Tetraphenylporphyrin
Tetraphenylporphyrin (TPP) is a synthetic porphyrin derivative with the chemical formula C44H30N4. It is a highly conjugated macrocyclic compound that is widely used in various fields of chemistry and materials science.
Structure and Synthesis[edit | edit source]
Tetraphenylporphyrin consists of a porphyrin core with four phenyl groups attached to the meso positions of the macrocycle. The porphyrin core is a planar, aromatic system that can coordinate metal ions in its central cavity, forming metalloporphyrins. The phenyl groups increase the solubility of TPP in organic solvents and can be further functionalized to introduce additional properties.
The synthesis of TPP typically involves the condensation of pyrrole with benzaldehyde in the presence of an acid catalyst, followed by oxidation. This process is known as the Adler-Longo method.
Properties[edit | edit source]
Tetraphenylporphyrin exhibits strong absorption in the visible region of the electromagnetic spectrum, with characteristic Soret and Q bands. These optical properties make TPP useful in various applications, including photodynamic therapy, organic photovoltaics, and as a fluorescent dye.
Applications[edit | edit source]
Photodynamic Therapy[edit | edit source]
In photodynamic therapy (PDT), TPP and its derivatives are used as photosensitizers. Upon irradiation with light of a specific wavelength, TPP generates reactive oxygen species that can kill cancer cells or pathogens.
Organic Photovoltaics[edit | edit source]
Tetraphenylporphyrin is used in the development of organic photovoltaics (OPVs) due to its ability to absorb light and convert it into electrical energy. TPP can be incorporated into the active layer of OPVs to enhance their efficiency.
Fluorescent Dye[edit | edit source]
TPP is also employed as a fluorescent dye in various analytical techniques, including fluorescence microscopy and flow cytometry. Its strong fluorescence and stability make it suitable for labeling and detecting biological molecules.
Metalloporphyrins[edit | edit source]
Tetraphenylporphyrin can coordinate with various metal ions to form metalloporphyrins. These complexes have diverse applications in catalysis, material science, and biochemistry. For example, iron(III) tetraphenylporphyrin is used as a model compound for studying the active sites of heme proteins.
See Also[edit | edit source]
References[edit | edit source]
External Links[edit | edit source]
Search WikiMD
Ad.Tired of being Overweight? Try W8MD's physician weight loss program.
Semaglutide (Ozempic / Wegovy and Tirzepatide (Mounjaro / Zepbound) available.
Advertise on WikiMD
WikiMD's Wellness Encyclopedia |
Let Food Be Thy Medicine Medicine Thy Food - Hippocrates |
Translate this page: - East Asian
中文,
日本,
한국어,
South Asian
हिन्दी,
தமிழ்,
తెలుగు,
Urdu,
ಕನ್ನಡ,
Southeast Asian
Indonesian,
Vietnamese,
Thai,
မြန်မာဘာသာ,
বাংলা
European
español,
Deutsch,
français,
Greek,
português do Brasil,
polski,
română,
русский,
Nederlands,
norsk,
svenska,
suomi,
Italian
Middle Eastern & African
عربى,
Turkish,
Persian,
Hebrew,
Afrikaans,
isiZulu,
Kiswahili,
Other
Bulgarian,
Hungarian,
Czech,
Swedish,
മലയാളം,
मराठी,
ਪੰਜਾਬੀ,
ગુજરાતી,
Portuguese,
Ukrainian
Medical Disclaimer: WikiMD is not a substitute for professional medical advice. The information on WikiMD is provided as an information resource only, may be incorrect, outdated or misleading, and is not to be used or relied on for any diagnostic or treatment purposes. Please consult your health care provider before making any healthcare decisions or for guidance about a specific medical condition. WikiMD expressly disclaims responsibility, and shall have no liability, for any damages, loss, injury, or liability whatsoever suffered as a result of your reliance on the information contained in this site. By visiting this site you agree to the foregoing terms and conditions, which may from time to time be changed or supplemented by WikiMD. If you do not agree to the foregoing terms and conditions, you should not enter or use this site. See full disclaimer.
Credits:Most images are courtesy of Wikimedia commons, and templates Wikipedia, licensed under CC BY SA or similar.
Contributors: Prab R. Tumpati, MD