Novel spiropyran amphiphiles and their application as light-responsive liquid crystalline components

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dc.contributor.authorTangso, KJen_AU
dc.contributor.authorFong, WKen_AU
dc.contributor.authorDarwish, TAen_AU
dc.contributor.authorKirby, Nen_AU
dc.contributor.authorBoyd, BJen_AU
dc.contributor.authorHanley, TLen_AU
dc.date.accessioned2014-06-19T04:26:41Zen_AU
dc.date.available2014-06-19T04:26:41Zen_AU
dc.date.issued2013-09-05en_AU
dc.date.statistics2014-06-19en_AU
dc.description.abstractLight-responsive materials formed by liquid crystalline lipids in water have potential application to drug delivery through inclusion of photochromic additives such as spiropyran. A series of novel analogues of spiropyran (SP) have been synthesized with an SP headgroup that possess a C8 (SP-OC), C12 (SP-L), and C16 (SP-P) tail to probe the influence of the length of the hydrophobic tail on their physicochemical properties and effect on behavior in liquid crystal matrices with a view to application as stimulus-responsive elements on ultraviolet irradiation. In addition, compounds possessing an oleyl (SP-OL) and phytanyl (SP-PHYT) tail, to mimic those of the ?parent? reverse bicontinuous cubic (V2) phase forming lipids, glyceryl monooleate (GMO) and phytantriol, were also prepared. The photochromic compounds were characterized by their melting points and photophysical behavior in solution using techniques including hot stage microscopy (HSM), differential scanning calorimetry (DSC), and UV?visible spectroscopy. Their effect on the equilibrium nanostructure of bulk V2 phases and phase-switching kinetics after exposure to UV light was assessed using small-angle X-ray scattering (SAXS). The melting point of the SP derivatives decreased linearly with increasing chain length, which suggests that interactions between the head groups governed their melting point, rather than the van der Waals interactions between the tails. Changing the R group did not influence the equilibrium rate constants for the isomerization of SP. Phase transition temperatures of liquid crystalline (LC) matrices were influenced significantly by incorporation of the SP derivatives and were greatest when the photochromic compound possessed an intermediate tail length substituent compared to the short alkyl or bulkier moieties. The level of disruption of lipid packing, and hence phase structure, were dependent on the duration of UV exposure. © 2013, American Chemical Society.en_AU
dc.identifier.citationTangso, K. J., Fong, W. K., Darwish, T., Kirby, N., Boyd, B. J., & Hanley, T. L. (2013). Novel spiropyran amphiphiles and their application as light-responsive liquid crystalline components. Journal of Physical Chemistry B, 117(35), 10203-10210. doi:10.1021/jp403840men_AU
dc.identifier.govdoc5447en_AU
dc.identifier.issn1520-6106en_AU
dc.identifier.issue35en_AU
dc.identifier.journaltitleJournal of Physical Chemistry Ben_AU
dc.identifier.pagination10203-10210en_AU
dc.identifier.urihttp://dx.doi.org/10.1021/jp403840men_AU
dc.identifier.urihttp://apo.ansto.gov.au/dspace/handle/10238/5699en_AU
dc.identifier.volume117en_AU
dc.language.isoenen_AU
dc.publisherAmerican Chemical Societyen_AU
dc.subjectDrugsen_AU
dc.subjectFilmsen_AU
dc.subjectNanostructuresen_AU
dc.subjectIn vitroen_AU
dc.subjectBehavioren_AU
dc.subjectLipidsen_AU
dc.titleNovel spiropyran amphiphiles and their application as light-responsive liquid crystalline componentsen_AU
dc.typeJournal Articleen_AU
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