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Langmuir-Blodgett Films
Published in Arthur T. Hubbard, The Handbook of Surface Imaging and Visualization, 2022
The porphyrin is one of the most important among biomolecules. The most stable synthetic porphyrin is 5, 10,15,20-tetraphenylporphyrin (TPP). The phthalocyanine (PC) is a very stable, planar, synthetic aromatic macrocycle. Many porphyrin and PC derivatives form good LB films, and in 1937, Langmuir and Schaefer built up multilayers from chlorophyll.36 LB films of both these molecules are important for applications, such as hole-burning, that may allow information storage using multiple frequency devices.
A greener tetraphenylporphyrin synthesis and metallation: an undergraduate teaching experiment
Published in Green Chemistry Letters and Reviews, 2023
Matthew A. Nitka, Katarina E. Zerbee, Julianne M. Dee, Matthew A. Cranswick, Edward P. Zovinka, John R. De Backere
The syntheses and reactions of porphyrins, such as meso-5,10,15,20-tetraphenyl-21H,23H-porphine (H2TPP, commonly referred to as tetraphenylporphyrin) shown in Scheme 1, are prevalent in undergraduate chemistry teaching laboratories worldwide (1–3). The H2TPP molecule is most widely used in this setting arguably due to its relative ease of synthesis and favorable physical properties for isolation and purification. The metallation of H2TPP to MTPP (M = metal ion, Scheme 1) is especially useful in inorganic teaching laboratories for discussing changes in electronic structure, coordination chemistry, bioinorganic chemistry, catalysis, and more (4–11). The synthesis of these highly colored compounds offers an instructive opportunity to expand lecture content within the laboratory, such as ring currents in aromatic systems, and electronic transitions through the use of 1H-NMR and UV-vis spectroscopies, respectively. Likewise, the importance of porphyrins and their derivatives in dye-sensitized solar cells, as photocatalysts, and in biology offers additional context for these compounds as timely and relevant advanced topics (12–14).