Synthesis of Triphenylene Derivatives by Rhodium-Catalyzed [2 + 2 + 2] Cycloaddition: Application to the Synthesis of Highly Fluorescent Triphenylene-Based Long Ladder Molecules.
英文:
Synthesis of Triphenylene Derivatives by Rhodium-Catalyzed [2 + 2 + 2] Cycloaddition: Application to the Synthesis of Highly Fluorescent Triphenylene-Based Long Ladder Molecules.
The convenient synthesis of substituted triphenylenes and azatriphenylenes has been achieved by the cationic rhodium(I)/H8-BINAP or BINAP complex-catalyzed [2 + 2 + 2] cycloaddn. under mild conditions. E.g., in presence of [Rh(cod)2]BF4 and H8-BINAP, cycloaddn. of biaryl-linked diyne (I) and MeC竕。CCO2Et gave 89% triphenylene (II). Photophys. properties of representative triphenylenes and azatriphenylenes were examd., which revealed that azatriphenylenes showed higher fluorescence quantum yields than triphenylenes. This method was successfully applied to the synthesis of highly fluorescent triphenylene-based long ladder mols. [on SciFinder(R)]