title: Mechanochemical click reaction as a tool for making carbohydrate-based triazole-linked self-assembling materials (CTSAMs).
abstract: Various glycosides in which glycosylated triazole residues are anchored on to a central phenyl ring have been prepared under green reaction conditions by a solvent-free mechanochemical method. Some of the glycosides exhibited the ability to form gels when in contact with long chain hydrocarbons, e.g. hexane, heptane and octane, and this property was phase-selective. Thus, from a mixture of hexane-water, the compounds preferably absorbed the alkane to form a gel. The gelation ability was found to increase with an increasing number of substituents on the phenyl ring but only up to tetra-substitution. The hexa-substituted phenyl derivative did not swell in the hydrocarbon solvents investigated. The spontaneous self-assembling properties of these compounds in hexane have been investigated by transmission electron microscopy (TEM). Molecular modelling was used to optimize the structural geometry of these carbohydrate-based triazole-linked self-assembling materials (CTSAMs) and to rationalize their behaviour.
authors.affiliation: Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Punjab, India.
authors.forename: Mohit
authors.initials: M
authors.lastname: Tyagi
authors.affiliation: Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Punjab, India.
authors.forename: Nikhil
authors.initials: N
authors.lastname: Taxak
authors.affiliation: Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Punjab, India.
authors.forename: Prasad V
authors.initials: PV
authors.lastname: Bharatam
authors.affiliation: Institute of Microbial Technology, Sector 39A, Chandigarh 160036, India.
authors.forename: Hemraj
authors.initials: H
authors.lastname: Nandanwar
authors.affiliation: Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Punjab, India. Electronic address: rkartha@niper.ac.in.
authors.forename: K P Ravindranathan
authors.initials: KP
authors.lastname: Kartha
mesh_terms: D002236:Carbohydrate Conformation; D005782:Gels / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis*; D006586:Hexanes / Q000737:chemistry*; D046529:Microscopy, Electron, Transmission; D008958:Models, Molecular; D014230:Triazoles / Q000737:chemistry*
chemical_list: D005782:Gels; D006027:Glycosides; D006586:Hexanes; D014230:Triazoles
keywords: CTSAMs; Mechanochemical click reaction; Nano bioorganomaterials; Organogelators