Synthesis of high molar extinction coefficient push-pull tricyanofuran-based disperse dyes: Biological activity and dyeing performance

Article abstract of DOI:10.1039/d0nj05510g

Several push-pull tricyanofuran-based disperse dyes with high molar extinction coefficient were synthesized and fully characterized. The dyes were preparedviaKnoevenagel reaction in dry pyridine under ambient conditions employing acetic acid as catalyst. The condensation process was carried out between the reactive methyl-bearing tricyanofuran moiety and tertiary amine-based arylaldehyde. The molecular structures of the synthesized chromophores were proved by Fourier transform infrared spectroscopy (FT-IR), nuclear magnetic resonance spectroscopy (¹H and¹³C NMR) and elemental analysis (C, H, N). The UV-Vis absorbance spectra of the synthesized dyes demonstrated interesting extinction coefficient values, which were found to be influenced by the aromatic-vinyl bridge and the tertiary amine donor group bonded to this aromatic-vinyl bridge moiety. The prepared tricyanofuran-based disperse colorants were dyed on polyester fabrics to afford satisfactory results. The substituents attached to the tertiary amine moiety influenced the absorption maxima. The fastness properties of the dyed polyester samples were measured. The biological activities of the synthesized dyestuffs against fungus (Candida Albican) as well as Gram-positive (S. Aureus) and Gram-negative (E. Coli) pathogens were also evaluated.

Full text of DOI:10.1039/d0nj05510g

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Synthesis of high molar extinction coefficient
push–pull tricyanofuran-based disperse dyes:
Biological activity and dyeing performance†
Cite this: New J. Chem., 2021,
45, 2208
Ali Aldalbahi,* Govindasami Periyasami
and Abdulaziz Alrehaili
Several push–pull tricyanofuran-based disperse dyes with high molar extinction coefficient were
synthesized and fully characterized. The dyes were prepared via Knoevenagel reaction in dry pyridine
under ambient conditions employing acetic acid as catalyst. The condensation process was carried out
between the reactive methyl-bearing tricyanofuran moiety and tertiary amine-based arylaldehyde. The
molecular structures of the synthesized chromophores were proved by Fourier transform infrared
spectroscopy (FT-IR), nuclear magnetic resonance spectroscopy (1H and 13C NMR) and elemental
analysis (C, H, N). The UV-Vis absorbance spectra of the synthesized dyes demonstrated interesting
extinction coefficient values, which were found to be influenced by the aromatic-vinyl bridge and the
tertiary amine donor group bonded to this aromatic-vinyl bridge moiety. The prepared tricyanofuran-
based disperse colorants were dyed on polyester fabrics to afford satisfactory results. The substituents
attached to the tertiary amine moiety influenced the absorption maxima. The fastness properties of the
dyed polyester samples were measured. The biological activities of the synthesized dyestuffs against
fungus (Candida Albican) as well as Gram-positive (S. Aureus) and Gram-negative (E. Coli) pathogens
were also evaluated.
Received 11th November 2020,
Accepted 6th January 2021
DOI: 10.1039/d0nj05510g
rsc.li/njc
strong and narrow absorbance that are suitable to evaluate
physical mechanisms which are proposed to enhance absorption
1. Introduction
Any electro-optical device that utilizes organic dyes requires in cavity configurations. The experimental processes and con-
that they be optimized in a variety of ways relevant to the figurations needed to create the cavity devices also create
particular technical application. The immediate applications independent demands on the materials that must be dealt
we are interested in here, including photovoltaics, organic with. Organic dyes studied for organic laser applications often
lasers, optical storage and nonlinear optical devices are no suffer from instability. Studies here attempt to take an already
exception.1–8 A pervasive requirement that applies to dyes in stable class of dyes and further enhance their thermal stability
virtually any application is stability (photochemical and ther- and photostability.15–20
mochemical). An exception, of course, is in the area of optical
Chromophores comprised of tricyanofuran (TCF) acceptors
storage wherein dyes may be designed and utilized which are and dialkylamine donors coupled by p-conjugated electron
inherently and intentionally photochemically and/or thermo- linkers have found extensive applications in electro-optics,
chemically labile.9–12 As such, a very general goal of our effort photorefractives and more recently in single molecule and
entails the design and synthesis of dyes that are optimized to super-resolution biological imaging.8,21,22 The TCF chromo-
provide the appropriate stability required for the specific phores developed for these particular applications were pur-
application. In addition to stability, in the case of photovoltaic sued due to their demonstrated superior stabilities relative to
devices the extinction coefficients of the dyes are also an numerous other structural options and therefore they are prime
important issue as this is a fundamental component in the candidates for extension into other areas, such as for photo-
light energy to electric energy conversion efficiency.13,14 Therefore, voltaics and organic lasers.23–25 Herein, we report the design,
another goal of our effort is to identify and prepare dyes with synthesis, and chemical characterization and intial photophy-
sical characterization which concentrate on TCF dyes intended
for use in photovoltaic devices, organic lasers and 3D optical
data storage. For the photovoltaic studies chromophores with
Department of Chemistry, College of Science, King Saud University, Riyadh 11451,
Saudi Arabia. E-mail: aaldalbahi@ksu.edu.sa
very large extinction coefficients and narrow bandwidths are
required and we find that dyes with Ar = phenyl or thiophene
† Electronic supplementary information (ESI) available. See DOI: 10.1039/
d0nj05510g
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(100%; 149 g mÀ2) were collected from the local market in Saudi
Arabia. The polyester substrates were scoured according to
literature procedure.27
Fig. 1 General representative structure of TCF-based chromophores
2.2. Dyeing process
The high temperature dyeing method28 was applied on the
[donor (tertiary amine)-aromatic-p-bridge acceptor (TCF)] with Ar
=
phenyl or thiophene based p-conjugated units. These dipolar push–pull
chromophores represent a broad category of organic materials studied for scoured polyester fabrics employing an infra-red dyeing
their optical and electronic properties wherein Ar, n, R1, R2, R3, and R4 are
machine. The dye (2 wt% relative to the fabric weight) was
dissolved in acetone (1 mL) and then added to the dye-bath
adjusted to tune the ancillary physical properties of the chromophore.
(stainless steel cup) with a 50 : 1 liquor ratio. Dispersing agent
(sodium lignin sulfonate; 2 wt% relative to the fabric weight)
was added to dye-bath. The pH was adjusted to B5.0 employing
an aqueous solution of acetic acid. The polyester fabric (50 : 1
and n = 1 provide nearly the desired function (such systems are
the most cyanine like with an intense absorption concentrated
in a narrow wavelength range) as shown in Fig. 1. Further
liquor ratio) was added to the dye-bath which was then closed,
modifications thus far in R1 and R2 have aided processing
heated up and maintained at 130 1C for 3 hours under pressure.
requirements and further modifications of these groups are
intended to further enhance both photochemical and thermo-
chemical stability. Additional functionality may be attached at
R1–4 such as groups containing hindered amines or phenols
The polyester substrates were washed and exposed to reduction
clear process at 80 1C for 45 minutes in an aqueous solution of
sodium hydrosulphite (Na2S2O4; 2 wt% relative to the fabric
weight) and sodium hydroxide (NaOH; 2 wt% relative to the
which may function in stabilization capacity.
fabric weight), followed by washing by nonionic detergent
(2 wt% relative to the fabric weight). The polyester samples
were rinsed with tap water, neutralized with acetic acid (1 g LÀ1
)
2. Experimental
2.1. Materials and methods
diluted in tap water for 5 minutes at 40 1C, rinsed with tap
water, and finally air-dried. The dye-uptake into fibers was
determined using Beer–Lambert law. This was assessed by
investigating samples from the dye-bath at different time
intervals (20, 40, 60, 80, 100, 120, 140, 160 and 180 minutes)
during the dyeing process.29
Melting points (1C) were recorded uncorrected employing
Stuart-SMP30. Fourier-transform infrared (FT-IR) spectra were
studied by Nexus-670 (Nicolet, USA). The elemental analysis (C,
H, N) was explored employing PerkinElmer-2400 (Norwalk, USA).
UV-Vis absorbance spectra were reported UNICAM-300. NMR
spectra were determined under ambient conditions utilizing
2.3. Colorfastness properties
BRUKER-AVANCE-400 at 400 MHz. Solvents (spectroscopic The fastness against washing (ISO-105-C02:1989), perspiration
grade) were obatined from Fluka and Aldrich. The progress of (ISO-105-E04:1989), rubbing (ISO-105-X12:1987), and light (ISO-
reactions was monitored by Merck aluminum TLC PF254 under 105-B02:1988) was examined using AATCC standard tests. The
an UN lamp (254 or 365 nm). The TCF moiety was synthesized fastness against light was evaluated under the blue-scale from 1
according to previously described procedure.26 Polyester fabrics for very poor to 8 for excellent, while fastness against perspiration,
Scheme 1 Synthesis of 3, 4 and 5 TH-TCF-X-V (X = 5, 6 and 8); A one-pot synthetic procedure has been developed for the preparation of
chromophores containing thiophene-vinyl in the p-system. Successful synthesis for the thiophene derivatives required formation of the imine as a
discrete intermediate.
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Scheme 2 Synthesis of phenyl vinyl-bridged TCF chromophores with a hydroxyl terminal group.
washing and rubbing was evaluated under the grey-scale from 1 3. Results and discussion
for very poor to 5 for excellent.
3.1. Synthesis and characterization
Different approaches have been pursued to design and develop
optimized chromophores for the relevant associated applications
including photovoltaic devices, organic lasers and 3D optical data
storage. The strong electron withdrawing TCF (tricyanofuran)
moiety was integrated into a variety of conjugated materials for
optoelectronic applications. This oxygen-containing heterocylic
intermediate was prepared in a 57% yield according to an early
literature method via condensation process of malononitrile with
3-hydroxy-3-methylbutan-2-one using ethanol as a solvent and
sodium ethoxide as a strong base. The TCF-based chromophores
employed in this study were synthesized in different procedure as
shown in Schemes 1–6.
2.4. Color strength
The color strength (K/S) was evaluated by Ultra-Scan-PRO
spectrometer (light source D65/101 observer).
2.5. Antimicrobial activity
The antimicrobial performance of the synthesized chromophores
was evaluated against Candida Albican (fungus), E. Coli (Gram-
negative) and S. Aureus (Gram-positive). The antimicrobial activity
was examined quantitatively employing AATCC 100-1999 standard
microbial counting procedure.
Scheme 3 Synthesis of thiophene vinyl-bridged TCF chromophores with a hydroxyl terminal group.
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acid as catalyst. The reaction was occurred between the active
methyl-bearing TCF head and tertiary cyclic amine based
arylaldehyde. A higher reaction rate and higher yields were
observed for tertiary cyclic amine based aryldehyde that have
displayed a high electrophilic reactivity compared to tertiary
acyclic amine based arylaldehyde. The 4-(4-hydroxypiperidin-1-
yl)benzaldehyde displayed a high yield for the final chromo-
phores compared to 2-alkylamino-5-formylthiophene. The
4-(4-hydroxypiperidin-1-yl)benzaldehyde was prepared from a
mixture of DMSO and water as shown in Scheme 2. On the
other hand, 2-alkylamino-5-formylthiophene was prepared
from a mixture of triethylamine and water as shown in
Scheme 3. The benzene bridged chromophores 8 and 9 were
prepared in high yield of 81-87%; while thiophene the bridged
chromophores 12 and 13 were obtained in a low yield of 18–21%.
3.1.3. Synthesis of phenyl vinyl-bridged TCF bis-chromo-
phores. Chromophores 8 and 9 reacted with aliphatic dicarboxylic
acid 14 via an esterification reaction (Steglich reaction) that was
performed in dichloromethane employing DCC and DMAP as
shown in Scheme 4. Bis-chromophores 15 and 16 were obtained
in low yields in the range of 33–39%. Bis-chromophore 18 was
prepared employing Knoevenagel reaction in dry pyridine at 40 1C
with acetic acid catalyst as shown in Scheme 5. The reaction was
performed between the active methyl-containing TCF head and
Scheme 4 Synthesis of phenyl vinyl ester-bridged TCF bis-
chromophores.
3.1.1. One-pot synthesis of thiophene vinyl-bridged TCF 1,4-bis(4-benzaldehyde)piperazine 17 to afford the corresponding
chromophores. This thiophene vinyl-bridged TCF chromo- bis-chromophore 18 in a high yield of 92%.
phores 6.3, 6.4 and 6.5 (TH-TCF-X-V; X = 5, 6, and 8) contain
3.1.4. Synthesis of phenyl-bridged TCF chromophores with
a vinyl-bridge between TCF moiety and thiophene ring as a 28 amine terminal group. For the synthesis of phenyl bridged
shown in Scheme 1. In a one-pot synthetic approach with a TCF chromophore 21 in which the TCF moiety is directly
28 to 48% overall yield (the yield increases with increasing the connected to a benzene ring without a vinyl-bridge, compound
alkyl chain length of the secondary amine), 2-bromo-5- 19,
2-(dicyanomethylene)-4-(4-fluorophenyl)-2,5-dihydro-5,5-
formylthiophene and dialkylamine were employed as starting dimethylfuran-3-carbonitrile, can be considered as a vital
materials followed by condensation with 4-chloroaniline to intermediate for a variety of TCF chromophores without a
afford the corresponding imine. Siegrist reaction was per- vinyl-bridge. It was found that the intermediate 19 easily reacts
formed between this highly reactive imine electrophile and with a variety of unhindered secondary amines 20 (added in
TCF head at room temperature. Siegrist reaction was employed excess) via a very facile aromatic nucleophilic substitution
due to the low reactivity of 2-alkylamino-5-formylthiophene.
reaction in dry pydridine at room temperature to afford the
3.1.2. Synthesis of phenyl and thiophene vinyl-bridged corresponding TCF chromophores 21 without a vinyl-bridge as
TCF chromophores with a hydroxyl terminal group. Phenyl- shown in Scheme 6. The phenyl bridged TCF chromophore 21
vinyl and thiophene vinyl-bridged TCF chromophores were was prepared in 63% yield at room temperature. The high
prepared directly via condensation employing Knoevenagel reactivity of compound 19 results from the activating TCF
reaction in dry pyridine under ambient conditions with acetic fragment bearing three electron withdrawing cyano groups.
Scheme 5 Synthesis of phenyl vinyl peprazine-bridged TCF bis-chromophores.
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Scheme 6 Synthesis of phenyl bridged TCF chromophores with a 21 amine terminal group.
Compound 19 was previously reported by our research group,
via efficient condensation reaction of aromatic a-
hydroxyketone, 1-(4-fluorophenyl)-2-hydroxy-2-methylpropan-1-
one, with malononitrile at room temperature using acetic acid
catalyst in pyridine. The aromatic a-hydroxyketone can be
synthesized from trimethylsilyl protected 2-hydroxy-2-
methylpropanenitrile and Grignard reagent of 1-bromo-4-
fluorobenzene.
3.2. Photophysical properties
In the past, p-conjugated linear push–pull chromophores have
been prepared to afford new electroactive architectures for bulk
heterojunction solar cells. However, weak acceptors such as
malononitrile moieties have been generally utilized, rather
than strong and more conjugated electron acceptors such as
TCF that has been broadly studied in push–pull molecular
systems of second order nonlinear dyes. Consequently, those
strong acceptors are linked to electron donating moieties by
Fig. 2 TCF-based chromophores with very large molar extinction coeffi-
cients; emax (TH-TCF-8V 5 in CH3CN) = 216 150 L molÀ1 cmÀ1
aromatic/heteroaromatic p-bridges such as thiophenes, fused-
thiophenes, and oligothiophenes, increasing the extension
coefficient and absorption wavelength to the red wavelengths
.
due to strong intramolecular interaction of the strong electron tunability of their energy levels employing a variety of donating
acceptors and donors. substituents and p-bridges. It was found that introduction of a
The molar extinction coefficient of a dye is an important thiophene-vinyl as p-bridge into the conjugation path in TCF-
issue related to the power conversion efficiency (PCE) of organic based chromophores provided the extremely high molar extinc-
photovoltaic devices. In this work, we report the results of an tion coefficients required for the photovoltaics studies (Table 1
investigation on the molecular design, preparation, spectral, and Fig. 2).
and photophysical properties of novel TCF dyes, with and
From our prior experience we know that generally these TCF
without a vinyl-bridge, with strong and narrow absorbance chromophores have substantially improved properties relevant
suitable to evaluate physical mechanisms which are proposed to single molecule optical imaging, especially in terms of their
to enhance absorption in cavity configurations. We designed photochemical stability. The UV-Vis absorbance established
and synthesized a series of novel push–pull chromophores via that the coupling of TCF with electron donor fragments
Knoevenagel reaction with formyl (hetero)aromatic donating resulted in an improved intramolecular charge transfer leading
moieties matched with TCF as a very strong electron acceptor. to long wavelength absorption (Fig. 3).
These TCF-based small dyes have afforded potential advantages
Overall, the structural variations of the TCF chromophores
for nonlinear optics, three dimensional optical data storage including different aliphatic chains on the donor amine group
and solar cells, as a result of their extremely high absorption display a little influence on the absorption spectra. The thio-
coefficient, polarizability, high dipole moments and simple phene bridged chromophores display much sharper absorption
Table 1 TCF-based chromophores and their photophysical properties; the dyes with di-n-alkyl tails (5 V; 3, 6 V; 4 and 8 V; 5) have particularly large
extinction coefficients
Chromophore
Molecular formula (g molÀ1
)
Melting point (1C)
lmax (nm) in CH2Cl2
emax in CH2Cl2
TH-TCF-5-V 3
TH-TCF-6-V 4
TH-TCF-8-V 5
TCF-5Cy3MOH-V 9
TH-TCF-5Cy4OH-V 12
TCF-6Cy3NH 21
C26H32N4OS; 448.62
C28H36N4OS; 476.67
C32H44N4OS; 532.78
C24H24N4O2; 400.47
C21H20N4O2S;392.47
C21H21N5O; 359.42
214–216
163–165
148–149
245–247
4300
624
622
624
579
621
496
166 787
161 908
194 024
61 200
94 191
87 645
208–211
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Fig. 3 Normalized UV-Vis absorbance and fluorescence spectra of TH-
TCF-8-V 5.
Fig. 4 Normalized UV-Vis absorbance spectra of some selected TCF
chromophores in dichloromethane.
peaks at longer wavelengths with higher extinction coefficient
values compared the phenyl bridged analogs. The UV-Vis absorp-
tion spectra in dichloromethane are listed in Tables 1 and 2. The One shortcoming of these dye monomers involves the fabrica-
normalized UV-Vis absorption spectra in dichloromethane are tion of thin glassy films required for physical studies. Solutions
shown in Fig. 4. The UV-Vis absorption spectra display a of sufficient viscosity are difficult to achieve to permit reliable
shoulder at the shorter wavelengths of the absorption peak of spin coating. So, in some refinements higher molecular weight
the produced dyes due to a dimeric aggregate as shown earlier by dyes (often just dimers) were made as an approach to dealing
our research group. This shoulder was not shown in dyes 6.8 and with the thin film preparation.
6.9 with a hydroxyl terminal group on the donor 21 amine as a
result of the expansion of the absorption peak.
3.4. Assessment of dyes uptake
Enhancement of the molecular weight of TCF-based chro-
mophores to facilitate the preparation of thicker films was The polyester fibers are hydrophobic substrates known by their
required for photophysical measurements. These ‘‘dimer’’ high affinity to disperse dyes, which are sparingly soluble in water
chromophores (Fig. 5) have been prepared and evaluated.
and exhibit non-ionic low molecular size. The synthesized chro-
mophores were applied to polyester fibers to introduce shades
between orange and blue. As depicted in Fig. 7, all dyes showed
3.3. Thermal properties
The thermal properties of a range of the obtained TCF-based high uptake into polyester fibers indicating high dye penetration
chromophores were studied via differential scanning calorimetry through the polyester fibers. This can be ascribed to the polyester
(DSC). The melting points Tm are strongly affected by the sub- affinity to the applied dyes which are characterized by small and
stituents on the donor amine groups displaying an increase of the planar molecular structures. Hence, the dyed polyester demon-
melting points Tm with reducing the aliphatic chain length on the strated high colorfastness against washing, perspiration, light and
donor amine groups. Incorporating an alkene group affects the rubbing as displayed in Table 3. The colorfastness to light
melting points Tm as the alkene-containing chromophores display depended on the aromatic-vinyl bridge and the tertiary amine
a lower melting points Tm compared to chromophores without an donor group bonded to those aromatic-vinyl bridge moieties,
alkene bridge. Many of the TCF chromophores display thermal which are capable to change the electron density over the whole
decomposition around 300 1C. Fig. 6 displays the DSC data dye molecule. Therefore, all dyes demonstrated good fastness to
evidence of glass formation of TH-TCF-8-V 5.
light except dyes bearing a thiophene moiety. However, the dyes
Neat samples of some of these TCF dyes also have the bearing a thiophene moiety displayed improved color strength
valuable property that they form relatively stable glasses upon compared to dyes bearing a phenyl moiety. The color shades of
quenching from the isotropic, as in the case of TH-TCF-8-V 5 the dyed polyester were in agreement with the observed wave-
(Fig. 6). These glasses are of high (linear) optical quality. length absorbance maxima of the synthesized dyes in solution.
Table 2 Some high molecular weight TCF chromophores and their photophysical properties
Bis-chromophore
Molecular formula (g molÀ1
)
Melting point (1C)
lmax (nm) in CH2Cl2
emax in CH2Cl2
15
16
18
C52H50N8O6; 883.00
C54H54N8O6; 911.05
C40H32N8O2; 656.73
218
227
4300
550
448
624
87 206
114 578
166 787
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Fig. 5 TCF chromophores for preparation of thicker films.
Fig. 6 DSC data evidence of glass formation of TH-TCF-8-V 5.
Fig. 7 Dye-uptake on polyester fibers.
3.5. Antimicrobial activity
The prepared dyes were tested against E. coli, S. aureus and
C. albican, employing the plate agar count procedure. The elemental analysis, DSC, UV-Vis absorption, and fluorescence
antimicrobial reduction percentage motivated by each synthe- emission spectroscopy. TCF chromophores containing a vinyl-
sized colorants is displayed in Table 4. Dyes with s phenyl-vinyl bridge were easily prepared via Knoevenagel condensation
bridge displayed low inhibition to the reduction percentage, between TCF moiety and the corresponding aromatic aldehyde.
while Dyes with a thiophene-vinyl bridge displayed moderate The TCF intermediate containing 4-fluorophenyl bridge can
antimicrobial activity.
directly react with a variety of unhindered secondary amines by
aromatic nucleophilic substitution to afford the corresponding
TCF chromophores without vinyl group. Most of the produced
TCF chromophores display high extinction coefficient values.
The highest extinction coefficient values were observed for the
thiophene vinyl-bridged chromophores. The produced materi-
als show promising characteristics suitable for different optoe-
lectronic applications such as photovoltaics, 3D optical data
4. Conclusion
Novel multifunctional push–pull architectures of small organic
TCF fluorophores have been synthesized, characterized and
structure optimized. They have been characterized with differ-
ent analysis techniques including 1H and 13C NMR, FT-IR,
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Table 3 Fastness, shade and color strength of dyed polyester fibers
Wash
Perspiration
Acidic
Alt.a
Rubbing
Dry
Basic
Alt.a
Dyes
Alt.a
St.a
St.a
St.a
Wet
Light
Shade
K/S
3
4
5
8
4–5
4
4
4–5
4
4–5
4
4–5
4–5
4
4
3–4
4
3–4
3
3
3–4
3
4
4
3–4
4
3–4
3
3–4
3–4
3
3
3
3–4
4
3
4
4–5
4
4
4–5
4
4–5
4
4–5
4
4–5
4–5
4
4
3–4
4
3–4
3–4
4
3–4
4
3
5
5
5
6–7
6
5–6
5
6–7
6
6–7
6–7
Blue
Blue
Blue
Red
17.04
19.92
23.57
9.78
12.27
15.43
18.71
10.06
13.43
9.76
4–5
4–5
4
4–5
4–5
4
4–5
4
4
4–5
3–4
3–4
4–5
4–5
4
4
4–5
4
4
9
4–5
4–5
4
4
4–5
4
Red
12
13
15
16
18
21
Blue
Blue
Red
Red
Red
3
3–4
4
4
4–5
3–4
4
4–5
4–5
Orange
8.66
a
Alt. = alteration in color; St. = staining on cotton.
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