A novel aggregation-induced emission platform from 2,3-diphenylbenzo[b]thiophene S,S-dioxide

Article abstract of DOI:10.1039/c6cc09892d

New aggregation-induced emission (AIE) luminogens with high solid-state emission efficiencies are developed by adopting a benzo[b]thiophene S,S-dioxide core, and steric and electronic effects on the AIE property are elucidated.

Full text of DOI:10.1039/c6cc09892d

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DOI: 10.1039/C6CC09892D
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A novel aggregation-induced emission platform from 2,3-
diphenylbenzo[b]thiophene S,S-dioxide
Received 00th January 20xx,
Accepted 00th January 20xx
Jingjing Guo,a Shimin Hu,a Wenwen Luo,a Rongrong Hu,a Anjun Qin,a Zujin Zhao,*a and Ben Zhong
Tang*ab
DOI: 10.1039/x0xx00000x
www.rsc.org/
New aggregation-induced emission (AIE) luminogens with high
Recently, we developed a new AIE system from 1,2,3-
solid-state emission efficiencies are developed by adopting a triphenylphosphindole 1-oxide (TPPIO, Scheme 1). The rotational
benzo[b]thiophene S,S-dioxide core, and steric and electronic motion of the phenyl rotors against the ring-fused phosphindole 1-
effects on the AIE property are elucidated.
oxide stator is proposed to nonradiatively deactivate the excited
state, making molecules nonluminescent in solutions. When
aggregate forms, such kind of intramolecular rotation is restricted
and the nonradiative decay of the excited state is suppressed,
which turn on the emission.2c If this hypothesis is universal, it
Organic luminogenic molecules play a key role in materials
chemistry, optics, electronics and bioscience. However, the
photoluminescence (PL) of many leading luminophors is often
weakened or totally quenched when exist as nanoaggregates
or solid films, presenting a thorny issue of aggregation-caused
quenching (ACQ). Aggregation-induced emission (AIE)1
represents an interesting photophysical phenomenon that the
nonluminescent molecules in solutions become highly emissive
via aggregate formation. Recent researches rationalize that
restriction of intramolecular motion (RIM), including rotation
(RIR), vibration (RIV), twisting and stretching, is the major
working mechanism of AIE.1,2 The AIE challenges ACQ problem
and paves a new avenue towards efficient aggregate-state
luminescent materials. Owing to the high academic
significance and bright practical prospect, AIE has currently
become a hot topic in materials and chemistry. A huge number
of luminogens with AIE property (AIEgens) have been
developed, such as siloles,3 tetraarylethenes,4 pyrroles,5
cyanostilbenes,6 phospholes,7 tetraphenylpyrazine,8 9,10-
should be applicable to similar systems with
a ring-fused
heterocyclic. To conform this and exploit new efficient luminescent
materials, in this work, we design and synthesize a series of new
luminogens by adopting
a
sulphur-containing heterocyclic,
benzo[b]thiophene S,S-dioxide (BTO). We find that 2,3-
diphenylbenzo[b]thiophene S,S-dioxide (DP-BTO) and its derivatives
indeed exhibit prominent AIE property, with excellent PL
efficiencies in solids. The substituent effects, including steric
hindrance and electronic push-pull effect, can exert significant
impacts on the AIE property.
The new luminogens consisting of a BTO core and substituents
with different volumes, and electron-donating and withdrawing
properties are synthesized facilely according to the synthetic routes
distyrylanthracenes,9
diphenyldibenzofulvenes,10
diphenylocarboranes,11 boron diiminates and ketoiminates,12
coumarins,2a,13 etc, exhibiting promising applications in
optoelectronics, chemical detection, biotechnology and
biomedicine.14
a.State Key Laboratory of Luminescent Materials and Devices, South China
University of Technology, Guangzhou 510640, China. E-mail:
mszjzhao@scut.edu.cn
b.Department of Chemistry, Hong Kong Branch of Chinese National Engineering
Research Center for Tissue Restoration and Reconstruction, The Hong Kong
University of Science & Technology, Clear Water Bay, Kowloon, Hong Kong,
China. E-mail: tangbenz@ust.hk
† Electronic Supplementary Information (ESI) available: Experimental details,
X-ray structure refinement data, packing pattern of DP-BTO in crystals,
electronic structures, UV and PL spectra and PL decay curves. See
DOI: 10.1039/x0xx00000x
Scheme 1. Molecular structures and syntheses of luminogens
based on benzo[b]thiophene S,S-dioxide. mCBPA
= 3-
chloroperbenzoic acid.
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DOI: 10.1039/C6CC09892D
73.80o
80.01o
55.09o
50.15o
38.15o
62.66o
54.18o
45.79o
77.36o
23.32o
p-DMP-BTO (I)
p-DMP-BTO (II)
o-DMP-BTO
DP-BTO (I)
DP-BTO (II)
60.28o
52.45o
59.68o
13.67o
67.42o
71.25o
25.12o
21.95o
22.97o
43.70o
DTFMP-BTO
DBP-BTO
DTBP-BTO
DMOP-BTO
DFP-BTO
Fig. 1 ORTEP drawings of the crystal structures of DP-BTO, p-DMP-BTO, o-DMP-BTO, DTBP-BTO, DMOP-BTO, DFP-BTO, DTFMP-BTO and
DBP-BTO (thermal ellipsoids are set at 50% probability).
outlined in Scheme 1. The details of synthesis and characterization crystals. In most of the new luminogens, α-Ph is better π-
are presented in Electronic Supplementary Information (ESI). 2,3- conjugated to the BTO with a much smaller torsion angle to build
Dibromobenzo[b]thiophene
chloroperoxybenzoic acid
was
(mCPBA)
oxidized
to
with
generate
3- the main molecular backbone. β-Ph is twisted out of the plane of
2,3- BTO, and contributes less to π-conjugation of the luminogen. Owing
dibromobenzo[b]thiophene S,S-dioxide (DBr-BTO), followed by to the presence of methyl groups at the ortho-positions of α-Ph and
Suzuki coupling with corresponding arylboronic acids to furnish β-Ph, o-DMP-BTO is spatial demanded and has to adopt a highly
target products (DAr-BTO) in good yields. The molecular structures twisted conformation to minimize the intramolecular repulsion,
are characterized by NMR and high resolution mass spectroscopy, resulting in large torsion angles of 80.01o and 73.8o for α-Ph and β-
with perfect results. Common organic solvents such as THF, CH2Cl2, Ph, respectively. Consequently, the π-conjugation of o-DMP-BTO is
CHCl3 and toluene are good solvents for the final products, but weakened. Meanwhile, the rotational motions of α-Ph and β-Ph
water and ethanol are poor solvents.
must be difficult and the molecule is rigidified because of the high
Through slow solvent evaporation, single crystals of DP-BTO, p- steric hindrance.
DMP-BTO, o-DMP-BTO, DTBP-BTO, DMOP-BTO, DFP-BTO, DTFMP-
The electronic structures of the luminogens are theoretically
BTO and DBP-BTO were cultured in CH2Cl2-ethanol mixtures, and calculated by density functional theory (DFT). Fig. 2 illustrates the
analyzed by X-ray crystallography. The obtained crystal structures representative molecular orbital amplitude plots of DP-BTO, DBP-
are displayed in Fig. 1. DP-BTO molecules adopt two kinds of BTO and DTPA-BTO, and Fig. S2 gives all electronic structures for
twisted conformations [DP-BTO (I) and DP-BTO (II)] in the same comparison. The HOMOs and LUMOs of DP-BTO and most of its
crystal lattice and align loosely (Fig. S1). The torsion angles between derivatives are located within the DP-BTO framework. The HOMO
thiophene S,S-dioxide and phenyl at the β-position (β-Ph) are close of DBP-BTO is apparently delocalized, mainly along the biphenyl at
(50.15o and 55.09o), but those between thiophene S,S-dioxide and the α-position, and that of DTPA-BTO shows major contributions
phenyl at the α-position (α-Ph) is varied from 38.15o in DP-BTO (I) to from the electron-rich triphenylamines. The LUMOs of DBP-BTO
77.36o in DP-BTO (II). p-DMP-BTO shows similar phenomenon in and DTPA-BTO are still mainly concentrated on the electron-
deficient BTO core.15 The separated distribution of HOMO and
LUMO indicates DTPA-BTO is prone to experience intramolecular
charge transfer (ICT) in polar environments.
DP-BTO shows absorption maximum at 334 nm, while with the
addition of the electron-donating groups, absorption maxima of p-
DMP-BTO (342 nm), DTBP-BTO (343 nm), DMOP-BTO (357 nm) and
DBP-BTO (354) are red-shifted (Fig. S3). In particular, DTPA-BTO
exhibits reddest absorption maximum at 391 nm, owing to its
strong ICT effect. But o-DMP-BTO absorbs at much bluer region of
313 nm because of its highly twisted conformation and weakened
π-conjugation. m-DMP-BTO shows almost identical absorption peak
(336 nm) to DP-BTO, because the meta-located methyls exert little
influence on the spatial and electronic properties of the molecule.
Fig. 2 Molecular orbital amplitude plots of DP-BTO, DBP-BTO
DFP-BTO and DTFMP-BTO that bear electron-withdrawing groups
and DTPA-BTO calculated by using the B3LYP/6-31G(d, p) basis
show absorption maxima at 335 and 331 nm, being close to that of
set.
2 | J. Name., 2012, 00, 1-3
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nonradiative decay of excited state is predominant, accounting for
the faint PL. On the contrary, o-DMP-BTO shows a relatively strong
View Article Online
DOI: 10.1039/C6CC09892D
fw (vol%)
99
fw (vol%)
99
B
A
90
80
70
60
50
40
30
20
00
99
0
99
95
90
80
70
60
50
40
30
PL at 431 nm, with a ΦF value of 19.2% in THF solution. The severe
steric hindrance imposed by the ortho-positioned methyls should
have retarded the intramolecular rotation of phenyls in o-DMP-BTO,
which frustrates the nonradiative decay of excited state, and allows
the molecule to emit more efficiently. The enhanced PL intensity of
o-DMP-BTO in solution actually provides evidences for the RIR
mechanism of AIE phenomenon.1 DTPA-BTO also provides
moderately strong PL at 555 nm in solution, with an enhanced ΦF
value of 33.3%. Similar PL red-shifts and enhancement were also
been reported for many other AIEgens built with strong electron-
donating and withdrawing groups, which is assumed to be mainly
caused by the electronic effec.16 And the two branched
triphenylamines may also contribute to emission enhancement by
RIR to some degree.
10
0
20
10
0
375
425
475
525
575
625
400
450
500
550
600
650
Wavelength (nm)
Wavelength (nm)
To validate the AIE characteristics, PL behaviors of these new
luminogens in the aggregated state are investigated. Their
nanoaggregates are readily formed by adding a large amount of
water to the THF solutions, for they are insoluble in water, and the
PL intensity is enhanced accordingly. Taking DBP-BTO as an example,
whereas its PL intensity increases slowly when the water fraction (fw)
in THF/water is low, the PL intensity boosts swiftly as the fw gets
higher than 80 vol% (Fig. 3B). The PL intensity is enhanced by 38-
fold higher from pure THF solution to aqueous medium,
demonstrating the AIE nature. As aggregates form, the
intramolecular rotations are restricted by spatial constraint from
neighbouring molecules. Therefore, the nonradiative decay is
blocked, and the PL intensity is enhanced. With regard to o-DMP-
BTO, its PL intensity changes little when fw is low, and intensifies
modestly when fw reaches 99 vol% (Fig. 3C), owing to the further
suppression of intramolecular rotations. However, DTPA-BTO
exhibits different PL behavior as the increase of fw. Its PL intensity
declines progressively as the addition of water, and then starts to
rise up when fw is higher than 60 vol%. The PL intensity exceeds the
initial one in pure THF when fw reaches 99 vol%, due to the
collective effects of ICT and RIR. 16
Fig. 3 PL spectra of (A) DP-BTO, (B) DBP-BTO, (C) o-DMP-BTO
and (D) DTPA-BTO in THF/water mixtures with different water
fractions (fw). Concentration: 10 μM. Inset: fluorescence photos
of the corresponding luminogens in THF/water mixtures (fw = 0
and 99 vol%), taken under the illumination of a UV lamp (365
nm).
DP-BTO. The PL property of DP-BTO is very poor in THF solution,
exhibiting a PL peak at 431 nm and a low fluorescence quantum
yield (ΦF) of 0.2%. Similarly, p-DMP-BTO, m-DMP-BTO and DTBP-
BTO also show faint PL peaking at 438, 426 and 429 nm, with low ΦF
values of 0.4%, 0.3% and 0.2%, respectively. DBP-BTO and DMOP-
BTO show apparently red-shifted PL peaks at 477 and 466 nm,
respectively, because of the increased ICT effect. DFP-BTO shows an
identical PL peak at 431 nm as DP-BTO, but the PL peak of DTMFP-
BTO with stronger electron-withdrawing trifluoromethyls is greatly
blue-shifted to 411 nm, owing to the weakened ICT effect. The ΦF
values of DBP-BTO, DMOP-BTO DFP-BTO and DTMFP-BTO are also
very low (0.2‒0.7%). According to molecular conformations of
present luminogens, the rotation of phenyls against the BTO core is
quite active without spatial restraint in solutions. Consequently, the
These new luminogens are highly emissive in the solid state. For
example, the solids of DP-BTO, and DBP-BTO exhibit PL peaks at 436
and 472 nm, very close to the PL peaks in THF solutions. The PL
peaks of the solids of p-DMP-BTO, m-DMP-BTO, DTBP-BTO, DFP-
Table 1. Optical properties of the luminogens based on BTO.
λem (nm)
ΦFb (%)
‹τ›d (ns)
λabs (nm) a
αAIE
c
solna
431
solid
436
soln
0.2
solid
57.3
soln
1.58
solid
3.38
4.52
3.91
7.27
DP-BTO
334
286.5
o-DMP-BTO
m-DMP-BTO
p-DMP-BTO
313
336
342
431
426
438
405
442
456
19.2
29.4
59.7
84.6
1.5
4.28
1.92
2.71
0.3
199.0
138.0
0.4
DTBP-BTO
DMOP-BTO
DFP-BTO
343
357
335
331
354
391
429
479
431
411
477
555
447
466
439
436
472
573
0.2
66.6
45.1
85.8
65.3
86.9
83.3
333.0
90.0
429
3.02
0.52
2.19
1.82
0.48
2.55
3.24
5.45
8.02
5.26
4.59
5.59
0.5
0.2
DTFMP-BTO
DBP-BTO
0.6
108.8
124.1
2.5
0.7
DTPA-BTO
33.3
a In THF solution (10−5 M). b Fluorescence quantum yield determined by a calibrated integrating sphere. c AIE activity calculated by F
(solid)/F (soln). d Fluorescence lifetime, measured under ambient conditions.
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Ed., 2009, 48, 7608; (c) Z. Li, Y. Dong, J. W. Y. Lam, J. Sun, A.
BTO, DTFMP-BTO and DTPA-BTO are in the range of 436‒573 nm,
being red-shifted relative to those in solutions to different extent.
The solid of DTPA-BTO shows the reddest PL peak at 573 nm (Fig.
S4). However, in solids, o-DMP-BTO and DMOP-BTO afford blue-
shifted PL peaks at 405 and 466 nm, respectively. The difference in
PL peaks should result from the varied molecular alignments and
intermolecular interactions. The ΦF values of all the luminogens in
solids except for o-DMP-BTO and DTPA-BTO are greatly advanced to
45.1%‒86.9%, which verifies again their AIE characteristics. The
lifetimes of these luminogens in solids are appaerently longer than
those in THF solutions (Table 1 and Fig. S5), which are consistent
with the ΦF values. The ΦF value of o-DMP-BTO is moderately
increased from 19.2% in solution to 29.4% in solid, which is
attributed to the further rigidified molecular structure by spatial
constraint in condensed phase. The ΦF value of DTPA-BTO is
enhanced apparently from 33.3% to 83.3%, suggesting the RIR
effect overcomes the ICT effect in solid. These results also reveal
that the steric and electronic effects can well modulate the PL
behaviors of BTO-based AIEgens.
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Qin, M. Häußler, Y. Dong, H. H. Y. Sung, I. D. Williams, H. S.
DOI: 10.1039/C6CC09892D
Kwok and B. Z. Tang, Adv. Funct. Mater., 2009, 19, 905.
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Chen, X. Meng and M.-Q. Zhu, Chem. Mater., 2014, 26, 4433;
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In summary, a series of BTO-based luminogens with prominent
AIE nature are facilely synthesized and characterized. Their AIE
properties are modulated effectively by controlling the conjugation,
steric and electronic effects of the substituents. The rotation of the
phenyls against the BTO core can nonradiatively deactivate the
excited state of the luminogen, leading to weak emission. The
restriction of intramolecular rotations can greatly improve emission,
which can be achieved by internal steric hindrance and/or external
constraint by aggregation. The AIE property is also sensitive to
strong ICT effect which increases the PL efficiency in solution. These
novel BTO-based AIEgens would be promising candidates for high-
tech applications in materials science and biotechnology, and
relevant in-depth studies are in progress.
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This work was financially supported by the National Natural
Science Foundation of China (51273053 and 21673082), the
National Basic Research Program of China (973 Program,
2015CB655004 and 2013CB834702), the Guangdong Natural
Science
Funds
for
Distinguished
Young
Scholar
(2014A030306035), the Guangdong Innovative Research Team
Program of China (201101C0105067115), the Natural Science
Foundation of Guangdong Province (2016A030312002), the
Innovation and Technology Commission of Hong Kong (ITC-
CNERC14SC01) and the Fundamental Research Funds for the
Central Universities (2015ZY013).
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