National Yang Ming Chiao Tung University

Industrial Technology Research Institute

Shih-Ching Chuang

Jayakumar Jayachandran

Yu-Wei Lin

Chih-Ping Chen

Yeu-Ding Chen

Fu-Wei Chan

The present invention provides 11-arylcinnolino[2,3-f]phenanthridinium salt compounds and method for producing the same by highly regioselective synthesis of 11-phenylimino[2,3-f]phenanthridin-9-ium salts from 2-azobiaryls and alkenes under catalysis of palladium, through double oxidative C—H coupling of alkenes, to give the polycyclic cinnolinophenanthridinium salts in moderate yields. The reaction mechanism involves ortho C—H olefination of 2-azobiaryls by alkenes, intramolecular aza-Michael addition, β-hydride elimination, electrophilic palladation followed by intramolecular C—H activation and reductive elimination. The prepared quaternary ammonium salts are candidate materials for solution-processable OLED and bioimaging materials.

11-arylcinnolino[2,3-f]phenanthridinium salts and method for producing the same

The present invention provides 11-arylcinnolino[2,3-f]phenanthridinium salt compounds and method for producing the same by highly regioselective synthesis of 11-phenylimino[2,3-f]phenanthridin-9-ium salts from 2-azobiaryls and alkenes under catalysis of palladium, through double oxidative C&#x2014;H coupling of alkenes, to give the polycyclic cinnolinophenanthridinium salts in moderate yields. The reaction mechanism involves ortho C&#x2014;H olefination of 2-azobiaryls by alkenes, intramolecular aza-Michael addition, &#x3b2;-hydride elimination, electrophilic palladation followed by intramolecular C&#x2014;H activation and reductive elimination. The prepared quaternary ammonium salts are candidate materials for solution-processable OLED and bioimaging materials.

Disclosed is a fullerene derivative having a formula of F-Cy, wherein F is an open-cage fullerene, and Cy is a chalcogenyl group. The fullerene derivative can be applied to hydrogen storage material and an optoelectronic device such as an organic light emitting diode (OLED), a solar cell, or an organic thin film transistor (TFT).

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Hsinchu, Taiwan

Shih-Ching Chuang