NDLI: Hierarchical self-assembly of switchable nucleolipid supramolecular gels based on environmentally-sensitive fluorescent nucleoside analogs

Content Provider	Royal Society of Chemistry (RSC)
Author	Srivatsan, Seergazhi G. Nuthanakanti, Ashok
Copyright Year	2016
Abstract	Exquisite recognition and folding properties have rendered nucleic acids as useful supramolecular synthons for the construction of programmable architectures. Despite their proven applications in nanotechnology, scalability and fabrication of nucleic acid nanostructures still remain a challenge. Here, we describe a novel design strategy to construct new supramolecular nucleolipid synthons by using environmentally-sensitive fluorescent nucleoside analogs, based on 5-(benzofuran-2-yl)uracil and 5-(benzo[b]thiophen-2-yl)uracil cores, as the head group and fatty acids, attached to the ribose sugar, as the lipophilic group. These modified nucleoside–lipid hybrids formed organogels driven by hierarchical structures such as fibers, twisted ribbons, helical ribbons and nanotubes, which depended on the nature of fatty acid chain and nucleobase modification. NMR, single crystal X-ray and powder X-ray diffraction studies revealed the coordinated interplay of various non-covalent interactions invoked by modified nucleobase, sugar and fatty acid chains in setting up the pathway for the gelation process. Importantly, these nucleolipid gels retained or displayed aggregation-induced enhanced emission and their gelation behavior and photophysical properties could be reversibly switched by external stimuli such as temperature, ultrasound and chemicals. Furthermore, the switchable nature of nucleolipid gels to chemical stimuli enabled the selective two channel recognition of fluoride and Hg2+ ions through visual phase transition and fluorescence change. Fluorescent organogels exhibiting such a combination of useful features is rare, and hence, we expect that this innovative design of fluorescent nucleolipid supramolecular synthons could lead to the emergence of a new family of smart optical materials and probes.
Starting Page	3607
Ending Page	3619
Page Count	13
File Format	HTM / HTML PDF
ISSN	20403364
Volume Number	8
Issue Number	6
Journal	Nanoscale
DOI	10.1039/c5nr07490h
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Fluorescence Nucleobase X-ray crystallography Fluoride Carboxylic acid Ribose Benzofuran Fatty acid Interplay Entertainment Nucleoside Organogels Carbohydrate Nuclear magnetic resonance Uracil Ultrasound Nanotechnology Lipophilicity Synthon Phase transition
Content Type	Text
Resource Type	Article
Subject	Nanoscience and Nanotechnology

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