US 10,947,232 B1 · 11-arylcinnolino[2,3-f]phenanthridinium salts and method for producing the same

Abstract

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.

Claims9

Dependent claims

A 11-arylcinnolino[2,3-f]phenanthridinium salt compound, having the structure of the following formula (1):

wherein
R1 is selected from hydrogen (H), deuterium (D), methyl (Me), isopropyl (iPr), phenyl (Ph), methoxy (OMe), oxytrifluoromethyl (OCF3), trifluoromethyl (CF3), fluorine (F), dimethylamino (NMe2), and cyano (CN);
R2 is selected from hydrogen (H), deuterium (D), methyl (Me), isopropyl (iPr), phenyl (Ph), methoxy (OMe), oxytrifluoromethyl (OCF3), trifluoromethyl (CF3), fluorine (F), dimethylamino (NMe2), and cyano (CN);
R is selected from the group consisting of ester (CO2R′), amide (CONR′2), keto (COR′), aryl (Ar), nitrile (CN), nitro (NO2), trifluoromethyl (CF3), phosphonate (P(═O)OR′2), phosphine oxide (P(═)R′2), sulfonyl (SOR′), and sulfur oxide (SO2R′), and R1 is selected from a group consisting of alkyl and aryl.

1 more element

Dependencies are inferred from the claim text.

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

Life of this patent

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

Life of this patent

Abstract

Claims9