Synthesis and properties of fluorescent coumarin/perylene-3,4,9,10-tetracarboxylic diimide hybrid as cold dye

Article abstract of DOI:10.1016/j.materresbull.2021.111500

Perylene-3,4,9,10-tetracarboxylic dianhydride (PTCDA) was modified by ethylenediamine to obtain perylene-3,4,9,10-tetracarboxylic diimide (PTCDI). PTCDI as an initial core was used to bond coumarin derivatives. Successful conjugating of coumarin derivatives onto PTCDI was confirmed by Fourier-transform infrared spectroscopy (FT-IR), proton nuclear magnetic resonance (¹H NMR), X-ray diffraction (XRD), and field emission scanning electron microscope (FE-SEM). XRD peaks of various samples showed that the crystalline structure of PTCDA retained during the modification processes. The morphology of the nanoparticles by FE-SEM showed that the dyes were fibrillar. Fluorescence microscopy was used to evaluate the fluorescence properties of the dyes. In order to determine the amount of absorption and reflection in the near-infrared region, NIR test was used in both white and black fields. High absorption on a white background and high reflection on a black background indicated the transparency of the dye in the near-infrared region. The synthesized dye was identified and reported as a cold dye.

Full text of DOI:10.1016/j.materresbull.2021.111500

Materials Research Bulletin 144 (2021) 111500
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Materials Research Bulletin
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Research Papers
Synthesis and properties of fluorescent coumarin/
perylene-3,4,9,10-tetracarboxylic diimide hybrid as cold dye
,
,
,b,
Erisa Ferasata b, Marzieh Golshana b, Mehdi Salami-Kalajahia *, Hossein Roghani-
,
b
Mamaqania
a Faculty of Polymer Engineering, Sahand University of Technology, P.O. Box 51335-1996, Tabriz, Iran
b Institute of Polymeric Materials, Sahand University of Technology, P.O. Box 51335-1996, Tabriz, Iran
A R T I C L E I N F O
A B S T R A C T
Keywords:
Cold dye
Perylene-3,4,9,10-tetracarboxylic dianhydride (PTCDA) was modified by ethylenediamine to obtain perylene-
3,4,9,10-tetracarboxylic diimide (PTCDI). PTCDI as an initial core was used to bond coumarin derivatives.
Successful conjugating of coumarin derivatives onto PTCDI was confirmed by Fourier-transform infrared spec-
troscopy (FT-IR), proton nuclear magnetic resonance (1H NMR), X-ray diffraction (XRD), and field emission
scanning electron microscope (FE-SEM). XRD peaks of various samples showed that the crystalline structure of
PTCDA retained during the modification processes. The morphology of the nanoparticles by FE-SEM showed that
the dyes were fibrillar. Fluorescence microscopy was used to evaluate the fluorescence properties of the dyes. In
order to determine the amount of absorption and reflection in the near-infrared region, NIR test was used in both
white and black fields. High absorption on a white background and high reflection on a black background
indicated the transparency of the dye in the near-infrared region. The synthesized dye was identified and re-
ported as a cold dye.
Coumarin
Fluorescence
Perylene
1. Introduction
brown, and black [11]. It is highly resistant to heat [12,13], light [14],
and changes in environmental conditions [15]. Different PTCDI de-
Fluorescence colorants such as coumarin, perylene, and rhodamine
often have advanced conjugate systems and a number of hybrid rings [1,
2]. One of the structural features of these dyes is relationship between
molecular structure and the intensity of fluorescence, which leads to an
increase in fluorescence efficiency [3]. Moreover, various factors
including solvent, concentration, and temperature affect the fluores-
cence emission spectrum [4]. In addition to their importance as one of
the brightest fluorescence dye groups, coumarins are one of most widely
used fluorescence compounds [5,6]. The most important colors of
coumarin fluorescence are reported to be yellow or green while they
absorb and emit the light in most parts of visible spectrum. Important
derivatives of coumarin dyes always have an electron-donor group in
position 7, such as the dialkylamine, hydroxyl, or methoxy groups [7,8].
Coumarin compounds are widely used for production of fluorescent dyes
due to their photophysical diversity and photochemical properties [8].
In recent years, perylene-3,4,9,10-tetracarboxylic diimide (PTCDI) is
well-known as one the main source of vat dyes [9] and pigments [10].
PTCDI has a wide range of colors including red, vinaceous, violet,
rivatives can be divided into two general categories [16,17]. The first
group is derivatives obtained from the bonding of different groups to the
nitrogen atoms in the imide groups [18] and the second category is the
derivatives with the bonding of different groups to the bay sides [19].
Altering substituents can significantly change the properties of the dye.
Not only PTCDI is often used as important dye in industries, but also has
interesting features such as high photochemical stability, fluorescence
quantum efficiency, and strong electron acceptance character [20].
The sun plays an important role in human life on earth. Solar energy
heats objects such as buildings and cars [21]. This extra energy leads to
an increase in indoor surface temperature and more energy consumption
for air conditioning [22]. Increasing energy consumption to cool the
interior has become a challenge for many years. The interaction of light
with matter in the visible region causes the color in the matter [23]. Due
to the very high reflection of sunlight, cold dyes effectively reduce the
internal temperature. Cold dyes absorb less solar energy in infrared light
and maintain a low surface temperature, transferring less energy to the
interior and storing energy for air conditioning. There are significant
* Corresponding author.
E-mail address: m.salami@sut.ac.ir (M. Salami-Kalajahi).
https://doi.org/10.1016/j.materresbull.2021.111500
Received 8 April 2021; Received in revised form 24 July 2021; Accepted 26 July 2021
Available online 30 July 2021
0025-5408/© 2021 Elsevier Ltd. All rights reserved.

E. Ferasat et al.
Materials Research Bulletin 144 (2021) 111500
Fig. 1. XRD patterns of PTCDA, PTCDI, HPTCDI-COUM, and DPTCDI-COUM.
differences in reports between cold dyes and regular dyes. Therefore, the
use of cold dyes is an effective way to save energy for pleasant condi-
tioning. Cold dyes can be organic and inorganic in nature [24]. Most
commercial cold dyes are inorganic in nature and the organic cold dyes
are very limited. Cold dyes include black dyes containing phthalocya-
nine, azo dyes, and a small number of perylene-based dyes such as
lumogen, dye black 3, and dye black 32 [25].
1H, d), 6.83 (d, 1H, e), 7.46 (d, 1H, c) [29].
2.1.2. Synthesis of 4-methyl-7-(carboxy methoxy) coumarin (MCMC)
MMEAC (1.0 g, 2 mmol) was dissolved in ethanol (25 mL). Then, 14
mL 5% NaOH solution was added to the reaction medium and the sol-
vent was removed from the reaction medium. After dissolving the pre-
cipitate in water, 6 N HCl was added to the solution and allowed to form
a white precipitate. Then, for purification, the precipitate was filtered
using filter paper and separated from the solvent, and white-cream solid
crystals were obtained by recrystallization from ethanol. Eventually, 4-
methyl-7-(carboxy methoxy) coumarin was dried in a vacuum oven at
room temperature for 24 h. The reaction for the preparation of MCMC is
shown in Scheme S2 [26]. Reaction yield was calculated ~ 60%
gravimetrically.
Although various derivatives of perylene diimide have been syn-
thesized and their properties have been investigated in various fields of
fluorescence and NIR reflectance, the effect of coumarin derivatives on
the structure of dye and hybridization with perylene chromophore has
not been studied in scientific sources. The purpose of this work is to
synthesize and investigate of optical and NIR reflectance properties of
the hybrid perylene-coumarin dye. Perylene diimide derivatives have
been prepared by modification of perylene-3,4,9,10-tetracarboxylic
dianhydride (PTCDA) by ethylenediamine. Then, PTCDI has been used
as a core, and coumarin derivative has been conjugated to synthesize a
perylene-3,4,9,10-tetracarboxylic diimide-coumarin hybrid (HPTCDI-
COUM). HPTCDI-COUM has been photodimerized to obtain another
dye. Finally, NIR reflectance and photophysical behavior of synthesized
dyes have been studied.
FT-IR of MCMC (KBr, cmꢀ 1, Fig. S4): (3400-3500 str. OH), (3068 CH
str. C=CH), (2987, 2916 assym. str. CH3, CH2), (1755 C=O), (1708
C=O), (1610, 1566, 1510 str. C=C), (1427, 1390 CH3, CH2 bend), (1253
C-O), (1147 C-O) [30,31].
1H NMR of MCMC (500 MHz, CDCl3, δ/ppm, Fig. S5): 2.39 (s, 3H, b),
4.78 (s, 2H, f), 6.06 (s, 1H, a), 6.21 (s, 1H, d), 6.98 (d, 1H, e), 7.69 (d, 1H,
c) [32,33].
2.1.3. Synthesis of hybrid perylene-3,4,9,10-tetracarboxylic diimide/
coumarin (HPTCDI-COUM)
2. Experimental section
MCMC (2.4 g, 2 mmol), DCC (0.1 g, 0.48 mmol), and DMAP (0.02 g,
0.16 mmol) were dissolved in THF (25 mL). Then, PTCDI (section S2, 0.2
g, 42 mmol) was dissolved in THF (5 mL) and added dropwise to the
reaction medium. The mixture was stirred at room temperature under
nitrogen for 7 days. On completion of the reaction, the product was
washed with diethyl ether (100 mL) and dried at 60◦C for 24 h in a
vacuum oven. Reaction yield was calculated ~ 70% gravimetrically. The
reaction route is shown in Scheme 1.
2.1. Synthesis steps
2.1.1. Synthesis of 4-methyl-7-(methoxy ethyl acetate) coumarin
(MMEAC)
Suspension of 4-methylumbelliferone (COUM) (2 g, 11.35 mmol),
anhydrous K2CO3 (8.5 g, 61.5 mmol), and ethyl bromoacetate (2.4 mL,
21.6 mmol) in THF (45 mL) was refluxed for 16 h at 60◦C. After filtra-
tion, MMEAC was dried in a vacuum oven at 40◦C and recrystallized in
ethanol [26]. Reaction yield was calculated ~ 80% gravimetrically.
FT-IR of MMEAC (KBr, cmꢀ 1, Fig. S4): (3076 CH str. C=CH), (2980,
2928 assym. str. CH3, CH2), (2872 sym. str. CH3), (1759 C=O), (1606,
1508 str. C=C), (1423, 1386 CH3, CH2 bend), (1220 C-O ester), (1197 C-
O lactone) [27,28].
FT-IR of HPTCDI-COUM (KBr, cmꢀ 1, Fig. S1): 1680 (
υ
asN-C=O),
1660 (
υ
sN-C=O), (3068 CH str. C=CH), (2987, 2916 assym. str. CH3,
CH2), (1726 C=O), (1708 C=O), (1610, 1510 str. C=C) [34,35].
1H NMR of HPTCDI-COUM (500 MHz, DMSO, δ/ppm, Fig. S6): 5.8 (s,
1H, a), 2.0 (s, 3H, b), 6.0 (s, 1H, c), 4.5 (s, 2H, d), 3.7 (m, 4H, CH2NH2, f),
3.3 (m, 4H, CH2NC=O, g), 7.9 (m, 8H, perylene, i).
1H NMR of MMEAC (500 MHz, CDCl3, δ/ppm, Fig. S5): 1.25 (t, 3H,
h), 2.33 (s, 3H, b), 4.23 (q, 2H, g), 4.63 (s, 2H, f), 6.06 (s, 1H, a), 6.69 (d,
13C NMR of HPTCDI-COUM (500 MHz, DMSO, δ/ppm, Fig. S7):
2

E. Ferasat et al.
Materials Research Bulletin 144 (2021) 111500
Fig. 2. FE-SEM images of PTCDI derivatives.
117.2 (CH, a), 20.8 (CH3, b), 158.0 (CCH3, c), 40.2 (CH, d), 72.4 (C-O,
e), 134.8 (CH, f), 103.1 (CH, g), 123.4 (CH, i), 150.1 (C-O, h),67.1
(OCH2, k), 168.6 (C=O, i), 36.4 (CH2NH2, m), 51.9 (CH2NC=O, n),
159.3 (CH2NC=O, o), 124.5, 130.9, 126.1 ((C) 1-naphthalene, r, q, s),
129.2 (CH (1-naphthalene, p).
substrate (black substrate) can qualitatively show the amount of
reflection, transfer, and absorption of dye.
3. Results and discussion
3.1. Synthesis of hybrid dyes
2.1.4. Photodimerization of HPTCDI-COUM (DPTCDI-COUM)
Photodimerization of HPTCDI-COUM was performed under UV light
at ʎ > 310 nm for 30 min with concentration of 0.2 mg mLꢀ 1 at H2SO4
(Scheme 1). The degree of dimerization was measured using UV-VIS-NIR
spectrum by Eq. (1) [36].
The dyes were designed with a perylene diimide core covered by
coumarin derivatives. XRD, UV-VIS-NIR, FS, FM, and FE-SEM analysis
were used to evaluate and confirm PTCDI-cored MCMC in each step. FT-
IR and 1HNMR, and 13C NMR spectra of different dyes including COUM,
MMEAC, MCMC, PTCDA, PTCDI, HPTCDI-COUM, and DPTCDI-COUM
are depicted in Figs. S1–S7 and the most important peaks are
mentioned in Section 2. Fig. 1 illustrates XRD patterns of different dyes
including PTCDA, PTCDI, HPTCDI-COUM, and DPTCDI-COUM in the
ranges of 10-70◦ and 10-30◦. In all patterns, sharp peaks due to the
crystalline phase were observed in the structure. The peak at 2θ = 24.8◦
is related to the stacking of PTCDI plates, which is also seen in other
aromatic plate structures (201) [37]. Also, the peaks at 2θ = 27.7◦ and
28.0◦ are related to the crystal structures (202) and (203) of perylene
layers, respectively. Therefore, all dyes contain amorphous and crys-
talline phases [38,39]. The crystallinity index of dyes was obtained ac-
cording to Eq. (2) [40].
At
A0
degreeofdim erization = 1 ꢀ
(1)
In this equation, A0 and At are initial absorption and absorption after
photodimerization, respectively.
2.2. Preparation of Dye
Nitrocellulose resin (64 wt. %), pigment (16 wt. %), and dye thinner
(20 wt. %) were mixed and ball-milled for 5 h. Then, resultant paints
were applied to Leneta checkerboard charts using a film applicator with
a thickness of 120 µm. This helped to prevent reflection of the substrate
and only reflection of paint was detected. Evaluation of dyes reflectance
on a highly reflective substrate (white substrate) and highly absorbent
Totalareaofcrystallinepeaks
Crystallinity(%) =
× 100
(2)
Totalareaofallpeaks
3

E. Ferasat et al.
Materials Research Bulletin 144 (2021) 111500
Fig. 3. Absorption and fluorescence spectra of synthesized colorants.
According to the results, crystallinity was obtained 85.7%, 62.9%,
HPTCDI-COUM, and DPTCDI-COUM samples. Quantum efficiency was
obtained for samples based on perylene (λex = 460 nm) and for coumarin
derivatives (λex = 320 nm) using Eq. (3) [44].
and 46.9% for PTCDA, PTCDI, and HPTCDI-COUM. Moreover, XRD
patterns of the dyes showed that the characteristic peaks of PTCDI de-
rivatives were similar to PTCDI that showed no significant change was
occurred in nature of PTCDI. After photodimerization reaction of
DPTCDI-COUM dye, the intensity of sharp crystalline peaks has
decreased sharply and a wide peak has been formed in the range of 10-
26◦.
(
)
2
ms ηs
Φs = Φ
(3)
rmr ηr
In this equation, Φ is the quantum yield of the standard dye (Rh6G),
ms is the slope of the lirnear fit for the integrated fluorescence intensity of
the fluorescent dye as a function of absorbence, and ηs and ηr are the
refractive indices of the fluorescent dye and the standard solutions,
respectively. The quantum fluorescence efficiencies of the samples were
obtained 25, 17.2, 11.7, 5.2, 13.7, and 10.6% for PTCDA, PTCDI, COUM,
MCMC, HPTCDI-COUM, and DPTCDI-COUM, respectively. The main
feature of the perylene core is that it has a high tendency to aggregate
Fig. 2 shows the FE-SEM images of PTCDA, PTCDI, HPTCDI-COUM,
and DPTCDI-COUM. The structure of dyes is almost all rod-shaped with
small sections and a glossy surface, which is due to the use of ultrasonic
devices for better dispersion during sampling [41]. After the reaction of
PTCDA with EDA, small aggregates were observed. Modification of
PTCDI by coumarin derivatives changed the morphology of
HPTCDI-COUM to fibrillar, and with the photodimerization reaction,
the morphology of DPTCDI-COUM appeared as a lump. In fact, the
change in structure causes the particles to become self-aggregating and
out of the fibrillar state [42].
through π-π bonds, which leads to the formation of molecular masses
that increases the rate of charge transfer in the sample. All these prop-
erties are attributed to perylene chromophore. One of the features of this
chromophore is the presence of perturbations in the absorption spec-
trum, which decreases the quantum efficiency by increasing the con-
centration. The reason for these properties is stacking through
π
-
π
bonds
interactions, it is
possible to achieve high concentrations with high fluorescence. There
are two main ways to prevent bond stacking. The first method is
modification through positions 1, 6, 7, and 12 of the non-core region of
perylene. By doing this modification, the tendency to stacking and
intermolecular dependence is reduced. Molecular isolation is another
3.2. Photophysical properties of hybrid dyes
or larger molecular aggregations. By preventing π-π
UV and FL spectra of samples are shown in Fig. 3. HPTCDI-COUM
dye was exposed to UV light irradiation in H2SO4 for the photo-
dimerization reaction. The presence of a coumarin derivative in the
PTCDI imide region led to a photodimerization reaction with photon
absorption at wavelengths above 310 nm [43]. Degree of dimerization of
coumarin derivatives was obtained by reducing the absorption peak
intensity in the range of 360-400 nm. Therefore, the degree of dimer-
ization for HPTCDI-COUM was about 80% for the coumarin section
according to Eq. (1). FL spectroscopy was used to evaluate the emission
and quantum fluorescence efficiency of PTCDA, PTCDI, COUM, MCMC,
π-π
π-π
effective method to reduce the intermolecular π-π bonds in perylene
diimide compounds, which is achieved by modifying the positions of 2,
8, 5, and 11 as ortho regions [45,46].
Fig. 4 displays fluorescence images of PTCDA, PTCDI, HPTCDI-
COUM, and DPTCDI-COUM in powder mode. Due to the blue emission
4

E. Ferasat et al.
Materials Research Bulletin 144 (2021) 111500
quite evident. After photodimerization, the DPTCDI-COUM sample
showed poor emission in the red filter.
3.3. Thermal stability
According to Figure S8, PTCDI and HPTCDI-COUM dyes were
examined by thermogravimetric analysis (TGA). Table 1 shows T10 and
T50 of PTCDI and HPTCD-COUM. According to the results, PTCDI
showed T10 of 484.7◦C whereas after hybridization with coumarin, T10
was decreased to 273.3◦C. However, both dyes showed T50 higher than
550◦C which confirmed thermal stability of synthesized hybrid dye. Due
to the thermal stability of these dyes, the use of these compounds in
various fields will increase in the future [47].
3.4. NIR properties of hybrid dyes
Fig. 5 illustrates UV–Vis-NIR reflectance of the PTCDI and HPTCDI-
COUM. In this research, two different optically substrates, black and
white, have been used to investigate the amount of radiation trans-
mission. These substrates play a key role in the classification of PTCDI
and HPTCDI-COUM in the NIR region. Howbeit, the dyes with similar
structures illustrate different reflectance in the UV–Vis-NIR region. The
difference in a reflection in the visible region is due to the difference in
color of the colorants and the difference in reflection in the NIR region
can be attributed to different crystal structures [23,24]. In view of the
above discussion, PTCDI and HPTCDI-COUM indicate absorption in
visible region (400-700 nm) due to the nature of dyes. However, in NIR
region (700-1000 nm) PTCDI shows high reflectance in white substrate
and low reflectance in the black substrate; so, it is NIR transparent. In
addition, integrals of UV-Vis-NIR curves in three regions are studied and
the data are summarized in Table 2. PTCDI had a reflection of 57% in
range of 700-1000 nm and showed good transparency, while
HPTCDI-COUM showed a weaker reflection. According to the results,
both synthesized dyes can be used as cold dyes in the construction and
military industries, depending on the required shade. For both dyes, a
near-zero reflection in the visible region was reported due to strong
adsorption by the synthesized dyes. It is noteworthy that the trans-
parency is more pronounced for the synthesized dyes, which is probably
due to the regular and fibrillar structure of the synthesized sample.
Furthermore, dyes were examined under an IR lamp. The results showed
that the color of dyes changed from dark to white (Figure S9).
4. Conclusions
Herein, a perylene-coumarin hybrid dye with a perylene core was
prepared. To prepare a coumarin derivative, 4-methyl-7-(carboxy
methoxy) coumarin was prepared by acid hydrolysis from 4-methyl-7-
(methoxy ethyl acetate) coumarin. XRD patterns of different samples
showed that the crystal structure of PTCDI derivatives was not destroyed
during various purification processes, after the photodimerization re-
action, and sample preparation. In DPTCDI-COUM, the intensity of
sharp crystalline peaks was drastically reduced and a wide peak was
formed in the range of 10-26◦. The fluorescence properties of the syn-
thesized dyes and their potential application as cold dyes were investi-
gated. Quantum fluorescence efficiency of samples was obtained 25,
17.2, 11.7, 5.2, 13.7, and 10.6% for PTCDA, PTCDI, COUM, MCMC,
HPTCDI-COUM, and DPTCDI-COUM, respectively. According to results,
properties of synthesized NIR dyes depend on the nature of nitrogen
exchange, and with the change in substitutions, the amount and type of
NIR properties of dyes were changed. The results of NIR spectrum of the
synthesized dyes showed that the synthesized dyes belong to transparent
category in NIR region.
Fig. 4. Fluorescence microscopy images of coumarin and PTCDI derivatives
Table 1
Decomposition temperatures of PTCDI and HPTCD-COUM.
Sample
T10
T50
PTCDI
484.7
273.3
749.7
559.6
HPTCD-COUM
of coumarin derivatives and the red emission of perylene derivatives, the
dyes were examined in two filters. According to the images, the stability
of the fluorescence emission of different samples in blue and red filters is
Data availability
The raw/processed data required to reproduce these findings cannot
5

E. Ferasat et al.
Materials Research Bulletin 144 (2021) 111500
Fig. 5. Reflectance UV-Vis-NIR integral of PTCDI and HPTCDI-COUM.
Scheme 1. Synthesis mechanism and photodimerization reaction of HPTCDI-COUM.
be shared at this time as the data also form part of an ongoing study.
Supporting information
Roghani-Mamaqani: Conceptualization, Validation, Resources, Visu-
alization, Supervision, Funding acquisition.
Materials, Instrumentation, FT-IR, 1H NMR, TGA, and IR lamp
results.
Declaration of Competing Interest
CRediT authorship contribution statement
The authors declare that they have no conflict of interest.
Supplementary materials
Erisa Ferasat: Formal analysis, Investigation, Investigation, Writing
– original draft, Visualization. Marzieh Golshan: Validation, Formal
analysis, Writing – original draft, Visualization. Mehdi Salami-Kala-
jahi: Conceptualization, Validation, Resources, Writing – review &
editing, Visualization, Supervision, Funding acquisition. Hossein
Supplementary material associated with this article can be found, in
the online version, at doi:10.1016/j.materresbull.2021.111500.
6

E. Ferasat et al.
Materials Research Bulletin 144 (2021) 111500
(2011) 2386–2407, https://doi.org/10.1021/jo2001963, https://chemistry-e
urope.onlinelibrary.wiley.com/doi/abs/10.1002/jlac.199519950366.
[18] K. Liu, Z. Xu, M. Yin, Perylenediimide-cored dendrimers and their bioimaging and
gene delivery applications, Prog. Polym. Sci. 46 (2015) 25–54, https://doi.org/
10.1016/j.progpolymsci.2014.11.005.
Table 2
Percentage of reflection of PTCDI and HPTCDI-COUM in different areas.
Sample
700-1000 (nm)
26819
1000-1500 (nm)
41188
1500-2500 (nm)
55577
White substrate
PTCDI
[19] A. Saeed, G. Shabir, J. Mahar, M. Irfan, Spectroscopic and electrochemical
behavior of newly synthesized high fluorescent symmetric 4′-nitrophenyl-3,4,9,10-
perylenebisdiimide-azo hybrid dyes, Spectrochim. Acta A 151 (2015) 72–79,
https://doi.org/10.1016/j.saa.2015.06.046.
15444
40909
60811
HPTCDI-COUM
Sample
12972
36754
58634
Reflection (%)
57%
Reflection (%)
99%
Reflection (%)
1%
PTCDI
¨
[20] O. Birel, A review on perylene-3,4,9,10-petracarboxylic acid diimide molecules,
HPTCDI-COUM
Sample
48%
89%
1%
Celal Bayar Univ. J. Sci 13 (2017) 379–386, https://doi.org/10.18466/
cbayarfbe.319879.
700-1000 (nm)
1981
1000-1500 (nm)
3297
1500-2500 (nm)
8223
Black substrate
PTCDI
[21] T. Prasankumar, S. Jose, P.M. Ajayan, M. Ashokkumar, Functional carbons for
energy applications, Mater. Res. Bull. 142 (2021), 111425, https://doi.org/
10.1016/j.materresbull.2021.111425.
4626
7684
15321
HPTCDI-COUM
Sample
2610
5180
12914
Reflection (%)
2.3%
Reflection (%)
2.3%
Reflection (%)
1.8%
[22] Y. Yin, Z. Wang, M. Zhu, Y. Zhang, J. Li, C. Dou, S. Sun, B. Teng, Y. Che, D. Zhong,
Full-visible-spectrum emission with high color rendering index and low correlated
PTCDI
HPTCDI-COUM
1.3%
1.5%
1.5%
color temperature enabled by a single-phased phosphor of α-Sr2V1.98P0.02O7:
0.5% Eu3+, Mater. Res. Bull. 141 (2021), 111344 https://doi.org/10.1016/j.
materresbull.2021.111344.
[23] M. Mazhar, M. Abdouss, K. Gharanjig, R. Teimuri-Mofrad, Synthesis,
characterization and near infra-red properties of perylenebisimide derivatives,
Prog. Org. Coat. 101 (2016) 297–304, https://doi.org/10.1016/j.
porgcoat.2016.08.018.
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