Trimellitic anhydride → 9,9-Bis{4-(4-carboxy-phthalimido)phenyl}fluorene

Participants

Reaction Steps

To a stirred mixture of 9,9-bis(4-aminophenyl)fluorene (13.9 g, 40 mmol) and 80 ml of m-cresol was added 1,2,4-benzenetricarboxylic anhydride (16.1 g, 84 mmol) over two minutes. The resulting mixture was stirred under gentle reflux (163°-170° C.) for three hours and then at ambient temperature for 16 hours. A pale yellow precipitate was filtered, washed with methanol, washed with toluene, and then dried in a vacuum oven at 100°-105° C. for 16 hours to provide the title compound as a pale yellow powder (24.7 g, 88.7% yield) that had a melting point of 328°-331° C. and a 1H NMR spectrum (DMSO d6) corresponding to δ8.39 (d,2H), 8.29 (br s, 2H), 8.05 (d, 2H), 8.00 (d, 2H), 7.61 (d, 2H), and 7.40 (m, 12H).

Provenance & Evidence