Reports: AC4
46355-AC4 Macrocyclic Scavengers of Chloroalkanes
Chloroalkanes such as methylene chloride and 1,2-dichloroethane are major non-fuel products of the petroleum industry. Although extremely useful, chloroalkanes are known to be carcinogenic and they can persist in the biosphere for a long time. There is an increasing need for the petroleum industry and its downstream petrochemical partners to invent novel methods of sensing and sequestering these potentially harmful chemicals; however, this is a very challenging task because the chemicals are inherently unreactive and difficult to trap. We have discovered that a simple macrocyclic amine can attack haloalkanes with unprecedented nucleophilic reactivity. A fluorescent version of the macrocycle, compound 1, was developed and used to monitor the alkylation reaction. One applied direction of this research is fluorescence detection systems for the presence of these carcinogenic chemicals in the biosphere. Therefore, we examined the ability of the 1 to react and sense alkylation agents in aqueous micellar solution. We discovered that fluorescence sensing does occur in neutral micelles and that reaction with the known carcinogen chloromethyl methyl ether exhibits autocatalysis. The data indicates that the source of the autocatalysis is different to that reported with other micellar systems.
