The study of perylene diimide-amino acid derivatives for the fluorescence detection of anions

Article abstract of DOI:10.1039/c7ra08005k

Four types of perylene diimide-amino acid derivatives (H₂PDIAla, H₂PDIGlu, H₂PDIPhe, H₂PDITyr) were chosen to interact with anions. The UV-vis, fluorescence (in DMF solution) and NMR spectra in DMSO-d₆

Full text of DOI:10.1039/c7ra08005k

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PAPER
The study of perylene diimide–amino acid
derivatives for the fluorescence detection of
anions†
Cite this: RSC Adv., 2017, 7, 42685
Chao-yuan Chen, Ke Wang, Lei-lei Gu and Hui Li
*
Four types of perylene diimide–amino acid derivatives (H
chosen to interact with anions. The UV-vis, fluorescence (in DMF solution) and NMR spectra in DMSO-d
solution were studied. The results indicated that the four types of derivatives exhibit specific selectivity
2 2 2 2
PDIAla, H PDIGlu, H PDIPhe, H PDITyr) were
6
Received 20th July 2017
Accepted 21st August 2017
ꢀ
ꢀ
ꢀ
ꢀ
and high sensitivity for F and OH ions. The NMR titrations of the derivatives with F and OH ions
DOI: 10.1039/c7ra08005k
confirmed the synergetic effect of hydrogen bonding and anion–p interaction between the derivatives
ꢀ
ꢀ
rsc.li/rsc-advances
and the anions (F , OH ). In addition, we made a simple test-paper to develop its potential applications.
to detect anions became a developing trend of research. Sourav
Introduction
Saha and co-workers used aliphatic chain modied PDI to
ꢀ
ꢀ
Hydrogen bonding is the most important and widespread detect F and OH , which demonstrated anion–p electronic
8
ꢀ
ꢀ
1
intermolecular interaction. The scientic branches involving interactions from OH and F ions to PDI in aprotic solvents.
the importance of hydrogen bonding are very diverse, including On the other hand, a type of PDI derivative incorporated with
inorganic and organic chemistry, supramolecular chemistry, functional groups of chloroacetamide (–NH–(C]O)–CH –Cl)
2
2
9
biochemistry, and medicine. It is operative in determining has been studied for uoride ion detection. It possesses
ꢀ
molecular conformation, molecular aggregation, and the func- a specic selectivity and high sensitivity for uoride ion (F )
tion of a vast number of chemical systems ranging from inor- among the halogen anions. The recognition was attributed to
ganic to biological and is emerging as a powerful tool in the the intermolecular proton transfer between a hydrogen atom on
3
design of functional materials. In recent years, receptors using the amide of the sensor and the uoride anion. Based on this
hydrogen bonding have been extensively developed, and result, a new colorimetric and ratiometric uorescent sensor for
a variety of functions have been investigated, including recog- naked-eye detection of uoride ion based on PDI–amide deriv-
10
nition, sensing, catalysis, and carrier-mediated transport across atives has been designed and synthesized. In consideration of
4
membranes.
the important effect of hydrogen bonding, the PDI derivatives
Perylene Diimide (PDI) is a valuable functional dye, which equipped with a –COOH group, such as amino acid, should
has numerous potential properties such as unique light- form a strong hydrogen bonding. However, there is no report of
harvesting, redox properties, high chemical persistency, PDI–amino acid derivatives applied in detection of anions in
thermal durability, and outstanding optical and electronic literature. Amino acids are essential structural units and phys-
properties. It has been applied as pigments, in uorescent iologically active substances of life and are environment
detectors, and semiconductors in organic electronics and friendly. The new material designed with amino acids has
5
photovoltaics.
advantages of being green and safe, low price, easy to synthesize
Anions are ubiquitous in environment and food samples and and so on.
play an important role in numerous types of biological and
medicinal processes. The design and development of synthetic (H
Herein, we report the studies of PDI–amino acid derivatives
6
PDIAAs) as uorescent sensors to detect anions, particularly
2
receptors to recognize specic anions selectively had received halogen ions, in organic solvents. Four types of H
more and more attention in recent years. Using PDI derivatives been selected, which are perylene diimides functionalized with
PDIAAs have
2
7
L-alanine (H
2
PDIAla), L-glutamic acid (H
2
PDIGlu), L-phenylala-
nine (H PDIPhe) and L-tyrosine (H
2
2
PDITyr) (Scheme 1). A
Key Laboratory of Clusters Science of Ministry of Education, Beijing Key Laboratory of comparative study and discussion on their uorescent proper-
Photoelectronic/Electrophotonic Conversion Materials, School of Chemistry and ties have been provided explaining their interaction with
Chemical Engineering, Beijing Institute of Technology, Beijing, 100081, China.
halogen ions in DMF as H PDIAAs have good solubility and
strong uorescence in DMF only. This work applies the PDI–
amino acid derivatives on the uorescent sensor to detect
anions based on hydrogen bonding for the rst time.
2
E-mail: lihui@bit.edu.cn
1
†
Electronic supplementary information (ESI) available: Spectra (IR, UV-vis,
H
13
NMR, C NMR, ESI-MS, uorescence life time), or other electronic format. See
DOI: 10.1039/c7ra08005k
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d 12.5 (br s, 4H), 8.43–7.94 (m, 8H), 5.66–5.53 (m, 2H), 2.61–2.47
1
3
(
m, 4H), 2.46–2.25 (m, 4H). C NMR (100 MHz, DMSO-d6):
d 174.0, 170.9, 162.3, 133.1, 130.7, 128.0, 124.6, 123.1, 121.8, 52.7,
3
0.8, 23.9. IR (lm): n ¼ 1751, 1697, 1642, 1591, 1363, 1255, 1168,
ꢀ1 +
0
8
09, 747 cm . ESI-MS: m/z ¼ 651 [M + H] . N,N -Bis-(L-phenyl-
PDIPhe).
PDIPhe (0.652 g, 74%). H NMR (400 MHz, DMSO-d ):
d 8.32–7.98 (m, 8H), 7.34–7.01 (m, 10H), 6.03–5.90 (m, 2H), 3.95–
alanine)-3,4,9,10-perylene tetracarboxylic diimide (H
Yields: H
2
1
2
6
1
3
3
1
5
1
6
.18 (m, 4H). C NMR (100 MHz, DMSO-d ): d 170.6, 162.18,
37.9, 133.8, 131.1, 129.1, 128.2, 128.1, 126.4, 125.2, 123.6, 121.7,
4.0, 34.3. IR (lm): n ¼ 1736, 1698, 1659, 1592, 1435, 1365, 1254,
ꢀ1
+
0
168, 810, 747 cm . ESI-MS: m/z ¼ 687 [M + H] . N,N -Bis-
Scheme
L-alanine (H
PDIPhe) and L-tyrosine (H
2
1
Structural representations of PDI functionalized with (L-tyrosine)-3,4,9,10-perlene tetracarboxylic diimide (H
PDIAla), L-glutamic acid (H PDIGlu), L-phenylalanine
PDITyr).
PDITyr).
PDITyr (0.593 g, 70%). H NMR (400 MHz, DMSO-d ):
d 8.29–7.75 (m, 8H), 7.15–7.97 (m, 4H), 6.64–6.51 (m, 4H), 5.99–
2
1
2
2
Yields: H
2
6
(
H
2
1
3
5
.85 (m, 2H), 3.58–3.46 (m, 2H), 3.44–3.31 (m, 2H). C NMR
100 MHz, DMSO-d ): d 170.8, 162.1, 155.9, 133.4, 130.9, 130.1,
127.9, 127.8, 124.9, 123.2, 121.6, 115.0, 54.1, 33.4. IR (lm): n ¼
(
6
Experimental
Materials and measurements
ꢀ1
1692, 1649, 1592, 14 434, 1402, 1367, 1253, 1009, 825, 745 cm .
+
ESI-MS: m/z ¼ 719 [M + H] .
All materials were reagent grade and obtained from commercial
sources and used without further purication. IR spectra were
recorded on a Nicolet-360 FT-IR spectrophotometer using KBr
pellets. Absorbance spectra were obtained with a Persee
TU-1950 spectrophotometer; the luminescent spectra were
recorded at room temperature on Hitachi F-7000 FL spectro-
photometer with a xenon arc lamp ashen light source spectra,
Preparation of solutions for absorbance and uorescence
detections
ꢀ5
The stock solution of H PDIAAs was prepared in DMF (1 ꢂ 10
2
M), and each inorganic salt (NaH PO , Na HPO , Na PO ,
2
4
2
4
3
4
Na P O (PPi), NaNO , NaHCO , Na CO , NaHSO , Na SO ,
4
2
7
3
3
2
3
4
2
4
tetrabutylammonium uoride (TBAF), tetrabutylammonium
chloride (TBACl), tetrabutylammonium bromide (TBABr), tet-
rabutylammonium iodide (TBAI), tetrabutylammonium
hydroxide (TBAOH)) was dissolved in DMF (1.5 ꢂ 10 M).
with the pass width of E
were recorded on a Bruker 400 MHz, and DMSO-d was used as
6
x
¼ 2.5 nm, E ¼ 2.5 nm. NMR spectra
m
the solvent, with TMS as the internal standard.
ꢀ
2
General procedure for H
2
PDIAAs
Test-paper measurement
The four types of H PDIAAs have been synthesized according to
2
2
1
1
The silica gel plate (2 ꢂ 1.5 cm ) was immersed in the DMF
the method reported in literature. Furthermore, 3,4,9,10-per-
ylene tetracarboxylic acid dianhydride (0.500 g, 1.28 mmol) in
DMSO (50 mL) was heated at 100 C with stirring. The amino
ꢀ
5
solution of H
2
PDIAla (1 ꢂ 10 M) by soaking half of it and then
ꢁ
dried using the blower. The letters (BIT) were written both in the
upper and lower panels with the TBAF solution and then put
under the visible light and UV light (l ¼ 365 nm).
acids, L-alanine (H
2
PDIAla) (0.341 g, 3.83 mmol), L-glutamic acid
(
(
H PDIGlu) (0.563 g, 3.83 mmol), L-phenylalanine (H PDIPhe)
0.632 g, 3.83 mmol) or L-tyrosine (H PDITyr) (0.594 g,
2
2
2
Fluorescence lifetime decay
3.83 mmol) was dissolved in 2 M KOH aq. (2.5 mL). The solution
of potassium amino acid salt was added to the mixture. The Fluorescence decay lifetime was measured using a time-
ꢁ
mixture was stirred for 3 hours at 100 C before cooling to the correlated single photon counting instrument. Only freshly
room temperature with the formation of a precipitate, which prepared solutions were used for the spectroscopic study, and
was recovered by ltration and recrystallized from hot water and all experiments were carried out at room temperature (298 K).
acetone to yield the dipotassium salt K PDIAAs. Moreover, 2 M Fluorescence lifetime was measured using Fluorolog-Tau-3
2
HCl aq. (5 mL) was added, recovered by ltration, and washed picosecond level uorescence spectroscopy.
extensively with water before being dried in vacuo (NMR,
0
ESI-MS, IR for H
2
PDIAAs in Fig. S1–S16†). N,N -Bis-(L-alanine)-
Results and discussion
UV-vis spectra
3,4,9,10-perylene tetracarboxylic diimide (H
2
PDIAla). Yields:
PDIAla (0.512 g, 75%). H NMR (400 MHz, DMSO-d ): d 7.88
1
H
2
6
(
d, J ¼ 7.7 Hz, 4H), 7.75 (d, J ¼ 8.1 Hz, 4H), 5.52 (dd, J ¼ 13.9, The UV-vis spectra of H
2
PDIAAs show the typical features of
1
3
12
6
d
1
8
.8 Hz, 2H), 1.67 (d, J ¼ 7.0 Hz, 6H). C NMR (100 MHz, DMSO- perylene absorption with three peaks. The interactions of
): d 172.2, 162.2, 133.2, 130.8, 127.9, 124.4, 123.5, 122.0, 49.5,
PDIAAs with different anions were studied by UV-vis
5.4. IR (lm): n ¼ 1747, 1695, 1653, 1592, 1437, 1343, 1256, 974, absorption spectroscopy, in which there was found to be an
H
2
6
ꢀ
1
+
0
ꢀ
ꢀ
ꢀ
09, 747 cm . ESI-MS: m/z ¼ 535 [M + H] . N,N -Bis-(L-glutamic obvious change in the presence of F and OH ions among Cl ,
ꢀ
ꢀ
ꢀ
2ꢀ
3ꢀ
ꢀ
ꢀ
2ꢀ
acid)-3,4,9,10-perylene tetracarboxylic diimide (H
Yields: H
2
PDIGlu). Br , I , H
2
PO
4
, HPO
4
, PO
4
, PPi, NO
3
, HCO
3
, CO
3
,
1
ꢀ
42ꢀ
2
PDIGlu (0.611 g, 73%). H NMR (400 MHz, DMSO-d
6
): HSO
4
, and SO ions (Fig. S17†). Fig. 1 exhibits the results of
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ꢀ
5
Fig. 1 UV-vis titration of H
2
PDIAAs with TBAF in DMF (1 ꢂ 10 M), (a) Fig. 2 Fluorescence emission of H PDIAAs with TBAF titration in DMF
2
ꢀ5
2
H PDIAla, (b) H
2
PDIGlu, (c) H
2
PDIPhe, (d) H
2
PDITyr. Inset: UV absor- (1 ꢂ 10 M) (lex ¼ 525 nm), (a) H PDIAla, (b) H PDIGlu, (c) H PDIPhe
2
2
2
ꢀ
bance intensity at 700 nm vs. concentration of F ion.
and (d) H PDITyr.
2
2
UV-vis titration by adding TBAF into H PDIAAs in DMF solution. theoretical quantum yield, shown in Table 1, in which the
Clearly, the typical absorption peaks red-shied, and a new peak quantum yield of H PDIPhe in the four compounds is the
2
appeared around 700 nm. With the same condition, the UV-vis largest one, and H PDITyr is the lowest. As a general rule, the
2
2
spectrometric titrations of H PDIAAs with other anions did not uorescence intensity is proportional to the uorescence
show any signicant change. Moreover, the inset pictures in Fig. 1 quantum yield. Therefore, this result is consistent with the
suggest that it has a good linearity between the absorbance at uorescence intensity measured with the same conditions, as
ꢀ
7
00 nm with the concentrations of F from 0.2 eq. to 6 eq., which shown in Fig. 2. The uorescence lifetime of H PDITyr is longer
2
ꢀ
indicates that H PDIAla can detect F quantitatively. The linear than that of the other three H PDIAAs.
2
2
equation was found to be y ¼ 0.0152x + 0.0008 (R ¼ 0.9991), where
As shown in Fig. 2, the H PDIAla has been found to have
2
ꢀ
“
y” is the absorbance at 700 nm measured at a given F concen- sensitivity higher than that of the other three compounds. The
ꢀ
ꢀ
tration, and “x” represents the equivalent of F added. When the OH ion also has similar phenomenon with the interaction of
ꢀ
concentration of F was less than 1 equivalent of PDI, there was H PDIAAs (Fig. S21†), and uorescence quenching can also be
2
no large absorbance around 700 nm, and the absorbance observed.
ꢀ
appeared aer the concentration of F was more than 1 equiva-
lent of PDI. The same trend in the detection was found using Fluorescent detectors for anions
H PDIPhe and H PDITyr (Fig. 1c and d inset), but H PDIGlu
2
2
2
Besides the UV-vis and uorescent spectra, the selectivity of
ꢀ
showed a different tendency in detection of F because it contains
ꢀ
ꢀ
H PDIAAs to F and OH ions can also be well identied by the
2
ꢀ
four carboxyl groups and has a capacity to accept more F ions
naked eye with colorimetric change (Fig. 3). The interactions of
ꢀ
(
Fig. 1b inset, S18†). The OH ion shows similar phenomenon
ꢀ
2ꢀ
3ꢀ
ꢀ
H PDIAla probe with various anions (H PO , HPO , PO
,
2
2
4
4
ꢀ
4
ꢀ
with F ion when it interacts with H
2
PDIAAs (Fig. S19†).
ꢀ
ꢀ
2ꢀ
ꢀ
42ꢀ
ꢀ
PPi, NO
3
, HCO
3
, CO
3
, HSO
4
, SO , Cl , Br , I )
ꢀ
compared with F were studied. Upon adding various anions to
Fluorescent properties
2
the blank solution of H PDIAla, no appreciable color change
was noticed under the visible light and UV light (Fig. 3a).
Therefore, it was inferred that there were no interactions
2
The interactions between H PDIAAs and various anions were
studied by uorescence spectra. There was an obvious change
ꢀ
between
H PDIAla and various anions mentioned.
2
in uorescence spectra of H PDIAAs in the presence of F and
2
ꢀ
OH ions as shown in Fig. S20.† Furthermore, uorescence
titration by adding standard solution of TBAF in DMF has been
Table 1 The quantum yield (F
F
) and lifetime of H
2
PDIAAs in DMF
ꢀ
ꢀ5
applied in investigation of H
OH ions (Fig. 2 and S21†). The four compounds have different
2
PDIAAs interacting with F and solution (1 ꢂ 10 M)
ꢀ
H
2
PDIAla
H
2
PDIGlu
H
2
PDIPhe
2
H PDITyr

uorescence intensity from the strongest 7500 (a.u., H
2
PDIPhe)
to the lowest 1500 (a.u., H PDITyr), which may be related to the
different substitutes on the branched chain of the four s (ns)b
2
a
Quantum yield (F
F
)
0.27
4.51
0.36
4.65
0.66
4.54
0.11
5.06
compounds. In order to understand the uorescence behavior
a
F
The quantum yield (F ) was measured relative to the uorescein
13
b
of H
2
PDIAAs in solution better, we measured the uorescence
solution in 0.1 M NaOH (F
F
¼ 0.79).
Fluorescence lifetime values
lifetime of these four compounds in DMF and calculated the (lem ¼ 541, 572 nm).
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Fig. 4 Photographs of test-paper of H
2
PDIAla solution in DMF (1 ꢂ
ꢀ5
1
0
M) of TBAF. (a) Visible light of the test-paper, (b) UV light (l ¼
365 nm) of the test-paper.
aer more than 1 equivalent of PDI. The results indicated that
ꢀ
when the concentration of F was equal or less than 1 equiva-
ꢀ
lent of PDI, the association between H
2
PDIAAs and F could be
+
Fig. 3 (a) The photographs of colorimetric identification by naked eye through the hydrogen bonding between the H of carboxylic
and fluorescence emission (l ¼ 365 nm) of H
2
PDIAla with various ions
ꢀ
ꢀ
acid (–COOH proton) and F (COO–H/F ). The formation of
hydrogen bonding followed by deprotonation of the –COOH
fragment could reduce the electron density on the carboxylic
moiety, which decreases the electron density of the core
benzene ring of PDI, deshielding the corresponding protons
(
6 eq., each). (b) The photographs of colorimetric identification by
ꢀ
naked eye and fluorescence emission (l ¼ 365 nm) of H
2
PDIAla–F ion
with various ions (6 eq., each).
ꢀ
14
Furthermore, with the addition of F ion to the above solution, and moving them to a low magnetic eld. Clearly, when the
the color of both blank solution and that containing various concentration of F is more than 1 equivalent of PDI, there is an
anion's solution changed from yellow to brown as observed by interaction between core structure and F . Moreover, UV-vis
ꢀ
ꢀ
the naked eye and uorescence quenching under UV light titration experiments indicated that the PDI anion radicals
ꢀ
ꢀ
(Fig. 3b). Clearly, the H
2
PDIAla can be a uorescent probe for F
were generated at high concentration of F . These results
ion even with the existence of various other anions. Moreover, indicated that anion–p interaction may play the leading role in
ꢀ
the detections by H PDIGlu, H PDIPhe and H PDITyr were the association between H PDIAAs and F at high concentra-
2
2
2
2
ꢀ
ꢀ
almost the same except for the difference of color changes with tions of F . A similar phenomenon for OH ion was observed
H PDIGlu from yellow to purple, H PDIPhe from yellow to brick (Fig. S32†). Based on the above observations and inferences, the
2
2
red, and H
2
PDITyr from jacinth to brown (Fig. S22–S24†). The synergetic effect of hydrogen bonding and anion–p interaction
ꢀ
detection for OH ion by the uorescent probe H
2
PDIAAs has in the uorescent detection of H PDIAAs could be proposed
2
been processed, and a similar phenomenon was observed with
uorescence quenching and a color change could be observed
by the naked eye (Fig. S25–S28†).

ꢀ
In order to improve the convenience and rapidity of F ion
detection out of the laboratory, we made a simple test-paper,
which used the existing H PDIAA solution with silica gel
2
plate. By soaking half of the silica gel plate in the solution and
drying, the letters “BIT” were written in both the upper and
lower panels with the TBAF solution. There was a signicant
difference between the soaked part and the control part. The
letters “BIT” could clearly be observed under the visible light
and UV light, but there was nothing on the control part (Fig. 4).
ꢀ
It suggests that this method can be used to detect F ion
conveniently and practically.
Mechanism of the uorescent detectors
The NMR titration experiment is very useful in studying the
mechanism of H PDIAAs to detect anions in solutions (Fig. 5).
2
According to our NMR titration experiment, when the addition
ꢀ
of F was equal or less than 1 equivalent of PDI, the signal of
core structure protons always existed, whereas the signal of
carboxylic acid moved to a low magnetic eld and became
broader. On the other hand, the signal of core structure protons
gradually disappeared with the increasing of F concentration Fig. 5 The H NMR titrations of H
ꢀ
1
2
PDIAla with TBAF in DMSO-d
6
.
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Scheme 2 Proposed mechanism of H
detect fluoride and hydroxide ions.
2
PDIAA fluorescent probe to
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5
6
, 61175–61179; (b) D. G ¨o rl, X. Zhang, V. Stepanenko and
and, the mechanism of uorescent detection of H
towards anions can be inferred to be a synergetic effect
Scheme 2). To the best of our knowledge, this is the rst report
2
PDIAAs
(
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of PDI–amino acid derivatives as uorescent probes to detect
anions.
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Conclusion
In summary, we have explored and discussed the uorescent
detection of anions using four types of PDI–amino acids deriva-
tives. The result indicates that they are sensitive to F and OH
ions in DMF solution with an obvious color change and uores-
cence quenching in a short time. The detecting mechanism has
been proposed according to the molecular structures and NMR
titrations. In addition, we made a simple test-paper to develop its
potential applications. These results constitute a promising
7
8
9
ꢀ
ꢀ
2786; (c) B. Vidya, G. Sivaraman, R. V. Sumesh and
D. Chellappa, ChemistrySelect, 2016, 1, 4024–4029.
(a) Y. Zhou, J. F. Zhang and J. Yoon, Chem. Rev., 2014, 114,
5
2
511–5571; (b) S. Guha and S. Saha, J. Am. Chem. Soc.,
010, 132, 17674–17677; (c) F. S. Goodson, D. K. Panda,
platform for the exploitation and applications of H PDIAAs as
2
S. Ray, A. Mitra, S. Guha and S. Saha, Org. Biomol. Chem.,
013, 11, 4797–4803.
uorescent probes, which are induced by the synergetic effect of
2
hydrogen bonding and anion–p interaction, and laid a solid
foundation for the PDI's development for uorescent detectors.
Y. S. Ma, Y. L. Zhao, F. X. Zhang, T. Y. Jiang, X. f. We, H. Shen,
R. Wang and Z. Q. Shi, Spectrochim. Acta, Part B, 2017, 241,
735–743.
Conflicts of interest
10 (a) Z. J. Chen, L. M. Wang, G. Zou, L. Zhang, G. J. Zhang,
X. F. Cai and M. S. Teng, Dyes Pigm., 2012, 94, 410–415; (b)
X. X. Chen, T. H. Leng, C. Y. Wang, Y. J. Shen and
W. H. Zhu, Dyes Pigm., 2017, 14, 299–305.
There are no conicts to declare.
Acknowledgements
1
1 S. A. Boer, C. S. Hawes and D. R. Turner, Chem. Commun.,
014, 50, 1125–1127.
2 (a) M. J. Farooqi, M. A. Penick, J. Burch, G. R. Negrete and
L. Brancaleon, Spectrochim. Acta, Part A, 2016, 153, 124–
2
This work was nancially supported by the National Natural
Science Foundation of China (no. 21471017).
1
1
31; (b) E. Kozma, G. Grisci, W. Mr ´o z, M. Catellani,
A. Eckstein-Andicsov `a , K. Pagano and F. Galeotti, Dyes
Pigm., 2016, 125, 201–209.
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