Electronic absorption spectroscopy was used to measure the molecular association of copper phthalocyanine tetrasulfonate in micellar solutions, a microemulsion made with cationic surfactant, and homogeneous solvents. Analysis of absorbance versus concentration data using a multiple-aggregation model and non-linear regression analysis gave values of association constants, molar absorptivities and estimates of average aggregation number. Microemulsions and aqueous micellar solutions made with alkylammonium surfactants inhibited aggregation, probably because of interactions between the phthalocyanine sulfonate groups and the cationic surfactant head groups at interfacial surfaces. Similar aggregation behavior was observed previously in multiple-bilayer films of cationic surfactants. Water and aqueous solutions containing tetraethylammonium bromide or anionic SDS micelles provide environments facilitating extensive aggregation of Cu II PcTS 4−. The major species are dimers in water and acetonitrile/water, but the formation of higher aggregates is promoted by addition of SDS or TEAB. Aprotic organic solvents provide environments intermediate between these two extremes, giving relatively large aggregation numbers (i.e. five to seven) but smaller association constants than aqueous media not containing cationic surfactants.

Previous synthetic processes for the preparation of sulopenem involved multistep linear sequences in which the chiral sulfoxide side chain was introduced early in the process. This contribution summarizes the development of a practical and convergent process for the large-scale preparation of 1. The key step in the synthesis involves cyclization of an oxalimide intermediate to provide the thiopenem core. This convergent strategy allows for late introduction of the expensive and labile chiral sulfoxide subunit. Additionally, a regioselective sulfur oxidation and an improved deprotection sequence were developed. The latter provides API of high purity without the need for recrystallization.

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