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Controlled Nanodimensional Supramolecular Self‐Assembly of Tetra‐Alkylated Naphthalene Diimide Derivatives
Author(s) -
Bhosale Sheshanath V.,
Ghule Namdev V.,
Al Kobaisi Mohammad,
Kelson Melissa M. A.,
Bhosale Sidhanath V.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201304117
Subject(s) - supramolecular chemistry , alkyl , diimide , solvophobic , self assembly , nanostructure , materials science , stacking , supramolecular assembly , naphthalene , non covalent interactions , chemistry , polymer chemistry , chemical engineering , nanotechnology , perylene , hydrogen bond , organic chemistry , molecule , engineering
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 (C 8 H 17 , C 12 H 25 , and C 16 H 33 ) 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 CHCl 3 /MeOH and CHCl 3 /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.