Controlled Nanodimensional Supramolecular Self‐Assembly of Tetra‐Alkylated Naphthalene Diimide Derivatives

Abstract

Construction of thermodynamically stable nanostructures on the nano- to millimeter scales through noncovalent bonding plays an important role in material science. The self-assembly of tetra-alkylamino core-substituted naphthalene diimides (cNDIs) with variable alkyl chains (C8H17, C12H25, and C16H33) added on to the core leads to the formation of a variety of controlled morphologies and well-defined nanostructures. Such structures include nanorods, vesicular, belts, twisted ribbons, and donutlike morphologies (formed in CHCl3/MeOH and CHCl3/hexane mixtures) generated through solvophobic control. UV/Vis absorption and fluorescence spectroscopy demonstrate molecular aggregation in solution. Furthermore, SEM was employed to visualize the supramolecular self-assembled nanostructures. The growth of these structures is mainly due to packing of hydrophobic alkyl chains and π-π stacking of the cNDI core. The present study paves the way to rational and controlled designs of nanostructures made of optically active dyes (naphthalene diimide); this may open a new avenue towards tuning nanodimensional morphology.

Right handed chiral superstructures from achiral molecules: self-assembly with a twist

“…Figure 3d illustrate, the Φ F in methanol/THF ( f M/H = 90%) and hexane/THF ( f H/T = 90%) was calculated to be 19.6 and 9.8%, respectively. The fluorescence emission spectroscopy suggests the formation of face-to-face π-stacks of TPE chromophores in a similar manner that is observed in the case of J- and H-aggregates of aromatic chromophores 38 39 40 .…”

“…Typically, in A W/T , a reduction in absorption peak intensity is observed. The absorption maximum in A A/T and A M/T (80%, v/v ) shows a significant blue-shift of 22 nm (365 nm), respectively, which is typical for J-type aggregates 38 . While, the absorption of 1 in A H/T (80%, v/v ) gives a 16 nm red-shift, similar to H-type aggregates 38 .…”

Chiral Assembly of AIE‐Active Achiral Molecules: An Odd Effect in Self‐Assembly

“…Figure A shows the absorption spectra of 1 – 4 in acetonitrile/THF (9:1 v/v). Typically, the absorption maximum shows a redshift with increasing number of methylene groups in the side chains: 6 nm for 1 , 12 nm for 2 , 17 nm for 3 and 22 nm for 4 in comparison to the peak for 4 in pure THF, which is typical for J‐type aggregates …”

Recent progress in the usage of tetrabromo-substituted naphthalenetetracarboxylic dianhydride as a building block to construct organic semiconductors and their applications

“…3a, a variety of well-defined nanoarchitectures, such as nanorods, vesicular, belts, twisted ribbons and donut-like morphologies, were produced via solvophobic control, which was mainly attributed to the packing mode of hydrophobic alkyl chains and the π-π stacking interaction of the TBNDI core. 109 Examples of self-assembly of the bilateral alkyl-annulated TBNDIs are shown in Fig. 3b.…”

“…Fig.3(a) Molecular structures of NDI-4N-alkyl and the respective SEM micrographs (A-D) revealing the formation of supramolecular nanostructures. Reproduced with permission 109. Copyright 2014, Wiley-VCH.…”