Novel tetrapodal molecules and reticular polyamides based on tetraphenylmethane

Lorenzi, Gian ; Manessis, Andreas ; Tirelli, Nicola ; Gramlich, Volker

In: Structural Chemistry, 1997, vol. 8, no. 6, p. 435-441

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    A series of tetrapodal derivatives of tetraphenylmethane were synthesized and characterized. Crystals obtained from tetrakis(4-acetamidophenyl)methane (1c) and from tetrakis[4-(4-aminobenzamido)phenyl]methane (2b) were analyzed by X-ray diffraction. The analyses pointed to the crystal packing problems faced by molecules of this kind by showing that the crystals, with composition1c·2DMF·2H2O and2b·2DMSO, respectively, contained cocrystallized solvent molecules. The solvent molecules were found in both cases to be held in place by H bonds; in the case of2b·2DMSO they occupied channels running along theb axis. Tetrakis(4-aminophenyl)methane (1b) was used in polycondensation reactions with terephthalic acid, under modified Yamazaki conditions, to produce rigid aromatic polyamide networks. The networks were obtained as gels encompassing the whole volume of the reaction mixture. The volume of the gels did not vary noticeably upon changing the solvent (1-methyl-2-pyrrolidone) with less polar solvents, but the gels collapsed upon drying. No crystallinity was observed