title: Amidophenol-modified amphiphilic calixarenes: synthesis, interfacial self-assembly, and acetaminophen crystal nucleation properties.
abstract: Three amidophenol-modified calixarenes have been produced reacting the parent 5,11,17,23-tetracarboxy-25,26,27,28-tetradodecyloxycalix[4]arene with o-, m-, and p-aminophenol. The produced amphiphiles have been shown to form stable monomolecular Langmuir layers on water. Working on subphases containing 1 mM acetaminophen (APAP), it has been demonstrated that the produced amphiphiles interact with this active pharmaceutically ingredient (API) with a relevant preference for the para-derivative that possesses in its structure substituents that are analogous to the target. Working at supersaturating concentrations of APAP, it has been demonstrated that the so-produced calixarene Langmuir monolayers do favor crystallization of APAP (polymorph I), with a clear effect of the packing density of the amphiphile at the interface on the quantity of produced crystals. Monolayers of the para-derivative have been transferred on solid substrates using the Langmuir-Blodgett technique; the so-produced ultrathin films have been shown to initiate surface crystal nucleation of APAP. The produced solids have been analyzed by single-crystal X-ray crystallography and shown to preferentially grow in the [010] direction.
authors.affiliation: School of Life Sciences, Institute of Chemistry and Bioanalytics, University of Applied Sciences Northwestern Switzerland, Gründenstrasse 40, CH-4132 Muttenz, Switzerland.
authors.forename: Negar
authors.initials: N
authors.lastname: Moridi
authors.forename: Dirk
authors.initials: D
authors.lastname: Elend
authors.forename: Oksana
authors.initials: O
authors.lastname: Danylyuk
authors.forename: Kinga
authors.initials: K
authors.lastname: Suwinska
authors.forename: Patrick
authors.initials: P
authors.lastname: Shahgaldian
mesh_terms: D000082:Acetaminophen / Q000737:chemistry*; D000388:Air; D047250:Calixarenes / Q000138:chemical synthesis* / Q000737:chemistry*; D003460:Crystallization; D008567:Membranes, Artificial; D008958:Models, Molecular; D015394:Molecular Structure; D010316:Particle Size; D010636:Phenols / Q000737:chemistry*; D013237:Stereoisomerism; D013499:Surface Properties; D014867:Water / Q000737:chemistry
chemical_list: D008567:Membranes, Artificial; D010636:Phenols; D014867:Water; D047250:Calixarenes; D000082:Acetaminophen