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The High‐Throughput Synthesis and Phase Characterisation of Amphiphiles: A Sweet Case Study
Author(s) -
Feast George C.,
Hutt Oliver E.,
Mulet Xavier,
Conn Charlotte E.,
Drummond Calum J.,
Savage G. Paul
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201303514
Subject(s) - amphiphile , degree of unsaturation , chemistry , cycloaddition , lyotropic , lyotropic liquid crystal , phase (matter) , combinatorial chemistry , azide , hydrogen bond , organic chemistry , materials science , polymer chemistry , crystallography , chemical engineering , polymer , catalysis , molecule , liquid crystalline , engineering , copolymer
A new method for the discovery of amphiphiles by using high‐throughput (HT) methods to synthesise and characterise a library of galactose‐ and glucose‐containing amphiphilic compounds is presented. The copper‐catalysed azide–alkyne cycloaddition (CuAAC) “click” reaction between azide‐tethered simple sugars and alkyne‐substituted hydrophobic tails was employed to synthesise a library of compounds with systematic variations in chain length and unsaturation in a 24‐vial array format. The liquid–crystalline phase behaviour was characterised in a HT manner by using synchrotron small‐angle X‐ray scattering (SSAXS). The observed structural variation with respect to chain parameters, including chain length and degree of unsaturation, is discussed, as well as hydration effects and degree of hydrogen bonding between head groups. The validity of our HT screening approach was verified by resynthesising a short‐chain glucose amphiphile. A separate phase analysis of this compound confirmed the presence of numerous lyotropic liquid–crystalline phases.