Communication
ChemComm
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4 D. Kristofıkova, V. Modrocka, M. Meciarova and R. Sebesta, Chem-
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dialysis for 3 days shows no asymmetric catalytic activity
(Table 1, entry 2). This indicates that dialysis could remove
all the liquid D-Pro. Dialysis is also a common method to purify
carbon dots reported in literature studies.36,37 Since the dialysis
conditions of CA-DP-CQDs are the same as those of D-Pro, even
if there are residues of D-Pro that are not carbonized, they can
be removed by dialysis. Therefore, the asymmetric catalytic
activity of CA-DP-CQDs should come from their asymmetric
structure, and not from the remaining uncarbonized raw
materials of D-Pro. Hereby, the asymmetric structure provides
the intrinsic asymmetric catalytic activity of CA-DP-CQDs. Since
CA-DP-CQDs were prepared by a one-step hydrothermal method
from citric acid and chiral D-Pro with asymmetric catalytic
activity, the intrinsic catalytic activity of carbon dots indicates
that they had a chiral catalytic memory effect.
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In summary, a CA-DP-CQD catalyst is prepared by a one-step
hydrothermal method using D-Pro and citric acid as raw materials.
It is composed of a graphite core with a mean size of 5.5 nm and
surface functional groups of N–H, C–H, CQO, C–O, and –CONR2.
CA-DP-CQDs display chiral character and show high asymmetric
catalytic performance in direct aldol reactions. When the hydro-
thermal time is 2 h (or 4 h), the obtained CA-DP-CQDs display high
asymmetric catalytic activity for the direct aldol condensation of
P-nitrobenzaldehyde and cyclohexanone, as shown by a yield of
98% (1H NMR results) and an ee% of 471%. Furthermore,
CA-DP-CQDs are reusable and can be used 4 times. This work
demonstrates that chiral CQDs have the memory effect of asym-
metric catalytic activity. The present work opens a new way to
prepare heterogeneous chiral catalysts.
Shuang Liu: data curation, and writing – original draft. Yu
He: data curation. Yu Liu: data curation. Shuaibin Wang: data
curation. Yajun Jian: writing – review and editing. Baoxin Li:
writing – review and editing. Chunli Xu: conceptualization,
formal analysis, funding acquisition, investigation, methodology,
project administration, resources, supervision, and writing –
review and editing.
`
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This work was supported by projects funded by the Science
and Technology Department in Shaanxi Province of China
(2019GY-165) and the Natural Science Foundation of China
(No. 21974082).
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Conflicts of interest
There are no conflicts to declare.
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Notes and references
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Chem. Commun., 2021, 57, 3680–3683 | 3683