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Polycyclic Aromatic Hydrocarbons (PAH)

Polycyclic Aromatic Hydrocarbons (PAH). Tobe Labo Ayumi Yoshizaki. Contents. ＊ Introduction - Carbon-carbon Bond - Planar Molecule ＊ PAH - What is PAH ? - Application of PAH ＊ History - Successive Synthesis Method

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Polycyclic Aromatic Hydrocarbons (PAH)

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  1. Polycyclic Aromatic Hydrocarbons(PAH) TobeLabo AyumiYoshizaki

  2. Contents ＊Introduction - Carbon-carbon Bond - Planar Molecule ＊PAH - What is PAH ? - Application of PAH ＊History - Successive Synthesis Method ＊New Synthesis Method - Recent Research ＊My Project ＊Summary

  3. Carbon-carbon Bond Because the carbon atom has four unpaired electrons, four bonds are necessary. Diamond and Graphite, the isotopes of the carbon, are described below. π-electron sp3 sp2 van der Waals' force Diamond Graphite

  4. Planar Molecule Conduction Band Wide Valence Band + Six sp2Carbons Six Hydrogens Benzene

  5. What is PAH ? ＊Polycyclic Aromatic Hydrocarbons (PAH) →Compound that one or more aromatic rings are condensed Azulene Naphthalene Anthracene Phenanthrene Perylene

  6. Semiconductor The curtain and the screen become the televisions. The display is printed on clothes.

  7. Application of PAH Pentacene Pentaceneis an organic compound that first exceeds the amorphous silicon level(Driving level of liquid crystal display) . Amorphous Silicon Level Career Mobility > 1.0 cm2/Vs Pentacene Level Career Mobility > 1.5cm2/Vs It is historical event of science and technology that organic semiconductor replaces inorganic semiconductor.

  8. Traditional Synthesis Method ＊Friedel-Crafts Reaction ＊Diels-Alder Reaction Perylene Postovoslii, I. et al. Zh. Obsch. Khim.1937, 7, 2919-2924. Perylene Coronene Clar, E. et al. J. Chem. Soc.1957, 4616-4619.

  9. Recent Synthesis Method Hexa-peri-hexabenzocoronene Diels-Alder Reaction Dehydro- genation

  10. New Synthesis Method Cyclic Structure → TransannularCyclization → TandemCyclization Hauptmann, H. et al. Tetrahedron Lett.1980, 21, 897-898. Non-cyclicStructure → Low Selectivity, Low Yield

  11. [N]annulene Cyclobutadiene [4]annulene Benzene [6]annulene [18]annulene Dehydrobenzo- [8]annulene Dehydrobenzo- [14]annulene Dehydrobenzo- [12]annulene

  12. Recent Research ①Nucleophile ②Charge Transfer ③TransannularCyclization Otera, J. et al. Chem. Lett. 2008, 37, 1296-1297.

  13. My Project

  14. Summary ＊Polycyclic Aromatic Hydrocarbons (PAH), Compound that one or more aromatic rings are condensed, are expected that replaces inorganic semiconductor. ＊ Traditionally, PAHs have been synthesized in stepwise synthesis methods which construct a ring one-by-one. ＊ In recent years, on the other hand, plural rings of PAHs are efficiently constructed. ＊ Recently, we have developed new single-step synthetic methods with high efficiency by tandem cyclization reaction of integrated acetylene.

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