A Metal–Organic Supramolecular Box as a Universal Reservoir of UV, WL, and NIR Light for Long-Persistent Luminescence

Article abstract of DOI:10.1002/anie.201812708

Long persistent luminescence (LPL) materials have a unique photophysical mechanism to store light radiation energy for subsequent release. However, in comparison to the common UV source, white-light (WL) and near-infrared (NIR) excited LPL is scarce. Herein we report a metal–organic supramolecular box based on a D–π–A-type ligand. Owing to the integrated one-photon absorption (OPA) and two-photon absorption (TPA) attributes of the ligand, the heavy-atom effect of the metal center, as well as π-stacking and J-aggregation states in the supramolecular assembly, LPL can be triggered by all wavebands from the UV to the NIR region. This novel designed supramolecular kit to afford LPL by both OPA and TPA pathways provides potential applications in anti-counterfeiting, camouflaging, decorating, and displaying, among others.

Full text of DOI:10.1002/anie.201812708

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International Edition Chemie
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Accepted Article
Title: Universal Reservior of UV, WL and NIR Light for Long Persistent
Luminescence from a Metal-Organic Supramolecular Box
Authors: Zheng Wang, Cheng-Yi Zhu, Shao-Yun Yin, Zhang-Wen Wei,
Jian-Hua Zhang, Ya-Nan Fan, Ji-Jun Jiang, Mei Pan, and
Cheng-Yong Su
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To be cited as: Angew. Chem. Int. Ed. 10.1002/anie.201812708
Angew. Chem. 10.1002/ange.201812708
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Angewandte Chemie International Edition
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COMMUNICATION
Universal Reservior of UV, WL and NIR Light for Long Persistent
Luminescence from a Metal-Organic Supramolecular Box
Zheng Wang, Cheng-Yi Zhu, Shao-Yun Yin, Zhang-Wen Wei, Jian-Hua Zhang, Ya-Nan Fan, Ji-Jun
Jiang, Mei Pan,* and Cheng-Yong Su
Abstract: Long persistent luminescence (LPL) materials have
unique photophysical mechanism to store light radiation energy for
subsequent release. However, in comparison to the common UV
source, white-light (WL) and near-infrared (NIR) excited LPL is
scarce. Here we report a metal-organic supramolecular box based
on a D-π-A type ligand. Due to the integrated one-photon absorption
purpose, numerous materials with TPEF potentials have been
developed. One of the designing concepts is to construct D-π-A
type molecules for the generation of excellent two-photon
absorption ability.[16-18] Bearing above considerations in mind, we
herein designed a unique D-π-A type organic ligand from
terpyridine derivatives, endowed with both good OPA and TPA
attributes. Further coordination with heavy metal Cd(II) ions
(OPA) and two-photon absorption (TPA) attributes of the ligand,
heavy atom effect of the metal-center, as well as π-stacking and J-
aggregation states in the supramolecular assembly, LPL can be
triggered by all wavebands from UV, WL to NIR region for the first
time. This novel designed supramolecular kit to afford LPL via both
OPA and TPA pathways provides potential applications in anti-
counterfeiting, camouflaging, decorating, displaying, and so on.
2 2
leads to M L rectangular box. As a whole, the inter- and intra-
molecular packing states among the boxes facilitate triplet
excitons and lead to unprecedented LPL with wide excitation of
UV, WL and NIR source via OPA or TPA pathways.
The D-π-A type organic ligand HTzDPTpy (L) was
synthesized by three steps (Figure 1 and Scheme S1), which
consists of a conjugated terpyridine, a biphenyl and a tetrazolyl
group, acting as the electron-acceptor, π-bridge and electron-
donor, respectively. Hydrothermal reaction of HTzDPTpy with
Long persistent luminescence (LPL), also known as
afterglow luminescence, is a fascinating optical phenomenon
which has certain amount time of emission after removing the
excitation light source.[1] In the past decades, a number of LPL
materials have been designed and synthesized by different
methods, and attracted considerable attention in various fields
including LEDs, displays and decorations, sensors, anti-
counterfeiting barcodes, military night-visions, bio-imaging lables
and so on. [2-4] However, most of the applicable LPL systems are
inorganics doped by rare earth or noble transition metals,[5-7]
which have limitations in structural and functional modification
and large-scale production due to expensive cost and harsh
synthetic conditions. Recently, organic-based LPL materials
have been gradually developed by several strategies, including
the construction of pure organic solids or host-guest co-crystals,
metal-organic hybrids and metal-organic frameworks, etc. [8-13]
However, the LPL in so far explored materials is dominantly
triggered by one-photon absorption (OPA) of UV light, although
some recent studies have expanded the radiation to visible
white-light.[3,5] In comparison, LPL excited by near-infrared (NIR)
source remains basically in blank, which might have the merits
of low energy and deep penetrability, and can be more
applicable in such fields as biological imaging and military anti-
counterfeiting.[14]
CdCl
block crystals, which were determined to have the formula of
Cd (TzDPTpy) (HCOO) ]·3H O (named as Cd , MOC-38).
Single crystal X-ray diffraction analysis reveals that Cd is
2 2
in DMF and H O for 2 days at 140 °C afforded yellow
[
2
2
2
2
2 2
L
2 2
L
crystallized in monoclinic crystal system belonging to C2/c space
group (Tables S1, S2). The phase purity is verified by PXRD,
and TGA shows good thermal stability up to ~300 oC (Figures
2 2
S1, S2). In the crystal structure of Cd L , two Cd(II) metal
centers link two TzDPTpy- ligands to form a rectangular
molecular box. Due to the simple yet unique structure of the
molecular box consisting of near-parallel sides with poly-
aromatics, strong π-π stacking interactions are formed. Further
intramolecular π-π, C-H…π and C-H…N interactions along
2 2
different directions stack Cd L boxes into a closely-packed 3D
framework, leading to J-aggregation conformations (Figures S3,
S4). This kind of intramolecular packing might promote the
population of lower-energy triplet states, as confirmed by the
redshift of solid state absorption in comparison with the solution
state (Figure S5). This is different from the H-aggregation
observed in pure organic LPL materials.[19] Meanwhile, the
abundant inter- and intramolecular interactions also bring
restricted molecular motions and reduced non-radiation energy
consumption. All these will be helpful to enrich and improve the
2 2
photophysical properties of Cd L , and encourage us for further
exploration.
Alternatively, two-photon excited fluorescence (TPEF)
provides the utilization of low energy visible/NIR excitation via a
two-photon absorption (TPA) pathway to produce higher-energy
HTzDPTpy shows rather broad absorption spectra extending
from 250 to 700 nm (Figure S5), and emits strong blue
luminescence centered at 495 nm in air at RT under the
excitation of 280 to 400 nm UV light (Figure S6), which can be
assigned to the typical π-π* singlet transitions of the ligand. A
short decay lifetime of 4.08 ns detected at the emission peak at
emissions, which is of practical importance for a wide range of
applications in optoelectronics and biological fields.[15] For this
Prof. M. Pan,* Z. Wang, C.-Y. Zhu, S.-Y. Yin, Z.-W. Wei, J.-H. Zhang, Y.-N.
Fan, J.-J. Jiang, Prof. C.-Y. Su, MOE Laboratory of Bioinorganic and
Synthetic Chemistry, Lehn Institute of Functional Materials, School of
Chemistry, Sun Yat-Sen University, Guangzhou 510275, China, E-mail:
panm@mail.sysu.edu.cn
495 nm confirms the attribution of fluorescence (F). After
pumped to vacuum, the emission intensity was decreased while
a broadened contour appears, showing some hints for the
emergence of lower energy triplet transitions, which are basically
Supporting information for this article is given via a link at the end of the
document.
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COMMUNICATION
obscure in air at room temperature (Figure S7). Additionally,
moderate increase of emission intensity and decay lifetime ( =
stabilize the molecular vibration and reduce non-irradiation loss.
Expectedly, as a wonderful D--A type organic molecule, TPEF
was obtained for HTzDPTpy using 780 nm laser radiation, with
similar attribute of the OPA luminescence (Figure S8).
9.7 ns) was detected as the temperature gradually decreases
from RT to 77 K. This is because the low temperature can
OPA& TPA Bifunctional Ligand
LPL by UV, WL & NIR Radiation
N
N
A
π
D
D
A
H
N
N
N
N
N
S
n
T
n
ISC
StabilizingT
n
’
OPA TPA
---
F
UV/WL/NIR
P
LPL
WLE
π-π
π-π
π-π
H-π
π-π
H-π
π-π
H-π
π-π
H-π
S
0
Cd
2
L
2
Molecular Box: - stacking & heavy metal effect
Intramolecular Packing & J-Aggregation
Figure 1 Design concepts for the targeted metal-organic molecular box with long persistent luminescence by UV, WL and NIR radiation. The inset shows
proposed energy transfer mechanism (F, fluorescence; P, phosphorescence; LPL, long persistent luminescence; WLE, white-light emission; OPA, one-photon
absorption; TPA, two-photon absorption; UV, ultraviolet; WL, white-light; NIR, near-infrared; S, singlet; T, triplet; ISC, intersystem crossing)
Intriguingly, for the assembled Cd
emissions can be distinguished obviously in the range of 400 to
00 nm under UV light excitation (Figure 2). The blue
luminescence centered at 460 nm has a quick decay lifetime of
.65 ns (RT), which can be assigned to ligand-centered (LC)
fluorescence similar to that observed for HTzDPTpy, with some
blue-shift due to the metal coordination. Whereas another
orange luminescence extends into long wavelength region, with
the center basically located at ~610 nm. This emission manifests
a slow decay lifetime of 21.4 ms at 298 K, and can be
unambiguously ascribed to room temperature phosphorescence
2
L
2
molecular box, dual
of 365 and 405 nm, respectively (Figures S11-13, Table S5).
When excited at 365 nm, the emission intensities of both blue
fluorescence and orange phosphorescence are gradually
decreased with the temperature increasing from 77 to 400 K.
Analysis of activation energy from Arrhenius equation gives an
activation energy to be 1829 J, corresponding to the difference
between energies of the two emission states. Nevertheless, the
overall emission color keeps basically unchanged in the blue
light region (Figure 2c). While at the excitation of 405 nm, as the
temperature increases from 77 to 300 K, the intensity of the blue
fluorescence shows an abnormal enhancement, in contrast with
the abatement of the orange phosphorescence. As a result, the
overall emission color is greatly switched from orange to blue
region (Figure 2d). This manifests that the emission property of
7
3
(
RTP) originating from the triplet excited states of the ligands.
The appearance of RTP in Cd metal-organic coordination box
2 2
L
which is obscure in pure HTzDPTpy ligand should be
contributed to multiple inter- and intra-molecular π-π*, C-H…N,
C-H…π packing interactions and J-aggregation as stated
above.[ Meanwhile, the heavy metal effect of Cd(II) ions also
helps to stabilize the triplet energy states and facilitate RTP.
2 2
Cd L is not only dependent on the excitation energy, but also
responds to the temperature, and the PL color changes can be
detected by naked eyes. The good linear relationship between
CIE coordinate and temperature due to the dual emissions
affords a prototype for ratio-dependent thermometer with self-
calibration ability. Time-dependent decay study reveals an
obvious increment of the phosphorescence lifetime at low
temperature (109.6 ms at 77 K, Figure S14). Time-gated
emission spectra show that, with different delayed times from
19]
2 2
The above dual-emission attributes of Cd L consisting of
both blue fluorescence and yellow phosphorescence
simultaneously provides possibility for single-component white-
light emission (SC-WLE). Adjustment of the excitation
wavelength can further modulate the relative intensities of the
dual emissions. As shown in Figures 2a and S9, with the steady
increase of excitation wavelength from 280 to 450 nm, the
0.05 to 15 ms, Cd
2
L
2
manifests the emission peak at
approximately 610 nm, corrpesonding to the room temperature
phosphorescence (RTP, Figure S15), further approving of its
triplet nature.
Based on the above one-photon excited emission, when
using 780 nm wavelength laser as the incident light, efficient
relative intensity of I
phosphorescence and fluorescence, respectively) is gradually
increased. As a consequence, the overall emitting color of Cd
P F P F
/I (I and I means for the intensity of
2
L
2
changes from blue to orange (Figures 2b and S10, Table S3,
S4). Noticeably, at the excitation of 405 nm, a pure white light
emission was obtained with the CIE coordinate of (0.33, 0.34).
2 2
TPEF was detected for Cd L sample. As shown in Figure S16,
a linear log(I)–log(P) relationship can be established between
the TPEF intensity (I) and laser power (P), proving the up-
converted luminescence is indeed induced by a nonlinear TPA
2 2
To further clarify the dual emissions of Cd L , variant-
temperature photoluminescence was detected at the excitation
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process. Notably, the TPEF excitation wavelength of Cd
2
L
2
can
while that for 365 nm changes little, which might be due to the
heat dissipationq effect is more significant in the former.
be extended from 780 to 900 nm (Figures 2e, f), showing good
adaptability to the excitation energy range, which has been
rarely reported in metal-organic coordination systems.
a
a
b
OPEF by UV
0
.1s
1s
3s
5s
7s
4
20 nm
05 nm
80-390 nm
4
1
0s
15s
20s
30s
60s
2
bb )
c
c
d
UV/WL/
NIRoff
UV/NIR
on
9
8
8
8
8
8
7
00
80
60
40
20
00
80
e
TPEF by NIR
f
0
.1s
0.35s
1.60s
0.60s
1.85s
0.85s
2.1s
1.1s
1
.35s
2.35s
Figure 3. a) LPL photos of Cd
the removal of WL radiation. b) Photos of Cd
powder (lower) samples at different irradiation source (from left to right, naked
eye-detectable yellow color under daylight (WL), OPA or TPA blue
luminescence by 365 or 780 UV/NIR excitation, and red LPL after the removal
2
L
2
bulk powders at different time interval after
single crystal (upper) and bulk
2 2
L
4
00 450 500 550 600 650
Wavelength (nm)
1
000
00
00
00
00
00
00
g
LPL by White light
h 9
8
7
6
5
4
2 2
of UV/NIR radiation. c) LPL photos of Cd L bulk powders at different time
interval after the removal of NIR radiation (room temperature).
Furthermore, more readily available white light, such as the
flashlight from a torch or cellphone was selected as the
irradiation source. And the red LPL can be triggered even more
efficiently and last for several minutes observable by naked eyes
after the WL off. The evolution spectra were also recorded by
time-dependent spectrophotometer (Figures 2g, 2h, 3a, S21,
and Video 2). For the generation of this strong white-light-
excited LPL, the overlapped region of the excitation spectrum of
0
2
4
6
8
10 12 14
Time (s)
2 2
Figure 1. OPA (a-d), TPA (e, f) and LPL (g, h) emissions of Cd L in solid
state at room temperature. a) OPA emission spectra, and b) CIE coordinates
at different excitation wavelength. c, d) variant-temperature emission at the
excitation wavelength of 365 and 405 nm. e, f) 1D and 2D TPA fluorescence
spectra. g, h) 1D and 2D LPL spectra after radiation of white light. Color from
red to blue indicates decrease in emission intensity within f and h.
Cd
might account. And the WL-excited LPL of Cd
mainly attributable to OPA pathway, similar with the UV-
kinds of irradiation source (Figures 2g, h, 3, S17-23, Videos 1-4). irradiation source. Photo-stability of Cd
has been approved
Typically, for a single-crystal of Cd with yellow color, prompt
by PXRD and repeatability of its LPL has been tested for eight
blue luminescence is emitted at the excitation of 365 nm UV light. runs (Figure S23), showing good consistence. Moreover, it is
2
L
2
and the irradiation spectrum of the flashlight (Fig. S22)
More fascinatingly, besides the above OPA and TPA
2 2
L
should still be
2 2
luminescence, Cd L can give LPL after the removal of different
2 2
L
2 2
L
While after the cease of UV-irradiation, long persistent red
luminescence is detected. Such is also the case for bulk powder
even delighted to find that, TPA process can also lead to LPL in
Cd . As discussed before, blue TPEF can be generated by
2 2
L
sample of Cd
2
L
2
(Figures 3b, S17). Changing the light source to
780 nm or longer wavelength laser excitation. And after
switching off the laser, red LPL appears, which is recorded and
can last for several seconds detectable by naked eyes (Figures
3b, 3c, S24, and Videos 3, 4). As far as we know, this is the first
report of LPL to be triggered by widebands covering UV, WL to
NIR region via either an OPA or TPA pathway, and represents
the first example of TPA-LPL.
405 nm, prompt white light emission is generated due to the dual
emissions, as discussed before in Figure 2b. While after turning
off the white light, red afterglow luminescence is observed to last
several seconds. By the aid of
spectrophotometer, we successfully recorded the evolution of
LPL spectra centered at about 650 nm for Cd after the
removal of 365 or 405 nm UV light for different irradiation time
Figures S18, 19). It can be concluded that basically, the 405 nm
a
time-dependent
2 2
L
TD-DFT calculation was performed to explore the
mechanism of the fluorescence and phosphorescence
(
irradiation leads to stronger initial LPL intensity than 365 nm light
source on equal basis of other conditions (Figure S20), showing
that the lower energy excitation might be more favorable for the
LPL generation. But notably, extending the irradiation time of
emissions of Cd . We can see that, the HOMO and LUMO
2
L
2
orbitals of Cd L are mainly resided on the biphenyl-tetrazole
2 2
and terpyridine groups, respectively, in accordance with the D-π-
A nature of the ligand. And as shown in Figure 4a and Table S6,
there exist multiple intersystem crossing channels from the
405 nm results in an obvious decrease of the LPL intensity,
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singlet to triplet transitions in Cd
favorable for the population of triplet exciton states, and
accounts for the generation of RTP and LPL in Cd , which is
absent in pure organic ligand. Summing up the above
experimental and theoretical results, we can deduce a proposed
energy transfer mechanism for Cd L as illustrated in Scheme 1:
2 2
first, the metal-organic supramolecules absorb UV/WL/NIR light
energy via either OPA or TPA pathway, and transfer to the
2
L
2
(S
1
→T
2
~T
7
).[11] This is
In summary, a M
2
L
2
metal-organic supramolecular box has
been successfully designed to possess multiple photophysical
attributes. Single phase white light and dual emissions
comprised of blue fluorescence and orange RTP (room
temperature phosphorescence) can be reached by adjusting the
excitation wavelength and temperature. OPA and TPA
properties of the D-π-A type ligand are well inherited by the
supramolecular box. And most importantly, LPL (long persistent
luminescence) can be triggered by wideband irradiation from UV,
WL to NIR light source via either OPA or TPA pathway. This
study brings forward a novel strategy to combine TPA with LPL
together, and successfully implements the idea of TPA-LPL for
the first time. The delicate design of such kinds of metal-organic
supramolecular assemblies provides a universal reservior of UV,
WL to NIR light energy for the persuit of LPL and other optical
potentials to be applicable in wide fields.
2 2
L
excited singlet states S
otherwisely, S states transit to the excited triplet states T
intersystem cross, which then emit orange phosphorescence.
And additionally, T states further relax to lower-energy T
states after ceasing of light radiation, leading to the unique LPL
phenomenon triggered by UV/WL/NIR light in Cd
3.0
n
, which can emit blue fluorescence. Or
n
n
via
n
n

2 2
L .
a
LUMO
b
S1
T
Acknowledgements
7
6
4
2
2
.5
.0
T
0
.25 eV
T ,T
5
3
This work was supported by NSFC (21771197, 21720102007,
T ,T
2
HOMO
2
1821003, 21573291), Local Innovative and Research Teams
Project of Guangdong Pearl River Talents Program
2017BT01C161). We thank Prof. Zhenguo Chi and Mr. Yingxiao
(
c
d
Mu for help with the test of time-interval-dependent LPL spectra.
Keywords: LPL • metal-organic box • TPA • white light• NIR
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COMMUNICATION
Entry for the Table of Contents
COMMUNICATION
By delicate design of D-π-A ligand
bearing both one-photon absorption
Zheng Wang, Cheng-Yi Zhu, Shao-Yun
Yin, Zhang-Wen Wei, Jian-Hua Zhang,
Ya-Nan Fan, Ji-Jun Jiang, Mei Pan,*
and Cheng-Yong Su
(
(
OPA) and two-photon absorption
TPA) attributes, LPL can be triggered
in the assembled metal-organic
supramolecular box by all wavebands
from UV, WL to NIR region, via either
OPA or TPA pathways.
Page No. – Page No.
Universal Reservior of UV, WL and
NIR Light for Long Persistent
Luminescence from a Metal-Organic
Supramolecular Box
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