Ionic interaction of tri-armed structure based on benzene ring: synthesis and characterization

Article abstract of DOI:10.1007/s00706-021-02768-w

Abstract: Liquid crystalline is a state of matter which combines the properties of liquid and a crystalline solid. Ionic liquid crystals are a new class of materials which exhibit phase transition at low temperature. A new structure was synthesized based on a benzene ring carrying three armed, two arms of triazine ring and the third arm is phenoxy benzene. The presence of alkyl chain groups on the periphery reduced the mesophase transitions which are desirable for low-temperature applications of liquid crystals. The substitution was achieved efficiently by Sonogashira coupling. The tri-armed compound was synthesized successfully through cross-coupling. However, it was oily and no transition phase was observed. Therefore, to increase the liquid crystal possibility, the compound was mixed with 4-(dodecyloxy)benzoic acid (4-DBA) with 1:1 ratio to produce an organic salt through hydrogen bonding. The organic salt obtained by ionic interaction between the tri-armed compound and 4-DBA exhibited a phase transition at low temperature. However, ionic liquid crystals are important class of mesomorphic materials and have considered as sealants due to their very low vapour pressure which demonstrated a proficient electrolyte systems for their anisotropic phase such as high ionic conductivity and diffusion along with excellent thermal stability. All the intermediate compounds and final compounds were confirmed by spectroscopic techniques (¹H NMR, ¹³C NMR, FT-IR, and HRMS). Graphic abstract: [Figure not available: see fulltext.].

Full text of DOI:10.1007/s00706-021-02768-w

Monatshefte für Chemie - Chemical Monthly (2021) 152:551–558
https://doi.org/10.1007/s00706-021-02768-w
ORIGINAL PAPER
Ionic interaction of tri‑armed structure based on benzene ring:
synthesis and characterization
Mohammed Hadi Ali Al‑Jumaili1 · Nihat Akkurt2 · Lokman Torun3
Received: 26 February 2021 / Accepted: 5 April 2021 / Published online: 22 April 2021
© Springer-Verlag GmbH Austria, part of Springer Nature 2021
Abstract
Liquid crystalline is a state of matter which combines the properties of liquid and a crystalline solid. Ionic liquid crystals
are a new class of materials which exhibit phase transition at low temperature. A new structure was synthesized based on a
benzene ring carrying three armed, two arms of triazine ring and the third arm is phenoxy benzene. The presence of alkyl
chain groups on the periphery reduced the mesophase transitions which are desirable for low-temperature applications of
liquid crystals. The substitution was achieved efciently by Sonogashira coupling. The tri-armed compound was synthesized
successfully through cross-coupling. However, it was oily and no transition phase was observed. Therefore, to increase the
liquid crystal possibility, the compound was mixed with 4-(dodecyloxy)benzoic acid (4-DBA) with 1:1 ratio to produce an
organic salt through hydrogen bonding. The organic salt obtained by ionic interaction between the tri-armed compound and
4-DBA exhibited a phase transition at low temperature. However, ionic liquid crystals are important class of mesomorphic
materials and have considered as sealants due to their very low vapour pressure which demonstrated a profcient electrolyte
systems for their anisotropic phase such as high ionic conductivity and difusion along with excellent thermal stability. All
the intermediate compounds and fnal compounds were confrmed by spectroscopic techniques (1H NMR, 13C NMR, FT-IR,
and HRMS).
Graphic abstract
Keywords Tri-armed structure · Triazine ring · Hydrogen bonding · Ionic interactions
Introduction
New compounds containing a 1,3,5-triazine unit showed
* Mohammed Hadi Ali Al-Jumaili
much in the synthesis of liquid crystals molecular and inves-
tigated their properties according to the literature [1]. The
liquid crystal state combines the properties of the liquid
phase (capacity of fowing) with the solid phase (capacity
of an ordered and crystalline structure) [2]. Star-shaped sys-
tems containing 1,3,5-triazine derivatives have been used as
acceptors in materials chemistry. The important structures
that contain the s-triazine core and other units as donors
mohammed.hadi@duc.edu.iq
1
Department of Medical Laboratory Techniques, Dijlah
University College, Baghdad, Iraq
2
Chemistry Department, Faculty of Science and Art,
Kırklareli University, Kırklareli, Turkey
3
TORKIM ARGE KimyaSanayi Tic. A. S. YTÜ Teknopark,
KuluckaMerkezi, Esenler, 34220 Istanbul, Turkey
Vol.:(0123456789)
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M. H. A. Al-Jumaili et al.
substituent’s allows the optoelectronic properties which led
these materials to use in luminescent liquid crystals [3, 4].
The donor substituent such as styryl benzene [5], thiophene
[6], 1,2,3-triazole [7], tetrathiafulvalene [8], ferrocene [9],
2-pyridyl [10], and bisphenylaminobenzene [11].
glassy nematic liquid crystals based on pentaerythritol as a
fexible core was investigated in detail [28].
Therefore, the aim of this research is to synthesize new
macromolecular structure based on benzene ring as a central
core, the central core connected to three armed, 1,3-dichloro-
5-phenoxybenzene arm, which obtained from the reaction of
1,3,5-trichlorobenzene and phenol and two arms of 2-chloro-
4,6-bis(3,7-dimethyloct-6-en-1-yloxy)-1,3,5-triazine which
obtain from the reaction between 1,3,5-triazine and citron-
ellol. These arms may be linked to the central core through
rigid linkers or fexible or semi-fexible.
Triazine has been also used as functional materials from
hard to soft porous frameworks [12], supported catalysts
[13], absorption of surfactants from the aqueous solution
[14], cathodes for lithium batteries [15], and nonporous
membranes for desalination [16]. The chemistry of triazines
since past two centuries has been studied intensively due to
their physical and chemical properties especially in pharma-
ceutical and industry. However, recently the research using
1,3,5-triazines unit as starting material carried out on the
antitumor activity [17, 18].
Results and discussion
1,3,5-Triazine has been used as a core [19]. Besides,
cyanuric chloride has been easily interacted with various
nucleophilic side groups to obtain liquid crystals molecu-
larly depending on their structures which can exhibitca-
lamitic morphological behaviours or discotic [20].
In this study, a new tri-armed compound was success-
fully obtained through cross-coupling starting from
2,4,6-trichloro-1,3,5-triazine and 1,3,5-trichlorobenzene as
a starting material. The target compound and the intermedi-
ate compounds were confrmed by spectroscopic techniques.
The result showed no liquid crystals of the tri-armed com-
pound. Therefore, it was reacted with 4-(dodecyloxy)benzoic
acid (4-DBA) resulting in an organic salt via intermolecular
hydrogen bonding to increase the possibility of liquid crys-
talline of the mixture. 4-DBA, its known compound which
already has liquid crystal properties. The obtained organic
salt is confrmed mainly by FT-IR, 1H NMR, 13C NMR, and
HRMS.
Soft materials of liquid crystals are unique groups that
have both the solid state and the liquid state and exhibit a
molecular organization [21]. The molecules display a long-
range order by occupying fxed positions at regular dis-
tances in the crystalline phase, while the molecules are free
to move around in both positional and orientational order
in the liquid phase [22]. Therefore, there is an exceptional
intermediate state demonstrated between isotropic liquids
and isotropic solids in the liquid crystalline materials. The
fourth state of matter was related to this intermediate which
is called a mesophase [23].
The ionic interaction between the tri-armed π-conjugated
system and the mesogenic carboxyl group was mainly stud-
ied by FT-IR. The carboxylic peak corresponding to 4-DBA
at 1680 cm−1 shifted to 1670 cm−1 in organic salt (Fig. 1)
[1].
Liquid crystal mesophases depends on the molecular
size, shape of the structure, the therapeutic objective and
the analytical signifcance for their identifcations well as
their applications in other felds [24]. Among these materi-
als, disc-like liquid crystals are particularly gathering atten-
tion especially concerning to their unique optical properties.
Triazine-based chemistry has a wide range of applications
as agrochemicals, inhibitors, industries, antitumor, and fame
retardants, but also shows a high afnity for liquid crystal
properties and the interest in triazine-containing processes
[25].
Additionally, the mass spectrometry was also confrmed
the molecular weight of the organic salt 11 by the presence
of (M + 2H)+2 peak at m/z = 650.43 (650 × 2–2 = 1299.8),
which calculated for C81H114N6O8 1299.8 (Fig. 2).
1,3,5-Triazine unit due to their high electron afnity and
symmetric structure is widely used to construct optoelec-
tronic materials as a strong electron-accepting canter. The
s-triazine and its derivatives have their importance in het-
erocyclic compounds due to their very good activities [26].
The heterocyclic compounds with nitrogen or sulfur atoms
have been an interest in the design of new drugs or material
due to their physiochemical properties [27]. Liquid crystals
are widely used both scientifcally and industrially; many
compounds based on triazine unit were employed as electron
injection and transport materials. The class of star-shaped
Fig. 1 FT-IR spectrum of 4-DBA, organic salt 11, compound 7
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Ionic interaction of tri-armed structure based on benzene ring: synthesis and characterization
553
Fig. 2 Mass spectrum of the
organic salt 11
Table 1 Chemical shifts (δ/ppm) of relevant protons in CDCl3 as the
Table 2 Chemical shifts (δ/ppm) of relevant carbon of 4-DBA before
solvents (25 °C)
and after interaction in CDCl3 as the solvents (25 °C)
Compound
Aromatic Ha/ Aromatic Hb/ –OCH2–/ppm
Compound
Aromatic Ca/ppm
Aro-
ppm
ppm
matic
Cb/ppm
Compound 7
4-DBA
Salt 11
–
4.05
4.15–3.97
3.75
4-DBA
Salt 11
171.6
166.7
163.6
163.9
8.05
7.80
6.95
6.73
Table 3 Phase transition as observed on heating (H→), cooling
(←C) of the organic salts 11 and 4-DBA
1H NMR showed the signals corresponding to the aro-
matic protons of an alkoxy benzoate unit in organic salt
observed at 7.8, 6.7 ppm as compared to pure benzoic acid
at 8.05, 6.95 ppm. These shifts of the aromatic protons
of organic salt compared to pure 4-DBA was due to the
ionic interaction between triazine and a carboxyl group of
the mesogenic unit which increased the electron density
of the aromatic ring. Besides, the signals of oxymethyl-
ene protons of 4-DBA in ion complex shift to higher feld
3.75 ppm as compared with the signals of pure 4-DBA at
4.05 ppm. Whereas, the protons corresponding to benzene
rings observed at 7.4, 7.3, 7.20 ppm (Table 1).
Compound
4-DBAb
T/°C/ΔH/kJ mol−1
H→: Cr 99.98 [39.01] SmC 132.43 [2.39] N
138.42 [2.05] Iso
OS (11)
H→: Cr 11.3 [− 35], 51.9 [− 11], 96 [− 42] Iso
The tri-armed compound was oily due to the citronel-
lyloxy chains which are positioned at the peripheries of
triazine. The compound showed no liquid crystals and no
transition phase of liquid properties in its pure state. There-
fore, the compound was mixed with 4-DBA in 1:1 ratio via
intermolecular hydrogen bonding to obtain the organic salt
through ionic interaction to increase the liquid crystal pos-
sibility. However, this method showed signifcant points in
producing liquid crystal molecules but at low temperature.
Ionic interactions through hydrogen bonding have a
propensity to be stable for lamellar mesophases. However,
ionic liquid crystals exhibit phase transition at low tempera-
ture which are more organized than the smectic A phase at
a lower temperature [29].
Also, the organic salt proved by the 13C NMR spec-
tra. The signal of the carbonyl carbon in an organic salt
shifted from 171.6 to 166.7 ppm. These changes in chemi-
cal shift due to increase of electron density after the ionic
interaction, whereas the aromatic carbon next to alkoxy
group shift slightly from 163.6 to 163.9 ppm, that’s lead
to decrease in electron density of carbon in case of ionic
interaction form. Also, the triazine ring carbon observed
at 172.01 and 170.98 ppm (Table 2).
The organic salt was investigated by diferential scan-
ning calorimeter (DSC). Upon heating curves, the organic
salt 11 shows two peaks at 51.9 °C and 11 °C. On cool-
ing from isotope phase, one peak was observed at 96.3 °C
(Table 3).
The ability of the molecular to show liquid crystals prop-
erties depends on the structure and side chains. In other
ways, increasing the length of the alkoxy chain leads to
decrease in the temperature of the transition phase. That
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554
M. H. A. Al-Jumaili et al.
is why the organic salt 11which obtained via ionic interac-
tion between tri-armed compounds and 4-DBA with a long
alkoxy side chain showed liquid crystal at low temperature
[30].
Ionic liquid crystal behaviour
Ionic liquid crystals can be considered as materials that
contain anions and cations which combine the properties of
liquid crystals and ionic liquids. However, the character of
the ionic liquid crystals are diferent from the conventional
liquid crystals. That ionic interactions play an important role
in the stabilization of mesophases.
Fig. 3 Ionic interaction of 4-DBA with triazines in tri-armed com-
Most of the ionic compounds that studied showed a smec-
tic A phase, but a columnar phase was observed for some of
the salts (containing 64 terminal NH2 groups).
pound [32]
The phase behaviour of liquid crystals are depending on
the degree of protonation of primary amino groups as com-
pared with that of the tertiary ones. Thus, protonation of the
tertiary amino groups of the compound is more pronounced
for the higher generation dendrimers than for the low genera-
tion dendrimers.
value which led to decreases the stability of mesophase mix-
ture, with increases of either the alkoxy chain of both 4-DBA
and tri-armed structure. Therefore, the shorter chain length
of the base and/or the acid resulted in the increment of the
lateral interaction to enhance the more ordered phases range
and stability (Fig. 4) [20].
Ionic liquid crystals based on benzene rings have been
created by the interaction of carboxylic acids in the com-
pound of 4-DBA with triazines that are functionalized on
their periphery with alkoxy chains. An ion pair is formed
by the transfer of the proton of the carboxylic acid to the
nitrogen, resulting in an organic salt. The salts obtained have
higher transition temperatures due to the presence of hydro-
gen bonds within the structure.
Conclusion
Ionic liquid crystals are organic salts having synergistic
properties of ionic liquids and liquid crystalline materials
endowed with non-covalently bound. The main driving force
for discovering ionic liquids is that these compounds have
too low vapour pressure to be candidates to replace vola-
tile organic solvents in organic reactions. Ionic liquids are
generally considered designer solvents. New star-shaped
compound was successfully obtained through cross-cou-
pling which composed 2,4,6-trichloro-1,3,5-triazine car-
rying dodecyloxy chains positioned at the peripheries and
1,3,5-trichlorobenzene. The tri-armed compound was a
non-liquid crystal. Therefore, the compound was mixed
with 4-DBA via ionic interaction and through hydrogen
bonding to obtain organic salt. The organic salt investigated
by diferential scanning calorimetry (DSC), two transition
phases was formed after the ionic interaction between the
compound 7 and 4-DBA resulting in an organic salt. All
the synthesis compounds were confrmed by spectroscopic
techniques (13C NMR, 1H NMR, FT-IR, and HRMS).
In hydrogen-bonded liquid crystals, thermotropic meso-
phases are displayed by associations of a hydrogen-bond
donor and a hydrogen acceptor. The building blocks of
hydrogen-bonded liquid crystals are often not mesomor-
phic themselves, but the resulting supramolecular aggregates
which exhibit a variety of ordered structures. These ionic
liquids could be also used to immobilize transition metal
catalysts in the liquid phase of two-phase catalytic reactions.
Other applications include their use as a solvent for extrac-
tion processes and as an electrolyte for batteries, fuel cells,
and dye sensitive solar cells [31] (Fig. 3).
The π–π stacking of the aromatic rings plays an important
role in the mesomorphic properties and thermal stabilities
of observed phases. The efect of changing the core moiety
of 4-DBA molecules on the mesophase behaviour of 1:1
molar mixtures, comparison was constructed between the
mesophase stabilities. Our study revealed that increasing the
length and rigidity of the acid mesogenic core resulted in an
increase of the stabilities and mesomorphic ranges of liquid
crystal properties. Although the chain length of the alkoxy
terminal of the carboxylic acid and the tri-armed compound
increases the dimensional parameters with considerable
Experimental
1,3,5-Trichlorobenzene, cyanuric chloride, dodecan-
1-ol, ethynyltrimethylsilane, copper iodide, tetrakis-
(triphenylphosphine) palladium, potassium carbonate,
1 3

Ionic interaction of tri-armed structure based on benzene ring: synthesis and characterization
555
Fig. 4 DSC of organic salt 11 (a), DSC of compound 4-DBA (b), and a typical texture of smectic C mesophase (c)
triethylamine, dimethylformamide, tetrahydrofuran, and
dioxane. Thin-layer chromatography was performed using
aluminium plates (20 × 20 cm) coated with silica gel 60
F254 (Merck), while column chromatography was carried
out using silica gel 60 (0.063–0.200 mm) from Merck. The
reagents and solvents were used without further purifcation.
The 1H and 13C NMR spectra were recorded on a Bruker
Avance III (500 MHz) in CDCl3. The chemical shift values
are expressed as δ value (ppm) down feld with residual pro-
tons of the solvents (CDCl3, δ=7.26 ppm) as internal stand-
ard. FT-IR (Shimadzu Prestige-21, KBr discs), and HRMS
(high-resolution mass spectrometry).
cm3 ethyl acetate and 10 cm3 water. The organic layer after
separation dried with sodium sulfate. Under vacuum, the
solvent was evaporated and the crude product purifed by
column chromatography with hexane/ethyl acetate (2.5%
EtOAc) as an eluent to yield 0.25 g (41%). 1H NMR: δ=5.14
(dd, J=7.1, 1.3 Hz, 2H), 4.5 (m, 4H, OCH2), 2.09 (m, 4H,
CH2), 1.9 (m, 6H, CH3), 1.8 (m, 6H, CH2), 1.6–1.3 (m, 10H,
CH2), 1.07–0.95 (m, 6H, CH3) ppm; 13C NMR: δ=172, 171,
131.5, 124, 69, 36.8, 35, 29, 25.7, 25.3, 19.2, 17.6 ppm;
HRMS: m/z calcd. for C23H38ClN3O2 (M+) 423.27, found
424.27 ([M+H]+), 441.311 ([M+NH4]+).
2,4‑Bis(3,7‑dimethyloct‑6‑en‑1‑yloxy)‑6‑(trimethylsilyleth‑
ynyl)‑1,3,5‑triazine (3) [20] 2-Chloro-4,6-bis(3,7-dimeth-
yloct-6-en-1-yloxy)-1,3,5-triazine (2, 1.2 g, 2.5 mmol),
0.29 g ethynyltrimethylsilane (2.96 mmol), 0.4 g K2CO3
(21.9 mmol), 0.28 g Pd(PPh3)4 (0.24 mmol), and 0.09 g CuI
(0.49 mmol) were dissolved in 10 cm3 of THF under argon
atmosphere then refuxed for 6 h (Scheme 1). The solution
2‑Chloro‑4,6‑bis(3,7‑dimethyloct‑6‑en‑1‑yloxy)‑1,3,5‑tri‑
azine (2) [1] 2,4,6-Trichloro-1,3,5-triazine (1, 0.29 g,
1.6 mmol), 0.5 g 3,7-dimethyloct-6-en-1-ol (3.2 mmol),
and 0.45 g K2CO3 (3.2 mmol) were dissolved in 10 cm3 of
THF under argon atmosphere and stirred at 50 °C overnight
(Scheme 1).The solution was poured into a mixture of 10
1 3

556
M. H. A. Al-Jumaili et al.
Scheme 1
was poured into a mixture of 20 cm3 ethyl acetate and 20
cm3 water. The organic layer after separation dried with
sodium sulfate. The solvent was removed under vacuum to
give brown oily material with yield 1.1 g (81%). HRMS:
m/z calcd. for C28H47N3O2Si (M+) 485.34, found 486.33
([M+H]+), 508.32 ([M+Na]+).
C12H8Cl2O (M+) 238.00, found 477.982 ([2 M]+), 715.988
([3 M]+).
6,6′‑[(5‑Phenoxy‑1,3‑phenylene)bis(ethyne‑2,1‑diyl)]‑
bis[2,4‑bis(3,7‑dimethyloct‑6‑en‑1‑yloxy)‑1,3,5‑triazine]
(7, C62H84N6O5) 1,3-Dichloro-5-phenoxybenzene (6, 0.2 g,
0.84 mmol), 0.46 g 2,4-bis(3,7-dimethyloct-6-en-1-yloxy)-
6-(trimethylsilylethynyl)-1,3,5-triazine (3, 1.1 mmol), 0.09 g
Pd(PPh3)4 (0.084 mmol), 0.031 g CuI (0.168 mmol), and
0.23 g K2CO3 (1.68 mmol) were dissolved in 10 cm3 of diox-
ane under argon atmosphere. The mixture was stirred for
16 h at 80 °C. The solution was poured into a mixture of 20
cm3 ethyl acetate and 20 cm3 water. The organic layer was
washed and dried over sodium sulfate. Under vacuum, the
solvent was removed and the residue by column chromatog-
raphy was purifed with hexane/ethyl acetate (5% EtOAc)
as an eluent to yield 0.30 g (60%). 1H NMR: δ=7.4 (s, 2H,
Ar–H), 7.3 (s, 1H, Ar–H), 7.25 (d, 2H, Ar–H), 7.0 (m, 3H,
Ar–H), 4.9 (s, 4H), 4.15 (t, 8H, OCH2), 1.8 (m, 14H, CH2),
1.6 (t, 8H, CH2), 1.4 (m, 12H, CH3), 1.25–0.9 (m, 42H,
1,3‑Dichloro‑5‑phenoxybenzene (6) [33] A mixture of
2.0 g 1,3,5-trichlorobenzene (4, 11.1 mmol), 1.04 g phenol
(5, 11.1 mmol), and 3.37 g K2CO3 (24.4 mmol) were dis-
solved in 10 cm3 of dioxane under argon atmosphere. The
mixture was stirred for 6 h at 70 °C, then the temperature
increased to 70 °C for 4 h (Scheme 2). The solution was
poured into a mixture of 10 cm3 ethyl acetate and 10 cm3
water. Then the organic layer was dried over sodium sulfate
and under vacuum the solvent was removed. The residue
was purifed by column chromatography with ethyl acetate/
hexane (5% EtOAc) as an eluent to give white solid material
(2.16 g, 81.8%). 1H NMR: δ=7.27 (s, 3H, Ar–H), 7.22 (d,
2H, Ar–H), 6.8 (d, 3H, Ar–H) ppm; HRMS: m/z calcd. for
1 3

Ionic interaction of tri-armed structure based on benzene ring: synthesis and characterization
557
Scheme 2
CH2), 0.75 (m, 12H, CH3) ppm; 13C NMR: δ=171.8, 170,
165, 164, 135, 133, 131, 124.9, 124.8, 123, 103, 64.6, 41.6,
41.4, 37.2, 35.9, 35.4, 29, 25, 19.5, 17.6, 13.5, 13.1 ppm;
FT-IR (KBr): v = 2967, 2925, 2850, 1742, 1570, 1522,
1504, 1429, 1340, 1340, 1299 cm−1; HRMS: m/z calcd. for
C62H84N6O5 (M+) 993.37, found 992.65, 993.66 (M+).
the precipitate fltered, washed with water, and recrystallized
from ethanol to obtain the pure product 4-dodecyloxyben-
1
zoic acid as white solid material (yield 4.55 g, 91%). H
NMR: δ=8.10 (d, 2H, Ar–H), 6.98 (d, 2H, Ar–H),4.07 (t,
2H, OCH2), 1.84 (m, 2H, CH2), 1.48 (m, 2H, CH2), 1.37–
1.28 (m, 16H, CH2), 0.91 (t, 3H, CH3) ppm; FT-IR (KBr):
v=2914, 2848, 2559, 1670, 1604 cm−1.
4‑(Dodecyloxy)benzoic acid (10) [34] A solution of
4-hydroxybenzoic acid (16.43 mmol), 11 cm3 1-bromodode-
cane (46 mmol, 2.8 eq), and 2.58 g KOH (46 mmol, 2.8 eq)
in 50 cm3 ethanol was heated under refux for 3 days. The
hydrolysis was carried out by adding 10% aqueous KOH
(25 cm3) and the mixture refuxed overnight. After cooling
down, the reaction mixture was acidifed with HCl (6 M),
6,6′‑[(5‑Phenoxy‑1,3‑phenylene)bis(ethyne‑2,1‑diyl)]‑
bis[2,4‑bis(3,7‑dimethyloct‑6‑en‑1‑yloxy)‑1,3,5‑triazine]
4‑(dodecyloxy)benzoate (11, C81H114N6O8) 4-DBA mes-
ogenic unit (10) and 6,6′-[(5-phenoxy-1,3-phenylene)
bis(ethyne-2,1-diyl)]bis[2,4-bis(3,7-dimethyloct-6-en-
1-yloxy)-1,3,5-triazine] (7), with one to one ratio. The
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M. H. A. Al-Jumaili et al.
14. Bhunia A, Dey S, Bous M, Zhang C, von Rybinski W, Janiak C
(2015) Chem Commun 51:484
sonication was done in dry THF for 10 min until a transpar-
ent solution was obtained. Then, the solvent was removed in
vacuum. 1H NMR: δ=7.8 (d, 2H, Ar–H), 7.4 (s, 2H, Ar–H),
7.25–6.9 (m, 6H, Ar–H), 6.7 (d, 2H, Ar–H), 4.8 (s, 4H),
4.15 (t, 8H,OCH2), 3.8 (t, 2H, OCH2), 1.75 (m, 12H, CH2),
1.6 (m, 8H, CH2), 1.4–1.3 (m, 24H, CH3), 1.1–0.9 (m, 28H,
CH2), 0.7 (m, 15H, CH3) ppm; 13C NMR: δ=172, 170, 166,
163, 151, 134, 133.6, 133.3, 132.5 131.4, 129.9, 126.7, 125,
123, 122, 121, 114, 69.3, 68.5, 41.6, 37.4, 37.1, 36.1, 35.4,
32.4, 29.98, 29.9, 29.8, 29.6, 29.5, 26.2, 25.99, 25.7, 25.6,
22.9, 19.7, 17.9, 14.4, 12 ppm; FT-IR (KBr): v=2914, 2849,
2560, 1670, 1604, 1577, 1469, 1430, 1331 cm−1; HRMS:
m/z calcd. for C81H114N6O8 (M+) 1299.8, found 650.43
([M+2H]+2).
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