerbee, Julianne M. Dee, Matthew A. Cranswick, E. Zovinka, John R. De Backere
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Abstract

ABSTRACT While porphyrin-related syntheses have become classic experiments in the undergraduate curriculum, traditional syntheses of the free-base meso-tetraphenylporphyrin (H2TPP) and its metallated derivatives can be energy-intensive, use hazardous solvents, and generate appreciable amounts of waste. In an attempt to make the synthesis of H2TPP and its metallated derivatives (MTPP where M = metal) better aligned with the principles of green chemistry, we optimized a microwave-assisted, microscale synthesis of H2TPP and alternative routes toward the metallation of H2TPP including solvent-substituted reflux and mechanochemical syntheses for the undergraduate teaching laboratory. The greenness of these syntheses were evaluated using various green metrics and qualitative comparison to previously reported syntheses. GRAPHICAL ABSTRACT
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来源期刊
Green Chemistry Letters and Reviews
Green Chemistry Letters and Reviews CHEMISTRY, MULTIDISCIPLINARY-GREEN & SUSTAINABLE SCIENCE & TECHNOLOGY
CiteScore
9.10
自引率
3.00%
发文量
48
期刊介绍: Green Chemistry Letters and Reviews is an Open Access, peer-reviewed journal focused on rapid publication of innovative new syntheses and procedures that reduce or eliminate the use and generation of hazardous materials. Reviews of state-of-the-art green chemistry technologies are also included within the journal''s scope. Green Chemistry Letters and Reviews is divided into three overlapping topic areas: research, education, and industrial implementation. The journal publishes both letters, which concisely communicate the most time-sensitive results, and reviews, which aid researchers in understanding the state of science on important green chemistry topics. Submissions are encouraged which apply the 12 principles of green chemistry to: -Green Chemistry Education- Synthetic Reaction Pathways- Research and Process Analytical Techniques- Separation and Purification Technologies- Renewable Feedstocks- Degradable Products
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