Abstract
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 16π system, which is divided into 10π and 6π aromatic systems. We also report a relatively easy protonation of INI, which occurs at a carbon, rather than nitrogen atom.
| Original language | English |
|---|---|
| Pages (from-to) | 16793-16803 |
| Number of pages | 11 |
| Journal | Journal of the American Chemical Society |
| Volume | 126 |
| Issue number | 51 |
| DOIs | |
| Publication status | Published - Dec 29 2004 |
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Cite this
Synthesis and properties of highly fluorescent indolizino[3,4,5-ab] isoindoles. / Mitsumori, Teruyuki; Bendikov, Michael; Dautel, Olivier; Wudl, Fred; Shioya, Takeshi; Sato, Hideki; Sato, Yoshiharu.
In: Journal of the American Chemical Society, Vol. 126, No. 51, 29.12.2004, p. 16793-16803.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis and properties of highly fluorescent indolizino[3,4,5-ab] isoindoles
AU - Mitsumori, Teruyuki
AU - Bendikov, Michael
AU - Dautel, Olivier
AU - Wudl, Fred
AU - Shioya, Takeshi
AU - Sato, Hideki
AU - Sato, Yoshiharu
PY - 2004/12/29
Y1 - 2004/12/29
N2 - 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 16π system, which is divided into 10π and 6π aromatic systems. We also report a relatively easy protonation of INI, which occurs at a carbon, rather than nitrogen atom.
AB - 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 16π system, which is divided into 10π and 6π aromatic systems. We also report a relatively easy protonation of INI, which occurs at a carbon, rather than nitrogen atom.
UR - http://www.scopus.com/inward/record.url?scp=11244344107&partnerID=8YFLogxK
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U2 - 10.1021/ja049214x
DO - 10.1021/ja049214x
M3 - Article
C2 - 15612718
AN - SCOPUS:11244344107
VL - 126
SP - 16793
EP - 16803
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 51
ER -