Abstract
Nanotubes are a fascinating kind of self‐assembled structure which have a wide interest and potential in supramolecular chemistry. We demonstrated that nanotubes of defined dimensions can be produced from dinucleobase monomers through two decoupled hierarchical cooperative processes: cyclotetramerization and supramolecular polymerization. Here we analyze the role of peripheral amide groups, which can form an array of hydrogen bonds along the tube axis, on this self‐assembly process. A combination of 1H NMR and CD spectroscopy techniques allowed us to analyze quantitatively the thermodynamics of each of these two processes separately. We found out that the presence of these amide directors is essential to guide the polymerization event and that their nature and number have a strong influence, not only on the stabilization of the stacks of macrocycles, but also on the supramolecular polymerization mechanism.
Highlights
Nanotubes are a fascinating kind of self-assembled structure which have a wide interest and potential in supramolecular chemistry
Self-assembled nanotubes and nanochannels built from organic molecules arise as promising materials that offer some distinct advantages with respect to carbon, inorganic or polymeric[3] materials
We recently reported on the self-assembly of dinucleobase rod-like monomers like GC1 (Figure 1a), comprising complementary G and C bases at the edges, into tubular structures[6] in alkane solvents.[6a]. Remarkably, this assembly process occurred through two decoupled cooperative steps of
Summary
General Methods: Mass Spectrometry (MS) and High ResolutionMass Spectrometry (HRMS) MALDI-TOF spectra were obtained from a BRUKER ULTRAFLEX III instrument equipped with a nitrogen laser operating at 337 nm. NMR spectra were recorded with a BRUKER AVANCE-II 300 MHz or a BRUKER DRX 500 MHz instrument. Emission spectra were recorded in a JASCO FP-8600 equipment using excitation and emission bandwidths of 5 nm in both cases, and a 50 ms response. CD spectra were recorded with a JASCO J-815 equipment. The slit width was set at 1000 μm and a DIT of 2 s was used. In all these three instruments the temperature was controlled using a JASCO Peltier thermostatted cell holder with a range of 263–383 K, adjustable temperature slope, and accuracy of 0.1 K. Transmission electron microscopy (TEM) images were obtained with a JEOL-JEM 1010 instrument operating at 100 kV for the stained samples and a JEM 1400K PLUS instrument operating at 100 kV for non-stained samples
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