Poly(N-isopropylacrylamide-co-monoalkyl itaconate)s crosslinked with tetraallylammonium bromide has structures including both hydrophobic and ionizable groups. In this research, Candan Erbil and colleagues discuss the effects of side chains on the compressive strengths of hydrogels in terms of physical crosslinks created by intermolecular interactions between octyl, cetyl and cyclohexyl groups. These POM images under bright field and between cross-polarizers also support the presence of ordered structures. Anisotropic phase of these hydrophobic side chains aligned perpendicularly to the main chain due to the possible rod-like, face-to-face and extended-coil conformations. These materials are excellent candidates for antimicrobial studies–due to improved mechanical properties and cationically modified-hydrophobic structures–and for the controlled release of hydrophilic and/or hydrophobic drugs because of improved mechanical properties and dual-responsive phase transitions. (DOI: 10.1002/app.45039)