Norbornene chaotropic salts as low molecular mass ionic organogelators (LMIOGs)

Jordan R Engstrom; Aramballi J Savyasachi; Marzieh Parhizkar; Alessandra Sutti; Chris S Hawes; Jonathan M White; Thorfinnur Gunnlaugsson; Frederick M Pfeffer

doi:10.1039/c8sc01798k

Norbornene chaotropic salts as low molecular mass ionic organogelators (LMIOGs)

Chem Sci. 2018 May 16;9(23):5233-5241. doi: 10.1039/c8sc01798k. eCollection 2018 Jun 21.

Authors

Jordan R Engstrom¹, Aramballi J Savyasachi², Marzieh Parhizkar³, Alessandra Sutti³, Chris S Hawes⁴, Jonathan M White⁵, Thorfinnur Gunnlaugsson², Frederick M Pfeffer¹

Affiliations

¹ School of Life and Environmental Sciences , Deakin University , Waurn Ponds , Victoria 3216 , Australia . Email: fred.pfeffer@deakin.edu.au.
² School of Chemistry and Trinity Biomedical Sciences Institute (TBSI) , Trinity College Dublin , The University of Dublin , Dublin 2 , Ireland . Email: gunnlaut@tcd.ie.
³ Institute for Frontier Materials , Deakin University , Waurn Ponds , Victoria 3216 , Australia . Email: asutti@deakin.edu.au.
⁴ School of Chemical and Physical Sciences , Keele University , Staffordshire , ST5 5BG , UK.
⁵ Bio21 Institute , School of Chemistry , University of Melbourne , Parkville , 3010 , Australia.

Abstract

Phenylalanine functionalised norbornene (9:Na) functions as a potent, low molecular-mass (M_W = 333 Da) ionic organogelator with a minimum gelating concentration of 0.5 wt% in THF, i-PrOH, 1,4-dioxane and n-BuOH. Fibrous crystals form in the gel and X-ray crystallography identified a cation mediated helical assembly process controlled by the chirality of the phenylalanine. In addition to excellent gelating properties 9:Na readily forms aqueous biphasic and triphasic systems.