Journal
INORGANIC CHEMISTRY
Volume 48, Issue 3, Pages 1173-1182Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ic801322x
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Funding
- National Science Foundation [0517782]
- UConn Research Foundation
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0517782] Funding Source: National Science Foundation
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The synthesis and in vitro evaluation of a squarate hydroxamate-coumarin conjugate, 12, as a chemodosimeter for Fe(III) and other oxidants, such as Cr(VI) and Ce(IV), is described. As 12 was originally designed to become a chelation-enhanced fluorescence (CHEF)-type sensor for Fe(III), the competence of the squarate diamide platform to relay a CHEF response was demonstrated using a zinc-binding, cyclen-substituted squarate coumarin amide. Due to a photo electron transfer process, 12 possesses a low fluorescence yield. Upon exposure of 12 to Fe(III) (or other oxidants), an irreversible 9-fold fluorescence intensity increase is observed as the result of an oxidation/hydrolysis reaction. The (aminomethyl)coumarin portion of 12 is oxidized to an iminocoumarin that hydrolyzes to produce a highly fluorescent coumarinaldehyde. Fe(III) acts as a catalyst in this transformation, thereby enhancing the sensitivity of the system for the detection of Fe(III) down to 1 ppm in aqueous buffer solution. The identities of the major reaction products between 12 and Fe(III) were proven by independent synthesis.
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