The self-assembly of diprotonated phenyl and 4-sulfonatophenyl meso-tetrasubstituted porphyrins gives a spontaneous chiral symmetry breaking, but only for H2TPPS3−, which forms helicoidal colloidal particles; the selection of the resulting chirality sign by the hydrodynamic forces of a stirring vortex can be demonstrated.
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Crusats et al. (2003) studied this question.
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