modification of nanostructure configuration through the manipulation of hydrogen bonded amphiphile self-association

• Published in: Soft matter 2016-05, Vol.12 (18), p.4221-4228
• Main Authors: Hiscock, Jennifer R, Bustone, Gianluca P, Wilson, Ben, Belsey, Kate E, Blackholly, Laura R
• Format: Article
• ISSN: 1744-683X; 1744-6848
• DOI: 10.1039/c6sm00529b

Herein, we report the synthesis of a novel amphiphilic salt containing a number of hydrogen bond donating (HBD) and accepting (HBA) functionalities. This amphiphile has been shown to self-associate via hydrogen bond formation in a DMSO solution, confirmed through a combination of NMR, UV-Vis and dynamic light scattering and supported by X-ray diffraction studies. The combination of different HBD and HBA functionalities within the amphiphile structure gives rise to a variety of competitive, self-associative hydrogen bonding modes that result in the formation of 'frustrated' hydrogen bonded nanostructures. These nanostructures can be altered through the addition of competitive HBD arrays and/or HBA anionic guests. The addition of these competitive species modifies the type of self-associative hydrogen bonding modes present between the amphiphilic molecules, triggering the in situ formation of novel hydrogen bonded nanostructures. Previously overlooked simple amphiphiles show an exciting capacity for complex hydrogen bond mediated self-association and diverse nanostructure formation.