Synthesis and study of N,N′-disubstituted derivatives of pyromellitic diimide

Article abstract of DOI:10.1007/s11172-020-2983-4

New N, N′-bis(4,6-dimethylpyrimidin-2-yl)- and N, N′-bis(2,3,5,6-tetrafluorophenyl)-substituted pyromellitic diimides were synthesized. Their properties were studied in comparison with the previously synthesized N, N′-bis(4-fluorophenyl)pyromellitic diimi

Full text of DOI:10.1007/s11172-020-2983-4

Russian Chemical Bulletin, International Edition, Vol. 69, No. 10, pp. 1944—1948, October, 2020
1944
Synthesis and study of N,N´-disubstituted derivatives
of pyromellitic diimide
E. A. Komissarova,a,b V. E. Zhulanov,b I. G. Mokrushin,b A. N. Vasyanin,b E. V. Shklyaeva,b and G. G. Abasheva,b
aInstitute of Technical Chemistry, Ural Branch, Russian Academy of Sciences,
Division of the Perm Federal Center of the Ural Branch of the Russian Academy of Sciences,
3 ul. Akad. Koroleva, 614013 Perm, Russian Federation.
Tel.: +7 (342) 237 8289. E-mail: gabashev@psu.ru
bPerm State National Research University,
15 ul. Bukireva, 614990 Perm, Russian Federation.
Tel.: +7 (342) 239 6231. E-mail: ekaterina.komva@gmail.com
New N,N´-bis(4,6-dimethylpyrimidin-2-yl)- and N,N´-bis(2,3,5,6-tetrafluorophenyl)-
substituted pyromellitic diimides were synthesized. Their properties were studied in comparison
with the previously synthesized N,N´-bis(4-fluorophenyl)pyromellitic diimide. Thermogravimetry,
UV spectroscopy, cyclic voltammetry, and quantum chemical calculations in the framework of
the density functional theory were used to characterize the synthesized compounds. The intro-
duction of the pyrimidine cycle significantly decreases the energy of the lowest unoccupied
molecular orbital. The highest occupied molecular orbitals in all compounds synthesized are
deep-lying (about –7 eV).
Key words: pyromellitic diimide, pyrimidine, fluoroaniline, tetrafluoroaniline, highest
occupied molecular orbital, lowest unoccupied molecular orbital, forbidden gap width, quantum
chemical calculations.
Targeted synthesis of organic electro- and photo-
conducting compounds necessary for the development
and design of modern materials used in organic electron-
ics is an urgent task. This is indicated by regularly published
research articles, reviews, reference books, and mono-
graphs.1—6 Substituted polycyclic carboxydiimides, such
as perylene-3,4,9,10-tetracarboxylic acid diimide and
naphthalene-1,4,5,8-tetracarboxylic acid diimide, are
referred to one of the promising class of small molecules
used for the fabrication of organic electronics devices, e.g.,
organic field-effect transistors,7,8 various sensors,9 and
solar cells.10 The studies devoted to the synthesis, proper-
ties, and application areas of the derivatives of benz-
ene-1,2,4,5- tetracarboxylic acid diimide, so-called pyro-
mellitic diimide (pyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-
tetraone) are presently published more frequently. N,N´-Di-
substituted pyromellitic acid diimides are also used in
the fabrication of materials for organic electronics de-
vices.8,9,11 In addition, it is known that the complexes of
N,N´-disubstituted pyromellitic diimide with electron-rich
compounds (tetrathiafulvalenes, pyrenes, and naphth-
alenes) have the properties of segnetoelectrics.12
—-interactions favoring an increase in the charge trans-
fer efficiency and, hence, an increase in the mobility of
charge carriers.8 In spite of the fact that the pyromellitic
diimide derivatives are most known as fragments of highly
insulating polyimide dielectrics, they are often used as
semiconductor materials in the structures of organic field-
effect transistors.13—17 Among the advantages of the pyro-
mellitic diimide derivatives is that its major precursor,
pyromellitic acid dianhydride, is commercially more ac-
cessible than naphthalene-1,4,5,8-tetracarboxylic acid
dianhydride or perylene-3,4,9,10-tetracarboxylic acid
dianhydride. In addition, it is fairly simple to purify the
substituted pyromellitic anhydrides.
The attachement of electron-withdrawing groups to
the nitrogen atom of the imide fragment of polycyclic
carboxydiimides increases the mobility of charge carriers
in these molecules.8 Fluorinated alkyl or substituted benzyl
groups are used most frequently as electron-withdrawing
groups, whereas carboxydiimides containing the electron-
withdrawing aromatic fragment directly linked to the ni-
trogen atom of the imide fragment are studied much
poorly.18—21 One of the aromatic electron-withdrawing
fragments promising for the incorporation into polycyclic
imide molecules is the pyrimidine cycle: its presence in
the structures of the -conjugated compounds decreases
the energy of the lowest unoccupied molecular orbital
High thermal stability and air stability are among the
main advantages of polycyclic carboxyimides. In addition,
these molecules are characterized by the planar structure
and stacked organization of the packing providing strong
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1944—1948, October, 2020.
1066-5285/20/6910-1944 © 2020 Springer Science+Business Media LLC

N,N´-Disubstituted pyromellitic dianhydride
Russ. Chem. Bull., Int. Ed., Vol. 69, No. 10, October, 2020
1945
(LUMO), thus favoring the achievement of a high electron
mobility.22
been described previously.27,28 2-Amino-4,6-dimethyl-
pyrimidine necessary for the synthesis of compound 1 was
synthesized by the condensation of acetylacetone with
urea.29 Reflux of pyromellitic dianhydride with 2-amino-
4,6-dimethylpyrimidine in glacial acetic acid gave (in
a yield of 65%) N,N´-bis(4,6-dimethylpyrimidin-2-yl)-
pyromellitic diimide 1 as a high-melting yellow crystalline
substance, which was recrystallized from DMF. Pyro-
mellitic diimide derivatives 2 and 3 containing the fluorine-
substituted benzene fragments were synthesized in high
yields of 68—70% by the reactions of pyromellitic di-
anhydride with the corresponding fluorine-substituted an-
ilines in refluxing DMF.30 The synthesized N,N´-disub-
stituted diimides 2 and 3 are high-melting crystalline sub-
stances, which were purified by recrystallization from ethanol.
In this work, we compared the thermal, optical,
electrochemical, and electronic properties of compounds
1—3. Thermal stability is an important characteristic of
materials for organic electronics, since it directly affects
the operation durability of the devices based on these
materials. The thermogravimetric analysis of compounds
1 and 3 shows that they are thermally stable highly melting
substances. The decomposition onset temperature of di-
imide 1 is 215 С, and that for tetrafluorophenyl-substi-
tuted diimide 3 is 288 С. Pyrimidine-containing diimide
1 is characterized by the two-step decomposition at 233
and 384 С accompanied by consecutive mass losses of
28.6 and 49.5% of the substance weight. The complete
decomposition of diimide 3 occurs at 380 С. It has previ-
ously27 been shown that diimide 2 containing the fluorine
atom in position 4 of the benzene cycle at the nitrogen
atom is also thermally stable: the range of its decomposi-
tion is 340—432 С.
The electronic absorption spectra in a DMF solution
(С = 4•10–5 mol L–1) were recorded for the studied carb-
oxydiimides 1—3 (Fig. 1). The absorption band maxima
(mах), absorption edge (onset), and molar absorption
coefficients () are given in Table 1. The character of the
absorption spectra of pyromellitic diimide 1 differs con-
siderably from the absorption spectra of fluorine-contain-
ing pyromellitic diimide derivatives 2 and 3. The intense
short-wavelength maximum of the absorption band of
bis(4,6-dimethylpyrimidin-2-yl)pyromellitic diimide 1
(mах = 293 nm) is red-shifted by 26 nm relative to the
maxima of the corresponding absorption bands of com-
pounds 2 and 3 (mах= 267 nm) (see Fig. 1, Table 1). In
addition, the absorption spectrum of compound 1 exhib-
its a pronounced low-intensity long-wavelength absorption
band at mах = 394 nm corresponding to the intramo-
lecular charge transfer. The absorption edge of compound
1 (onset) is also bathochromically shifted, due to which
diimide 1 is characterized by the lowest optical width of
the forbidden gap equal to 2.99 eV. The spectra of com-
pounds 2 and 3 exhibit broadened absorption bands in
a range of 320—330 nm.
Polycyclic carboxydiimides are synthesized most fre-
quently by the acylation of primary amines by the corre-
sponding di- or tetracarboxylic acid anhydrides under
various conditions, which depend on the nature of the
reactants and their solubility.23—25 It is known that the
reactions characteristic of amines, including acylation,
are impeded if the amino group is in the structure of azines,
in particular, pyrimidine, which is due to its deactivation
by the electron-withdrawing pyrimidine cycle. This com-
pletely concerns the reactivity of the amino group of
2-amino-4,6-dimethylpyrimidine. Nevertheless, we earlier
synthesized and studied N-(4,6-dimethylpyrimidin-2-yl)-
phthalimide and N-(4,6-dimethylpyrimidin-2-yl)-1,8-
naphthalimide and products of their condensation with
aromatic aldehydes.26 The nature of the central imide
fragment of the synthesized chromophores was shown to
exert a significant effect on the LUMO energy of these
molecules. The purpose of the present study is the synthe-
sis of the new pyrimidine-containing N,N´-bis(4,6-di-
methylpyrimidin-2-yl)pyromellitic diimide and study of
its optical and thermal properties in comparison with the
properties of N,N´-disubstituted pyromellitic diimides
bearing the 4-fluorophenyl and 2,3,5,6-tetrafluorophenyl
electron-withdrawing groups at the nitrogen atoms of the
diimide cycle. The determination of the energies of
the highest occupied (EHOMO) and lowest unoccupied
(ELUMO) molecular orbitals and optical width of the for-
bidden gap (Egopt) using both the experimental methods and
quantum chemical calculations was also a task of the work.
Target compounds 1—3 were synthesized by the reac-
tions of pyromellitic dianhydride with the amines con-
taining the electron-withdrawing groups, namely, with
2-amino-4,6-dimethylpyrimidine, 4-fluoroaniline, and
2,3,5,6-tetrafluoroaniline (Scheme 1).
Scheme 1
or
R =
(1),
(2),
(3)
Reagents and conditions: i (for 1), glacial AcOH, reflux, 24 h;
ii (for 2 and 3), DMF, reflux, 8 h.
Compounds 1 and 3 were synthesized and described
for the first time, and the synthesis of compound 2 has

Komissarova et al.
I/mA
1946
Russ. Chem. Bull., Int. Ed., Vol. 69, No. 10, October, 2020
A (arb. units)
E/V –2.0
–1.5
–1.0
–0.5
0
1.0
0.8
1
–0.5
–1.0
–1.5
–2.0
–2.5
–3.0
3
0.6
0.4
0.2
1
I/mА
2.5
2
2
1
2.0
1.5
1.0
0.5
2
3
3
0.5 1.0 1.5 2.0 Е/V
310
360
410 /nm
Fig. 1. Normalized absorption spectra of the DMF solutions of
compounds 1—3 (С = 4•10–5 mol L–1). The spectra were nor-
malized to the maximum absorption intensity in this spectrum.
Fig. 2. CV curves of compounds 1—3 (DMF—CH2Cl2 (1 : 4))
recorded in the cathodic potential range (glassy carbon working
electrode, platinum wire as an auxiliary electrode, Ag/AgCl
reference electrode, Et4NClO4 supporting electrolyte, scan
=
= 100 mV s–1). Inset: CV curves detected in the anodic poten-
tial range.
The energies of the HOMO (EHOMO) and LUMO
(ELUMO) of compounds 1—3 were estimated from the data
obtained by cyclic voltammetry (Fig. 2). In addition, the
HOMO and LUMO energies were calculated using the
density functional theory (DFT) (see Table 1).
fragment of the molecule, while at the LUMO+1 level the
electron density is also distributed over the nitrogen atom
and over the pyrimidine or fluorophenyl substituents at
the nitrogen atoms of pyromellitic diimide (see Fig. 3). As
it was expected, the introduction of the pyrimidine frag-
ment into the chromophore structure resulted in an de-
crease in the HOMO energy by –3.75 eV and a decrease
in the optical bandgap value to 2.99 eV as compared with
the corresponding parameters determined for the fluorine-
containing derivatives of pyromellitic diimide.
Thus, the N,N´-disubstituted derivatives of pyro-
mellitic diimide, two of which were not described previ-
ously, were synthesized in this work. Their electronic
absorption spectra were recorded, the electrochemical
properties were studied by the CV method, and the ener-
gies of the frontier orbitals were estimated. The quantum
chemical calculations of the main energy characteristics
of molecules of the synthesized compounds were per-
formed. It is shown experimentally and by the quantum
Diimide 1 containing two electron-withdrawing pyr-
imidine cycles (see Table 1) has the lowest LUMO energy
calculated from the experimental data (ELUMO = –3.75 eV).
The close ELUMO values equal to –3.57 and –3.58 eV were
obtained for diimides 2 and 3, respectively, containing
fluorinated phenyl rings at the nitrogen atom. These val-
ues of the LUMO energies are confirmed by the quantum
chemical calculations: ELUMO = –3.49 (1) and –3.44 eV
(compounds 2 and 3). According to the experimental data,
carboxydiimides 1—3 have the deep-lying HOMO, which
was also confirmed by the quantum chemical calculation
(see Table 1). The energies of the neighboring HOMO and
HOMO–1 orbitals, as well as those of LUMO and
LUMO+1, were shown to be very close (degenerated)
(Fig. 3). According to the quantum chemical calculations,
the electron density of the LUMO is localized on the
naphthalene fragment and carbonyl group of the imide
Table 1. Optical characteristics and the HOMO/LUMO energy values (E) for compounds 1—3
opt
Compound
mах/nm
onset
/nm
Eg
–ЕHOMO/eV
experimenta calculationb
ЕLUMO/eV
experimenta calculationb
E
/eV
(/L mol–1 cm–1
)
/eV
1
2
3
293 (12760), 394 (890)
267 (16500)
414
345
352
2.99
3.59
3.52
6.74
7.16
7.10
7.87
7.16
7.58
3.75
3.57
3.58
3.49
3.44
3.44
4.38
3.72
4.14
267 (12950)
Notes: mах is the absorption band maximum,  is the molar absorption coefficient, onset is the absorption edge wavelength,31 and
Egopt is the optical bandgap value (Egopt = 1240/onset).32
a
red
red
Calculated by the CV data: ЕLUMO = [–e(Eonset – E1/2
+ 4.80)], where e is the electron charge, Eonset is the
Fc/Fc+vsAg/AgCl
onset reduction potential,31 E1/2
is the experimentally determined half-wave potential of the Fc/Fc+ pair vs Ag/Ag+
electrode33 equal to 0.68 V, and ЕHOMO
Fc/Fc+vs=AgЕ/ALgUCMl O – Eg
.
opt
b Data of quantum chemical calculations (PBE0-D3/Def2-TZVPD).

N,N´-Disubstituted pyromellitic dianhydride
Russ. Chem. Bull., Int. Ed., Vol. 69, No. 10, October, 2020
1947
E/eV
LUMO+1
–2.40 eV
–2.40 eV
LUMO
–2.34 eV
–3.44 eV
–3.49 eV
–3.54 eV
–7.58 eV
–7.87 eV
–7.89 eV
–7.16 eV
–7.31 eV
HOMO
–7.59 eV
HOMO–1
3
1
2
Fig. 3. Shapes of the frontier molecular orbitals of compounds 1—3 calculated by the PBE0-D3/Def2-TZVPD method (controlling
value of the isocontour 0.02 a.u.).
analysis was carried out on an STA 449 F1 Jupiter® instrument
chemical calculations that the synthesized N,N´-disub-
for simultaneous thermal analysis (Netzsch-Geratebau GmbH,
stituted carboxyimides have deep-lying LUMO and HOMO.
Germany) coupled with a QMS 403 C Aëolos® mass spectrom-
In addition, pyrimidine-containing pyromellitic diimide
eter using DSC/TG pan Al2O3 crucible, and the heating rate was
is characterized by a deeper-lying LUMO (–3.75 eV),
5 C min–1. Quantum chemical calculations were performed at
a higher-lying HOMO (–6.74 eV), and a narrower band-
the PBE0-D3/Def2-TZVPD level in a DMF medium using the
gap (2.99 eV) than pyromellitic diimides containing fluoro-
Firefly program partially based on the initial code of the GAMESS
phenyl substituents.
system (US) using a PSU-Kepler supercomputer.
2,6-Bis(4,6-dimethylpyrimidin-2-yl)pyrrolo[3,4-f]isoindole-
1,3,5,7(2H,6H)-tetraone (1). A mixture of pyromellitic dian-
hydride (0.18 g, 0.8 mmol) and 2-amino-4,6-dimethylpyrimidine
(0.2 g, 1.6 mmol) in glacial AcOH (10 mL) was refluxed for 12 h.
The reaction mixture was cooled down to room temperature and
poured to water, and the formed precipitate was filtered off,
washed with water on the filter, and dried in air. The product was
recrystallized from DMF. The yield of compound 1 as a yellow
crystalline substance was 0.22 g (65%), m.p. 235 C. Found (%):
C, 61.41; H, 3.82; N, 19.04. Calculated (%): C, 61.68; H, 3.76;
N, 19.62. 1Н NMR (DMSO-d6), : 2.25 (s, 12 H, 4 CH3); 6.46
(s, 2 H, Pyrim), 8.16 (s, 2 H, PDI). 13С NMR (DMSO-d6), :
22.8, 108.9, 130.2, 134.9, 161.51, 166.8, 167.1. UV (DMSO),
mах/nm (/L mol–1 cm–1): 293 (12 750), 394 (890).
Experimental
1Н and 13С NMR spectra were recorded on a Bruker Avance
Neo IIIHD spectrometer (400 MHz) using Me4Si as the internal
standard. The signals from the pyrimidine cycle protons are
designated as Pyrim, and the signals of the pyromellitic diimide
protons are designated as PDI. Elemental analysis was carried
out using a CHNS-932 LECO Corp analyzer. UV spectra were
recorded on a Shimadzu UV-2600 UV-VIS spectrophotometer
using a concentration of the solutions of 10–5 mol L–1. Electro-
chemical studies were carried out at room temperature on
a Potentiostat/Galvanostat/ZRA Interface 1000 in a standard
three-electrode cell using a glassy carbon working electrode, an
auxiliary platinum electrode (wire, ERL-02), and silver chloride
reference electrode. A DMF—CH2Cl2 (1 : 4) mixture ser-
ved as the solvent, and Et4NClO4 was used as the supporting
The thermal decomposition of the samples occurred in two
stages. A mass loss of 28.6% of the sample weight occurred in an
endothermal range of 180—270 C. The peak of the decomposi-
tion rate was 11% per min and was observed at 233 C. In a range
of 270—410 C, the sample underwent endothermal decomposi-
electrolyte (Сsup = 0.1 mol L–1, Сcompd = 1•10–3 mol L–1
potential sweep rate (vscan) = 100 mV s–1). Thermogravimetric
,

Komissarova et al.
1948
Russ. Chem. Bull., Int. Ed., Vol. 69, No. 10, October, 2020
tion with a mass loss of 49.5%. The peak of the decomposition
rate in this temperature range was observed at 384 C (11% per
min). The further mass loss (11.5%) occurred in a range of
410—540 C and corresponded to the decomposition of the
carbonized residue.
Synthesis of compounds 2 and 3 (general procedure). A mix-
ture of pyromellitic dianhydride (0.28 g, 1.3 mmol), the corre-
sponding fluorine-substituted aniline (2.6 mmol), and anhydrous
DMF (10 mL) was refluxed for 12 h. The reaction mixture was
cooled down to room temperature and poured to water, and the
formed precipitate was filtered off, washed with water on the
filter, dried in air, and recrystallized from EtOH.
2,6-Bis(4-fluorophenyl)pyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-
tetraone (2). The yield of compound 2 as a light green crystalline
substance was 0.35 g (68%). The physicochemical and spectral
characteristics coincide with the previously published values.27,28
UV (DMSO), mах/nm (/L mol–1 cm–1): 267 (16 500).
2,6-Bis(2,3,5,6-tetrafluorophenyl)pyrrolo[3,4-f]isoindole-
1,3,5,7(2H,6H)-tetraone (3). The yield of compound 3 as a light
yellow crystalline substance was 0.46 g (70%), m.p. 274 C.
Found (%): C, 51.41; H, 0.95; N, 5.06. Calculated (%): C, 51.58;
H, 0.79; N, 5.47. 1Н NMR (DMSO-d6), : 8.11—8.20 (m, 2 H,
2 С6F4H); 8.38 (s, 1 H, PDI); 8.62 (s, 1 H, PDI). 13С NMR
(DMSO-d6), : 108.7, 116.7, 118.2, 119.8, 136.1, 136.8, 137.8,
162.5, 162.8, 165.8. UV (DMSO), mах/nm (/L mol–1 cm–1):
267 (12 950).
The thermal decomposition of the sample proceeds in three
stages. A mass loss of 2.8% of the sample weight occurs in an
endothermic range of 110—220 C along with the removal of the
solvent and low-molecular-weight impurities. A minor broad
endoeffect (H  2 J g–1) is observed at 218 C, after which
(in a range of 220—390 C) the sample endothermally de-
composed with a mass loss of 84.9%. The melting of the sample
(H  90 J g–1) is observed at 274 C in the DSC curve. At this
stage, a mass loss of 10% of the sample weight occurs at 295 C.
The maximum decomposition rate is observed at 350 C (16%
per min). The further mass loss in a range of 390—540 C cor-
responds to the decomposition of the carbonized residue (4%).
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Received December 24, 2019;
in revised form January 29, 2020;
accepted March 2, 2020