An Easy Access to Organic Salt-Based Stimuli-Responsive and Multifunctional Supramolecular Hydrogels.
By exploiting orthogonal hydrogen bonding involving supramolecular synthons and hydrophobic/hydrophilic interactions, a new series of simple organic salt based hydrogelators derived from pyrene butyric acid and its β-alanine amide derivative, and various primary amines has been achieved. The hydrogels were characterised by microscopy, table-top rheology and dynamic rheology. FTIR, variable-temperature (1) H NMR and emission spectroscopy established the role of various supramolecular interactions such as hydrogen bonding and π-π stacking in hydrogelation. Single-crystal X-ray diffraction (SXRD) studies supported the conclusion that orthogonal hydrogen bonding involving amide-amide and primary ammonium monocarboxylate (PAM) synthons indeed played a crucial role in hydrogelation. The hydrogels were found to be stimuli-responsive and were capable of sensing ammonia and adsorbing water-soluble dye (methylene blue). All the hydrogelators were biocompatible (MTT assay in RAW 264.7 cells), indicating their suitability for use in drug delivery.
Department of Organic Chemistry, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Kolkata, 700032, India.
Joydeb
J
Majumder
Department of Organic Chemistry, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Kolkata, 700032, India. ocpd@iacs.res.in.
Parthasarathi
http://orcid.org/0000-0002-1011-2386
P
Dastidar
D000327:Adsorption; D000641:Ammonia / Q000032:analysis; D000818:Animals; D001672:Biocompatible Materials / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity; D002470:Cell Survival / Q000187:drug effects; D018360:Crystallography, X-Ray; D004337:Drug Carriers / Q000737:chemistry; D020100:Hydrogels / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D006860:Hydrogen Bonding; D057927:Hydrophobic and Hydrophilic Interactions; D009682:Magnetic Resonance Spectroscopy; D008751:Methylene Blue / Q000737:chemistry; D051379:Mice; D011721:Pyrenes / Q000737:chemistry*; D000067996:RAW 264.7 Cells; D012212:Rheology; D017550:Spectroscopy, Fourier Transform Infrared; D015091:beta-Alanine / Q000031:analogs & derivatives / Q000737:chemistry
D001672:Biocompatible Materials; D004337:Drug Carriers; D020100:Hydrogels; D011721:Pyrenes; D015091:beta-Alanine; C002218:1-pyrenebutyrate; C012731:beta-alanine amide; D000641:Ammonia; D008751:Methylene Blue
dye adsorption; gels; self-assembly; sensors; supramolecular chemistry