Ultrafast broadband nonlinear optical properties and excited-state dynamics of two bis-chalcone derivatives

Article abstract of DOI:10.1039/d0ra01592j

The development of organic nonlinear optical (NLO) chromophores is vital for various fields such as two-photon biomedical imaging, optical limiting, etc. In this work, two bis-chalcone molecules 1,4-bis[3-(2,4-dimethoxyphenyl)-2-acryloyl]benzene (C1) and

Full text of DOI:10.1039/d0ra01592j

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Ultrafast broadband nonlinear optical properties
and excited-state dynamics of two bis-chalcone
derivatives
Cite this: RSC Adv., 2020, 10, 15199
a
b
d
a
*
*
Junyi Yang
Lei Shen,
Zhongguo Li, Xingzhi Wu,c Wenfa Zhou,
ae
*
and Yinglin Song
The development of organic nonlinear optical (NLO) chromophores is vital for various fields such as two-
photon biomedical imaging, optical limiting, etc. In this work, two bis-chalcone molecules 1,4-bis[3-(2,4-
dimethoxyphenyl)-2-acryloyl]benzene (C1) and 4,40-bis[3-(2,4-bimethoxy phenyl)-2-acryloyl]biphenyl (C2)
were synthesized and characterized. The excited-state dynamics of these two chromophores were studied
using femtosecond transient absorption (TA) measurements. And their broadband nonlinear absorption
properties and optical limiting (OL) response were investigated by femtosecond open-aperture Z-scan
and intensity-dependent transmittance measurements in the wavelength range from 515 nm to 800 nm,
respectively. The TA results demonstrate that C2 has strong excited-state absorption behavior and
longer lifetime. In addition, the nonlinear absorption response of C2 was found to be superior to that of
C1 in the visible range after 500 nm, which is attributed to a two-photon-absorption induced excited-
state absorption mechanism. These results indicate that the nonlinear optical response and excited-state
dynamics in bis-chalcone compounds could be enhanced via intramolecular charge-transfer.
Received 19th February 2020
Accepted 31st March 2020
DOI: 10.1039/d0ra01592j
rsc.li/rsc-advances
biology and medical science.11–14 In recent years, they have
received much interest due to the high tendency to crystallize
and notable second and third-order NLO responses.15–17 Dhar-
1. Introduction
Organic nonlinear optical (NLO) materials have attracted
considerable attention in recent years due to their intriguing
properties, such as structural exibility, large p-conjugated
systems, and biocompatibility, and are highly promising for
applications in all-optical switching, optical limiting, bio-
imaging, and so on.1–5 It is well known that the NLO response
of conjugated organic materials is closely related to the struc-
ture of the molecule, such as the size of the p-conjugated
system and the introduction of electron donor and electron
acceptor.6–10 Hence, designing novel organic chromophores
exhibiting superior NLO response is of great scientic and
technological interest not only for shedding light on the
nonlinear light–matter interaction but also for the development
of novel photonic devices. Chalcone derivatives are a kind of p-
conjugated molecules and have been widely investigated in
maprakash et al. have synthesized numerous chalcone deriva-
tives and mainly investigated the crystalline perfection, third-
order NLO and OL properties.18–22 Despite these effects,
however, the NLO mechanism and excited-state dynamics of
these chalcone chromophores remains elusive.23 Gu et al.
studied the NLO properties of chalcone derivatives and
proposed that their NLO response could be attributed to the
multi-photon absorption induced excited-state absorption
mechanism (MPA induced ESA).24–26 Bis-chalcone is a derivative
of chalcone, which has a larger p-conjugated electron system in
its molecule skeleton. Although advances have been made
towards investigating the NLO properties of bis-chalcones
derivatives, however, the novel bis-chalcones compound with
broadband ultrafast NLO response remains elusive.27–30
Albota et al. reported that symmetric charge transfer from
the end of a conjugated system to the middle or vice versa can
lead to large two-photon cross-section.31 Following this idea,
two bis-chalcone derivatives C1 (ref. 32) and C2 (Scheme 1) were
synthesized and characterized. Their ultrafast excited-state
dynamics were investigated using femtosecond TA measure-
ments. And their broadband NLO responses and mechanism
were also studied via femtosecond Z-scan technique in the
visible regime. Our results show that the introduction of
benzene ring to the bis-chalcone compound has a substantial
impact on the excited-state absorption spectra and dynamics of
aSchool of Physical Science and Technology, Soochow University, Suzhou 215006,
China. E-mail: 15962196650@163.com
bSchool of Electronic and Information Engineering, Changshu Institute of Technology,
Changshu 215500, China. E-mail: claes.lee@gmail.com
cJiangsu Key Laboratory of Micro and Nano Heat Fluid Flow Technology and Energy
Application, School of Mathematics and Physics, Suzhou University of Science and
Technology, Suzhou 215009, China
dSchool of Optoelectronic Science and Engineering, Soochow University, Suzhou
215006, China
eDepartment of Physics, Harbin Institute of Technology, Harbin 150001, China. E-mail:
ylsong@hit.edu.cn
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NMR d/ppm (150 MHz, CDCl3): 190.57, 163.14, 160.50, 143.83,
140.76, 138.25, 131.09, 129.15, 127.35, 120.31, 117.14, 105.46,
98.49, 55.60, 55.54. LC-MS (ESI, m/z): 535.20 [M + H]+. Calcd. for
C
34H30O6: 535.21 (Scheme 2).
2.2 Quantum chemical calculations
In order to investigate the inuence of molecular structure on
the NLO properties of the two compounds, quantum chemical
calculation of density functional theory (DFT) was performed
using the Gaussian 09 program package to obtain frontier
molecular orbital distributions. The structures of the
compounds was optimized by the B3LYP/6-31G (D, P) model.
The energy and electron cloud distribution of frontier molec-
ular orbitals were calculated. To further analyse the electron
transition, the time-dependent density functional theory (TD-
DFT)33 was performed using the CAM-B3LYP functional34 and
the b3lyp/6-311g(d) basis set. The type of electron transition can
be characterized through hole–electron analysis which was
performed using Multiwfn 3.7 program.35 The data of the
density isosurface were extracted from Multiwfn and visualized
by the VMD program.36
Scheme 1 Molecular structure of C1 and C2.
these chromophores. And the nonlinear absorption properties
of C2 is greatly enhanced compared to that of C1, indicating C2
compound is a promising OL material.
2. Experimental section and
theoretical calculation
2.1 Synthesis and characterization of C1 and C2
Synthesis of 1,4-bis[3-(2,4-dimethoxyphenyl)-2-acryloyl]
benzene (C1). A mixture of 1,4-diacetylbenzene (350 mg, 2
mmol) and 2,4-dimethoxy benzaldehyde (720 mg, 4 mmol) were
placed in a 250 cm3, three-necked, round-bottom ask. Meth-
anol (45 ml) was added to it, and the ask was heated until the
mixture dissolved completely. Sodium hydroxide (600 mg) as
the catalyst was added to the reaction system. The reaction time
was about 8 h (until the color of reaction liquid changes from
light yellow to yellow). The reaction mixture was extracted and
ltered, and the lter cake was washed with water and anhy-
drous ethanol twice, respectively. Aer recrystallized by anhy-
drous ethanol, 0.81 g of yellow powder solid crude product was
obtained. The compound C1 (350 mg, 35%) was obtained by
column chromatography separation. 1H NMR d/ppm (600 MHz,
DMSO-d): 8.225 (s, 4H), 8.053–8.027 (d, 2H, J ¼ 15.6 Hz), 7.971–
7.957 (d, 2H, J ¼ 8.4 Hz), 7.816–7.790 (d, 2H, J ¼ 15.6 Hz), 6.666–
6.649 (d, 4H, J ¼ 11.2 Hz), 3.920 (s, 6H), 3.859 (s, 6H). 13C NMR d/
ppm (150 MHz, DMSO-d): 189.35, 163.86, 160.63, 141.46,
140.00, 130.84, 129.05, 119.51, 116.26, 106.96, 98.78, 56.37,
56.07. LC-MS (ESI, m/z): 459.15 [M + H]+. Calcd. for C28H27O6:
459.18.
Synthesis of 4,40-bis[3-(2,4-bimethoxy phenyl)-2-acryloyl]
biphenyl (C2). A mixture of 4,4-diacetyl biphenyl (476 mg, 2
mmol) and 2,4-dimethoxy benzaldehyde (730.4 mg, 4.4 mmol)
were placed in a 250 cm3, three-necked, round-bottom ask.
Absolute ethyl alcohol (90 ml) was added to it, and the ask was
heated until the mixture dissolved completely. Sodium
hydroxide (10%, 5 ml) as the catalyst was added to the reaction
system. The reaction time was about 40 h. The reaction mixture
was extracted and ltered, and the lter cake was washed with
2.3 Transient optical nonlinearity
Ultrafast TA measurements were performed in ambient atmo-
sphere at room temperature. A detailed description of the
experimental system is reported elsewhere.27 In brief, the
400 nm pump pulse was generated by an optical parametric
amplier (OPA, ORPHEUS, light conversion) pumped by
a mode-locked Yb: KGW based ber laser (PHAROS, light
conversion). The laser pulse duration and repetition rate were
190 fs and 6 kHz, respectively. The probe light was the white-
light supercontinuum generated using sapphire crystal. The
instrument response function (IRF) was estimated to be around
250 fs. In order to minimize the high-order dynamics, the pump
energy was kept below 12 mW.
2.4 Nonlinear absorption experiments
The nonlinear absorption and optical limiting properties of C1
and C2 were measured by open-aperture Z-scan37 and intensity-
dependent transmittance measurement with the same femto-
second laser source in fs TA experiments. The pulse duration
and laser repetition rate were 190 fs and 20 Hz, respectively. The
sample compounds were diluted in DMSO solvent with
a concentration of 4 ꢀ 10ꢁ3 M and contained in 2 mm quartz
cells. The neat DMSO solvent was also measured under the
same experimental condition and the solvent's NLO response
was removed in the data analysis.
3. Results and discussions
3.1 UV-vis absorption and orescence spectra
anhydrous ethanol. The compound C2 (100 mg, 10%) was ob-
1
tained by column chromatography separation. H NMR d/ppm The UV-vis absorption spectra and uorescence spectra of bis-
(600 MHz, CDCl3): 8.146–8.132 (d, 4H, J ¼ 8.4 Hz), 8.105 (s, 2H), chalcone derivatives C1 and C2 are shown in Fig. 1. The
7.799–7.785 (d, 4H, J ¼ 8.4 Hz), 7.630–7.616 (d, 2H, J ¼ 8.4 Hz), measurements were carried out in dilute DMSO (2 ꢀ 10ꢁ5 M) at
7.616–7.604 (d, 2H, J ¼ 7.2 Hz), 6.585–6.571 (t, 2H, J ¼ 4.2 Hz), room temperature. The results demonstrate that the change in
6.567–6.512 (t, 2H, J ¼ 16.5 Hz), 3.941 (s, 6H), 3.890 (s, 6H). 13
C
absorption peak of C1 and C2 is rather small (387 nm vs. 378
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Scheme 2 Synthetic route of target compounds C1 and C2.
nm), but their emission maximum have dramatic changes spectra (EADS) for C1 and C2 are plotted in Fig. 4(c) and (d),
(536 nm and 490 nm). The uorescence spectrum band of C2 respectively. In Fig. 4(c), the TA spectrum at a delay of 0.55
showed blue-shied compared to that of C1, which indicate the picosecond (ps) aer 400 nm laser excitation is characterized by
strong intramolecular charge-transfer character in C2.38 This an excited state absorption (ESA) band with peak before 460 nm
charge-transfer character can also be supported by the DFT and a stimulated emission (SE) peak at about 540 nm. The
calculation results in Fig. 2.
transient spectrum evolves in 20 ps, exhibiting a dynamic red
As can be seen in Fig. 2, the electron moiety transition is cor- shi of the SE band maximum to 610 nm which may attribute to
responded with the maximum absorption peak on the absorption the vibrational relaxation of S1. With further time delay, the ESA
spectra from HOMO to LUMO ability. The HOMO–LUMO energy band and SE band decays up to about 400 ps. The TA spectral
gap of C1 and C2 are 3.40 eV and 3.46 eV, respectively. And these evolution of C1 suggests three distinct relaxation processes
results corresponded to the UV-vis absorption.
which occur in 0–0.25 ps, 0.25–20 ps, 20–350 ps, 350 ps–ns time
Fig. 3 shows the hole and electron distributions of the two scales. Through global analysis39 (see Fig. 5(a)), we obtain four
compounds. Red and grey isosurfaces denote where electrons dynamic processes and the lifetimes are about 0.25 ps, 4.9 ps,
increase (electron) and where electrons decrease (hole), respec- 142.8 ps and 2.9 ns, respectively. The rst content is unable to
tively. The transition energies (between S0 and S1) of the two be distinguished as the time resolution of our experiment is
compounds were calculated to be 2.956 and 3.034 eV, respectively. 0.25 ps. So we assign the ultrafast process of 0.25 ps to the
The results of Fig. 3 clearly show that C2 has strong intramolecular internal conversion in the rst singlet state (S1). The next
charge-transfer. And compared with C1, C2 has more p-electrons. component with a 4.9 ps lifetime corresponds to the vibrational
relaxation of S1. The last two times are then assigned to the
inter-system crossing (ISC) process between singlet and triplet
state (142.8 ps) and lifetime of the triplet state (2.9 ns).40,41
3.2 Transient absorption spectrum
Fig. 4(a) and (b) show the TA spectra of C1 and C2 in DMSO
solution, respectively. The evolution associated difference
As shown in Fig. 4(d), the TA spectra of C2 underwent
dramatic changes compared to the TA spectra of C1. Following
400 nm laser excitation, the TA spectrum at 0.2 ps is charac-
terized by an excited state absorption (ESA) band with peak at
around 540 nm. The valley at about 485 nm attributes to the
competition between ESA and the effect of uorescence. The
ESA peak at 540 nm exhibits a red shi with a decrease in
Fig. 1 UV-vis absorption (solid lines) and emission spectrum (dashed
lines) of C1 (black) and C2 (blue).
Fig. 2 Frontier molecular orbital distributions of C1 and C2.
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Fig. 3 Hole and electron distributions of C1 and C2.
intensity within 1.4 ps. With further time delay, a new ESA band 10ꢁ3 mol Lꢁ1. The contribution of solvent's NLO response was
grows in the 450–550 nm region. Aer 12 ps, on further delay, subtracted in the data tting. The experimental results show
ESA decay in the 1100 ps time scale. And then follows a much that C2 has larger reverse saturation absorption (RSA) than C1
longer ESA decay in the time scale of ns. Through global anal- in the whole wavelength range. Due to the fs laser pulses used in
ysis (see Fig. 5(b)), we obtain four similar dynamic processes the Z-scan measurements, the main RSA mechanism should be
with C1 and the lifetimes are about 0.25 ps, 7.5 ps, 144.8 ps and intrinsic multi-photon absorption. To further analyze the
7 ns, respectively. It can be easily seen in Fig. 5, unlike C1, with mechanism of the observed optical nonlinearities, all Z-scan
the improvement of the molecule, the relaxation process of measurements were carried out under different laser inten-
excited state has been changed and the lifetime becomes longer sity. And the variation of nonlinear absorption coefficient with
(from 2.9 ns to 7 ns). Furthermore, there's no SE in the TA different laser irradiance at 600 nm was plotted in Fig. 6(c).
spectrum of C2. And the intensity of ESA of C2 is stronger than
By tting to the Z-scan theory,37 the effective nonlinear
that of C1 in the visible range aer 500 nm which means the absorption beff at different intensities were obtained. From
nonlinear optical properties of C2 can be improved because of Fig. 6(c), the extracted beff of C1 is observed to remain
more p-electrons in C2.42–44 The TA spectra indicate that the substantially unchanged, indicating that 2 PA may be the only
excited-state relaxation processes change dramatically with the mechanism under this wavelength. In contrast, the beff of C2 is
molecule structure change from C1 to C2, which could be nearly a proportionally increasing function of the intensity I0,
related to the stronger intramolecular charge-transfer character which means there was higher-order nonlinear absorption. Due
in C2.
to the laser wavelength is far away from the potential 3PA
window (>1100 nm), the higher-order nonlinear absorption can
be attributed to the 2PA-induced ESA.45–47 Therefore, the Z-scan
results in Fig. 6 agree well with the fs TA measurements of the
two compounds. According to the 2PA-induced ESA theory, the
nonlinear absorption coefficient can be expressed as a ¼ a0 + bI
+ gI2, where a0, b and g represent the linear absorption, TPA,
3.3 Femtoseconds Z-scan experiment
To investigate the nonlinear optical response of these two
compounds, open-aperture Z-scan measurements were carried
out at different laser intensity in wavelength range of 515–
800 nm. The concentration of C1 and C2 were about 5.2 ꢀ
Fig. 5 (a and b) Temporal dynamics of C1 and C2 in DMSO following
Fig. 4 TA spectra of C1 (a) and C2 (b) diluted in DMSO at excitation femtosecond laser excitation at 400 nm, respectively. Inset figures
wavelength of 400 nm. (c and d) Plots of the TA spectra at various time show early stage dynamics of the same (within the first 20 ps). Circles
delays of C1 and C2, respectively.
are experimental data, and solid lines represent theoretical fitting.
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Fig. 6 (a and b) Open-aperture Z-scan curves of C1 and C2 at 600 nm under 190 fs excitation, respectively. Circles are experimental data, and
solid lines represent theoretical fitting. (c) Example of the intensity dependence of the nonlinear absorption coefficient for C1 and C2.
and the effective h-order nonlinear absorption coefficients,
respectively. And the TPA cross section sTPA can be achieved by
the equation sTPA ¼ hub/N. Both b and g can be determined by
theoretical tting the Z-scan curves in different laser intensity.
All NLO parameters of the two compounds are summarized in
Table 1. The experimental error was less than 10%.
From Table 1, it is shown that both compounds exhibit TPA
induced ESA in the whole wavelength window from 515 nm to
800 nm, except for C1 compound in around 600 nm. The results
also demonstrate that the two-photon absorption coefficients
b and TPA cross section sTPA of C2 are substantially larger than
C1, which indicate that C2 has promising nonlinear absorption
response in the visible regime.
Fig. 7 Ultrafast OL of C2 as a function of the input fluence at 480 nm,
532 nm, 600 nm, 700 nm and 800 nm with 190 fs excitation.
3.4 Optical limiting behaviour
From previous analysis, C2 compound has strong ICT and
exhibits favorable TPA and ESA,45,46 which means it may have
strong optical limiting response in the visible wavelength
regime. Fig. 7 shows the variations of the transmittance of C2
diluted in DMSO as a function of the input laser uence at 480,
532, 600, 700 and 800 nm. The sample solution was contained
in a 10 mm thick cuvette. Fig. 7 shows that the C2 shows high
linear transmittance at all wavelengths (0.85–0.98). And the
transmittance of C2 solution decreases with increasing input
Table 1 The experimental results of TPA and TPA induced ESA at different wavelength from open-aperture Z-scan measurements
C1
C2
Wavelength
(nm)
b (10ꢁ2 cm GWꢁ1
)
sTPA (GM)
g (10ꢁ4 cm3 GWꢁ2
)
b (10ꢁ2 cm GWꢁ1
)
sTPA (GM)
g (10ꢁ4 cm3 GWꢁ2
)
515
532
580
600
650
700
800
0.50
0.95
0.9
1.19
0.4
80.2
139.7
128.2
163.8
50.8
2.0
2.5
0.75
0
0.2
0.15
0.17
0.63
1.1
1.99
1.99
0.7
101.0
170.7
283.4
274.0
88.9
2.9
2.7
2
2.4
0.25
0.2
0.25
0.66
0.6
77.9
67.1
0.95
0.9
112.1
92.9
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Table 2 Summary of the OL parameters of C2 and other materials
Sample
l/pulse
Wavelength (nm)
T (%)
Threshold (10ꢁ3 J cmꢁ2
)
Ref.
C2/DMSO
190 fs
480
85
4.9
This work
532
98
6.5
600
98
5.9
700
98
10.3
800
98
12.9
Pyrene-based molecules/DMSO
Hydrazone derivatives/DMF
Fluorescent stilbene dye/CHCl3
Silver nanoparticle-embedded polymer
lm
190 fs
190 fs
100 fs
110 fs
515–900
515–800
800
>91
72–98
—
z19
2.75–10.6
30 100
154
45
46
38
48
800
94
a-Se doped silica
QD
Grapheme/water
CNT/water
100 fs
8 ns
8 ns
3–80 ns
3–80 ns
800
85
—
70
—
—
450
>720
>500
70–947
13–740
49
50
51
52
52
532, 1064
532, 1064
430–1064
430–1064
CNT/chloroform
irradiance. The properties of OL material is shown as the OL
threshold, which is the laser uence when the transmittance of
the sample decreases to 50% of the original value. The OL
threshold of C2 and other organic materials reported in recent
literatures are summarized in Table 2.38,45,46,48–52 The results in
Table 2 show that the C2 compound has strong OL response
compared to other organic compounds and inorganic nano-
materials, which means it's a promising ultrafast broadband
optical limiter. Based on the fs TA and Z-scan measurements
above, the OL response of C2 can be attributed to the TPA
induced ESA mechanism.
Acknowledgements
The authors gratefully acknowledge the support of the NSAF
(Grant No. U1630103), Special Fund from State Key Laboratory
of Intense Pulsed Radiation Simulation and Effect (Grant No.
SKLIPR1715) and National Natural Science Foundation of
China (Grant No. 11704048, 11804244).
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