Covalent Capture of Self-Assembled Rosette Nanotubes

Abstract

Rosette nanotubes (RNTs) are self-assembled tubular architectures which have extensive chemical and physical tuning capabilities, owing to their ease of surface functionalization and flexible inner channel design. To marry these tunable features of the RNTs with the enhanced stability of a covalent polymer, here we demonstrate the covalent capture of the RNT supramolecular structure by polymerizing alkyldiamine functional groups expressed on their outer periphery in the presence of adipoyl chloride (nylon-6,6 process). The resulting polymeric materials were characterized using proton nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, dynamic light scattering, and differential scanning calorimetry. Transmission and scanning electron microscopy revealed the formation of fibers and films composed of RNTs.

Hydrogen‐Bonded Macrocyclic Supramolecular Systems in Solution and on Surfaces

“…They created a heterobicyclic G C monomer containing the Watson–Crick DDA H‐bond array of guanine and the AAD array of cytosine (Figure a). Because of the asymmetry of its H‐bonding edges, the G C monomer undergoes self‐assembly in water as well as in polar solvents to form a six‐membered macrocycle maintained by 18 H‐bonds. The resulting hexameric rosette then self‐organizes hierarchically to produce tubular stacks (named rosette nanotubes, RNs) with tunable dimensions and properties (Figure b).…”

Porphyrin derivatives as potent and selective blockers of neuronal Kv1 channels

“…This task was complemented using a model of the rat homologous Kv1.1 channel, derived from the crystallographic structure of Kv1.2, 12 to perform molecular modelling of its interaction with the porphyrins. The porphyrins examined in this (10)(11)(12)(13)(14)(15)(16)(17)(18) study are shown in Scheme 1. Of particular interest was to determine the effects on Kv1 selectivity of porphyrin substituent chain length (10-13), amide linkage (14), primary amine groups (17,18) and multiple charged groups (15,16).…”

“…The porphyrins examined in this (10)(11)(12)(13)(14)(15)(16)(17)(18) study are shown in Scheme 1. Of particular interest was to determine the effects on Kv1 selectivity of porphyrin substituent chain length (10-13), amide linkage (14), primary amine groups (17,18) and multiple charged groups (15,16). Four of the compounds purified were shown electrophysiologically to inhibit Kv1.1, 1.2 or both homo-tetrameric channels expressed in mammalian cells.…”

“…In the case of 6, the required diprotected triamine was prepared according to the procedure of Leonor et al 15 and then treated with TCPP using the EDCI procedure described above; this resulted in a yield of 35% after silica gel chromatography. For porphyrin 7, the required diprotected triamine was prepared 16 and coupled to TCPP using the EDCI protocol to give 7 in 66% yield after silica gel chromatography. The same EDCI coupling was employed for making porphyrins 8 and 9 from the corresponding amines (N,N-ethylenediamine and N,N-dimethyl-1,3-diaminopropane) in 62% and 59% yield, respectively.…”