posted on 2004-12-29, 00:00authored byTeruyuki Mitsumori, Michael Bendikov, Olivier Dautel, Fred Wudl, Takeshi Shioya, Hideki Sato, Yoshiharu Sato
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.