Issue 48, 2013

Self-assembly of a set of hydrophilic–solvophobic–hydrophobic coil–rod–coil molecules based on perylene diimide

Abstract

The self-assembly and the resulting morphology of a set of asymmetrically substituted perylene diimide is discussed. We synthesized perylene diimides with hydrophilic Jeffamine® (PEO/PPO co-oligomer) attached to the imide nitrogen on one side and (hydrophobic) alkyl chains of different lengths on the other. Although studies on asymmetrically substituted perylene diimides have been reported by various authors, both side chains in this work are linear and we discuss the effect of the length of the hydrophobic alkyl side chain on the self-assembly in water and aqueous mixtures and the resulting morphology. We find that self-assembly occurs in water in a range of concentrations (from 10−7 to 10−4 M), and the mode of packing of the H-stacked molecules changes with concentration for the propyl substitution. Although self-assembly does not occur in non-aqueous solvents such as acetone, it does upon addition of water. While other authors observed nano-belts and nano-fibers with asymmetrically substituted perylene diimides, the morphology of drop-cast films in our work consists of folded sheets and hollow tubes, of a few microns in diameter. Such folding in a non-chiral system such as the present case is attributed to predominant asymmetry of interactions between the molecules in the three directions, as we discussed in our previous work on an hydrogen bonded system (S. Khanna, M. K. Khan and P. Sundararajan, Langmuir, 2009, 25, 13183–13193).

Graphical abstract: Self-assembly of a set of hydrophilic–solvophobic–hydrophobic coil–rod–coil molecules based on perylene diimide

Supplementary files

Article information

Article type
Paper
Submitted
26 Jun 2013
Accepted
07 Nov 2013
First published
07 Nov 2013

Phys. Chem. Chem. Phys., 2013,15, 21058-21069

Self-assembly of a set of hydrophilic–solvophobic–hydrophobic coil–rod–coil molecules based on perylene diimide

M. R. Islam and P. R. Sundararajan, Phys. Chem. Chem. Phys., 2013, 15, 21058 DOI: 10.1039/C3CP52680A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements