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Chiral inversion and enhanced cooperative self-assembly of biosurfactant-functionalized porphyrin chromophores

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Abstract

A new self-assembling di-conjugated sophorolipid–(Zn)porphyrin was synthesized with a short lipid chain length connecting the porphyrin and disaccharide moieties in order to influence the self-assembled state. In dilute solution, circular dichroism measurements of the ordered molecules exhibited Cotton effects indicative of right-handed exciton-coupling; a chirality inversion compared to our previous report on (long-chain) sophorolipid–(Zn)porphyrins that formed a left-handed system. The self-assembly process was investigated by variable-temperature CD. Cooling curve profiles exhibited simultaneous evolution of net helicity and aggregation that corresponds with the cooperative assembly model. Analysis revealed a 3-fold increase in enthalpy of polymerization compared to long-chain species implying that shortening the distance between porphyrin and disaccharide moieties enhance the cooperative self-assembly. The morphology of assembled aggregates was examined by electron microscopy and showed mesoscopic cup-staked structures and nanofibrils.

Graphical abstract: Chiral inversion and enhanced cooperative self-assembly of biosurfactant-functionalized porphyrin chromophores

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Article information


Submitted
13 Dec 2019
Accepted
26 Feb 2020
First published
02 Mar 2020

J. Mater. Chem. C, 2020, Advance Article
Article type
Communication

Chiral inversion and enhanced cooperative self-assembly of biosurfactant-functionalized porphyrin chromophores

K. C. Peters, S. Mekala, R. A. Gross and K. D. Singer, J. Mater. Chem. C, 2020, Advance Article , DOI: 10.1039/C9TC06829E

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