No abstract

The influence of gaseous chlorine on monolayers of metal-free meso-tetra(4-amino sulfonyl)phenylporphyrin is discussed. These films exhibit characteristic intense optical absorption bands in the region 400-700 nm. Upon exposure to chlorine vapour in the concentration range 0.1-10 ppm, the Soret and Q-bands decrease in intensity and new bands at ∼455 nm and ∼660 nm appear. The rate of response has been measured as a function of deposition surface pressure and gas concentration. Repeated dosing experiments have shown that reversible and reproducible sensing action occurs provided that a threshold concentration is not exceeded. The recovery of the original optical spectrum can be accelerated with moderate heat treatment (60°C for 10 min). Ageing experiments have shown that the basic response of the monolayer is not effected over a time period of at least 5 months.

New sulfonamide and sulfonic ester porphyrins were prepared and their in vitro characteristics as sensitizers for photodynamic therapy were assessed. Fluorescence spectra were characterised by two main peaks, located between 650-680 nm and 705-740 nm, respectively. Some of these new porphyrins (three out of nine) showed good photodynamic properties in the in vitro assays. In the absence of light, these porphyrins are not toxic. With 50 J.cm−2 illumination light (514 nm) they induced mortality in 50% of HT29 cells with 2 to 4.5 μg/ml. Comparison of in vitro phototoxic efficacy of these three compounds with other photosensitizers already described confirms interest in their phototoxic properties.

In this laboratory experiment, students synthesize and investigate the properties of a stable porphyrinogen. Porphyrinogens are an important class of porphyrin precursors as well as important macrocycles for the preparation of coordination compounds. The acid-catalyzed cyclization of pyrrole and acetone uses common, inexpensive reagents to afford the meso-octamethylporphyrinogen in a near-analytical grade in one step, directly from the reaction medium.

Scheme I. Synthesis of meso-diethyl-2,2´-dipyrromethane from 3pentanone and pyrrole.