Chiral Sign Selection on the J-Aggregates of Diprotonated Tetrakis-(4-sulfonatophenyl)porphyrin by Traces of Unidentified Chiral Contaminants Present in the Ultra-Pure Water Used as Solvent

Traces of biological contaminants that cannot be detected, but are expected to be present, in ultra-pure water suffice to select the emerging chiral sign in the spontaneous mirror symmetry breaking that takes place during the formation of the J-aggregates of the amphiphilic diprotonated tetrakis-(4-sulfonatophenyl)porphyrin (H4TPPS42-). This is demonstrated by competition experiments with a chiral cationic surfactant. The sensitivity of the detection depends on the hierarchical control of the H4TPPS42- self-aggregation. Chirality 21:408-412, 2009. (C) 2008 Wiley-Liss, Inc.