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The fluorescence counts for coumarin could only be used qualitatively since we found that part of the coumarin emission was quenched by the NC (not shown).
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We found similar results with 72 Å NC covered with ligand 2. Thus, coumarin was efficiently formed from these NC using 620 nm light. However, the tendency for the thiol ligands to detach upon dissolution was dramatically higher for these NC than for the 31 Å NC. Therefore, 72 Å NC are of limited use and are not explicitedly discussed in this paper.
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Interestingly, electrolysis of 8 at +0.9 V was accompanied by vast decomposition of the radical cation, thereby excluding any mechanisms that involve the radical cation in explaining the coumarin formation from the NC.
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33748360519
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At wavelengths < 440 nm, the same proposed mechanisms will hold true but now isomerization can also occur by direct absorption of the light by the surface cinnamates. The latter pathway was predictable and not of high interest.
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The rate of coumarin formation from cinnamates in solution can be increased as much as 1000-10 000-fold by simply switching from DMF to water or ethanol instead. This is a result of acid-catalysis of the lactonization step.
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