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Issue 38, 2011
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Ionic liquid induced spontaneous symmetry breaking: emergence of predominant handedness during the self-assembly of tetrakis(4-sulfonatophenyl)porphyrin (TPPS) with achiral ionic liquid

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Abstract

The self-assembly and supramolecular chirality of a dianionic tetrakis(4-sulfonatophenyl) porphyrin (TPPS) in the presence of ionic liquids, 1-alkyl-3-methylimidazolium tetrafluoroborate (alkyl = C2, C4 or C6, abbreviated as C2mimBF4, C4mimBF4 and C6mimBF4, respectively), have been investigated. It has been confirmed that mimBF4 ionic liquids significantly promoted the J-aggregation of TPPS and the alkyl chain length in the imidazolium cation was closely related to the TPPS aggregation, the inducing ability of which decreased in the order of C2, C4 or C6 in side chain. Interestingly, the formed TPPS assemblies with the ionic liquids showed supramolecular chirality although both TPPS and ionic liquids are achiral. It was found that the supramolecular chirality of the TPPS/IL system always appeared after the formation of the J aggregate. The dynamic process of the emergence of the handedness in the initial achiral system was monitored by the time-dependent CD spectra. A mechanism for the transformation of the conventional J-aggregate to the chiral J-aggregate was proposed. The work will lead to a deeper understanding of the chiral symmetry breaking in the supramolecular system.

Graphical abstract: Ionic liquid induced spontaneous symmetry breaking: emergence of predominant handedness during the self-assembly of tetrakis(4-sulfonatophenyl)porphyrin (TPPS) with achiral ionic liquid

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Publication details

The article was received on 01 Jun 2011, accepted on 11 Jul 2011 and first published on 30 Aug 2011


Article type: Paper
DOI: 10.1039/C1CP21767D
Citation: Phys. Chem. Chem. Phys., 2011,13, 17205-17209
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    Ionic liquid induced spontaneous symmetry breaking: emergence of predominant handedness during the self-assembly of tetrakis(4-sulfonatophenyl)porphyrin (TPPS) with achiral ionic liquid

    L. Zhang, Y. Tian and M. Liu, Phys. Chem. Chem. Phys., 2011, 13, 17205
    DOI: 10.1039/C1CP21767D

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