Bis[N-(4-carboxyphenyl)phtalimidyl]dimethylsilane prepared by the reaction between bis(3,4-dicarboxyphenyl)dimethylsilane anhydride and p-aminobenzoic acid has been used to built three novel hydrogen-bonded supramolecular polymers as a result of cocrystallization with pyridine derivatives: 4,4'-bipyridyl (SP1), 1,2-bis(4-pyridyl)ethylene (SP2), and 4,4'-azopyridine (SP3). The structures of the dianhydride, diacid, and derived supramolecular polymers were investigated by Fourier transform infrared (FTIR) and proton magnetic resonance (1H NMR) spectroscopy. Self-assembling was proved by the presence of the IR absorption bands around 1900 and 2400 cm-1 specific for hydrogen bond. The association constant values were estimated by using FTIR spectroscopy in solid state. According to X-ray diffraction study, the bis(3,4-dicarboxyphenyl)dimethylsilane anhydride (1) has an isolated molecular structure. Bis[N-(4-carboxyphenyl)phtalimidyl]dimethylsilane (2) molecules are associated in the crystal structure via dimeric O?H center dot center dot center dot O hydrogen bonds resulting in the wavy 1D supramolecular chain. The main packing motif for SP1 and SP3 is represented by wavy chain formed by alternating sequences of 4,4'-bipyridyl or 4,4'-azopyridine and bis[N(4-carboxyphenyl)phtalimidyl]dimethylsilane molecules linked by O?H center dot center dot center dot N hydrogen bonds. Thermal behavior was studied by differential scanning calorimetry and thermogravimetric analysis. The ability for the structuration in film was emphasized by atomic force microscopy. The molecular transport ability of the reversible associations was estimated by dynamic water vapor sorption (DVS) analysis. (c) 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012