Phenylcarboxyl-decorated tetraphenylethene with diverse molecular RIM-induced emission from host-guest inclusion and aggregation formation

Article abstract of DOI:10.1039/c5ra27292k

A novel synthesized 4-carboxylphenoxy-decorated tetraphenylethene and α-cyclodextrin could form a host-guest inclusion complex with molecular RIM-induced Emission. On the basis of this, the TPE-COOH?α-CD inclusion complex exhibits a reversible fluorescence intensity change response to the photo-isomerization of 4-(phenylazo)benzoic acid (PBA) under alternate UV- and visible-light irradiation.

Full text of DOI:10.1039/c5ra27292k

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Phenylcarboxyl-decorating Tetraphenylethene with Diverse
Molecular RIM-induced Emission from Host-guest Inclusion and
Aggregation Formation
Received 00th January 20xx,
Accepted 00th January 20xx
a
a
b
a
a
DOI: 10.1039/x0xx00000x
Yan Gao, Bin Han , Yuting Chen , Xi Wang , Ming Bai*
www.rsc.org/
1
1
A
novel
synthesized
4-carboxylphenoxy-decorating
The inclusion of hydrophobic guest species inside the cavity
tetraphenylethene and α-cyclodextrin could form a host-guest of CD may restrict the free rotation of corresponding guest
inclusion complex with molecular RIM-induced Emission. On the species such as AIE-active tetraphenylethene (TPE) molecule.
base of this, the TPE-COOH⊂α-CD inclusion complex exhibits an As
a consequence, a few of CD-consisting host-guest
reversible fluorescence intensity change response to the photo- complexes with TPE derivatives were fabricated to investigate
isomerization of 4-(phenylazo)benzoic acid (PBA) under alternate the RIM effect of AIE-active guest molecules. Tang and
UV- and visible-light irradiation.
coworkers reported a series of α-, β-, or γ-CD-decorating TPEs
with high emission efficiency in dimethylsulfoxide (DMSO)
1
2a
Luminogenic molecules with aggregation-induced emission
(AIE) nature have been attracting increasing research interests
solution due to the intramolecular host-guest inclusion.
They revealed that the diboronic acid-containing TPE can be
utilized to recognize -CD from - or -CD based on host-guest
interaction-aided boronic acid/diol-binding.
in the past decade owing to their various potential applications
in optoelectronic devices such as photoelectric conversion,
β
α
γ
1
2b
Zheng et al.
1
,2
biological probes, and organic light-emitting diodes (OLEDs).
found that oligo ethylene glycol-modified TPE exhibit an
enhanced monomer emission and a decreased aggregate
In contrast to the fluorophores showing notorious
aggregation-caused quenching (ACQ) characteristics in solid
state, the AIE luminogens (AIEgens) become to emit efficiently
1
3
emission when they were included in the cavity of γ-CD. It is
noteworthy that despite a few reports on RIM process of CD-
consisting host-guest complex with TPE moiety, systemic
exploration on RIM-induced emission from host-guest
inclusion and the difference from aggregation induced
emission has not yet been reported out thus far.
3
in concentrated state due to the aggregate formation. The
fluorescence enhancement for AIEgens is mainly attributed to
the restriction of intramolecular motions (RIM) in aggregate
state, which can block the radiationless relaxation channel and
open the radiative decay pathway, switching on fluorescence
emission of AIEgens. This RIM-induced emission mechanism
for rotor-carrying AIEgens has been approved by manipulating
external experiment conditions (like increasing solvent
viscosity, decreasing solution temperature, or pressurizing
solid film) or by modulating such internal control experiments
as introducing sterically bulky groups and cross-locking with
In the present paper, a 4-carboxylphenoxy-decorated TPE
(
TPE-COOH) luminogen was designed and synthesized. This
compound exhibited typical AIE characteristics in the mixed
solvent of DMSO (or THF) and water. Meanwhile, addition of
the
α-CD into TPE-COOH in the basic DMSO/H O (1/1, v/v)
2
solution switches on its molecular fluorescence emission
centered at 455 nm due to the RIM process associated with
host-guest inclusion, which is slightly different from its red-
shifted emission (466 nm) attributed to the AIE process in
1
,4-6
tethering units.
Additionally, the intermolecular network
structures which canconfine the intramolecular motions of
7
AIEgen such as microporous polymers and metal-organic
8
framework were also employed to reach this goal.
DMSO/H O (1/9, v/v). Particularly, on the basis of the RIM-
2
induced emission from host-guest inclusion, TPE-COOH⊂α-CD
Cyclodextrin (CD) are well-known for its unique inclusion
9
property toward a wide range of hydrophobic guest species.
complex exhibits a reversible fluorescence intensity response
to the azobenzene derivatives under alternate UV- and visible-
light irradiation.
-
The synthesis of 4-carboxylphenoxy substituted TPE
a.
Marine College, Shandong University at Weihai, Weihai 264209, People’s Republic
of China.
derivative
(
TPE-COOH
)
was shown Scheme 1. 1-(4-
b.
Key Laboratory of Coordination Chemistry and Functional Materials in Universities
of Shandong, Dezhou University, Dezhou 253023, People’s Republic of China.
Electronic Supplementary Information (ESI) available: Materials and instruments,
(Bromomethylphenyl)-1,2,2-triphenylethylene was prepared
14
according to the precious report with some modification.
†
synthesis and characterization of the compounds 1-4, additional spectra and
experimental details. See DOI: 10.1039/x0xx00000x
This compound was then treated with methyl 4-
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Fig. 2 Change in fluorescence intensity of TPE-COOH at 455 nm upon addition of
Scheme 1. Synthesis of compound TPE-COOH(4).
2
2
equiv. α-CD in different water fraction DMSO-H O mixtures. Concentration: 30
ꢀM (contain 1.1 equiv. NaOH) ; λex: 330 nm (10 nm, 10 nm); 283 K .
2 3
hydroxybenzoate in the presence of K CO in DMF, affording
compound 3. Further hydrolysis was performed in saturated
NaOH solution of THF and H O to get TPE-COOH 4. All the
molecule hardly get into the cavity of host to form host-guest
1
1,12
2
complex.
As a consequence, it is essential to determine an
1
13
compounds were characterized by H NMR, C NMR, 2D COSY,
and ESI-MS spectroscopies (Figs. S1-12, ESI†).
appropriate ratio of organic/water mixture, whose solvation
effect can just endow TPE-COOH with weakly non-aggregated
emission but synchronously is sufficient to facilitate the
formation of TPE-COOH-based host-guest complex with RIM-
induced emission after adding CD.
To investigate whether the synthesized TPE-COOH is
endowed with the same AIE characteristics as those exhibited
1
by other TPE derivatives, the fluorescence emission behavior
of this compound in the THF-H
fraction (f , the volume percentage of H
DMSO-H O mixture) was studied. As shown in Fig. S13 (ESI†),
when the water fraction f is below 75%, TPE-COOH is almost
non-emissive. However, along with the increase of f from 75
2
O mixture with different H
2
O
Since the alkaline media can enhance the amphiphilicity of
guest with carboxylic acid group which will be beneficial to the
w
2
O in the THF or
1
1
2
formation of host-guest complex, NaOH (1.1 equiv, relative
to TPE-COOH) was added into the experimental solution(the
apparent pH value is 7.94). In the preliminary experiments, we
w
w
to 90%, weak fluorescence emission of this compound is
swiftly enhanced due to the aggregation formation, which
restricts the free motions of TPE moiety and in turn switches
on its fluorescence emission, revealing the AIE nature of TPE-
2
tried to use the basic THF-H O mixture with different water
fraction as solvent. As shown in Fig. S14 (ESI†), the
fluorescence emission behavior of TPE-COOH upon addition of
α-CD (2 equiv.) takes little change relative to that without
addition of -CD in basic THF-H O mixture, suggesting that the
1
COOH at high water fraction.
α
2
Since host-guest inclusion can restrict the intramolecular
motions (RIM) of guest inside the cavity of host, to study the
spectroscopic properties of RIM process associated with host-
guest inclusion with AIE-active guest, the fluorescence
emission spectrum of TPE-COOH upon addition of CD was
recorded with the excitation of 330 nm. It is well known that
the solvent choice plays a very important role in studying RIM-
induced emission of AIE-active host-guest complex. In general,
the aqueous media is preferable to form the host-guest
inclusion owing to the favorable hydrophobic interaction
investigation on RIM-induced emission of TPE-COOH-based
host-guest complex in this media is not suitable for THF’s
strong solvated effect. Taking it into account that DMSO could
be miscible with water and sometime is utilized as
experimental media in the formation of host-guest complex,
the fluorescence emission property of TPE-COOH upon
addition of
Similar to that in basic THF-H
exhibits an obvious aggregation-induced emission effect when
the f of basic DMSO-H O mixture is above 50% (Fig. 1). In
α
-CD was probed in the basic DMSO-water mixture.
2
O mixture, TPE-COOH also
w
2
1
2
between guest molecule and CD. Meanwhile molecular
aggregation is very common for AIE-active luminogen in high
water fraction. As a result, it seems very puzzling to exactly
attribute the fluorescence enhancement of AIE-active host-
guest complex to the AIE effect or the host-guest inclusion
inhigh water media. Similarly, the organic solvent was rarely
utilized because the strong solvated effect can make the guest
other words, TPE-COOH in this media is weak emissive.
Notably, the weak emission of TPE-COOH in this medium is
found to be obviously increased upon addition of
equiv.), despite little optical change occurring in other ratio of
basic DMSO-H O mixture (Fig. 2). Nevertheless, in neutral
DMSO-H O mixture with different f being from 0 to 90%,
addition of -CD (2 equiv.) into TPE-COOH induces little optical
change relative to that without addition of -CD (Figs S15-16,
ESI†). These results show that the basic DMSO-H O mixture (f
50%) can be employed as experimental medium to
investigate the RIM effect of TPE-COOH-based host-guest
complex with -CD. The fluorescence increase of TPE-COOH
upon addition of -CD (2 equiv.) in this medium is attributed
to the formation of TPE-COOH-based host-guest complex with
-CD, which can restrict the phenyl motions of TPE moiety in
sufficiently and in turn lead to the fluorescence emission of
TPE-COOH
To explore the binding stoichiometry between TPE-COOH
and -CD in TPE-COOH-based host-guest complex with -CD,
α-CD (2
2
2
w
α
α
2
w
=
α
α
α
Fig. 1 (A) Fluorescence spectra and (B) plots of the fluorescence intensity at 455
nm of TPE-COOH in DMSO-H O mixtures with different water fractions.
2
.
Concentration: 30 ꢀM (contain 1.1 equiv. NaOH); λex: 330 nm (10 nm, 10nm); 283
K.
α
α
2
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Fig. 4 Change in fluorescence intensity of TPE-COOH upon addition of 2
equiv. -CD, -CD, and -CD in DMSO-H mixture (f 50%).
ex: 330 nm (10 nm, 10
α
β
γ
2
O
w
=
Fig. 3 (A) Change in fluorescence spectrum of TPE-COOH upon titration
with -CD in DMSO-H O (f = 50%) and (B) plots of the fluorescence
intensity at 455 nm against [ -CD]/[TPE-COOH]. Concentration: 30 μM
contain 1.1 equiv. NaOH); ex: 330 nm (10 nm, 10 nm); 283 K.
Concentration: 30 μM (contain 1.1 equiv. NaOH);
λ
α
2
w
nm); 283 K.
α
(
λ
TPE-COOH and
the quantitative fluorescent titration experiments of TPE- TPE-COOH -CD
-CD (0-1.5 equiv.) adamantanecarboxylate (AD-COOH) was investigated in basic
α
-CD, the fluorescence emission behaviors of
⊂
α
(1:1) system after adding 1-
COOH (30
ꢀ
M) with increasing amount of
α
1
5
were carried out in a basic H
2
O-DMSO mixture (f
w
2 w
= 50%). As DMSO-H O mixture (f
= 50%). As expected, the fluorescence
-CD complex at 455 nm is weakened
at 455 nm is gradually enhanced (60-fold) along with the to be almost quenched along with the increasing amount of
increasing amount of
-CD from 0 to 1 equiv. Then further AD-COOH added from 0 to 1.5 equiv. (Fig. S22, ESI†), probably
increase in the
-CD amount added even to 1.5 equiv leads to because the phenyl rings of TPE moiety in TPE-COOH were
almost no change in the emission spectrum. Moreover, the driven out from the cavity of -CD owing to the strong and
fluorescence intensity of this compound increases linearly specific interaction of AD-COOH with -CD. In addition, the
based on Benesi-Hildebrand plot of 1/(F-F ) against 1/[
-CD] effect of cavity size of the CD on the RIM process of host-guest
Fig. S17, ESI†), implying the possible 1:1 binding stoichiometry complex was also investigated under the same experimental
shown in Fig. 3, the weak fluorescence emission of TPE-COOH emission of TPE-COOH-α
α
α
α
α
0
α
(
between TPE-COOH and
α
-CD in TPE-COOH-based host-guest condition as mentioned above. As shown in Fig. 4, different
) being close to from that of -CD, the weak fluorescence emission of TPE-
.81×105 M . This is further confirmed by fluorescent Job’s COOH at 455 nm upon addition of - or -CD keeps almost
plot (Fig. S18, ESI†). By plotting the intensity of the unchanged, revealing that the small cavity of -CD can more
fluorescence peak at 455 nm versus the mole fraction of TPE- efficiently restrict the phenyl motions of TPE-COOH than the
COOH (total concentration = 50
M), the curve clearly showed larger-sized one in - or -CD. These results give an additional
a maximum at 0.5. In addition, ESI-MS spectrum for the support for the formation of TPE-COOH -CD complex upon
mixture of TPE-COOH and
-CD displays an obvious molecular addition of -CD into TPE-COOH, which in turn leads to RIM-
ion peak at 1452.75 designated to TPE-COOH
-CD complex induced fluorescence emission in basic DMSO-H O mixture (f
calcd 1453.50[M-H] ), (Fig. S19, ESI†), again approving the 1:1 = 50%).
complex, with the association constant (K
a
α
-1 16
1
β
γ
α
ꢀ
β
γ
⊂
α
α
α
-α
2
w
-
(
chelating model between TPE-COOH and
α
-CD in TPE-COOH
-
To investigate the potential application of RIM-induced
fluorescence emission from TPE-COOH -CD inclusion complex,
based host-guest complex with
α
-CD.
-α
It is noteworthy that the maximum emission of TPE-COOH 4-(phenylazo)benzoic acid (PBA) with the reversible photo-
at 455 keeps almost unchanged along with increasing the isomerization effect between trans and cis isomers under
amount of
α
-CD added from 0 to 1.5 equiv in basic DMSO-H O alternate UV- and visible-light irradiation was employed as the
2
mixture (fw = 50%) despite the obvious enhancement in its recognition guest in basic DMSO-H
2
O mixture (f
As shown in Fig. S23 (ESI†), the fluorescence emission of
maximum absorption of this compound at ca. 300 nm (Fig. S20, TPE-COOH -CD complex is obviously decreased upon
ESI†). In contrast, the aggregate-induced fluorescence addition of trans-PBA (1.5 equiv.) in basic DMSO-H O (f
emission for TPE-COOH not only is increased but also takes 50%), suggesting more favorably chelating affinity of the -CD
slight red-shift from 455 to 466 nm (11 nm) along with with trans-PBA than with TPE-COOH, which in turn induces the
increasing the fw of H O-DMSO from 50 to 90% (Fig. dissociation of TPE-COOH from the cavity of -CD in their
w
= 50%), Fig.
1
8-20
fluorescence intensity (Fig. 3A). This is also true for the 5.
⊂
α
2
w
=
α
α
2
1A),meanwhile a slight red-shift (8 nm) is also observed in its
maximum absorption (Fig. S21, ESI†), due probably to the
strong intermolecular interactions in the aggregate state of
1
7
this compound. These results clearly indicate that the
fluorescence emission of TPE-COOH ascribed to its host-guest
complex with α-CD is obviously different from the one due to
the AIE process of this compound in H O-DMSO mixture.
2
It is well known that adamantane enters preferentially into
the cavity of CD in comparison with phenyl derivatives due to
1
1
its strong and specific interaction with CD. As a consequence, Fig. 5 Schematic illustration of the preparation of the TPE-COOH/α-CD/PBA
composite and its photoreversible behavior with UV and visible light.
tofurther reveal the host-guest inclusion between AIE-active
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inclusion, TPE-COOH
⊂
α
-CD complex can be utilized as a
reversible fluorescence intensity responsive sensor for the
azobenzene derivatives under alternate UV- and visible-light
irradiation.
Notes and references
1
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Tang, Adv. Mater., 2014, 26, 5429; (b)Y. Hong, J. W. Y. Lam
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J. W. Y. Lam and B. Z. Tang, Chem. Commun., 2009, 4332.
D. Ding, K. Li, B. Liu and B. Z. Tang, Acc. Chem. Res., 2013,
46, 2441.
Z. Zhao, J. W. Y. Lam and B. Z. Tang, J. Mater. Chem., 2012,
22, 23726.
Fig. 6 Reversible switching of fluorescence intensity at 455 nm under alternate
2
3
4
UV (365 nm) and visible (> 435 nm) light irradiation.
inclusion complex. It is well known that PBA exhibits the
reversible photo-isomerization effect between trans and cis
isomers under alternate UV- and visible-light irradiation (Fig.
S24, ESI†). Based on the above-mentioned results, one TPE-
(a) J. Q. Shi, N. Chang, C.H. Li, J. Mei, C.M. Deng, X. L. Luo, Z.
P. Liu, Z. S. Bo, Y. Q. Dong and B. Z. Tang, Chem. Commun.,
2
012, 48, 10675; (b) H. Tong, Y. Dong, Y. Hong, M. Haussler,
J. W. Y. Lam, H. H.-Y. Sung, X. Yu, J. Sun, I. D. Williams, H. S.
Kwok and B. Z. Tang, J. Phys. Chem. C, 2007, 111, 2287; (c) C.
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Zheng, X. -L. Yang and H. -B. Xu, Angew. Chem. Int. Ed., 2015,
COOH
investigate the photoresponsive effect on RIM-induced
emission of host-guest inclusion in basic DMSO-H O (f = 50%).
/α-CD/PBA (1:1:2) ternary system is fabricated to
2
w
54, 9244.
T. Noguchi, B. Roy, D. Yoshihara, Y. Tsuchiya, T. Yamamoto
and S. Shinkai, Chem. Eur. J., 2014, 20, 381.
J. Zhao, D. Yang, Y. Zhao, X. -J. Yang, Y. -Y. Wang and B.Wu,
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Am. Chem. Soc., 2011, 133, 17622; (b) E. Preis, W. Dong, G.
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A. F. Cozzolino, V. K. Michaelis, R. G. Griffin and M. Dinca, J.
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Lustig, F. Wang, H. Wang, S. J. Teat, D. Banerjee, D. Zhang
and J. Li, Chem. Commun., 2015, 51, 3045.
As shown in Fig. S25 (ESI†), upon irradiation with UV light (365
5
6
7
nm) for 120 s, the quenched fluorescence emission for TPE-
COOH-α-CD complex is restored probably due to the
formation of cis-PBA associated with its isomerization from
trans- to cis-isomer, which is hard to be included into the
cavity of
them, inducing the reformation of TPE-COOH
In contrast, the fluorescence emission of TPE-COOH
α
-CD owing to the mismatch interaction between
-CD complex.
-CD
-α
8
⊂
α
complex is obviously decreased after adding trans-PBA for 120
s under visible-light (435 nm) irradiation, as a result of the
formation of α-CD-trans-PBA inclusion as just mentioned (Fig.
S26, ESI†). Then upon further irradiation with UV light, the PBA
9
1
S. Li, W. C. Purdy, Chem. Rev., 1992, 92, 1457.
0 VT D’Souza, KB Lipkowitz. Cyclodextrins: Introduction. Chem.
Rev., 1998,98,1741.
returns to the cis state and TPE-COOH is included into the
cavity of
α-CD instead. Moreover, this fluorescence responsive
of TPE-COOH
⊂α
-CD complex to PBA can be recycled many 11 V. Mikhail and Y. I. Rekharsky, Chem. Rev., 1998, 98, 1875.
1
2 (a) G. Liang, J. W. Y. Lam, W. Qin, J. Li, N. Xie and B. Z. Tang,
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X. Y. Shen, L. Tong, R. Hu,J. Z. Sun and B. Z. Tang, Chem. Eur.
J., 2011, 17, 14736.
complex with RIM-induced emission as reversible photo-times
under alternate UV- and visible-light irradiation, Fig. 6,
suggesting the potential application of the TPE-COOH⊂α-CD
responsive fluorescence sensor.
13 S. Song, H. -F. Zheng, D. -M. Li, J. -H. Wang, H. -T. Feng, Z. -H.
Zhu, Y. -C. Chen and Y. -S. Zheng, Org. Lett., 2014, 16, 2170.
1
1
1
4 Y. Liu, A. Qin, X. Chen, X. Y. Shen, L. Tong, R. Hu, J. Z. Sun and
B. Z. Tang, Chem. Eur. J., 2011, 17, 14736.
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193.
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,
A 4-carboxylphenoxy-decorating TPE derivative (TPE-COOH
with obvious AIE characteristics has been designed and
synthesized. In basic DMSO-H O (f = 50%) mixture, the
inclusion of TPE-COOH inside the cavity of -CD switches on
)
1
2
949, 71, 2703; (b) A. D. Bani-Yaseen, Spectrochim. Acta, A,
015, 148, 93.
2
w
α
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7 B. Z. Tang, Y. Geng, J. W. Y. Lam, B. Li, X. Jing, X. Wang, F.
Wang, A. Pakhomov and X. X. Zhang, Chem. Mater., 1999, 11
1581.
the non-aggregated emission of TPE-COOH at 455 nm owing to
restricting phenyl motions of AIE-active TPE moiety, which is
different from the aggregate-induced emission red-shifted to
,
1
1
8 B. Pietro and M. Sandra, J. Phys. Chem., 1987, 91, 5046.
9 D. -H. Qu, Q. -C. Wang, Q. -W. Zhang, X. Ma and H. Tian,
Chem. Rev., 2015, 115, 7543.
2 w
466 nm in H O-DMSO (f = 90%) mixture. The clarification of
this slight difference provides the basis for the application of
TPE derivatives in host-guest inclusion induced emission
system, such as the utilization of fluorescence titration to
distinguish the change of the emission is difficult and changing
the molecular state to achieve the obvious emission
wavelength shift is hopeless. Additionally, based on the RIM-
induced fluorescence emission mechanism of host-guest
2
0 Z. -Q. Dong, Y. Cao, X. -J. Han, M.-M. Fan, Q.-J. Yuan, Y. -F.
Wang, B. -J. Li and S. Zhang, Langmuir, 2013, 29, 3188.
4
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Graphical abstract:
Phenylcarboxyl-decorating Tetraphenylethene with Diverse Molecular
RIM-induced Emission from Host-guest Inclusion and Aggregation Formation
Basing on an amphiphilic TPE luminogenic molecule, host-guest complexation
with α-CD could be obtained and for the hydrophobic cavity restrict the motions of
AIE molecules the RIM induced fluorescence turn on could be confirmed which
clarified the slightly difference (an 11 nm red-shifted emission) from its AIE process.