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3140565 
Journal Article 
Self-Assembly of Coronene Bisimides: Mechanistic Insight and Chiral Amplification 
Kulkarni, C; Munirathinam, R; George, SJ 
2013 
Yes 
Chemistry: A European Journal
ISSN: 0947-6539
EISSN: 1521-3765 
19 
34 
11270-11278 
English 
23813722 
WOS:000323098100026 
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. 
chirality; coronene bisimides; isodesmic systems; liquid crystals; organic electronics; self-assembly