Synthesis and Properties of Highly Fluorescent Indolizino[3,4,5-ab]isoindoles
| Autor: | Michael Bendikov, Yoshiharu Sato, Hideki Sato, Takeshi Shioya, Fred Wudl, Olivier Dautel, Teruyuki Mitsumori |
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| Přispěvatelé: | Department of Chemistry and Biochemistry, Exotic Materials Institute, University of California, Los Angeles (UCLA), University of California [Los Angeles] (UCLA), University of California-University of California, Science and Technology Research Center (MCC), Mitsubishi Chemical Corporation |
| Rok vydání: | 2004 |
| Předmět: |
Isoindoles
[CHIM.ORGA]Chemical Sciences/Organic chemistry 010405 organic chemistry General Chemistry 010402 general chemistry 01 natural sciences Biochemistry Fluorescence Medicinal chemistry Catalysis Cycloaddition 0104 chemical sciences chemistry.chemical_compound Colloid and Surface Chemistry Acetylene chemistry Molecule Organic chemistry Organic synthesis Luminescence Isoindole |
| Zdroj: | Journal of the American Chemical Society Journal of the American Chemical Society, American Chemical Society, 2004, 126 (51), pp.16793-16803. ⟨10.1021/ja049214x⟩ |
| ISSN: | 1520-5126 0002-7863 |
| Popis: | International audience; We report here the synthesis, X-ray structures, optical and electrochemical properties, fabrication of light-emitting devices, and density functional calculations for indolizino[3,4,5-ab]isoindole (INI) derivatives. Strongly luminescent heterocycles based on the INI unit were synthesized by 1,3-dipolar cycloaddition reactions between pyrido[2,1-a]isoindole (PIS) and acetylene or ethylene derivatives. They are indolizino[3,4,5-ab]isoindoles 2-9 and 14-15, benzo[1',2'-1,2]indolizino[3,4,5-ab]isoindoles 10, pyridazino[4',5':1,2]indolizino[3,4,5-ab]isoindoles 12-13, and 2,3-hydropyridazino[4',5':1,2]indolizino[3,4,5-ab]isoindole-1,4-dione 11. The relative luminescence quantum yield can be as high as 90%. Their reduction and oxidation potentials and high luminescence can make these heterocycles possible alternatives to tris(8-hydroxyquinolinato)aluminum (Alq3). The brightness of the light-emitting device reached as high as 104 cd/m2 and indolizino[3,4,5-ab]isoindole 3 emits beautifully blue light. The X-ray crystal structures of INI derivatives were obtained for the first time. The geometries obtained from X-ray data and density functional theory calculations shed more light on an interesting formally antiaromatic 16 system, which is divided into 10 and 6 aromatic systems. We also report a relatively easy protonation of INI, which occurs at a carbon, rather than nitrogen atom. |
| Databáze: | OpenAIRE |
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