reported that the indole CL mechanism proceeds via the
oxidation of CQC (dioxetane) with skatole.85–88 From the
investigation of products after the CL reaction of compound 7
using 1H-NMR and FAB MS, compound 16 should be
produced (Fig. 9). Compound 16 was a fluorescent compound
(excitation maximum wavelength, 250 nm; emission maximum
wavelength, 287 nm) (ESI).w Thus, the IMs having the CQC
bond of the maleimide moiety also emitted light via dioxetane
(Fig. 9). We proposed that the CL intensities were low because
the FL intensities of FL compounds produced after CL
reactions were weak. The CL reaction conditions (NaOH,
H2O2 conc.) inducing the maximum CL intensity for the
IMs are shown in Table 3. A large difference in CL intensities
was observed for the IMs.This fact indicates that some IMs
can be useful for the on–off switching of CL.
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The synthesis of the IMs in this study was facile. Interesting
FL and CL properties of various IMs were found. The
introduction of a naphthyl or phenyl group at the 2-position
in the indole ring and the 3- or 4-position in the maleimide
moiety caused an obvious increase and decrease in the FL and
CL of the IMs. The CQC bond in the maleimide moiety in the
IMs without substitution at the 2-position of the indole ring
was needed for strong CL. Significant information for the
rational design of the IMs for FL and CL probes was
provided.
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Acknowledgements
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This work was supported in part by a Grant-in-Aid for
Scientific Research from the Ministry of Education, Culture,
Sports, Science and Technology of Japan (Grant No. 17590034).
The authors thank Prof. Dr Kiyoshi Sakai (Redox Navi
Institute, Kyushu University) for his helpful discussions about
the synthetic methods. The authors thank Prof. Dr Fumito
Tani (Institute for Material Chemistry and Engineering,
Kyushu University) and Prof. Dr Katsuhiko Nishiyama
(Applied Chemistry and Biochemistry, Kumamoto University)
for the FAB MS measurements and CV measurements. The
computations were mainly performed at the Research Institute
for Information Technology (Kyushu University, Fukuoka,
Japan) and the computer facilities in the Research Center for
Computational Science of National Institutes of the Natural
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