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Issue 13, 2012
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Hydrogen bond directed self-assembly of cyclic dipeptide derivatives: gelation and ordered hierarchical architectures

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Abstract

Cyclo(Gly-L-Lys) ε-amino derivatives (1 and 2) were synthesised and exploited as low molecular weight (LMW) gelators and ordered hierarchical structures. Cyclic dipeptide (CDP) derivative 1 forms organogels in hexane, carbon tetrachloride, toluene and chloroform at minimal gelation concentrations (MGC) 5.5 wt%, 4.4 wt%, 2.6 wt% and 3.2 wt% respectively. Organogel (toluene) and hydrogel were obtained using CDP 2 at a MGC of 3.2 wt% and 2.5 wt% respectively. Interestingly, CDP 2 exhibits excimer emission in chloroform and self-assembles into ordered microporous hierarchical structures. The insight into supramolecular self-assembly of CDPs into nanofibres and ordered hierarchical structures was achieved by microscopy analysis. Presence of a network of strong intermolecular hydrogen bonding and aromatic π–π interactions was validated through concentration and temperature dependent NMR studies.

Graphical abstract: Hydrogen bond directed self-assembly of cyclic dipeptide derivatives: gelation and ordered hierarchical architectures

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Publication details

The article was received on 23 Feb 2012, accepted on 29 Apr 2012, published on 01 May 2012 and first published online on 01 May 2012


Article type: Communication
DOI: 10.1039/C2RA20342A
Citation: RSC Adv., 2012,2, 5539-5542
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    Hydrogen bond directed self-assembly of cyclic dipeptide derivatives: gelation and ordered hierarchical architectures

    S. Manchineella and T. Govindaraju, RSC Adv., 2012, 2, 5539
    DOI: 10.1039/C2RA20342A

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