Geminal cross-coupling synthesis, ion-induced emission and lysosome imaging of cationic tetraarylethene oligoelectrolytes

Article abstract of DOI:10.1039/c8cc00533h

Neutral conjugated tetraarylethenes OF_n (n = 1-3) and the corresponding cationic conjugated oligoelectrolytes OF_n+ (n = 1-3) with aggregation-induced emission activity have been designed and synthesized using geminal cross-coupling.

Full text of DOI:10.1039/c8cc00533h

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Marilyn M. Olmstead, Alan L. Balch, Josep M. Poblet, Luis Echegoyenet al.
Reactivity differences of Sc3N@C2n (2n 68 and 80). Synthesis of the
first methanofullerene derivatives of Sc N@D5h-C80
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DOI: 10.1039/C8CC00533H
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Geminal cross-coupling synthesis, ion-induced emission and
lysosome imaging of cationic tetraarylethene oligoelectrolytes
Qi-Yuan Zhou,# Bo Xin,# Ya-Long Wang,# Chong Li,* Ze-Qiang Chen, Qi Yu, Zhen-Li Huang, and
Ming-Qiang Zhu*
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
www.rsc.org/
Neutral conjugated tetraarylethene OFn (n
=
1-3) and
corresponding cationic conjugated oligoelectrolytes OFn+ (n = 1-3)
with aggregating-induced emission activity have been designed
and synthesized using geminal cross-coupling. OFn+ (n = 1-3)
exhibit featured ion-induced emission in aqueous solution. They
are used for lysosomal fluorescence imaging and tracing of
lysosome events.
Scheme 1 Synthetic route to OFn and OFn+.
Most conventional fluorophores suffer from aggregation
caused quenching (ACQ), in which the fluorescence at solid
state diminishes relative to that in dilute solution. The latter
state represents isolated molecules and does not suffer from
detrimental aggregation effects that can decrease the
fluorescence quantum yields. Considering the fact that many
applications of light-emitting materials are in the solid-state,
i.e. OLEDs, the efficient ways to alleviate solid-state
fluorescence quenching have become important research
topics. One excellent example of this is aggregation induced
emission (AIE)1-3 whose solid-state fluorescence increases
dramatically relative to its solution-state fluorescence. A
phenomenon that is the exact opposite of ACQ was
unexpected. The benefits from this strategy in improving
fluorescence properties in the “aggregate” state have been
exploited in several research areas, including OLEDs, sensors
and bioimaging.4-6 It is noteworthy that few reports on ionic
AIE fluorogens in aqueous solution, which may be more
beneficial in biosensors or bioimaging.7-9
have demonstrated remarkable fluorescence quenching in
solution with enhanced emission in the “aggregate” state of an
analogous series of fluorene oligomers end-capped with TPE.13
It is concluded that as the length of central oligofluorene unit
increases between the two end-capped TPE groups, the AIE-
effect of the associated material gradually decreases,
indicating that the TPE units have a reduced influence on the
AIE-effect as the conjugation length increases.15 On the basis
of these results, here,
a series of neutral conjugated
fluorogens OFn and corresponding cationic conjugated
oligoelectrolytes OFn+ (n = 1-3, ‘O’ presents the 9-methylene-
9H-xanthene as it has an oxygen bridge between two benzene
rings, while ‘Fn’ or ‘Fn+’ represents the number of the Fluorene
repeating unit at each side of ‘O’ segment, as shown in Scheme
1), where two oligofluorenes and one 9-methylene-9H-
xanthene in each molecule construct
a
AIE-active
tetraarylethene structure, have been designed and
synthesized using geminal cross-coupling (GCC) reaction of 1,1-
dibromoolefins with aryl boric acid ester.16
One archetypal AIE-active material is tetraphenylethene
(TPE) and has been extensively reported in the literatures due
to its prominent AIE properties, high solid-state fluorescence
quantum yields and ease of synthesis/modification.10-12
Recently, we have reported intriguing AIE-active adducts and
investigated the optical and photophysical properties.13,14 We
The synthetic procedures of the neutral conjugated
fluorogens OFn (n
= 1-3) and corresponding cationic
conjugated oligoelectrolytes OFn+ (n = 1 - 3) are shown in
Scheme 1 and Scheme S1-S3. The neutral conjugated
fluorogens OFn (n = 1-3) were synthesized by the standard
palladium-mediated GCC between oligofluorenes borate
derivatives Fn and 9-(dibromomethylene)-9H-xanthene with a
isolated yield higher than 64%. The corresponding cationic
conjugated oligoelectrolytes OFn+ were prepared through
treatment of the precursor OFn with trimethylamine in ethonal.
The chemical structures of the neutral conjugated fluorogens
Wuhan National Laboratory for Optoelectronics, School of Optical and Electronic
Information, Huazhong University of Science and Technology, Wuhan, 430074,
Hubei, China, E-mail: mqzhu@hust.edu.cn, chongli@hust.edu.cn; Fax: +86-27-
87793419.
†
Electronic Supplementary Information (ESI) available: experimental
procedures/characterization, optical spectra, and molecular simulation. See
DOI: 10.1039/x0xx00000x
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respectively, which is in consistence with theiVriewabArstioclrepOtniolinne
wavelengths. The Eg becomes more and more narrow from
0%
0%
a
b
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90%
99%
OF1
10%
20%
30%
40%
50%
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99%
OF2
6x104
DOI: 10.1039/C8CC00533H
1x104
OF1 to OF3, which explains the successively absorption redshift
of OFn (n = 1-3). OFn (n = 1-3) show blue emission in THF with
the maximum emission peaks centered at 428 nm, 430 nm,
418 nm and yellow emission in water with the maximum
emission peaks centered at 586 nm, 582 nm, 572 nm (Fig. S2b).
The blue emission of OFn (n = 1-3) in THF is originated from the
oligofluorenes while the yellow emission is attributed to TAE
structure17where the oligo-fluorene segment has increased the
conjugation length, which is not ascribed to keto defects or
excimers in poly- and oligofluorenes.18 (Fig. S4) Due to the ACQ
feature of oligofluorenes, the blue emission peak of OFn totally
disappears when aggregated in water. It is noteworthy that
the Stock shifts of OFn at aggregated state are larger than 200
nm, which is beneficial to sensing and imaging applications.
OFn exhibit the complementary AIE and ACQ effect in THF-
water binary solvents which is demonstrated by measuring the
photoluminescence (PL) of OFn. OFn as hydrophobic
luminogens can be easily dissolved in THF but perform
aggregated state in water. The OFn molecules aggregate to
different extent in the different volume ratios of THF-water
binary solvents. Fig. 1a-1c show the PL spectra of OFn in THF-
water mixtures with increasing water fraction. The PL intensity
at around 420 nm decreases in high water fraction binary
solvents while that of around 570 nm increases. The emission
of around 570 nm remains weak until up to 80% of water is
added to the THF solution. Nevertheless, it increases
dramatically at 90% water content. Fig. 1d shows the plot of
3x104
5x103
0
0
400
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400
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700
Wavelength (nm)
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0%
c
d2000
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OF3
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OF2
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e3x104
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90%
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OF2+
OF3+
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50
0
1x105
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0
20
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80
100
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Water fraction (%)
Fig. 1 AIE effect of OFn in water-THF and OFn+ in DMSO-THF binary solvents with
various THF volume fractions Fluorescence spectra of (a) OF1, (b) OF2, (c) OF3, (e) normalized fluorescence intensity ratio ([I550/I420]’/[I550/I420]0)
OF1+, (f) OF2+, (g) OF3+. The changes of normalized emission intensity ratio at 550
nm and 420 nm [I550/I420]’/[I550/I420 0 versus water fractions of (d) OFn and (h) OFn+
.
versus water fraction. The [I550/I420]’/[I550/I420
] of OF3 at 99%
0
]
.
water content is 2062 which is 5 and 3 times as much as those
of OF2 and OF1, respectively. The relative quantum yield (QY)
of OF3 is estimated to be 1.69% in THF and 35.85% in water
relative to quinine sulfate (QY = 55% in 0.1 M H2SO4) (Table S1),
which are both higher than those of OF2 and OF1. The
transformation from blue emission to yellow emission of OF3 is
more intense than those of OF2 and OF1 when aggregated in
poor solvent. Hence, we draw a conclusion that OF3 exhibits
the most distinctive ratiometric fluorescence response to a
poor solvent.
We further investigate the AIE properties of organic
quaternary ammonium OFn+ (n = 1-3). As cationic compounds,
OFn+ are well soluble in water and highly polar organic
solvents like DMSO, methanol and ethanol but insoluble in low
polar solvents such as THF. In particular, OFn+ (n = 1-3) are
better soluble in highly polar organic solvents (DMSO and
methyl alcohol) than in water which is due to the amphiphilic
character of OFn+ (n = 1-3). Thus, we choose DMSO as the
good solvent and THF as the poor solvent for the PL
examination to investigate the AIE effect of OFn+ (n = 1-3). As
shown in Fig. 1e-1g, the blue emissions of OFn+ (n = 1-3) in
DMSO are not significant compared to their yellow emission in
THF. With increasing the poor solvent fraction, the blue
emission at around 430 nm decreases meanwhile the yellow
emission at around 560 nm increases. The fluorescence color
The concentrations of OFn and OFn+ are 2 µM. The excitation wavelength is 380 nm.
OFn and corresponding cationic conjugated oligoelectrolytes
1
OFn+ (n = 1-3) were studied by H NMR spectra (Fig. S1). They
were estimated to have high quaternization degree of 99.5%,
97.0% and 95.9%, respectively by calculating the ratio of the
integrated area of the H atoms on Xanthone moiety (6.7 ppm)
to that of -CH2 N(CH3)3 (3.0 ppm). Due to the high charge
density, the cationic conjugated oligoelectrolytes OFn+ (n = 1-3)
exhibit good solubility in both aqueous media and highly polar
organic solvents.
The normalized UV-vis absorption and photoluminescence
(PL) spectra of OFn (n = 1-3) in THF or in water are depicted in
Fig. S2. The absorbance of OFn (n = 1-3) at 344 nm (a shoulder
peak), 345 nm, 360 nm are ascribed to the fluorense segments.
Compared to OF1, the maximum absorption peaks of OF2, OF3
red shift 31 nm and 46 nm which is attributed to the more π-
conjugated fluorine units (Fig. S2a). The optimized molecular
structures and HOMO /LUMO energy levels of OFn are shown
in Fig. S3. The HOMO and LUMO of OFn are contributed by
both the orbitals of TAE and oligofluorenes. The effective
conjugation length becomes longer with increasing the length
of oligofluorenes incorporating to the tetraarylethylene (TAE)
segment. Through theoretical calculations, the energy
bandgap Eg for OFn (n = 1-3) is 3.84 eV, 3.64 eV and 3.56 eV,
sensitivity to poor solvent than OF1+ and OF2+. The relative
2 | J. Name., 2012, 00, 1-3
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NH4Cl
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DOI: 10.1039/C8CC00533H
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Fig. 2 Fluorescence spectra of OF1+ in aqueous solution of different sodium salt
(concentration unit: mM). (a) NaBr, (b) NaNO3, (c) NaCl, (d) Na2CO3, (e) Na2SO4. (f) The
enhancement of emission peak intensity at 550 nm versus Na+ concentration [Na+] with
various anions. The concentration of OF1+ is 2 µM. The excitation wavelength is 380 nm.
Fig. 3 Fluorescence spectra of OF1+ in aqueous solution of different chloride salt
(concentration unit: mM). (a) NaCl, (b) NH4Cl, (c) KCl, (d) CaCl2, (e) MgCl2. (f) The
enhancement of emission peak intensity at 550 nm versus Cl- concentration ([Cl-]) with
various cation. The concentration of OF1+ is 2 µM. The excitation wavelength is 380 nm.
QYs of OFn+ (n = 1-3) are estimated to be 2.89%, 2.09%, 4.20%
sensitivity to poor solvent than OF1+ and OF2+. The relative
QYs of OFn+ (n = 1-3) are estimated to be 2.89%, 2.09%, 4.20%
in DMSO and 29.95%, 32.85%, 38.62% in THF relative to
quinine sulfate (QY = 55% in 0.1 M H2SO4) (Table S1).
which may be attributed to the less extent of interaction
between the identical electrical charges of salt cations and
cationic oligoelectrolyte OF1+.
In the molecular structure of OFn+ (n = 1-3), the 9-C position
of each fluorene is replaced by a pair of six-carbon
hydrophobic alkyl chains containing positively charged,
quaternary ammonium head groups which will interact with
anionic cell membrane, intercalate into the cell membrane and
increase the membrane permeability by distorting the
arrangement of membrane phospholipids. OFn+ (n = 1-3) are
assessed for their ability to localize and stain subcellular
structures in living cells by fluorescence microscope. Cervical
cancer HeLa cells are incubated with 5 μM OFn+ (n = 1-3) for 2
h, followed by 50 nM LysoTracker Red (a commercial probe for
Lysosomes) for another 45 mins. OFn+ (n = 1-3) staining the
HeLa cells (Fig. 4a, 4e and 4i) overlaps well with the containing
LysoTracker Red (Fig. 4b, 4f and 4j). The Pearson's correlation
coefficients between the green-yellow emissions from OFn+ (n
= 1-3) and the red emissions from LysoTracker Red were
determined to be 92.9% (OF1+), 90.1% (OF2+) and 68.7% (OF3+),
respectively, demonstrating the specific targeting of OFn+ (n =
1-2) to lysosomes. Compared with OF3+, both OF1+ and OF2+
show better imaging results, which may be attributed to the
smaller molecular scale and higher lipophilicity of them. The
colocalization experiment of OFn+ (n = 1-3) with MitoTracker
Red (A commercial probe for mitochondria) was also carried
out (Fig. S6). The blue signal of OFn+ (n = 1-3) overlaps poor
with the red signal of MitoTracker Red. These experiment
results indicate that OFn+ (n = 1-3) with high cell membrane
permeability could specifically target lysosomes. The cells still
An interesting discovery for these hydrophilic cationic
oligoelectroytes is that OFn+ (n = 1-3) exhibit strong salt or
ionic effect (Fig. S5 and Note S1). The emission spectra of
organic quaternary aminated OF1+ in aqueous solution of
different sodium salts are measured (Fig. 2). As shown in Fig.
2a-2e, the blue emission of OF1+ in water decreases
significantly while its yellow emission increases abruptly along
with ion concentration increasing. The emission enhancement
2-
2-
of OF1+ become stronger in the order of SO4 (x 12), CO3 (x
14), Cl- (x 14), NO3 (x 45) and Br- (x 50) at the same normality
-
of Na+. The univalent anions, especially large-volume anions
such as NO3- and Br- exhibit better emission enhancement than
divalent anions. It is noteworthy that Br- causes 50 times of
fluorescence enhancement of OF1+, which is higher than Cl-
and even has the highest sensitivity to fluorescence than all
other anions.
The similar experiments about ion effect of different
chloride salts are studied. The emission spectra of organic
quaternary aminated OF1+ in aqueous solution of different
chloride salts are also investigated (Fig. 3). As shown in Figure
3a-3e, the blue emission of OF1+ in water decreases
significantly while their yellow emission increases abruptly
along with ion concentration increasing. The emission
enhancement of OF1+ is similar, i.e., Na+ (x 14), Ca2+ (x 15),
+
Mg2+ (x16), K+ (x 16) and NH4 (x 17). There is no much
difference due to ion concentration effect of different cations, have a good morphology and life activity which can be seen
J. Name., 2013, 00, 1-3 | 3
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(peaked at around 550 nm) and aggregation-induced
a
b
f
c
g
k
d
h
l
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quenching (ACQ) characteristics (peakeDdOaI:t10a.r1o03u9n/Cd84C2C000n53m3H),
which significantly increase the ratiometric fluorescence
contrast above 2000. OFn+ (n = 1-3) exhibit excellent ion-
induced emission in aqueous solution, in which monovalent
ions show better fluorescence enhancement than divalent ions.
OFn+ (n = 1-2) exhibit excellent colocalization to lysosomes of
living HeLa cells, which are also used for fluorescence imaging
and tracing of lysosome events.
OF1+
20 μm
e
OF2+
This work was supported by the National Basic Research
Program (973) of China (2015CB755602 and 2013CB922104),
the Natural Science Foundation of China (51673077, 21474034
and 51603078) and the Fundamental Research Funds for the
Central Universities (HUST: 2016YXMS029). We also thank to
the facility support of the Analytical & Testing Center of
Huazhong University of Science & Technology, the Center of
Micro-Fabrication & Characterization (CMFC) and the Center
for Nanoscale Characterization & Devices (CNCD) of WNLO.
i
j
OF3+
Fig. 4 Confocal images of Hela cells stained with 5.0 µM OFn+ and 50 nM LysoTracker
Red. The 1st column: distribution of OFn+ on Channel 1 (λex = 405 nm, λem = 415-475
nm); The 2nd column: distribution of LysoTracker Red on Channel 2 (λex = 561 nm, λem
580-650 nm). The 3rd column: the Merged image of 2nd and 3rd columns; The 4th
column: bright-field image. Scale bar = 20 µm.
=
a
b
c
d
Notes and references
1
J. Luo, Z. Xie, J. W. Y. Lam, L. Cheng, H. Chen, C. Qiu, H. S.
Kwok, X. Zhan, Y. Liu, D. Zhu, B. Z. Tang, Chem. Commun.,
2001, 1740-1741.
0 min
e
5 min
f
10 min
g
15 min
h
2
3
J. Mei, N. L. C. Leung, R. T. K. Kwok, J. W. Y. Lam and B. Z.
Tang, Chem. Rev., 2015, 115, 11718-11940.
N. Zhao, Z. Yang, J. W. Y. Lam, H. H. Y. Sung, N. Xie, S. Chen, H.
Su, M. Gao, I. D. Williams, K. S. Wong and B. Z. Tang, Chem.
Commun., 2012, 48, 8637-8639.
J. Huang, N. Sun, P. Chen, R. Tang, Q. Li, D. Ma and Z. Li,
Chem. Commun., 2014, 50, 2136-2138.
G.-F. Zhang, M. P. Aldred, W.-L. Gong, C. Li and M.-Q. Zhu,
Chem. Commun., 2012, 48, 7711-7713.
L. Yan, Y. Zhang, B. Xu and W. Tian, Nanoscale, 2016, 8, 2471-
0 min + 5 min
10 min + 15 min
5 min + 10 min
0 min + 15 min
4
5
6
7
Fig. 5 Confocal images of a HeLa cell stained with 5.0 µM OF1+ and stimulated using 5
µM chloroquine. Different pseudocolors are used to display the fluorescence images at
different stimulation times: (a) 0 min, (b) 5 min, (c) 10 min, (d) 15 min; Merged images
at two different moments: (e) 0 min and 5 min, (f) 5 min and 10 min, (g) 10 min and 15
min and (h) 0 min and 15 min. The white arrows in (e)-(h) are used to trace the
movement direction of lysosome. Scale bar = 5 µm.
2487.
Y. Yuan, W. Wu, S. Xu and B. Liu, Chem. Commun., 2017, 53
5287-5290.
,
8
9
C. Li and S. Liu, Chem. Commun., 2012, 48, 3262-3278.
C. Chen, Z. Song, X. Zheng, Z. He, B. Liu, X. Huang, D. Kong, D.
from the bright field (Fig. 4d, 4h and 4l). This indicates a
relatively low cytotoxicity of OFn+ (n = 1-3).
Ding and B. Z. Tang, Chem. Sci., 2017, 8, 2191-2198.
10 X. Y. Shen, Y. J. Wang, H. Zhang, A. Qin, J. Z. Sun and B. Z.
Tang, Chem. Commun., 2014, 50, 8747-8750.
11 Z. Zhao, J. W. Y. Lam and B. Z. Tang, J. Mater. Chem., 2012,
22, 23726-23740.
12 N.-H. Xie, C. Li, J.-X. Liu, W.-L. Gong, B.-Z. Tang, G. Li and M.-
Q. Zhu, Chem. Commun., 2016, 52, 5808-5811.
13 M. P. Aldred, C. Li, G.-F. Zhang, W.-L. Gong, A. D. Q. Li, Y. Dai,
D. Ma and M.-Q. Zhu, J. Mater. Chem.2012, 22, 7515-7528.
14 Z.-Q. Chen, T. Chen, J. X. Liu, G. F. Zhang, C. Li, W.-L. Gong, Z.
As the spatial and temporal distribution of lysosomes can
also help to diagnose the lysosomal storage diseases or
tracking lysosomal movements (Fig. 5). The cells are stimulated
using 5.0 µM of chloroquine, which can drive lysosomal
migration without inducing any other apparent disturbance in
the cells.19 The movement of lysosomes is subsequently
monitored by confocal microscopy. As shown in Fig. 5, the
slight movement could be observed in Fig. 5a-5d and
unambiguously traced in the merged images (Fig. 5e-5h) at any
time interval. Such a good image quality of OF1+ for tracing
lysosomes should be ascribed to the superior fluorescence
photostability of OF1+ independent of pH environment within
lysosomes.
J. Xiong, N.-H. Xie, B. Z. Tang and M.-Q. Zhu, Macromolecules,
2015, 48, 7823-7831.
15 R. Hu, N. L. C. Leung and B. Z. Tang, Chem. Soc. Rev., 2014,
43, 4494 – 4562.
16 G.-F. Zhang, H. Wang, M. P. Aldred, T. Chen, Z.-Q. Chen, X.
Meng and M.-Q. Zhu, Chem. Mater., 2014, 26, 4433-4446.
17 J. Shi, N. Chang, C. Li, J. Mei, C. Deng, X. Luo, Z. Liu, Z. Bo, Y. Q.
Dong and B. Z. Tang, Chem. Commun., 2012, 48,
10675-10677.
18 Y. Honmou, S. Hirata, H. Komiyama, J. Hiyoshi, S. Kawauchi, T.
Iyoda and M. Vacha, Nat. Commun., 2014, 5, 4666.
19 Y. Cai, C. Gui, K. Samedov, H. Su, X. Gu, S. Li, W. Luo, H. H. Y.
Sung, J. W. Y. Lam, R. T. K. Kwok, I. D. Williams, A. Qin and B.
In conclusion, by means of GCC, we have designed and
synthesized two series of xanthene-contained AIE lumingens,
hydrophobic neutral conjugated tetraarylethene OFn (n = 1-3)
and
corresponding
hydrophilic
cationic conjugated
oligoelectrolytes OFn+ (n = 1-3) with aggregating-induced
emission activity. Both OFn (n = 1-3) and OFn+ (n = 1-3) exhibit
synergistical ratiometric aggregation-induced emission (AIE)
Z. Tang, Chem. Sci., 2017, 8, 7593-7603.
4 | J. Name., 2012, 00, 1-3
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DOI: 10.1039/C8CC00533H
Table of contents entry
Novel ratiometric AIE–active tetraarylethene oligoelectrolytes synthesized by
Geminal cross-coupling show ion-induced emission and are applied as
bioprobes for lysosome tracing.