Synthesis and combustion catalytic activity of ferrocene-based energetic compounds

Article abstract of DOI:10.1002/jhet.3994

Ammonium perchlorate (AP) is a common oxidizer in composite solid rocket propellants due to its excellent burning characteristics, good processability, and storability. Owing to their outstanding catalytic effects, ferrocene, and its derivatives have become the most widely used burning rate catalysts (BRCs). The addition of ferrocene and its derivatives to AP rendered performance optimization. In this study, azole-based ferrocenyl compounds were successfully synthesized. The compounds were characterized by single-crystal X-ray diffraction, UV-vis spectroscopy, and other techniques. The thermal degradation of AP catalyzed by these compounds was evaluated by differential scanning calorimetry and thermogravimetric analysis. Results revealed that the decomposition peak temperature of AP dramatically decreases and that the released heat of AP significantly increases with the new compounds as additives. Hence, the six azole-based ferrocenyl BR catalysts are favorable for the combustion catalytic activity.

Full text of DOI:10.1002/jhet.3994

Received: 8 February 2020
DOI: 10.1002/jhet.3994
Revised: 17 March 2020
Accepted: 21 March 2020
A R T I C L E
Synthesis and combustion catalytic activity of
ferrocene-based energetic compounds
Shiqi Huang1 | Rong Yang1 | Jiaodan Wang1 | Shuai Chang2
|
Xiaofeng Gou1
| Chengwen Hua1 | Junlong Zhao1
1Key Laboratory of Synthetic and Natural
Functional Molecule Chemistry of
Ministry of Education, College of
Chemistry and Materials Science,
Northwest University, Shaanxi, China
2School of Physics, Northwest University,
Shaanxi, China
Abstract
Ammonium perchlorate (AP) is a common oxidizer in composite solid rocket
propellants due to its excellent burning characteristics, good processability,
and storability. Owing to their outstanding catalytic effects, ferrocene, and its
derivatives have become the most widely used burning rate catalysts (BRCs).
The addition of ferrocene and its derivatives to AP rendered performance opti-
mization. In this study, azole-based ferrocenyl compounds were successfully
synthesized. The compounds were characterized by single-crystal X-ray diffrac-
tion, UV-vis spectroscopy, and other techniques. The thermal degradation of
AP catalyzed by these compounds was evaluated by differential scanning calo-
rimetry and thermogravimetric analysis. Results revealed that the decomposi-
tion peak temperature of AP dramatically decreases and that the released heat
of AP significantly increases with the new compounds as additives. Hence, the
six azole-based ferrocenyl BR catalysts are favorable for the combustion cata-
lytic activity.
Correspondence
Junlong Zhao, Key Laboratory of
Synthetic and Natural Functional
Molecule Chemistry of Ministry of
Education, College of Chemistry and
Materials Science, Northwest University,
Shaanxi 710127, China.
Email: zhaojunlong327@163.com
Funding information
the National Natural Science Foundation
of China, Grant/Award Number:
21703171; the Natural Science Basic
Research Plan in Shaanxi Province of
China, Grant/Award Number:
2018JQ2043; the Foundation of Shaanxi
Educational Committee, Grant/Award
Number: 19JS063
1 | INTRODUCTION
widely used in several fields such as medicine,[9] biology,
agriculture, catalysis,[10] and materials;[11] especially, Fc-
Solid propellants are important in the military and aero-
space fields.[1] An excellent solid propellant must exhibit
an extremely stable burning rate between certain bound-
aries at a given operating pressure, a low pressure index,
and a low characteristic signal during burning.[2] The
addition of a burning rate catalyst (BRC) into a solid
propellant is key to achieving these goals.[3] Several BRCs
have been reported, including metal complexes,[4] carbon
black, and related compounds,[5] transition-metal
oxides,[6] nanomaterials,[7] and ferrocene and its deriva-
tives.[8] Ferrocene (Fc) and its derivatives have been
based BRCs have attracted considerable attention due to
their excellent BRC activity, broad range of BR adjust-
ments, and facile compatibility with an organic binder.
Their efficient BR catalytic performance is derived from
highly active Fe2O3, which decomposes during combus-
tion.[12] In recent years, several nitrogen-rich ferrocene
compounds have been synthesized. These compounds
not only exhibit an excellent combustion catalytic
activity and favorable mechanical performance but also
exhibit a low pressure index.[13] In 2013, Bian and co-
workers[14] have prepared complexes with 1,2,3-(NH)-
triazolylferrocene derivatives and copper(II) and zinc(II),
and their catalytic performance for the thermal
Shiqi Huang and Rong Yang contributed equally to this study.
J Heterocyclic Chem. 2020;1–8.
wileyonlinelibrary.com/journal/jhet
© 2020 Wiley Periodicals LLC
1

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HUANG ET AL.
decomposition of ammonium perchlorate (AP) has been
investigated by thermogravimetric analysis and differen-
tial thermal analysis. Results revealed that the com-
plexes exhibit a distinct effect on the high-temperature
decomposition (HTD) of AP, and the temperature shifts
down to 32.3ꢀC to 61.9ꢀC. In 2015, Zhang[15] has intro-
duced novel ionic compounds synthesized using
1-(ferrocenylmethyl)-imidazolium cations and the poly-
cyano anion, and the results revealed that the decompo-
sition temperature span of the AP is narrowed; HTD
peaks shift down to 74.2ꢀC to 120.7ꢀC; and the release
heat is 1156.6 to 2164.0 J/g. In 2016, Zhang[16] has used
alkali hydroxides or carbonates to deprotonate
5-ferrocenyl-1H-tetrazole, affording the corresponding
metal salts. Results revealed that the complexes exhibit
a distinct effect on HTD and HTD peaks with a down-
ward shift to 61.3ꢀC to 85.2ꢀC, and the release heat is in
the range of 1339.9 to 1946.3 J/g. In 2019, Zhang and co-
workers[17] synthesized more than 20 ferrocene com-
pounds, which were synthesized by copper-catalyzed
azide alkyne cycloaddition reactions. Results revealed
that the new ferrocene-based compounds have high
thermal stability and the new ferrocenyl compounds
exhibit high catalytic activity in the thermal degradation
of AP during their combustion. Energetic combustion
catalysts are very distinctive in many types of BRCs.[18]
Energetic compounds have been widely used in solid
propellants due to their high nitrogen content, high ten-
sion, high heat of formation, facile oxygen balance, and
environmental friendliness.[19] Novel high-nitrogen
energetic derivatives such as azoles, dioxazines, and pol-
ynitro compounds have provided a new research direc-
tion for energetic compounds in new types of BRCs.
Generally, novel BRCs should exhibit a well-controlled
BR of propellants, excellent mechanical performance,
low signal characteristics, and environmental friendli-
ness. As typical nitrogen-rich energy compounds, azoles
comprise several N N bonds and C N bonds. They can
maintain a high energy level, high density, and good
thermal stability, in addition, they can increase the
nitrogen content and provide energy for solid propel-
lants. In this study, ferrocenyl-based energetic com-
pounds and a ferrocenyl-based energetic oligomer are
prepared using two novel BR catalysts, where the
ferrocenyl groups are modified with azoles: Class A,
2 | RESULTS AND DISCUSSION
2.1 | Single-Crystal Determination
To obtain structural information about the new com-
pounds, their single crystals were grown, but only single
crystals of two compounds A1 and B2 were successfully
collected and characterized by single X-ray crystallogra-
phy. A1 exhibited a cis structure and crystallized in the
monoclinic space group P21/c (Figure 1). The pyrazole
ring, carbonyl group, and ferrocene Cp rings were almost
present in the same plane. The distances of C N bonds
(C15-N3, C6-N1) generated by 1,10-ferrocenedicarbonyl
chloride and pyrazole were 1.405(5) and 1.401(5) Å,
respectively. The distance between two pyridines was
3.5749 Å, with strong π-π stacking interactions.
B1 crystallized in the hexagonal space group P65. The
comparison of B2 with A1 revealed different structures.
1,2,4-Triazole and the Cp ring were almost present in the
vertical plane. The distances of C N bonds (C14-N5,
C6-N1) generated by 1,10-ferrocenedicarbonyl chloride
and 4-amine-1,2,4-triazole were 1.351(7) and 1.365(7) Å,
respectively. The C N bond of A1 was shorter than that
of B1, so the bond of A1 is more stable. B2 and water
molecules participated in intramolecular strong hydrogen
bonding [N5-H6ꢁꢁꢁO4, O3-H3AꢁꢁꢁO1, O4-H4BꢁꢁꢁN4, and
N1-H1ꢁꢁꢁN8] to form a two-dimensional supramolecular
structure. The presence of a large number of hydrogen
bonds in the molecules led to stable compounds
(Figure 2).
2.2 | UV-vis absorption spectra
Figure 3 shows the UV-vis absorption spectra of all com-
pounds in DMSO. Absorption bands were observed near
280 nm for A1-A3, corresponding to π-π* transitions of
comprising
a nitrogen-containing heterocyclic ring
directly linked to 1,1-ferrocenyl methanone and class B,
where the amino group on the nitrogen-containing het-
erocyclic ring is connected to 1,10-ferrocenyl methanone.
In addition, catalytic effects of the compounds on the
thermal decomposition of AP were investigated to con-
firm their potential BRC activities.
FIGURE 1 Single-crystal structure of compound A1

HUANG ET AL.
3
FIGURE 2 a, Single-crystal structure of compound
B2, b, two-dimensional supramolecular structure of B2
(The green dashed line represents the hydrogen bond.)
FIGURE 3 UV–vis spectra of compounds A1-A3
FIGURE 4 UV–vis spectra of compounds B1-B3
Cp rings and absorption bands near 350 nm cor-
responded to the MLCT transition. Strong, broad bands
observed from 320 to 420 nm corresponded to n-π* transi-
tions of the carbonyl group, which red-shifted due to the
conjugation of the carbonyl group with nitrogen-
containing heterocycles Broad, weak bands ranging from
400 to 550 nm corresponded to d-d transitions of the
Fe atom.
Absorption bands near 280 nm for B1-B3 cor-
responded to π-π* transitions of Cp rings and absorption
bands near 350 nm corresponded to the MLCT transition.
Broad, weak bands in the range from 400 to 550 nm

4
HUANG ET AL.
corresponded to the d-d transitions of the Fe atom
(Figure 4).
B1 exhibited a slow weight-loss process, where it was
stabilized before 143ꢀC. With the increase in the tempera-
ture, a mass loss of 44.7% at 497ꢀC was observed due to
the dissociation of the amide bond. B2 was divided into
two stages. The first stage was observed at 158ꢀC to
257ꢀC, with a mass loss of 31.4%, corresponding to the
dissociation of the amide bond. The second mass loss of
~25% was observed at 256ꢀC to 441ꢀC, corresponding to
the collapse of ferrocene. B3 exhibited a slow weight-loss
process at 208ꢀC to 475ꢀC, with a mass loss of ~62% cau-
sed by the collapse of ferrocene.
2.3 | Thermal stability studies of
ferrocenyl-based energetic compounds
Thermal stability is an important property for energetic
catalytic materials, where the effect of materials under a
specific temperature program can be examined. Figures 5
and 6 show the TG curves of A1-A3 and B1-B3, respec-
tively. A1 and A2 exhibited three weight-loss processes,
first starting from 118ꢀC to 119ꢀC and ended at 171ꢀC;
second at 186ꢀC with a mass loss of 7.1%; and third at
11.1%, possibly related to the volatilization of water. The
second weight loss was observed from 215ꢀC, 230ꢀC, and
ended at 328ꢀC, 457ꢀC, with mass losses of ~18.5% and
19.6%, related to the dissociation of the amide bond. The
third weight loss was observed at 380ꢀC, from 671ꢀC to
601ꢀC, 761ꢀC with mass losses of ~14.3% and ~13.0%,
probably related to the collapse of ferrocene. The first
stage for A3 was observed at 169ꢀC to 197ꢀC, displaying a
rapid weight loss process of ~36.2% due to the dissocia-
tion of the amide bond; the second stage from 458ꢀC to
662ꢀC, with a weight-loss process of ~16.7% caused by
the collapse of ferrocene. The final residues for each com-
pound should be Fe2O3 and carbon. The thermal decom-
position of class A was a rapid process, where the amide
bond was first dissociated during the temperature
increase. With the further increase in the temperature,
ferrocene collapsed. In the five-membered aromatic het-
erocyclic system, all nitrogen atoms belonged to pyri-
dines, with the aromatic ring being the electron-deficient
system. With the increase in the amount of nitrogen
atoms, the conjugated effect became increasingly weaker,
and the stability of the compound deteriorated.
2.4 | Catalytic effect on the
decomposition of ammonium perchlorate
AP is the most widely used high-energy oxidant in solid
propellants. The combustion of a composite solid propel-
lant is strongly dependent on the thermal decomposition
of AP. Generally, the catalytic performance of BRCs in a
solid propellant is typically evaluated by their effects on
the thermal decomposition of AP according to DSC. The
DSC curve for the thermal decomposition of pure AP rev-
ealed one endothermic peak and two exothermic peaks
(Figure 7). The endothermic peak at 242ꢀC corresponded
to the morphological transition from an orthorhombic to
a cubic phase of AP. The first exothermic peak at 337 cor-
responded to low-temperature decomposition (LTD). The
second exothermic peak at 442ꢀC corresponded to HTD.
The mass ratio of the ferrocene energetic compound to
AP was 1:3. The morphological-transition endothermic
peak of A1-A3 disappeared, and two exothermic peaks
were observed; both LTD and HTD stages of AP were sig-
nificantly changed by the inclusion of additives
(Figure 8). The additive led to the narrowing of the
decomposition temperature span of AP; two exothermic
FIGURE 5 TG curves of compounds A1-A3
FIGURE 6 TG curves of compounds B1-B3

HUANG ET AL.
5
FIGURE 9 DSC curves of B1-B3
FIGURE 7 DSC curve of pure AP
decreased to ~153ꢀC. The released heat values for AP
added B1 and B2 were 2493 J/g and 2895 J/g, respec-
tively. B3 exhibited two closed peaks with LDT and HDT
peaks, which shifted down to ~70ꢀC and 151ꢀC, respec-
tively, with a released heat of 2589 J/g. With the increase
in the nitrogen content, the energy released by these
three compounds also increases. At the same nitrogen
content, irrespective of the presence of absence of the
methyl group, heat release was affected, containing
methyl can decrease heat.
3 | CONCLUSIONS
In summary, six azole-based ferrocenyl compounds were
successfully synthesized and characterized. Single-crystal
X-ray diffraction analysis and other characterization tech-
niques confirmed the molecular structures of the pre-
pared products. These azole-based ferrocenyl compounds
exhibited high catalytic activity for the thermal degrada-
tion of ammonium perchlorate. Both A and B com-
pounds advance the thermal decomposition peak
temperature of AP, but A compounds advance more. In
terms of releasing heat, Class B compounds release more
concentrated heat than class A compounds, because
Class A compound is more rigid than Class B compound,
so the molecular structure is more likely to collapse after
heating, interacting with AP, and forming Fe atoms
when exposed the highly active ferric oxide catalyzes the
further decomposition of AP.
FIGURE 8 DSC curves of A1-A3
peaks in A1 were combined into one broad exothermic
peak; and two exothermic peaks of A2 did not completely
merge, but the exothermic peak was the sharpest. The
exothermic peak of A3 was the most decentralized. Thus,
these new compounds exhibit a distinct positive catalytic
effect on the LDT and HDT stages of AP. From the
released heat of AP added into A1 (2875 J/g), A2 (2931 J/
g), and A3 (2976 J/g), the catalytic activity of A1 was
weaker than that of A2, and that of A2 was weaker than
that of A3. With the increase in the nitrogen content, the
three compounds released more heat. B1, B2, and B3
exhibited no effect on the morphological transition peak,
and the temperature was constant at 244ꢀC to 247ꢀC
(Figure 9). The two exothermic peaks in B1 and B2 at
300ꢀC and 289ꢀC, respectively, combined into one sharp
exothermic peak. Compared to pure AP, B1 LDT peaks
shifted up to ~37ꢀC, HDT peaks shifted down by ~142ꢀC;
B2 LDT peaks shifted down by ~48ꢀC, and HDT peaks
Experimental Section Caution: Azole compounds are
hazardous materials, and explosion may occur under cer-
tain conditions. Necessary safety precautions (such as
safety glasses, a face shield, and a plastic spatula) should
be used during the experiment, especially during the
large-scale preparation of such compounds.

6
HUANG ET AL.
3.1 | Materials and instruments
3.4 | Synthesis of new compounds
All commercially available reagents were used without
any purification. The IR spectrum of compounds was
recorded by the KBr pellet method on a Bruker FTIR
spectrometer. NMR spectra were recorded on a Bruker
AVANCE III-400 MHz spectrometer and
a Bruker
Ascend 400 MHz spectrometer. TG and DSC analyses
were performed on a Netzsch STA 449C instrument using
nitrogen gas as the atmosphere. First, 1 to 3 mg of sam-
ples was added into the crucible for measurements. Spe-
cific procedures were described as follows: Standard
weights were used for the calibration of the balance. At
25ꢀC to 800ꢀC, the baseline was calibrated by using an
empty crucible at a heating rate of 20ꢀCꢁmin−1 and a
nitrogen gas flow rate of 10 mLꢁmin−1
.
3.2 | Synthesis
For the preparation of ferrocene dicarbonyl chloride, acyl
chloride was easily hydrolyzed; hence, the solvent needs
to be dried, and the reaction is carried out under dry con-
ditions to increase the yield. Acetonitrile and
triethylamine were selected as the solvent and acid-
binding agent, respectively, and the temperature was
maintained at 40ꢀC during the reaction.
FDC was prepared by using an optimized procedure.[21]
Synthetic procedures for compounds A1-A3 as well as
B1-B3 were similar; hence, the preparation for A1 is
shown as an example. First, 15 mL of acetonitrile with
1,10-ferrocenedicarbonyl chloride (15.547 g, 0.05 mol)
was added with stirring into a 50 mL round-bottom flask
with containing acetonitrile (15 mL) and 1H-pyrazole
(6.808 g, 0.1 mol). Second, the mixed solution was stirred
at 40ꢀC for 10 hours. All procedures are monitored by
TLC. The precipitate was collected by filtration and dried
at 40ꢀC under vacuum.
3.3 | Synthesis of ferrocene dicarbonyl
chloride (FDC)
FDC was synthesized by an optimized procedure.[20] First,
1,10-ferrocenedicarboxylic acid (2.74 g, 0.01 mmoL) was
dissolved in
a dry dichloromethane (50 mL) and
dimethylformamide (0.15 mL) solution. After adding
20 mL of dry dichloromethane into a constant-pressure
dropping funnel, 3 mL of oxalyl chloride was rapidly
added. This mixed solvent was controlled to drip within
0.5 hour. Next, the mixture solution was stirred at 25ꢀC for
0.5 hour, followed by heating at reflux for 10 hours. All
procedures were monitored by TLC. The precipitate was
collected and dried by reduced pressure distillation. To
obtain a high-purity product, the precipitate was rec-
rystallized using a mixture of 50 mL of petroleum ether-
dichloromethane(petroleumether:dichlorome-thane=1:1),
affording a red solid in 95% yield.
3.4.1 | 1,10-Ferrocenylbis ((1H-pyrazol-
1-yl) methanone) (A1)
The product was obtained though recrystallization from
acetonitrile, as a red blocks, yield: 80%, m.p. 119ꢀC to
121ꢀC; 1H NMR (400 MHz, DMSO-d6) δppm: 8.39 (s, 2H,
CH), 7.81 (s, 2H, CH), 6.56 (s, 2H, CH), 5.38 (s, 4H,
C5H4), 4.77 (s, 4H, C5H4); 13C NMR (100 MHz, DMSO-

HUANG ET AL.
7
d6) δppm: 168.2 (CO), 144.7 (NCH), 129.8 (NHCH), 109.5
(NHCHCH), 75.2, 74.5, 73.1 (C5H4). IR (KBr): 3120, 2880,
2642, 2556, 1687, 1505, 1410, 1295, 1171, 1027, 913, 827,
731 cm−1. HRMS (ESI) m/z calculated for C18H14FeN4O2
[M + Na+]: 397.0364; found: 397.0354.
3.4.4 | N,N0-bis(4H-1,2,4-triazol-4-yl)
ferrocenecarbo-xamide (B1)
The product was obtained though recrystallization from
the mixture (VEtOH: VH2O = 1:1), as a red needles, yield:
95%, m.p. 240ꢀC to 242ꢀC; 1H NMR (400 MHz, DMSO-d6)
δppm: 11.61(s, 2H, NH), 8.72(s, 4H, CH), 5.06 (s, 4H,
C5H4), 4.70 (s, 4H, C5H4); 13C NMR (100 MHz, DMSO-
d6) δppm: 168.8 (CO), 144.3 (NCH), 73.9, 73.2, 71.0
(C5H4). IR (KBr): 3425, 3196, 3120, 1659, 1496, 1391,
1286, 1208, 1123, 1046, 1066, 923, 875, 817 cm−1. HRMS
(ESI) m/z calculated for C16H14FeN8O2 [M + H+]:
407.0667; found: 407.0678.
3.4.2 | 1,10-Ferrocenylbis ((1H-
1,2,4-triazol-1-yl) methanone) (A2)
The product was obtained though recrystallization from
acetonitrile, as a red blocks, yield: 83%, m.p. 160ꢀC to
162ꢀC; 1H NMR (400 MHz, DMSO-d6) δppm: 9.33 (s, 2H,
CH), 8.25 (s, 2H, CH), 5.39 (s, 4H, C5H4), 4.89 (s, 4H,
C5H4); 13C NMR (100 MHz, DMSO-d6) δppm: 166.8
(CO), 153.6 (CONNCH), 145.8 (CONCH), 75.7, 75.3, 72.2
(C5H4). IR (KBr): 3110, 2880, 2642, 2556, 1678, 1487,
1440, 1305, 1162, 1037, 904, 827, 741 cm−1. HRMS (ESI)
m/z calculated for C16H12FeN6O2 [M + Na+]: 399.0269;
found: 399.0278.
3.4.5 | N,N0-bis(3-amino-1H-1,2,4-triazol-
5-yl)ferrocenecarboxamide (B2)
The product is obtained from the reaction without fur-
ther purification, as a red solid, yield: 93%, m.p. 136ꢀC
1
to 138ꢀC; H NMR (400 MHz, DMSO-d6) δppm: 4.70 (s,
4H, C5H4), 4.46 (s, 4H, C5H4); 13C NMR (100 MHz,
DMSO-d6) δppm: 171.2 (CO), 73.9, 72.9, 72.3 (C5H4).
IR(KBr): 3408, 3129, 2633,S 2548, 1689, 1495, 1409,
1301, 1172, 1044, 914, 840, 753 cm−1. HRMS (ESI) m/z
calculated for C16H16FeN10O2 [M + H+]: 437.0885;
found: 437.0887.
3.4.3 | 1,10-Ferrocenylbis ((1H-tetrazol-
1-yl) methanone) (A3)
The product was obtained though recrystallization from
acetonitrile, as a red blocks, yield: 70%, m.p. 169ꢀC to
1
171ꢀC; H NMR (400 MHz, DMSO-d6) δppm: 10.13 (s,
2H), 5.45 (s, 4H, C5H4), 5.07 (s, 4H, C5H4); 13C NMR
(100 MHz, DMSO-d6) δppm: 165.4 (CO), 144.1 (NCH),
76.8, 75.2, 71.8 (C5H4). IR(KBr): 3120, 2871, 2642, 2556,
1677, 1486, 1295, 1151, 1018, 913, 827, 741 cm−1. HRMS
(ESI) m/z calculated for C14H10FeN8O2 [M + Na+]:
401.0174; found: 401.0179.
3.4.6 | N,N0-bis(1-methyl-1H-tetrazol-
5-yl)ferroce-necarboxamide (B3)
The product was obtained though recrystallization from
the mixture(VEtOH: VH2O = 1:1), as a yellow needles,
yield: 94%, m.p. 142ꢀC to 144ꢀC; 1H NMR (400 MHz,
DMSO-d6) δppm: 4.71 (s, 4H, C5H4), 4.47 (s, 4H, C5H4),
3.76 (s, 6H, CH3); 13C NMR (100 MHz, DMSO-d6) δppm:
171.7 (CO), 155.3 (NHC), 73.9, 73.0, 71.8 (C5H4), 32.3
(CH3). IR (KBr): 3320, 3138, 2984, 1668, 1591, 1477, 1285,

8
HUANG ET AL.
1171, 1085, 894, 741 cm−1. HRMS (ESI) m/z calculated
for C16H16FeN10O2 [M + H+]: 437.0885; found: 437.0887.
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The financial support by the National Natural Science
Foundation of China (project 21703171), the Natural Sci-
ence Basic Research Plan in Shaanxi Province of China
(project 2018JQ2043), and the Foundation of Shaanxi
Educational Committee (project 19JS063) is gratefully
acknowledged.
ORCID
Xiaofeng Gou https://orcid.org/0000-0002-2946-9457
Junlong Zhao https://orcid.org/0000-0002-6204-8929
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article.
How to cite this article: Huang S, Yang R,
Wang J, et al. Synthesis and combustion catalytic
activity of ferrocene-based energetic compounds.
J Heterocyclic Chem. 2020;1–8. https://doi.org/10.
1002/jhet.3994