Supramolecular helical nanostructures from self-assembly of coil–rod–coil amphiphilic molecules incorporating the dianthranide unit

Abstract

Coil-rod-coil amphipathic oligomers composed of a rigid dianthranide unit and a hydrophilic branched oligoether as the coil segment were synthesized. These amphiphilic molecules self-assemble into clew-like aggregates composed of fibres or helical nanofibers in aqueous solution. Subsequently, supramolecular polymers were produced from the above objects through charge-transfer interactions by adding 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (4F-TCNQ). Interestingly, temperature-sensitive supramolecular chirality was induced by lateral methyl units located at the interface of the rigid and flexible segments. However, upon addition of the electron-acceptor molecule, 4F-TCNQ, strong donor-acceptor interactions restrict any change in supramolecular chirality with temperature.

Supramolecular nanostructures of coil–rod–coil molecules containing a 9,10-distyrylanthracene group in aqueous solution and their optical properties of assemblies

“…This may be attributed to the formation of the charge transfer complex between the DSA derivatives and TNF, resulting in quenching fluorescence of the system. 51–53 The formation of the charge transfer complex was further verified by 1 H-NMR measurements (Fig. S7a, S7c, and S7e, ESI†).…”

Construction of nanoaggregates from amphiphilic supramolecules containing barbiturate and Hamilton wedge units

“…Rod–coil molecules further have strong self‐organizing capacities to produce well‐defined supramolecular nanostructures. This may be attributed to the microseparation of rigid and flexible domains combined with the intermolecular interactions related to hydrogen bonds, and electrostatic, hydrophobic/hydrophilic and π – π interactions 29–36 . In related work, the current authors have also reported the construction of n‐shaped 37, 38 and bent‐shaped 39 rod–coil molecular assemblies in aqueous solutions.…”

Photoresponsive reversible self-assembly of rod-coil amphiphiles containing spiropyran groups

“…[39][40][41] Various assembly nanostructures have been constructed by adjusting the chain length, rod shape of the amphiphilic rodcoil molecules, or modifying their molecular structures with functional groups. [42][43][44] Lee et al, for example, constructed 2D porous nanosheets, toroids, and helical fibers from bent and disk-shaped molecules in water/methanol or water/tetrahydrofuran (THF) mixed solutions. 45,46 We recently reported that rodcoil molecules with pyrene and anthracene units assembled in an aqueous solution into fibers, nanoparticles, multilayer nanotubes, and nanosheets and used them as nanoreactors for the Suzuki cross-coupling reaction.…”