Affordable Access

deepdyve-link deepdyve-link
Publisher Website

Self-assembly of coronene bisimides: mechanistic insight and chiral amplification.

Authors
  • Kulkarni, Chidambar
  • Munirathinam, Rajesh
  • George, Subi J
Type
Published Article
Journal
Chemistry - A European Journal
Publisher
Wiley (John Wiley & Sons)
Publication Date
Aug 19, 2013
Volume
19
Issue
34
Pages
11270–11278
Identifiers
DOI: 10.1002/chem.201301251
PMID: 23813722
Source
Medline
Keywords
License
Unknown

Abstract

The study of the organization of small π-conjugated molecules is imperative to understanding and controlling its properties for various applications. Coronene bisimides (CBIs) are potential candidates for novel liquid-crystalline materials and active n-type semiconductor molecules in organic electronics. To understand the self-assembly of this seldom-studied chromophore, we have designed two derivatives of CBIs bearing chiral and achiral 3,4,5-trialkoxyphenyl groups at the imide position, named as CBI-GCH and CBI-GACH, respectively. CBI-GCH self-assembles mainly through π-stacking and van der Waals interactions in nonpolar methylcyclohexane to result in long 1D fibrillar stacks. The mechanism of supramolecular polymerization was probed by using chiroptical studies, which showed an isodesmic pathway for CBI-GCH. The thermodynamic parameters that govern the self-assembly are detailed. CBI-GACH also shows similar self-assembly behavior as its chiral counterpart. X-ray diffraction studies of both molecules reveals a 2D hexagonal columnar arrangement. The coassembly of CBI-GCH and CBI-GACH shows chiral amplification (sergeant and soldiers experiment) with saturation at 30-50 % of the chiral derivative, which was further used to study the dynamics of the assembly. Thus, this study presents a rare report of chiral amplification in an isodesmic system.

Report this publication

Statistics

Seen <100 times