A styrene based water soluble polymer as a reaction medium for photodimerization of aromatic hydrocarbons in water |
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Affiliation: | 1. Department of Chemistry, University of Miami, 1301 Memorial drive, Coral Gables, FL 33124, United States;2. Department of Chemistry, University of Massachusetts, Amherst, MA 01003, United States |
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Abstract: | A styrene based water soluble polymer (polymer-A) has been explored as a host for solubilizing otherwise insoluble aromatic hydrocarbons in water. The increased local concentration of encapsulated aromatic hydrocarbons within the hydrophobic pockets of polymer-A was utilized for performing efficient photodimerization of acenaphthylene (1) and six 9-substituted anthracenes [AnCOOH, AnCHO, AnCH2OH, AnCH3, AnBr and AnCN] in water. Photodimerization of these aromatic hydrocarbons were more efficient than in water and yielded dimers even at low concentrations (∼10−4 M). At the same concentration of anthracenes in organic solvents such as benzene and methanol, no dimers were formed even after 48 h of irradiation. Although the polymer-A was able to increase the local concentration of the reactant aromatics it was unable to orient them towards a single dimer. |
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