Abstract
In this work, we describe the synthesis, characterization, and self-assembly properties of a new tetrathiafulvalene (TTF)–triglycyl low-molecular-weight (LMW) gelator. Supramolecular organogels were obtained in various solvents via a heating–cooling cycle. Critical gelation concentrations (CGC) (range ≈ 5–50 g/L) and thermal gel-to-sol transition temperatures (Tgel) (range ≈ 36–51 °C) were determined for each gel. Fourier transform infrared (FT-IR) spectroscopy suggested that the gelator is also aggregated in its solid state via a similar hydrogen-bonding pattern. The fibrillar microstructure and viscoelastic properties of selected gels were demonstrated by means of field-emission electron microscopy (FE-SEM) and rheological measurements. As expected, exposure of a model xerogel to I2 vapor caused the oxidation of the TTF unit as confirmed by UV-vis-NIR analysis. However, FT-IR spectroscopy showed that the oxidation was accompanied with concurrent alteration of the hydrogen-bonded network.
Highlights
Oligonucleotide conjugates carrying aromatic systems are important tools for a large number of applications due to their enhanced hybridization properties and their special fluorescence and chemical properties coming from the aromatic moieties [1,2,3,4,5,6]
Tetrathiafulvalene (TTF) derivatives have been incorporated in oligonucleotides demonstrating the fluorescence-quenching properties of the DNA–TTF conjugates upon hybridization [7], the preservation of the electrochemical properties of TTF [8], an enhanced affinity to complementary sequences [9], and compatibility with the RNA
In this communication we describe the synthesis, characterization, and gelation properties of a new TTF–triglycyl-based LMW organogelator (Figure 1)
Summary
Oligonucleotide conjugates carrying aromatic systems are important tools for a large number of applications due to their enhanced hybridization properties and their special fluorescence and chemical properties coming from the aromatic moieties [1,2,3,4,5,6]. Tetrathiafulvalene (TTF) derivatives have been incorporated in oligonucleotides demonstrating the fluorescence-quenching properties of the DNA–TTF conjugates upon hybridization [7], the preservation of the electrochemical properties of TTF [8], an enhanced affinity to complementary sequences [9], and compatibility with the RNA interference mechanism for gene inhibition [10]. In the field of materials chemistry, TTF and its derivatives constitute electron donors that can form charge-transfer (CT) complexes and have been widely studied for the development of electrically conducting materials [11,12].
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