Many supramolecular naturally occurring machines can self-assemble into nanostructures that sense environmental changes and respond to them accordingly. In thermosensitive materials, when hydrophilic substances are modified to increase their hydrophobicity, the resulting material reaches a composition where it shows a lower critical solution temperature (LCST) before becoming entirely insoluble.  Most examples of this are polymers that experience a coil to globule shift and/or self-assembling into aggregates upon reaching a transition temperature (Tt).  It's essential that we modulate the three-dimensional configuration of said systems in order to create a selection of Tt's. Recently, we discovered non-polymeric supramolecular G-quadruplexes made from 8-aryl-2'-deoxyguanosine (8ArG) derivatives that show this phenomenon. Our interest is to control the three-dimensional distribution of hydrophobic patches affecting the LSCT by using constitutional isomers of 8ArG derivatives.  We will present the synthesis and characterization of two isomeric 8ArG derivatives via Differential Scanning Calorimetry, Dynamic Light Scattering, Mass-Spectrometry, IR and NMR.

Hydrophobic modulation of lower critical solution temperature of nonpolymeric thermosensitive supramolecules

243rd National Meeting (2012)

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