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SAFH was oxidized to a fluorescent product by Pd
2+
and KBrO
3
.
Reproduced with permission from Ref. 57. Copyright 2004 Taylor &
Francis.
Figure 16.12
(a)
(b)
Figure 16.13
(a) SQ1:SEt reacted with Pd(II) to form the fully conjugated product
SQ1, showing a distinct absorption spectrum from that of the starting
material. (b) Compound 38 was prepared by a Suzuki-Miyaura cross-
coupling and analyzed for its palladium content using the method
shown in (a).
Adapted from Ref. 58.
recognize the importance of sample preparation when trace palladium was
quantified in synthetic organic molecules. Namely, acid digestion of syn-
thetic samples played a critical role in the quantification of palladium
species.
16.4.2.3 Chemodosimeters Based on Deallylation
16.4.2.3.1 2007 Version from Koide's Group. In 2007, Koide's group dis-
covered that a hydroxymethyl variant of O-alkylated dichlorofluorescein, A,
(Figure 16.14a) was nearly non-fluorescent.
59
In contrast, the dealkylated
product of A, Pittsburgh Green, was about 400 times more fluorescent
than A, making its green fluorescence signal as intense as that of fluor-
escein. Pittsburgh Green was strongly fluorescent in the pH range 5.5-10
(Figure 16.14b);
60
therefore, the fluorescence-based assays were developed
within this range.
Koide and co-workers hypothesized that the palladium-catalyzed deal-
lylation of allyl Pittsburgh Green ether (APE, Figure 16.15) could be used for
the fluorimetric detection of palladium. This ether was synthesized ac-
cording to the synthetic scheme depicted in Figure 16.15.
61
They were able to
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