Dual Upconverted and Downconverted Circularly Polarized Luminescence in Donor–Acceptor Assemblies

Article abstract of DOI:10.1002/anie.201804402

Through mimicking both the chiral and energy transfer in an artificial self-assembled system, not only was chiral transfer realized but also a dual upconverted and downconverted energy transfer system was created that emit circularly polarized luminescence. The individual chiral π-gelator can self-assemble into a nanofiber exhibiting supramolecular chirality and circularly polarized luminescence (CPL). In the presence of an achiral sensitizer Pd^II octaethylporphyrin derivative, both chirality transfer from chiral gelator to achiral sensitizer and triplet-triplet energy transfer from excited sensitizer to chiral gelator could be realized. Upconverted CPL could be observed through a triplet–triplet annihilation photon upconversion (TTA-UC), while downconverted CPL could be obtained from chirality-transfer-induced emission of the achiral sensitizer. The interplay between chiral energy acceptor and achiral sensitizer promoted the communication of chiral and excited energy information.

Full text of DOI:10.1002/anie.201804402

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Accepted Article
Title: Dual upconverted and downconverted circularly polarized
luminescence in donor-acceptor assemblies
Authors: Dong Yang, Pengfei Duan, and Minghua Liu
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To be cited as: Angew. Chem. Int. Ed. 10.1002/anie.201804402
Angew. Chem. 10.1002/ange.201804402
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Angewandte Chemie International Edition
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COMMUNICATION
Dual upconverted and downconverted circularly polarized
luminescence in donor-acceptor assemblies
[
a,b,c]
[a]
[a,b,c]
Dong Yang,
Pengfei Duan* and Minghua Liu*
Abstract: Chirality and energy transfer represent two important
aspects of structure and function in biological system. Here, through
the mimic of both the chiral and energy transfer in an artificial self-
assembled system, we not only realized the chiral transfer but also
created a dual upconverted and downconverted energy transfer
system that emit circularly polarized luminescence. It is found the
individual chiral π-gelator can self-assemble into nanofiber exhibiting
supramolecular assemblies and revealed a new insight into the
interplay between the two processes. That is, dual
upconverted and downconverted CPL can be realized
simultaneously.
Photon upconversion, the population of higher-energy
excited state with excitation at lower-energy light, provides a
novel view for achieving higher-energy emission. In this work,
a
supramolecular chirality and circularly polarized luminescence (CPL). we conceived an idea to integrate chiral assembly with photon
In the presence of an achiral sensitizer Pd(II) octaethylporphyrin
derivative, both chirality transfer from chiral gelator to achiral
sensitizer and triplet-triplet energy transfer from excited sensitizer to
chiral gelator could be realized. Specifically, upconverted CPL could
be observed through a triplet-triplet annihilation photon upconversion
upconversion (UC) based on triplet-triplet annihilation (TTA)
[
6]
mechanism,
and design a self-assembly system based on
anthracene derived chiral gelator (LGAn or DGAn) and achiral
Pd(II) octaethylporphyrin derivative (PdOEP-C18) as sensitizer
(Figure 1). Here, the achiral PdOEP-18 experiences the chiral
environment of LGAn or DGAn after incorporation into the
LGAn/DGAn fibers, which generates supramolecular chirality of
PdOEP-18 due to the spatial nonsymmetric arrangement of
PdOEP-18 in the co-assembly. In term of energy transfer, LGAn
or DGAn works as energy acceptor and PdOEP-18 as energy
donor in the TTA-based upconversion process. It is found that
when chiral LGAn or DGAn assembled with the achiral PdOEP-
C18, the chirality transfer from LGAn or DGAn to PdOEP-C18
and triplet-triplet energy transfer from PdOEP-C18 to LGAn
(TTA-UC) process, while downconverted CPL could be obtained
from chirality-transfer-induced emission of the achiral sensitizer.
The interplay between chiral energy acceptor and achiral sensitizer
promoted the communication of chiral and excited energy
information.
Chirality and energy transfer represent two important
aspects of structure and function in biological system. Chiral
molecules such as L-amino acids and D-sugars formed the
covalent polymers and then self-assembled into helical proteins
(DGAn) can happen simultaneously. The co-assembly exhibited
dual upconverted (460 nm) and downconverted CPL (550-750
nm) emission under excitation of a 532 nm laser. With such
design, we have successfully integrated with two channels of
chirality and energy transfer process and revealed the interplay
[
1]
and DNA through non-covalent bond.
During such process,
molecular chirality was transferred to the supramolecular system,
which is crucial for the well-implementation of their sophisticated
functions like catalytic and replication activity in life process. In
addition, the transfer of information in living organisms is
multichannel, not only through the chirality-based structural
information but also through the electron-, ion-, photon-based
of energy and chirality transfer to produce
simultaneously.
a dual CPL
[
2]
energy types.
Many researches have tried to mimic the
[
3]
process through self-assembly strategy.
Unfortunately, most
of the researches only focused one aspect, either chirality or
energy transfer. Only a limited efforts have been devoted to
construction of the supramolecular systems containing both
[
4-5]
chirality and energy transfer.
In these two chirality-related
energy transfer systems, high-energy excitation resulted in low-
energy circularly polarized luminescence (CPL). Here, we
combined both the chirality and energy transfer in the
[
a]
Dr. Yang, Prof. P. Duan, Prof. M. Liu
CAS Center for Excellence in Nanoscience, CAS Key Laboratory of
Nanosystem and Hierarchical Fabrication, Division of
Nanophotonics
National Center for Nanoscience and Technology (NCNST)
No. 11 ZhongGuanCun BeiYiTiao, Beijing 100190, P. R. China
E-mail: duanpf@nanoctr.cn, liumh@iccas.ac.cn
Dr. Yang, Prof. M. Liu
Beijing National Laboratory for Molecular Science, CAS Key
Laboratory of Colloid Interface and Chemical Thermodynamics
Institute of Chemistry, Chinese Academy of Sciences
No. 2 ZhongGuanCun BeiYiJie, Beijing 100190, P. R. China
Dr. Yang, Prof. M. Liu
Figure 1. (a) Chemical structures of the chiral gelator LGAn (DGAn) and
achiral sensitizer PdOEP-C18 and schematic representation of chirality
transfer from chiral gelator to achiral PdOEP-C18 during the coassembly
process. (b) Dual upconverted and downconverted CPL emission for donor-
acceptor coassembly in deaerated condition under excitation of 532 nm laser.
The upconverted CPL at 460 nm results from the successful triplet-triplet
energy transfer from energy donor (PdOEP-C18) to energy acceptor (LGAn or
DGAn assembly), while the downconverted CPL in the range of 550-750 nm
results from the successful chirality transfer from LGAn or DGAn to PdOEP-
C18.
[
[
b]
b]
University of Chinese Academy of Sciences, Beijing 100049, P. R.
China
The designed chiral gelator LGAn or DGAn was shown in
Figure 1a, which contains an anthracene unit conjugating with a
gelator moiety N,N’-bis(dodecyl)-L(D)-amine-glutamic diamide.
The detailed synthetic route was shown in Figure S1. The
Supporting information for this article is given via a link at the end of
the document.
[
7]
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Angewandte Chemie International Edition
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COMMUNICATION
individual self-assembly and properties were first investigated.
LGAn or DGAn showed excellent gel ability in various organic
solvents. Among them, the gel formed in toluene was
transparent. In order to minimize the interference of light
scattering in the later research, all the studies were focused on
the self-assembly in toluene. The self-assembly behavior of
LGAn in solution and gel were studied by absorbance and
emission spectra. As shown in Figure S2, the absorbance
spectra in solution exhibited three well-resolved absorption
peaks at 347, 364 and 384 nm, which can be attributed to the
Cotton effect displayed a left-handed CPL, while the DGAn a
right-handed CPL. The magnitude of CPL was evaluated by the
[
12]
luminescence dissymmetry factor (glum), which were about 1.3
-
3
-3
× 10 and -1.1 × 10 for LGAn or DGAn gel, respectively,
[
13]
comparable to many organic self-assembly system.
Sergio
Abbate and co-authors have stressed that the measured CPL
should be corrected when fluorescence (and CPL) of the
targeted sample is too close in wavelength to absorption (and
[
14]
CD).
In our present study, the absorption (and CD) of our gel
sample has only a slight overlap with the fluorescence (and
CPL). Therefore, the correction equations shown in the two
references were not applied for our present case due to different
setup.
[8]
S
0
–S
spectrum in solution exhibited well-defined peaks at 412 and
26 nm. When increasing the concentration to 2.5 mM,
1
transition with different vibronic peaks. The emission
4
transparent gel formed. The absorption of the gel broadened
and still exhibited some well-resolved vibronic peaks. The
emission spectrum had a bathochromic shift to 445 nm with the
disappearance of vibronic peaks, which indicated the formation
of ordered self-assemblies in the gel. When the concentration
was further increased to 5 to 20 mM, the vibronic peaks tended
to disappear and the emission spectra shifted to 455 nm,
indicating a dense molecular packing. We further measured the
variable temperature photoluminescence spectrum to confirm
the self-assembly. As shown in Figure S3, the emission peak
gradually hypsochromic shifted upon heat-driven disassembly
o
and moved to 428 nm at 60 C. It should be noted that the
emission intensity of the system decreased with the increase of
temperature, which was suggestive of the aggregation induced
[
9]
fluorescence enhancement for LGAn system.
The self-
assembled structures of the gel were further investigated by
transmission electron microscopy (TEM), scanning electron
microscopy (SEM) and atomic force microscopy (AFM). As
shown in Figure S4-5, thin and entangled fibers were formed.
Since the gelators have chiral centers, the gel were
characterized by CD spectra, as shown in Figure 2a. LGAn gel
showed positive Cotton effect at 375 nm, which is corresponding
to the absorption region of anthracene chromophore, indicating
that molecular chirality could be amplified through the
Figure 3. (a) Normalized absorption (solid line) and luminescence (dotted line)
spectra for PdOEP-C18 solution (2.8×10 M, red line, λex = 532 nm) in
-5
deaerated toluene and LGAn gel (10 mM, blue lines, λex = 350 nm). (b)
Upconversion emission spectra of LGAn/PdOEP-C18 = 100/1 (mol/mol) gel in
deaerated toluene excited with different incident power intensity of 532 nm
laser at room temperature. A notch filter at 532 nm was used to remove the
scattered incident light in front of the detector. (c) Dependence of UC intensity
at 460 nm on the excitation density. The solid lines are fitting results with slope
of 1.7 (blue) and 1.2 (red) in the low- and high-power density regimes,
respectively. (d) Time resolved upconverted emission at 460 nm of the
LGAn/PdOEP-C18=100/1 gel in deaerated toluene under 532 nm laser
excitation at room temperature. The tail fit (red circle), [LGAn] = 10 mM. The
[
10]
supramolecular self-assembly. The DGAn gel showed mirror-
imaged CD signal with LGAn, suggested that the
supramolecular chirality followed the molecular chirality. The
-
2
temperature-dependent CD spectra
confirmed such chirality transfer.
(Figure S6) further
excitation density of 532 nm laser was 930 mW cm .
We then investigated the co-assembly behavior and energy
transfer in the cogel of LGAn (DGAn) with PdOEP-C18. PdOEP
is a typical energy donor for sensitizing the triplet of acceptor in
[
6e, 6i, 6j, 15]
TTA-UC process.
Here, for improving the coassembly
ability of sensitizer with the energy acceptor LGAn (DGAn), two
long alkyl chains were introduced. As a typical sensitizer for
TTA-UC, PdOEP-C18 in deaerated toluene exhibited a typical
Soret band at 391 nm and Q bands at 525 nm and 556 nm in the
absorption spectrum, and one phosphorescence peak at 670
[6e, 6i, 15]
nm (Figure 3a).
LGAn gel doped with PdOEP-C18 excited under various incident
32 nm laser power. Blue UC emission were observed upon
Figure 3b shows upconverted emission of
Figure 2. (a) CD (up) and UV-vis spectra (down) of LGAn and DGAn gel. (b)
CPL spectra of LGAn and DGAn gel. For the measurement of CD and CPL,
the [LGAn] = [DGAn] = 10 mM. λex = 350 nm.
5
excitation of the cogel system by 532 nm green laser. The
location of the UC emission (λex = 532 nm) is similar to that of
the normal fluorescence (λex = 350 nm). The phosphorescence
of sensitizer PdOEP-C18 was severely quenched regardless of
the excitation power, indicating the efficient TTET from sensitizer
The gel was further found to show circularly polarized
luminescence (CPL), which is used to evaluate the chirality of
[
11]
excited-state.
As shown in Figure 2b, CPL signals with
[
6b, 16f]
to the acceptor LGAn.
This can be further confirmed by the
different handedness and emission at 460 nm could be
observed. It further revealed that LGAn gel with a positive
reduced phosphorescence lifetime of PdOEP-C18 in the
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COMMUNICATION
presence of LGAn compared with that in the absence of LGAn
to PdOEP-C18 occurred in LGAn/PdOEP-C18 co-gel. In order to
clarify the chirality transfer in co-gel more clearly, we conducted
the CD measurement at 20/1 ratio. The CD spectrum of the co-
assembly of LGAn/PdOEP-C18 showed two negative CD bands
in the range of 500-600 nm, while DGAn/ PdOEP-C18 showed
two positive ones in the same range (Figure 4a). In
LGAn/PdOEP-C18 assembly, two exciton type Cotton effects
(Figure S7). To gain insight into the TTA-based UC mechanism,
the dependence of UC emission intensity to the excitation power
density was investigated. Figure 3c presents a double logarithm
plot for the UC emission intensity of PdOEP-C18-doped gel as a
function of incident light power density (λex = 532 nm). The blue
line and red line are the fitting results with slopes of 1.7 and 1.2
in the low and high excitation power density regime, respectively. were observed, which is strongly suggestive that PdOEP-C18
It provides decisive experimental evidence for TTA-based
could capture the supramolecular chirality from the chiral
assemblies. Temperature-dependent absorption spectra further
confirmed this (Figure 4b). The absorption peaks located at 560
nm and 523 nm in gel at 25℃ gradually hypsochromic-shifted to
549 nm and 514 nm when the temperature was increased to 80
[
6b, 16]
photon UC in the hybrid gel system.
A high crossover
-
2
threshold 4350 mW cm was obtained, above which TTA
becomes the main triplet deactivation channel for the acceptor.
A long UC emission lifetimes at 460 nm for LGAn/PdOEP-C18
o
(τUC = 135 μs, Figure 3d) and DGAn/PdOEP-C18 (τUC = 126 μs,
C, indicating a certain J-aggregation for PdOEP-C18 in the
[
4, 18]
Figure S8) were observed, which is significantly longer than the
pure acceptor LGAn (18.5 ns; λex = 350 nm; Figure S9). Such
prolonged luminescence decay is characteristic of the TTA-UC
cogel.
FTIR was further used to gain insight into the driving
force for the gel formation. As shown in Figure S11, strong
-
1
vibrations were observed at 3296, 1636 and 1554 cm , which
can be ascribed to N-H stretching vibration, amide I and II band
[
6b, 17]
processes.
Thus, a light-harvesting supramolecular system
[
4,
19]
with high UC efficiency was successfully fabricated based on
donor-acceptor (D-A) self-assembled system.
in hydrogen bonding state, respectively.
As for
LGAn/PdOEP-C18, the amide I band and II band were identical
to that of pure LGAn, which further confirmed that the addition of
PdOEP-C18 did not destroy the well-ordered packing of LGAn.
The co-assembly showed upconverted circularly polarized
luminescence (UC-CPL). As shown in Figure 4c, LGAn/PdOEP-
C18 cogel in deaerated toluene exhibited positive UC-CPL
signal at 460 nm under 532 nm laser excitation with excitation
2
density at 7847 mW/cm , while DGAn/PdOEP-C18 cogel
exhibited the mirror-imaged signal. The signs of UC-CPL at 460
nm were the same as that excited with 350 nm (Figure 2b). To
date, the only study on upconverted circularly polarized
[
6d]
luminescence was reported in our recent published work.
Here, we realize the upconverted circularly polarized
luminescence in supramolecular self-assembly system again.
More interestingly, the energy donor PdOEP-C18 exhibited a
weak phosphorescence emission at 670 nm due to high TTET
efficiency in the LGAn/PdOEP-C18 cogel system, as shown in
Figure 4c. If we increase the excitation laser power, to say, 23
2
W/cm , then we can see the CPL more clearly. As shown in
Figure 4d, the cogel system exhibited obvious emission intensity
in the wide range of 550-750 nm and strong CPL signal. This
strongly suggested that PdOEP-C18 can emit downconverted
CPL in the assembly at deaerated condition. Thus, a dual CPL
emission including upconverted CPL at 460 nm and
downconverted CPL in the range of 550-750 nm was succefully
realized in donor-acceptor co-assembly.
Figure 4. (a) CD (up) and absorption (down) spectra for gels of LGAn/PdOEP-
C18 = 20/1 (molar ratio) and DGAn/PdOEP-C18 = 20/1 (molar ratio); (b)
Temperature-dependent UV-vis absorption spectra of LGAn/PdOEP-C18=20/1
co-gel. The measurement was conducted in 1mm sealed quart cell. The
absorption of LGAn in this condition was too large, so the spectra just shown
the absorption region of PdOEP-C18. (c) CPL spectra of LGAn/PdOEP-C18 =
1
00/1 (molar ratio) and DGAn/PdOEP-C18 = 100/1 (molar ratio) in deaerated
2
toluene excited by 532 nm laser with excitation density at 7847 mW/cm ; 532
nm notch filter was placed between the sample and detector perpendicular to
the optical path; (d) CPL spectra of LGAn/PdOEP-C18 = 100/1 (molar ratio)
and DGAn/PdOEP-C18 = 100/1 (molar ratio) in deaerated toluene excited by
2
5
32 nm laser with excitation density at 23439 mW/cm ; 532 nm long pass filter
was used. [LGAn] = [DGAn] = 10 mM. During the measurement of CPL, a low
slit width value at 500 µm in detector was used to reduce the stray light, thus a
hole in emission at 532 nm could be clearly observed.
Since LGAn (DGAn) as energy acceptor exhibited
supramolecular chirality in the self-assembly, we further studied
the interplay between the chirality and energy transfer. We first
measured the CD spectra of LGAn/PdOEP-C18 at 100/1 molar
ratio. As shown in Figure S10, the absorption and CD signal of
PdOEP-C18 in this low concentration is weak but observable,
which indicated that the successful chirality transfer from LGAn
Figure 5. The symbol “D” and “A” represent the energy do-nor PdOEP-C18
and energy acceptor LGAn or DGAn in TTA-UC process. (a) In the
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COMMUNICATION
coassembly system, the chirality can be transferred from LGAn or DGAn to
PdOEP-C18 through entanglement of hydrophobic chains. (b) In the
adsorption assembly system, chirality transfer was blocked due to weak
interaction between LGAn (DGAn) and PdOEP-C18.
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PdOEP-C18 solution was allowed to freely diffuse into the gel
matrix. In this case, the chirality transfer from LGAn (DGAn)
gelator to PdOEP-C18 could not be realized (Figure 5b). In
addition, LGAn/PdOEP-C18 or DGAn/PdOEP-C18 in deaerated
toluene formed by adsorption pathway showed only upconverted
CPL at 460 nm excited with 532 nm, while without
downconverted CPL (see the experimental details in Figure S12).
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Acknowledgements
This work was supported by the Strategic Priority Research
Program of the Chinese Academy of Sciences (XDB12020200),
National Natural Science Foundation of China (51673050 and
91027042); The Ministry of Science and Technology of China
[
[
(2016YFA0203400) and New Hundred-Talent Program research
13] a) J. Kumar, T. Nakashima, T. Kawai. J. Phys. Chem. Lett. 2015, 6,
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Dual upconverted and
Dong Yang, Pengfei Duan*,Minghua
downconverted circularly polarized
luminescence could be realized in a
composite self-assembly system,
which integrated with chirality and
triplet-triplet energy transfer process.
Liu*
Page No. – Page No.
Dual upconverted and
downconverted circularly polarized
luminescence in donor-acceptor
assemblies
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