Efficient synthesis of 3-phenylnaphtho[2,3-b]furan-4,9-diones in water and their fluorimetric study in solutions

Article abstract of DOI:10.1002/cjoc.201200499

A simple and efficient protocol has been developed for the synthesis of 3-phenylnaphtho[2,3-b]furan-4,9-diones by domino reaction of α-bromonitroalkenes to 2-hydroxynaphthalene-1,4-dione. With the optimal reaction conditions [NaOAc (120 mol%), water, 70°C, 7 h], the scope of the domino reaction was explored and the green approach provided the desired products in moderate to good yields at elevated temperature under aqueous-mediated conditions. A mechanistic rationalization for this reaction is also provided. The absorption characteristics of the compounds were examined by UV-Vis spectra and fluorescence spectroscopy. All compounds were fluorescent in solution emitting at blue light (432-433 nm), green light (512-536 nm), or yellow light (591 nm).

Full text of DOI:10.1002/cjoc.201200499

COMMUNICATION
DOI: 10.1002/cjoc.201200499
Efficient Synthesis of 3-Phenylnaphtho[2,3-b]furan-4,9-diones
in Water and Their Fluorimetric Study in Solutions
Zhang, Renzun(张仁尊)
Xu, Dongcheng(徐东成)
Xie, Jianwu*(谢建武)
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry and Life
Sciences, Zhejiang Normal University, Jinhua, Zhejiang 321004, China
A simple and efficient protocol has been developed for the synthesis of 3-phenylnaphtho[2,3-b]furan-4,9-diones
by domino reaction of α-bromonitroalkenes to 2-hydroxynaphthalene-1,4-dione. With the optimal reaction condi-
tions [NaOAc (120 mol%), water, 70 ℃, 7 h], the scope of the domino reaction was explored and the green ap-
proach provided the desired products in moderate to good yields at elevated temperature under aqueous-mediated
conditions. A mechanistic rationalization for this reaction is also provided. The absorption characteristics of the
compounds were examined by UV-Vis spectra and fluorescence spectroscopy. All compounds were fluorescent in
solution emitting at blue light (432—433 nm), green light (512—536 nm), or yellow light (591 nm).
Keywords domino reaction, naphthoquinones, fluorescence, Michael addition, 2-hydroxynaphthalene-1,4-dione
Introduction
this paper we describe an efficient protocol for the syn-
thesis of new 3-phenylnaphtho[2,3-b]furan-4,9-diones
under mild conditions. In addition, it was revealed that
3-phenylnaphtho[2,3-b]furan-4,9-diones exhibit fluo-
rescence in CHCl3.
Naphthoquinones and their derivatives occur in
various families of plants, fungi, bacteria and insects.[1]
Many of these naturally occurring naphthoquinones and
their synthetic analogues are important precursors for
the synthesis of natural products and pharmaceuticals.[2]
And naphthoquinone derivatives have been broadly ex-
plored for their anti-inflammatory,[3] antifungal,[4] try-
panocida,[5] molluscicidal,[6] leishmanicidal[7] and anti-
tumor biological activities.[4,8] Moreover, naphtho-
quinone derivatives owe their importance to their suffi-
cient fluorescence in the visible yellow, large Stokes
shift, high quantum yield of photoluminescence and
reasonable solubility, which gives rise to one of the
most extensively investigated and commercially sig-
nificant organic dyes.[9] For example, 2-hydroxy-
1,4-naphthoquinone (HNQ; Lawsone) is the principal
natural dye in the leaves of Henna, Lawsonia inermis. In
recent years, some semipermanent hair dyes containing
Henna as well as its pure dye ingredient HNQ are
widely used and have become increasingly popular due
to their natural origin.[10] Many pigments (strepto-car-
pone, α-dunnione, dunniol and dunnione), which con-
tain naphthoquinone skeleton, have been isolated and
characterized from Streptocapus dunnii.[11] In view of
their importance in pharmaceuticals and dyes, different
approaches toward the synthesis of naphthoquinone de-
rivatives have been reported.[12,13] Recently, the synthe-
ses of quinones in water have also been reported.[14] In
In the course of our investigations on the use of
α-bromonitroalkenes in organic synthesis, this reagent
turned out to be highly reactive and versatile.[15,16] Es-
pecially, the bromo or nitro group could behave as a
better leaving group in the nucleophilic substitution re-
action in comparison with bromoalkenes or nitroalkenes,
α-bromonitroalkenes have become important intermedi-
ates in the synthesis of heterocycles. Organic solvents
can cause significant air pollution, land contamination
and water pollution in many synthetic organic processes,
and the development of efficient synthetic methodolo-
gies for organic reactions, in the absence of organic
solvents, is an important challenge toward reducing the
amount of waste.[17,18] An ideal organic reaction would
proceed in an environmentally benign solvent, such as
water. Considering the above reports, the development
of new and simple synthetic methods for the efficient
preparation of heterocycles and new dyes containing
nahthoquinone moiety is therefore an interesting chal-
lenge. Herein, we present a simple and efficient protocol
for the synthesis of 3-phenylnaphtho[2,3-b]furan-4,9-
diones[19] by domino reaction of α-bromonitroalkenes to
2-hydroxynaphthalene-1,4-dione under aqueous-medi-
ated conditions and their fluorimetric study in solutions.
*
E-mail: xjw@zjnu.cn; Tel./Fax: 0086-0579-82282610
Received May 22, 2012; accepted July 1, 2012.
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/cjoc.201200499 or from the author.
1690
© 2012 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim Chin. J. Chem. 2012, 30, 1690—1694

Synthesis of 3-Phenylnaphtho[2,3-b]furan-4,9-diones in Water and Their Fluorimetric Study
－
1
Experimental
(KBr) ν: 2922, 1678, 1589, 1198, 836 cm ; ESI-HRMS
calcd for C19H12O4＋H 305.0814, found 305.0813.
3-(4-Chlorophenyl)naphtho[2,3-b]furan-4,9-dione
All reactants were commercially available and used
without further purification. All melting points were
uncorrected. Nuclear magnetic resonance spectra were
recorded on Bruker DRX 400 and chemical shifts are
expressed relative to TMS as an internal standard.
ESI-HRMS spectra were measured with a Finnigan
LCQDECA ion trap mass spectrometer. Absorption spec-
tra were recorded on an Shimadzu UV-2550 spectro-
photometer. Fluorescence spectra were obtained on a
Perkin-Elmer LS55 spectrofluorometer. The widths of
the excitation slit and the emission slit were both set to
1
(3d) Yield 81%; yellow solid; m.p. 212—214 ℃; H
NMR (400 MHz, DMSO) δ: 8.59 (s, 1H, CH＝), 8.13—
8.07 (m, 2H, ArH), 7.88 (dd, J＝5.6, 3.4 Hz, 2H, ArH),
7.80 (d, J＝8.5 Hz, 2H, ArH), 7.54 (d, J＝8.5 Hz, 2H,
ArH); 13C NMR (100 MHz, DMSO) δ: 180.9, 173.7,
153.9, 147.8, 134.8, 134.6, 133.8, 133.6, 132.1, 131.0,
128.8, 128.3, 127.2, 126.5, 125.5; IR (KBr) ν: 2922,
1675, 1588, 1197, 835 cm－1; ESI-HRMS calcd for
C18H9ClO3＋H 309.0318, found 309.0317.
3-(4-Bromophenyl)naphtho[2,3-b]furan-4,9-dione
(3e) Yield 83%; yellow solid; m.p. 228—230 ℃; H
－
1
10 nm with the scanning speed at 200 nm•min .
1
NMR (400 MHz, CDCl3) δ: 8.25 (d, J＝5.6 Hz, 1H,
ArH), 8.19 (d, J＝2.9 Hz, 1H, ArH), 7.87 (s, 1H, CH＝),
7.79 (d, J＝3.3 Hz, 1H, ArH), 7.78 (d, J＝3.5 Hz, 1H,
ArH), 7.61 (s, 4H, ArH); 13C NMR (100 MHz, CDCl3) δ:
180.7, 173.9, 153.9, 145.4, 134.2, 133.9, 133.7, 132.0,
131.7, 130.5, 127.7, 127.3, 126.8, 126.6, 123.1; IR (KBr)
General procedure for the synthesis of 3-phenyl-
naphtho[2,3-b]furan-4,9-diones (3a—3h)
To a solution of 2-hydroxynaphthalene-1,4-dione (26
mg, 0.15 mmol) and α-bromonitroalkene 2c (77 mg, 0.3
mmol) in water (1 mL) was added NaOAc (15 mg, 0.18
mmol) and TBAB (tetrabutylammonium bromide) (10
mg, 0.03 mmol) at 70 ℃ for 7 h. The crude product
was isolated by filtration, washed with water, and re-
crystallized from EtOAc to give naphtho[2,3-b]furan-
4,9-dione (3a—3h).
－
1
ν: 2922, 1673, 1586, 1172, 839 cm ; ESI-HRMS calcd
for C18H9BrO3＋H 352.9813, found 352.9811.
3-(4-Fluorophenyl)naphtho[2,3-b]furan-4,9-dione
1
(3f) Yield 77%; yellow solid; m.p. 208—210 ℃; H
NMR (400 MHz, CDCl3) δ: 8.22 (dd, J＝5.2, 3.7 Hz,
1H, ArH), 8.19—8.16 (m, 1H, ArH), 7.83 (s, 1H, CH＝),
7.76 (dd, J＝5.5, 3.5 Hz, 2H, ArH), 7.72—7.66 (m, 2H,
ArH), 7.15 (t, J＝8.7 Hz, 2H, ArH); 13C NMR (100
MHz, CDCl3) δ: 180.7, 173.8, 164.3, 161.8, 153.8,
145.3, 134.1, 133.9, 133.7, 132.0, 130.8, 130.7, 127.2,
126.7, 126.7, 124.8, 115.7, 115.4; IR (KBr) ν: 2921,
1677, 1589, 1167, 837 cm－1; ESI-HRMS calcd for
C18H9FO3＋H 293.0614, found 293.0614.
3-Phenylnaphtho[2,3-b]furan-4,9-dione
(3a)
1
Yield 78%; yellow solid; m.p. 192—194 ℃; H NMR
(400 MHz, CDCl3) δ: 8.26—8.23 (m, 1H, ArH), 8.21—
8.18 (m, 1H, ArH), 7.87 (s, 1H, CH＝), 7.78—7.76 (m,
2H, ArH), 7.72—7.70 (m, 2H, ArH), 7.50—7.43 (m, 3H,
ArH); 13C NMR (100 MHz, CDCl3) δ: 180.7, 174.0,
153.8, 145.5, 134.1, 133.8, 132.1, 128.9, 128.8, 128.7,
128.5, 127.6, 127.2, 127.0, 126.7; IR (KBr) ν: 2922,
1675, 1585, 1194, 832 cm－1; ESI-HRMS calcd for
C18H10O3＋H 275.0708, found 275.0705.
3-(2-Chlorophenyl)naphtho[2,3-b]furan-4,9-dione
1
(3g) Yield 47%; yellow solid; m.p. 224—226 ℃; H
3-p-Tolylnaphtho[2,3-b]furan-4,9-dione
(3b)
1
NMR (400 MHz, CDCl3) δ: 8.26—8.23 (m, 1H, ArH),
8.16—8.12 (m, 1H, ArH), 7.84 (s, 1H, CH＝), 7.78—
7.74 (m, 2H, ArH), 7.55—7.51 (m, 1H, ArH), 7.46 (dd,
J＝7.1, 2.0 Hz, 1H, ArH), 7.41—7.35 (m, 2H, ArH); 13C
NMR (100 MHz, CDCl3) δ: 180.3, 173.9, 153.0, 146.8,
134.0, 133.8, 133.5, 132.3, 131.7, 130.1, 129.8, 128.1,
127.1, 126.8, 126.6, 123.5; IR (KBr) ν: 2923, 1675,
Yield 76%; yellow solid; m.p. 193—195 ℃; H NMR
(400 MHz, CDCl3) δ: 8.23 (dd, J＝5.8, 3.1 Hz, 1H,
ArH), 8.19 (dd, J＝5.4, 3.6 Hz, 1H, ArH), 7.83 (s, 1H,
CH＝), 7.77 (d, J＝3.6 Hz, 1H, ArH), 7.75 (d, J＝3.2
Hz, 1H, ArH), 7.59 (d, J＝7.9 Hz, 2H, ArH), 7.29 (s, 1H,
ArH), 7.26 (s, 1H, ArH), 2.42 (s, 3H, CH3); 13C NMR
(100 MHz, CDCl3) δ: 178.7, 173.2, 149.7, 135.0, 134.6,
133.4, 131.9, 130.2, 129.9, 128.2, 127.9, 127.6, 127.2,
125.6, 125.2, 29.7; IR (KBr) ν: 2921, 1673, 1587, 1195,
－
1
1581, 1196, 822 cm ; ESI-HRMS calcd for C18H9ClO3
＋H 309.0318, found 309.0316.
－
1
3-(2-Bromophenyl)naphtho[2,3-b]furan-4,9-dione
838 cm ; ESI-HRMS calcd for C19H12O3＋H 289.0865,
found 289.0865.
1
(3h) Yield 54%; yellow solid; m.p. 215—217 ℃; H
NMR (400 MHz, CDCl3) δ: 8.26—8.23 (m, 1H, ArH),
8.15—8.11 (m, 1H, ArH), 7.83 (s, 1H, CH＝), 7.78—
7.74 (m, 2H, ArH), 7.72 (dd, J＝7.4, 0.6 Hz, 1H, ArH),
7.41 (dd, J＝8.4, 1.6 Hz, 2H, ArH), 7.34—7.29 (m, 1H,
ArH); 13C NMR (100 MHz, CDCl3) δ: 180.3, 173.9,
152.9, 146.7, 134.0, 133.8, 133.5, 133.0, 132.3, 131.7,
3-(4-Methoxyphenyl)naphtho[2,3-b]furan-4,9-dione
(3c) Yield 64%; red solid; m.p. 214—216 ℃; H
1
NMR (400 MHz, CDCl3) δ: 8.24 (dd, J＝5.8, 3.1 Hz,
1H, ArH), 8.20 (dd, J＝5.5, 3.5 Hz, 1H, ArH), 7.83 (s,
1H, CH＝), 7.78 (d, J＝3.3 Hz, 1H, ArH), 7.76 (d, J＝
3.3 Hz, 1H, ArH), 7.67 (d, J＝1.8 Hz, 1H, ArH), 7.66 (d,
J＝2.1 Hz, 1H, ArH), 7.02—7.00 (m, 2H, ArH), 3.88 (s,
3H, OCH3); 13C NMR (100 MHz, CDCl3) δ: 180.8,
173.9, 160.1, 153.8, 145.0, 134.0, 133.9, 133.7, 132.1,
130.2, 127.4, 127.2, 126.9, 126.6, 121.0, 114.0, 55.4; IR
130.3, 130.2, 128.1, 127.2, 127.1, 126.8, 125.2, 124.2;
IR (KBr) ν: 2922, 1678, 1588, 1196, 822 cm －
;
1
ESI-HRMS calcd for C18H9BrO3＋H 352.9813, found
352.9812.
Chin. J. Chem. 2012, 30, 1690—1694
© 2012 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cjc.wiley-vch.de
1691

Zhang, Xu & Xie
COMMUNICATION
Results and Discussion
temperature and reaction time on the reactivity, and
found out that the best yield was obtained at 70 ℃ af-
ter 7 h (Table 1, Entry 10). In fact, similar results were
obtained when other bases were used at 70 ℃ (Table 1,
Entries 12—14). However, when the stronger base
NaOH, was used at 70 ℃, the reaction became very
complicated and low yield was isolated (Table 1, Entry
11). When the reaction temperature was increased, the
reaction became a little complicated, somewhat low
yield was isolated (Table 1, Entry 15). Compared with
TBAB, lower yield was obtained (only 17%) using SDS
(sodium dodecyl sulfate) as PTC (Table 1, Entry 16).
With the optimal reaction conditions [NaOAc (120
mol%), water, 70 ℃, 7 h] in hand, the scope of the
Synthesis of 3-phenylnaphtho[2,3-b]furan-4,9-diones
(3)
We started our original studies by screening a series
of bases for the domino reaction of α-bromonitroalkene
2c with 2-hydroxynaphthalene-1,4-dione (1) in water.
As shown in Table 1, various bases such as NaOH,
DABCO, NaHCO3 and Na2CO3, were screened and
similar results were achieved when the reaction was
carried out at room temperature (Table 1, Entries 1—5).
When the base NaOAc was used as the catalyst, the
yield of the desired product was higher than those by
using NaOH, DABCO, NaHCO3 and Na2CO3 as cata-
lysts (Table 1, Entry 3). Subsequently, we evaluated the
effects of solvent on the reaction. It was found that,
various solvents such as CH3CN, toluene and EtOH,
were all tolerated to afford product 3c, and H2O was
identified as the best solvent for this reaction (Table 1,
Entries 3, 6—8). Finally, we investigated the effects of
domino reaction of α-bromonitroalkenes
2 with
2-hydroxynaphthalene-1,4-dione (1) was explored. The
results are summarized in Table 2. In general, the de-
sired product can be prepared in moderate to good
yields under standard conditions from the corresponding
α-bromonitroalkenes 2 and 2-hydroxynaphthalene-1,4-
dione (1). Good yields were obtained when there was
electron-withdrawing group on para positions of aro-
matic ring of α-bromonitroalkenes 2 (Table 2, Entries
4—6). On the contrary, α-bromonitroalkenes 2 with
electron-donating substituents on the para positions of
aromatic ring afford 3-phenylnaphtho[2,3-b]furan-4,9-
diones 3 with slightly inferior yields (Table 2, Entries
2—3). Only moderate yields were obtained with elec-
tron-withdrawing group on the ortho positions of aro-
matic ring of α-bromonitroalkenes 2 (Table 2, Entries
7—8).
Table 1 Optimizing reaction conditionsa
O
MeO
OH
Br
Base
Solvent
+
NO2
O
2c
1
O
O
OMe
O
Table 2 Reaction of 2-hydroxynaphthalene-1,4-dione (1) with
different α-bromonitroalkenes 2a
3c
Entry Base
1b NaOH
2b Na2CO3 H2O
3b NaOAc
H2O
4b DABCO H2O
5b NaHCO3 H2O
Solvent
H2O
Tem./℃
Time/h
Yieldd/%
O
O
O
OH
+
Br
25
25
25
25
25
25
25
25
50
70
70
70
70
70
100
70
24
24
24
24
24
24
24
24
12
7
30
33
38
28
36
20
27
34
37
64
21
55
64
62
44
17
Ar
NaOAc, TBAB
H2O, 70 oC
Ar
NO2
O
O
3
2
Yieldb/%
2
Entry
Ar
Prod. 3
6
7
8
NaOAc
NaOAc
NaOAc
CH3CN
Toluene
EtOH
H2O
1
2
3
4
5
6
7
C6H5
2a
2b
3a
3b
3c
3d
3e
3f
78
76
64
81
83
77
47
54
p-MeC6H4
p-MeOC6H4 2c
9b NaOAc
10b NaOAc
11b NaOH
12b Na2CO3
13b DABCO H2O
14b NaHCO3 H2O
p-ClC6H4
p-BrC6H4
p-FC6H4
o-ClC6H4
o-BrC6H4
2d
2e
2f
H2O
H2O
7
H2O
7
2g
2h
3g
3h
7
8
7
a
Unless otherwise noted, reactions were performed with 0.15
mmol of 1, 0.3 mmol of α-bromonitroalkene, 20 mol% TBAB in
1 mL water at 70 ℃ for 7 h. b Isolated yield.
15b NaOAc
16c NaOAc
H2O
H2O
7
7
a
Unless otherwise noted, reactions were performed with 0.15
b
mmol of 1, 0.3 mmol of 2c in the indicated solvent (1 mL). 20
mol% TBAB was added. 20 mol% SDS was added. Isolated
yield.
A mechanistic rationalization for this reaction is
provided in Scheme 1. The domino reaction of
α-bromonitroalkenes 2 with 2-hydroxynaphthalene-
c
d
1692
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© 2012 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2012, 30, 1690—1694

Synthesis of 3-Phenylnaphtho[2,3-b]furan-4,9-diones in Water and Their Fluorimetric Study
4
1,4-dione (1) gives the Michael addition product I cata-
lyzed by NaOAc. Then, the enolate anion was formed
under the basic conditions and the subsequent in-
tramolecular nucleophilic displacement of I affords in-
termediate II. Subsequently, elimination of the nitro
group leads to the formation of 3-phenylnaphtho[2,3-b]-
furan-4,9-diones (3).
Table 3 UV/Vis data for compounds 3 in CHCl3 (4×10－
mol/L)
Entry
λ
max/nm
Molar absorptivity (log ε)
3
1
2
3
4
5
6
7
8
3a
3b
3c
3d
3e
3f
335.5, 387.5
338.0, 397.0
337.0, 405.5
330.0, 388.0
328.5, 385.5
331.0, 385.0
336.0, 380.5
337.0, 380.0
2.065, 1.409
1.411, 1.096
1.474, 1.073
2.532, 1.197
1.839, 0.798
1.826, 0.944
1.705, 1.038
1.752, 1.077
Scheme 1 Formation mechanism of 3-phenylna-phtho[2,3-b]-
furan-4,9-diones (3)
3g
3h
O
O
O
Br
OH
+
Ar
NaOAc, TBAB
NO2
Ar
H2O, 70 oC
O
2
O
measured in CHCl3 (Figure 2) and the relevant data are
listed in Table 4. As shown in Table 4, compound 3e
and 3g are fluorescent in solution emitting at blue light.
Compounds 3a, 3b, 3d, 3f and 3h are fluorescent in so-
lution emitting at green light. Compound 3c presents a
yellow emission of fluorescence. Although the fluores-
cence of these compounds is not very excellent. In the
future, the structure of these compounds will be modi-
fied through the introduction of the different functional
groups to improve the properties of fluorescence. We
hope these can expand the range of the application in
the field of fluorescent materials.
3
1
Michael additon
- HNO2
O
O
O
O
Br
intramolecular SN2
NO2
- HBr
NO2
H
H
Ar
O
Ar
O
B-
B-
I
II
3a
3b
2.5
2.0
1.5
1.0
0.5
0.0
3a
3b
3c
3d
3e
3f
3g
3h
bl
180
3c
3d
3e
3f
3g
3h
170
160
150
140
130
120
110
100
90
80
70
60
50
40
30
20
300
400
500
600
700
800
10
0
Wavelength/nm
nm
700
400
450
500
550
600
650
Figure 1 UV/Vis spectra of compounds 3 in CHCl3 (4×10－
4
Figure 2 Emission spectra of selected compounds (2×10－
mol/L in CHCl3).
4
4
mol/L).
Spectral properties
Table 4 Fluorescence data for compound in CHCl3 (2×10－
mol/L)
Compounds 3a—3h are stable solids whose struc-
tures are fully supported by IR, H and 13C NMR spec-
1
troscopy and ESI-HRMS. Electronic absorption spectra
Entry
3
λ
ex, max/nm
400
396
398
400
376
451
366
448
λem, max/nm
512
Stoke’s shift/nm
of 4×10－ mol/L solutions of 3a—3h in chloroform
4
1
2
3
4
5
6
7
8
3a
3b
3c
3d
3e
3f
112
140
193
118
56
78
67
84
were measured (Figure 1). Data are summarized in Ta-
ble 3. All compounds 3a—3h showed similar absorp-
tions, with maximum wavelengths in the range of 328.5
—405.5 nm and the substituents have little effect on the
electronic absorption.
536
591
518
432
529
433
532
3g
3h
Fluorimetric properties
The fluorescence spectra of all compounds were
Chin. J. Chem. 2012, 30, 1690—1694
© 2012 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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Zhang, Xu & Xie
COMMUNICATION
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Conclusions
We have reported a simple and clean methodology
for the synthesis of new 3-phenylnaphtho[2,3-b]furan-
4,9-diones by domino reaction of α-bromonitroalkenes
to 2-hydroxynaphthalene-1,4-dione under aqueous-me-
diated conditions. This green approach provided the
desired products in moderate to good yields at elevated
temperature. The absorption characteristics of the com-
pounds were examined by UV-Vis spectra and fluores-
cence spectroscopy. All compounds were fluorescent in
solution emitting at blue light (432—433 nm), green
light (512—536 nm), or yellow light (591 nm).
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Acknowledgement
We are grateful for the financial support from the
National Natural Science Foundation of China (No.
20902083).
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