Abstract
Isophthalic acid derivatives (CnIP), bearing alkylamide chains (–CONHCnH2n+1: n = 6, 10, 14, and 18) at the 5-position that can participate in hydrogen bonding, were prepared and evaluated for their hydrogen-bonding molecular assembly structures for organogelation and liquid crystal formation. The hydrogen-bonding carboxylic acid (–COOH) groups form a ring-shaped (CnIP)6 hexamer or a one-dimensional (1D) zig-zag (CnIP)∞ chain. Although neither organogelation nor liquid crystal formation was observed in the isophthalic acid derivative bearing an alkoxy (–OC14H29) chain, C14IP and C18IP derivatives could form both organogel and liquid crystal states through intermolecular N–H⋯O = amide-type hydrogen-bonding interactions. A discotic hexagonal columnar liquid crystal (Colh) phase was observed in hydrated (C14IP)6·(H2O)n and (C18IP)6·(H2O)n, whereas a lamella-type liquid crystal (La) phase was confirmed in the unhydrated C18IP. In the Colh phase, O–H⋯O hydrogen-bonding ring-shaped (C14IP)6 and (C18IP)6 hexamers assembled to form the tubular molecular assembly stabilized by intermolecular–N–H⋯O = hydrogen-bonding interactions along the tube growth direction, where H2O molecules were contained within the hydrophilic space. On the other hand, the N–H⋯O = hydrogen-bonding interactions between the 1D zig-zag (CnIP)∞ chains formed a layer-type molecular assembly of the La-phase in the absence of water molecules.
Highlights
Amide-type N–H/O 1⁄4 hydrogen-bonding in polypeptide chains plays an important role in forming the secondary protein structures of a-helices and b-sheets, which are further assembled to form ternary protein structures through weak van der Waals interactions.[1]
Isophthalic acid derivatives (CnIP), bearing alkylamide chains (–CONHCnH2n+1: n 1⁄4 6, 10, 14, and 18) at the 5-position that can participate in hydrogen bonding, were prepared and evaluated for their hydrogenbonding molecular assembly structures for organogelation and liquid crystal formation
In the Colh phase, O–H/O hydrogen-bonding ring-shaped (C14IP)[6] and (C18IP)[6] hexamers assembled to form the tubular molecular assembly stabilized by intermolecular–N–H/O 1⁄4 hydrogen-bonding interactions along the tube growth direction, where H2O molecules were contained within the hydrophilic space
Summary
Amide-type N–H/O 1⁄4 hydrogen-bonding in polypeptide chains plays an important role in forming the secondary protein structures of a-helices and b-sheets, which are further assembled to form ternary protein structures through weak van der Waals interactions.[1]. Isophthalic acid derivatives (CnIP), bearing alkylamide chains (–CONHCnH2n+1: n 1⁄4 6, 10, 14, and 18) at the 5-position that can participate in hydrogen bonding, were prepared and evaluated for their hydrogenbonding molecular assembly structures for organogelation and liquid crystal formation.
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
