Achievement of persistent and efficient organic room-temperature phosphorescence with temperature-response by adjusting the proportion of excited-state configurations in coupled molecules

Article abstract of DOI:10.1039/c9tc01870k

Organic materials with persistent room-temperature phosphorescence (pRTP) have played an important role in many fields. However, it is difficult to simultaneously improve the efficiency and lifetime of pRTP via the introduction of simple groups. Herein, w

Full text of DOI:10.1039/c9tc01870k

View Article Online
View Journal
Journal of
Materials Chemistry C
Accepted Manuscript
This article can be cited before page numbers have been issued, to do this please use: J. Chen, N. U.
Rahman, Z. Mao, J. Zhao, Z. Yang, S. Liu, Y. Zhang and Z. Chi, J. Mater. Chem. C, 2019, DOI:
10.1039/C9TC01870K.
This is an Accepted Manuscript, which has been through the
Volume
4 Number 1 7 January 2016 Pages 1–224
Royal Society of Chemistry peer review process and has been
accepted for publication.
Journal of
Materials Chemistry C
Accepted Manuscripts are published online shortly after
Materials for optical, magnetic and electronic devices
www.rsc.org/MaterialsC
acceptance, before technical editing, formatting and proof reading.
Using this free service, authors can make their results available
to the community, in citable form, before we publish the edited
article. We will replace this Accepted Manuscript with the edited
and formatted Advance Article as soon as it is available.
You can find more information about Accepted Manuscripts in the
author guidelines.
Please note that technical editing may introduce minor changes
to the text and/or graphics, which may alter content. The journal’s
standard Terms & Conditions and the ethical guidelines, outlined
in our author and reviewer resource centre, still apply. In no
event shall the Royal Society of Chemistry be held responsible
for any errors or omissions in this Accepted Manuscript or any
consequences arising from the use of any information it contains.
ISSN 2050-7526
PAPER
~
Nguyên T. K. Thanh, Xiaodi Su et al.
Fine-tuning of gold nanorod dimensions and plasmonic properties using
the Hofmeister effects
rsc.li/materials-c

Please do not adjust margins
Page 1 of 6
Journal of Materials Chemistry C
View Article Online
DOI: 10.1039/C9TC01870K
ARTICLE
Achieving persistent and efficient organic room-temperature
phosphorescence with temperature-response by adjusting the
proportion of excited-state configurations in coupled molecules
Received 00th January 20xx,
Accepted 00th January 20xx
Junru Chen, Naveed Ur Rahman, Zhu Mao, Juan Zhao,* Zhiyong Yang, Siwei Liu, Yi Zhang,*
Zhenguo Chi*
DOI: 10.1039/x0xx00000x
Organic persistent room temperature phosphorescence (pRTP) materials have played an important role in many fields.
However, the efficiency and lifetime for pRTP are difficult to improve simultaneously through the introduction of simple
groups. Herein, we synthesized OMe-SPh (=58.1 ms, P=4.47%), in which the methoxy group was introduce based on SPh
(=43.2 ms, P=2.48%). And further extension of the conjugate chain by dibenzothiophene, OMe-SPhT was achieved with
both high efficiency and long lifetime (=171 ms, P=4.71%). In this case, we desired a balance of different excited-state
configurations (n*and *), which were verified from single crystal X-ray diffraction analysis and theoretical time-
dependent density functional theory calculations. In addition, the pRTP from neighbouring molecules exhibits higher
stablility character than the phosphorescence from traditional single molecule, especially for temperature. Based on this
property, OMe-SPhT achieved the real-time change of phosphorescence color to temperature.
for pRTP, and can be divided by two kinds: one way is to create a
rigidity environment to suppress the non-radiative pathways, and
Introduction
Light-emitting materials are widely used in devices and biological
engineering. Particularly, phosphors with persistent luminescence
have attracted the wide spread attention because of a variety of
potential applications, such as biological imaging,[1-4] optoelectronic
devices,[5-6] sensors,[7-8] data storage[9] and anti-counterfeiting.[10] So
far, the realization of phosphorescence is mostly limited to metal-
containing materials.[11-13] Compared with the organometallic or
inorganic compounds, metal-free organic phosphorescence
materials have more merits including good stability and
processability, low cost and toxicity. Considering these factors,
more substitute organic phosphorescence materials have been
achieved to perform their advantages, resulting in wide application
areas[14]. However, the persistent phosphorescence in organic
materials are more easily observed under low temperature or inert
conditions, because the emission from the triplet excitons tends to
quench, owing to high sensitivity to oxygen and temperature.
Therefore, the persistence room temperature phosphorescence
(pRTP) is still rare (typically > 100 ms). Until now, many effective
approaches have been proposed to obtain mental-free pRTP,
another way is to introduce heavy atoms and heteroatoms with n
electrons to promote the intersystem crossing (ISC) rate.[25-26] Most
importantly, Adachi et al.[27] even reported a material that lasts for
more than one hour at room temperature through using a simple
mixture of two organic molecules. Despite of that, it is rarely
reported about organic pRTP with both high efficiency and ultra-
long lifetime, because of the process of non-radiative transition and
the spin-forbidden transfer from singlet to triplet excited states.
Recently, Tang et al.[28] reported on molecular-orbital
investigation to balance the lifetime and efficiency of single
luminogenic molecules. To obtain the organic RTP materials with
high efficiency and persistent lifetime, the materials should realize a
fast rate of ISC (kst) from the lowest singlet (S1) to triplet excited
state (Tn) and a slow rate of phosphorescence (kp) or reduce the
rate of nonradiative decay. According to EI-Sayed rule, spin-orbit
coupling occurring in transition between n* and * states could
promote the process of ISC. While the efficient ISC process is
achieved, the radiative rate from the lowest triplet state (T1) to the
ground state (S0) is also increased because of the enhancement of
spin−orbital coupling (SOC). In contrary, the transition between two
different * states could lead to long lifetime but weak
phosphorescence (Figure 1a).[29-30] Therefore, it is challenging to
improve efficiency and lifetime simultaneously.
including host-guest doping,[15-16] crystallization,[17-18]
H-
aggregation[19-20] and so on.[21-24] All of these strategies aim to
enhance efficiency and lifetime, which are two critical parameters
In this research work, we expect to adjust the proportion of
excited-state configurations to balance the efficiency and lifetime.
In the first step, we introduced a simple methoxy group on SPh
(Figure 1b), the existence of the long-pair electrons could increase
kst through the transition between n* and * states, resulting in
the higher phosphorescence efficiency (4.47%). In the second step,
PCFM Lab, GD HPPC Lab, Guangdong Engineering Technology Research Center for
High-performance Organic and Polymer Photoelectric Functional Films, State Key
Laboratory of Optoelectronic Material and Technologies, School of Chemistry, Sun
Yat-sen University, Guangzhou, 510275, P. R. China. E-mail:
zhaoj95@mail.sysu.edu.cn, chizhg@mail.sysu.edu.cn, ceszy@mail.sysu.edu.cn.
†Electronic Supplementary Information (ESI) available: CCDC 1905615, 1834499
and 1835838. For ESI and crystallographic data in CIF or other electronic format
see DOI: 10.1039/x0xx00000x
Please do not adjust margins

Please do not adjust margins
Journal of Materials Chemistry C
Page 2 of 6
ARTICLE
Journal Name
emission bands of the molecules in THF are peaked atV3ie0w6Anrtmicle(OSPnlhin)e,
309 nm (OMe-SPh) and 377 nm (OMe-SDPOhTI:)10r.e10s3p9e/cCt9ivTeCly0.18T7h0Ke
phenomenon of redshift could be explained by the theoretical
calculation, which reveals the distribution of energy level (Figure
S12). The electronic cloud distributions of SPh and OMe-SPh have
no obvious changes, leading to large energy level difference
between S1 and T1 (1.44 eV for SPh and 1.28 eV for OMe-SPh). In
contrast, OMe-SPhT has two electron-donating groups including
dibenzothiophene and anisole. The overlapping between the
electron clouds of HOMO (highest occupied molecular orbital) and
LUMO (lowest unoccupied molecular orbital) becomes smaller,
showing the energy level between S1 and T1 is 0.82 eV. Besides, the
lowest S1 energy level of OMe-SPhT (3.89 eV) presents a significant
bathochromic shift in comparison to that of SPh and OMe-SPh.
Similarly, the decrease of the energy level of T1 causes the single
phosphorescence of OMe-SPhT, which moves towards longer
wavelength (ca. 530 nm) (Figure S13).
All the crystalline powders were achieved by recrystallization
from dichloromethane and N-hexane solvents, and the crystal
purity was confirmed by powder X-ray diffraction (Figure S14). As
shown in Figure 2a, the fluorescence emissions of SPh, OMe-SPh
and OMe-SPhT are peaked at 337 nm (ca. 2.3 ns), 318 nm (ca. 1.8 ns)
and 389 nm (ca. 3.8 ns). Because of the larger conjugated structure,
the prompt fluorescence of OMe-SPhT exhibits a red-shift. After
turning off the excitation lamp, green phosphorescence from SPh
(at ca. 529 nm, p=2.48%) is observed, which is relatively weak and
lasts in a short interval of time (43.2 ms) (Figure 1b and Figure S15).
On the contrary, both of OMe-SPh and OMe-SPhT exhibit orange
RTP by stopping the excitation, which contributes to new emission
peaks at 580 nm with a shoulder at 625 nm and 563 nm with a
shoulder at 606 nm respectively. The corresponding lifetime of the
emission in OMe-SPh (580 nm) and in OMe-SPhT (563 nm) is 58.1
ms (p=4.47%) and 171 ms (p=4.71%) respectively at room
temperature (Figure 2b and Figure S16-S17). The phosphorescence
emission spectra of the three compounds had been investigated at
77 K to further identify the attribution of RTP (Figure S18). It is
worth noting that SPh crystal powder shows the similar
phosphorescence spectra at different temperatures (ca. 507 nm).
But for OMe-SPh and OMe-SPhT, compared with phosphorescence
spectra at 300 K, the new bands (476 nm and 530 nm) at 77 K for
them are observed. Because the molecular motion is limited, the
Figure 1. (a) Equations for phosphorescence efficiency and
phosphorescence lifetime. (b) Strategies for achieving high-
efficiency pRTP compounds with a long lifetime.
we used dibenzothiophene to extend the conjugation of OMe-SPh
and successfully synthesized a compound namely OMe-SPhT with
longer phosphorescence lifetime through increasing the proportion
of excited state with * configuration (Figure 1b). Taking
advantage of electron with long phosphorescence lifetime
achieved OMe-SPhT with the longest lifetime (171ms). As expected,
based on combining the advantages of different excited-state
configurations in coupled intermolecular units, OMe-SPhT has as
much phosphorescence quantum efficiency as OMe-SPh. Moreover,
pRTP OMe-SPhT has a longer phosphorescence lifetime originated
from coupled molecule which has more stable triplet excitons than
traditional single phosphorescence, resulting in temperature-
response for OMe-SPhT.
Results and discussion
Two molecules OMe-SPh and OMe-SPhT were synthesized as shown
in Scheme S1, where SPh was purchased from Aldrich. Their
chemical structures were fully characterized by NMR, high-
resolution EI mass, and X-ray single-crystal analyses (Figure S1-S9).
The photophysical properties of the molecules were measured in
solution and crystal powder. The absorption and emission spectra
of SPh, OMe-SPh and OMe-SPhT in tetrahydrofuran (THF) are
shown in Figure S10. In dilute solution (1 × 10-5 mol/L), the UV-vis
absorption displays the peaks at 254 nm, 266 nm and 286nm for
SPh, OMe-SPh and dibenzothiophene respectively, which are mainly
stemmed from * transition. Through comparing the spectra of
dibenzonthiophene, OMe-SPh and OMe-SPhT, the main absorption
peaks for OMe-SPhT are located at 290 nm and 334 nm, attributing
to * transition from dibenzonthiophene and intramolecular
charge transfer (ICT) respectively. The emission spectra of OMe-
SPhT measured in different polar solvents are shown in Figure S11.
The emission band shows a bathochromic shift (ca. 42 nm) with
increasing the solvent polarity. Therefore, the absorption and
emission bands can be ascribed to ICT transition. In addition, the
Figure 2. (a) Steady-state photoluminescence (blue line) and
persistent phosphorescence (orange line) spectra of SPh, OMe-SPh
and OMe-SPhT. (b) The persistent phosphorescence photograph of
SPh, OMe-SPh and OMe-SPhT after removing the excitation.
2 | J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins

Please do not adjust margins
Page 3 of 6
Journal of Materials Chemistry C
Journal Name
ARTICLE
View Article Online
DOI: 10.1039/C9TC01870K
Figure 3. (a) The extracted adjacent dimer (the intermolecular
interaction between two methoxys) and packing style of OMe-SPh
in single crystal. (b) The ISC channels between S1 and Tn of OMe-SPh
dimer (the red lines represent the major ISC channels and grey lines
represent energy gap over 0.4 eV). (c) The persistent
phosphorescence photograph of SPh and OMe-SPh with different
decay times.
Figure 4. (a) The extracted adjacent dimer (the intermolecular
interaction between methoxy and dibenzothiophene) and packing
style of OMe-SPhT in single crystal. (b) The ISC channels between
the S1 and Tn of OMe-SPhT dimer (the red lines represent the major
ISC channels and grey dashed lines represent energy gap over 0.4
eV). (c) The persistent phosphorescence photograph of OMe-SPhT
with different decay times.
single phosphorescence intensity is sharply increased. It indicates
that there are two probably types of phosphorescence in OMe-SPh
and OMe-SPhT. Moreover, the phosphorescence spectra of the
three compounds in glass state (THF) at 77 K (Figure S13) exhibit the
single phosphorescence peaked at 507 nm, 460 nm and 536 nm,
which is corresponding to new peaks observed from their spectra in
solid powder at 77 K (Figure S18). From discussed above, we
attribute the room temperature phosphorescence of SPh to single
molecule, and OMe-SPh and OMe-SPhT to coupled molecules.
To further investigate the mechanism of the enhanced persistent
RTP, the single crystal X-ray diffraction (XRD) analysis were
performed for SPh, OMe-SPh and OMe-SPhT. All of them are
monoclinic crystal system. SPh and OMe-SPh are in the P21/c space
group, while OMe-SPhT is in the P21/n space group. For SPh, the
intermolecular interaction is mainly C-H···, which can restrict the
molecule motions to certain extent. Nevertheless, such week van
der Waals force has little contribution to ultra-long
phosphorescence. But for OMe-SPh and OMe-SPhT, abundant
intermolecular interactions are observed in their adjacent
molecules. The main performance of C-H···O intermolecular
interactions are originated from methoxy and sulfonyl. In the single
crystal of OMe-SPh, the compact interactions (2.588 Å) are
detected between the oxygen atom and hydrogen atom of the two
adjacent methoxy groups, liking the circular chain to immobilize the
molecule (Figure 3a and Figure S19). Similarly, we found more
different distances of C-H···O intermolecular interactions (2.665 Å,
2.539 Å, 2.582 Å, 2.656 Å and 2.640 Å) in OMe-SPhT crystal (Figure
4a and Figure S13). Especially, OMe-SPhT shows C-H···S with a short
Furthermore, the theoretical time-dependent density functional
theory (TD-DFT) calculations were used to verify our conjecture. For
instance, the monomers of OMe-SPh and OMe-SPhT involve one
major and two minor the same orbital composition respectively to
finish the progress of ISC (Figure S20). To gain further insight into
the influence of the coupling of typical n and  units in the crystal
state to pRTP for coupled molecules, the adjacent dimer was
extracted from three crystals of SPh, OMe-SPh and OMe-SPhT.
Consistent with previous results, there is no channel found in any
coupled SPh for ISC transition. Considering the probability of ISC
between the S1 and Tn states, there are more ISC channels in
coupled OMe-SPh and OMe-SPhT molecules, resulting in more
efficient phosphorescence. As shown in Figure 3b, in the aggregated
OMe-SPh dimer, two molecules are interacting with each other
through hydrogen bonds. In this case, two possible ISC main
channels from S1 to T7 and T8 are obtained by calculation,where all
the channels containing the same transition configurations
including HOMO-1 → LUMO+1 and HOMO → LUMO. Further
results reveal that the number of the main ISC channels for coupled
OMe-SPhT molecules is increased into four possible channels. The
T3, T4, T9, and T10 states of the coupled molecules involve the same
orbital composition as the S1 state (HOMO-1 → LUMO and HOMO
→ LUMO+1, Figure 4b), indicating more efficient channels for ISC.
And the hot excitons decay to the lowest triplet state through
internal conversion and then to ground state, resulting in
persistence phosphorescence at room temperature. Through
combining the photophysical properties and the ISC channels in the
single crystals, we have proposed a mechanism for the pRTP in
OMe-SPhT. The long-lived phosphorescence owing to the presence
of a new lower-lying triplet energy level, which is formed by the
interaction of adjacent molecules.[26,34] Because of the existence of
distance (2.993 Å). Moreover,
a large overlapping on the
dibenzothiophene group for OMe-SPhT dimer is observed to form
π···π stacking. As previously reported, the abundant hydrogen
bonding stabilizes the energy and restricts the molecule motion,
resulting in the enhancement of persistence RTP.[10,31-33] The
compact stacking in OMe-SPhT crystal further suppresses the non-
radiative transition and brings about a longer lifetime.
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 3
Please do not adjust margins

Please do not adjust margins
Journal of Materials Chemistry C
Page 4 of 6
ARTICLE
Journal Name
from green to orange. This temperature-response characteristic is
View Article Online
not detected in OMe-SPh, due to the weak sDinOgIl:e10p.h10o3s9p/hCo9rTeCs0c1e8n7c0eK.
As shown from previous TD-DFT calculations of isolate OMe-SPh
and OMe-SPhT, only one main ISC channel to achieve ISC is
observed in isolated OMe-SPh, while there are more main channels
for OMe-SPhT, which is also associated with the abundant
intermolecular interactions in the crystal of OMe-SPhT. Therefore,
these characters enable the organic molecule phosphorescence
with more potential applications such as in anti-counterfeiting and
data storage.
Conclusions
In summary, we synthesized OMe-SPhT for achieving the pRTP
materials with high efficiency and long lifetime. Among these
compounds, the molecules with methoxy provide the long pair
Figure 5. (a) Phosphorescence spectra of OMe-SPhT under different
temperatures. (b) The CIE coordination of phosphorescence during
the temperature increase from 77 K to 300 K for OMe-SPhT. (c)
Illustration of the character “R” arranged by OMe-SPhT in different
aggregation states, and the changes of persistent phosphorescence
as the temperature increases.
electrons and enhance the transition between n
states. Furthermore, the large conjugated system of
dibenzothiophene improves the portion of n * transition by
adjusting the proportion of an excited state with hybrid n
* and *


*
and * for the purpose of achieving a balance between
efficiency and lifetime. Moreover, more stabilized triplet
excitons in coupled OMe-SPhT molecule realize higher stability
of phosphorescence to temperature rather than that
phosphorescence from single molecule. It is observed that the
persistent phosphorescence of OMe-SPhT experiences color
variations from cyan to green and finally orange with the
temperature increasing from 77 K to 300 K. This work proposes
an effective strategy for achieving high-efficiency pRTP with a
long lifetime to broaden more possible applications.
the coupling of n and  units in the crystal state, the bright pRTP by
combining their advantage including the fast rate of ISC and slow
rate of phosphorescence (Figure 4c).
Generally, the rigid crystalline state could provide a condition to
generate the RTP emissions and isolate it from inert atmosphere
such as heat and oxygen.[35] For OMe-SPhT, the crystallization not
only prevents phosphorescence quenching by oxygen but also
immobilize the molecule because of multiple intermolecular
interactions. Intermolecular hydrogen bonding even has impeded
the progress of thermal relaxation or other non-radiative pathways
to enhance the phosphorescence. Besides, the adjacent molecules
in OMe-SPhT combined with hydrogen bonding produce the lower
triplet energy level.[36,37] Meanwhile, the movement is limited by
weak interactions of coupled molecule, which have few effects
related to temperature. However, the traditional phosphorescence
from single molecule depends on the temperature more than the
dimer. Based on this characteristic, we investigated color changes
of the persistence phosphorescence at different temperatures. For
OMe-SPhT crystal powder, the persistent phosphorescence
emission is orange by removing the excitation light. However, the
initial orange color becomes cyan under 77 K because the single
molecular phosphorescence is more sensitive to the temperature.
According to Figure 5a, the single phosphorescence gradually
weakens as the temperature increases from 77 K to 300 K and its
lifetime changes from 373 ms to 198 ms correspondingly (Figure
S21). At the same time, the lifetimes of emission peaks at 563 nm
and 603 nm are 375 ms and 403 ms respectively at 77 K, which is
very close to the lifetime of single phosphorescence. For better
performance regarding the temperature-response of OMe-SPhT, a
pattern of “R” is designed for crystal powder and ground sample
(Figure 5c). After removing the excitation, the cyan persistent
phosphorescence “R” could be detected. As the temperature
increases, the single molecule phosphorescence from the part of
ground sample is gradually diminished, and the green persistent
phosphorescence displayed as a “P”. When the temperature
increases to room temperature (ca. 300 K), the color of “P” changes
Conflicts of interest
The authors declare no conflict of interest.
Acknowledgements
The authors gratefully acknowledge the financial support from
the NSF of China (51733010, 21672267, 61605253, and
51603232), the Fundamental Research Funds for the Central
Universities, and Guangdong Science and Technology Plan
(2015B090913003).
Notes and references
1
2
3
G. Liu, S. Zhang, Y. Shi, X. Huang, Y. Tang, P. Chen, W. Si, W.
Huang, X. Dong, Adv. Funct. Mater., 2018, 28, 1804317.
Fateminia, S. M. A., Z. Mao, S. Xu, Z. Yang, Z. Chi, B. Liu,
Angew. Chem. Int. Ed., 2017, 56, 12160-12164.
X. Chen, C. Xu, T. Wang. C. Zhou, J. Du, Z. Wang, H. Xu, T. Xie,
G. Bi, J. Jiang, X. Zhang, J. N. Demas, C. O. Trindle, Y. Luo, G.
Zhang, Angew. Chem. Int. Ed., 2016, 55, 9872-9876.
A. S. Mathew, C. A. DeRosa, J. N. Demas, C. L. Fraser, Anal.
Methods, 2016, 8, 3109-3114.
R. Kabe, N. Notsuka, K. Yoshida, C. Adachi, Adv. Mater., 2016,
28, 655-660.
Z. Lin, R. Kabe, N. Nishimura, K. Jinnai, C. Adachi, Adv. Mater.,
2018, 30, 1803713.
4
5
6
4 | J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins

Please do not adjust margins
Page 5 of 6
Journal of Materials Chemistry C
Journal Name
ARTICLE
7
C. Li, X. Tang, L. Zhang, C. Li, Z. Liu, Z. Bo, Y. Q. Dong, Y.-H. 37 L. Gu, H. Shi, C. Miao, Q. Wu, Z. Cheng, S. Cai, M. Gu, C. Ma,
View Article Online
Tian, Y. Dong, B. Z. Tang, Adv. Opt. Mater., 2015,
3
, 1184-
W. Yao, Y. Gao, Z. An, W. Huang, J. Mater. Chem. C, 2018, 6,
DOI: 10.1039/C9TC01870K
1190.
226-233.
8
9
L. Xu, G. Li, T. Xu, W. Zhang, S. Zhang, S. Yin, Z. An, G. He,
Chem. Commun., 2018, 54, 9226-9229.
L. Gu, H. Shi, M. Gu, K. Ling, H. Ma, S. Cai, L. Song, C. Ma, H.
Li, G. Xing, X. Hang, J. Li, Y. Gao, W. Yao, Z. Shuai, Z. An, X. Liu,
W. Huang, Angew. Chem. Int. Ed., 2018, 57, 8425-8431.
10 M. Li, K. Ling, H. Shi, N. Gan, L. Song, S. Cai, Z. Cheng, L. Gu, X.
Wang, C. Ma, M. Gu, Q. Wu, L. Bian, M. Liu, Z. An, H. Ma, W.
Huang, Adv. Opt. Mater., 2019, 1800820, DOI
:
10.1002/adom.201800820.
11 Y. Li, M. Gecevicius, J. Qiu, Chem. Soc. Rev., 2016, 45, 2090.
12 B. Viana, A. J. J. Bos, P. Dorenbos, M. Bessodes, D. Gourier, D.
Scherman, C. Richard, Nat. Mater., 2014, 13, 418.
13 H. Mieno, R. Kabe, N. Notsuka, M. D. Allendorf, C. Adachi,
Adv. Opt. Mater., 2016, 4, 1015-1021.
14 Q. Li, Y. Tang, W. Hu, Z. Li, Small, 2018, 14, 1801560.
15 R. Gao, D. Yan, Chem. Sci., 2017, , 590-599.
8
16 S. Hirata, K. Totani, J. Zhang, T. Yamashita, H. Kaji, S. R.
Marder, T. Watanabe, C. Adachi, Adv. Funct. Mater., 2013,
23, 3386-3397.
17 W. Yuan, X. Shen, H. Zhao, J. W. Y. Lam, L. Tang, P. Lu, C.
Wang, Y. Liu, Z. Wang, Q. Zheng, J.Sun, Y. Ma, B. Z. Tang., J.
Phys. Chem. C, 2010, 114, 6090–6099.
18 Y. Gonga, L. Zhao, Q. Peng, D. Fan, W. Yuan, Y. Zhang, B. Z.
Tang, Chem. Sci., 2015, 6, 4438-4444.
19 Z. An, C. Zheng, Y. Tao, R. Chen, H. Shi, T. Chen, Z. Wang, H. Li,
R. Deng, X. Liu, W. Huang, Nat. Mater., 2015, 14, 685.
20 L. Paul, S. Chakrabarti, K. Ruud, J. Phys. Chem. Lett., 2017, 8,
1253-1258.
21 Y. Xiong, Z. Zhao, W. Zhao, H. Ma, Q. Peng, Z. He, X. Zhang, Y.
Chen, X. He, J. W. Y. Lam, B. Z. Tang, Angew. Chem. Int. Ed.,
2018, 57, 7997-8001.
22 Y. Xie, Y. Ge, Q. Peng, C. Li, Q. Li, Z. Li, Adv. Mater., 2017, 29
,
1606829.
23 Y. Shoji, Y. Ikabata, Q. Wang, D. Nemoto, A. Sakamoto, N.
Tanaka, J. Seino, H. Nakai, T. Fukushima, J. Am. Chem. Soc.,
2017, 139, 2728-2733.
24 J. Yang, X. Zhen, B. Wang, X. Gao, Z. Ren, J. Wang, Y. Xie, J. Li,
Q. Peng, K. Pu, Z. Li, Nat. Commun., 2018, 9, 840.
25 H. Shi, L. Song, H. Ma, C. Sun, K. Huang, A. Lv, W. Ye, H. Wang,
S. Cai, W. Yao, Y. Zhang, R. Zheng, Z. An, W. Huang, J. Phys.
Chem. Lett., 2019, 10, 595–600.
26 Z. Yang, Z. Mao, X. Zhang, D. Ou, Y. Mu, Y. Zhang, C. Zhao, S.
Liu, Z. Chi, J. Xu, Y. Wu, P. Lu, A. Lien, M. R. Bryce, Angew.
Chem. Int. Ed., 2016, 55, 2181 –2185.
27 R. Kabe, C. Adachi, Nature, 2017, 550, 384–387.
28 W. Zhao, Z. He, J. W.Y. Lam, Q. Peng, H. Ma, Z. Shuai, G. Bai, J.
Hao, B. Z. Tang, Chem, 2016, 1, 592–602.
29 H. Ma, Q. Peng, Z. An, W. Huang, Z. Shuai, J. Am. Chem. Soc.,
2019, 141, 1010–1015.
30 S. Tian, H. Ma, J. Li, X. Wang, A. Lv, H. Shi, Y. Geng, F. Liang, Z.
Su, Z. An, W. Huang, Angew. Chem. Int. Ed., 2019, 58, 6645–
6649.
31 J. Chen, T. Yu, E. Ubba, Z. Xie, Z. Yang, Y. Zhang, S. Liu, J. Xu,
M. P. Aldred, Z. Chi, Adv. Opt. Mater., 2019, 7, 1801593.
32 X. Ma, C. Xu, J. Wang, H. Tian, Angew. Chem. Int. Ed., 2018,
57, 10854.
33 M. Fang, J. Yang, X. Xiang, Y. Xie, Y. Dong, Q. Peng, Q. Li, Z. Li,
Mater. Chem. Front., 2018, 2, 2124-2129.
34 Z. Mao, Z. Yang, Z. Fan, E. Ubba, W. Li, Y. Li, J. Zhao, Z. Yang,
M. P. Aldreda, Z. Chi, Chem. Sci., 2019, 10, 179-184.
35 O. Bolton, K. Lee, H. J. Kim, K. Y. Lin, J. Kim, Nat. Chem., 2011,
3
, 205–210.
36 S. Cai, H. Shi, Z. Zhang, X. Wang, H. Ma, N. Gan, Q. Wu, Z.
Cheng, K. Ling, M. Gu, C. Ma, L. Gu. Z. An, W. Huang, Angew.
Chem. Int. Ed., 2018, 130, 4069-4073.
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 5
Please do not adjust margins

Journal of Materials Chemistry C
Page 6 of 6
View Article Online
DOI: 10.1039/C9TC01870K
Achieving bright pRTP compound OMe-SPhT with temperature-response by adjusting the
proportion of excited-state configurations in coupled molecules.