Dielectric phase transition triggered by the order-disorder transformation of cyclopropylamine in a layered organic-inorganic halide perovskite

Article abstract of DOI:10.1039/C8TC03517B

Cyclic organic amines are emerging as excellent building blocks to assemble organic-inorganic hybrid phase transition materials due to their flexible cyclic structure. Herein, we used a three-membered ring organic amine, cyclopropylamine, assembling a layered organic-inorganic hybrid dielectric phase transition compound ([C₃H₅NH₃]₂[CdCl₄], CPA) that displays a remarkable switchable dielectric response induced by an order-disorder transformation of the organic moiety. More specifically, the dielectric constant of CPA can be tuned between high- and low-dielectric states at ～273 K, which demonstrates its potential application in a switchable dielectric field. In addition, theoretical analysis of electronic band structures suggests that CPA exhibits a direct-band-gap with the value of 5.20 eV. This solid-state structural phase transition triggered by ordering of a three-membered ring organic amine is reported for the first time, and it highlights a new potential strategy to design switchable dielectric materials.

Full text of DOI:10.1039/C8TC03517B

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ISSN 2050-7526
PAPER
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Nguyên T. K. Thanh, Xiaodi Su et al.
Fine-tuning of gold nanorod dimensions and plasmonic properties using
the Hofmeister effects
rsc.li/materials-c

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JPolueransael odfoMnaotetraiadljsuCsht emmairsgtriynsC
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DOI: 10.1039/C8TC03517B
Journal Name
ARTICLE
Dielectric Phase Transition Triggered by the Order-disorder
Transformation of Cyclopropylamine in a Layered Organic-
inorganic Halide Perovskite
Received 00th January 20xx,
Accepted 00th January 20xx
Shiguo Han,ab Xitao Liu,a Jing Zhang,a Chengmin Ji,a Zhenyue Wu,ab Kewen Tao,a Yuyin Wang,ab
Zhihua Sun*a and Junhua Luo*a
DOI: 10.1039/x0xx00000x
www.rsc.org/
Cyclic organic amines are emerging as excellent building blocks to assemble organic-inorganic hybrid phase transition
materials due to their flexible cyclic structure. Herein, we used three-membered ring organic amine, cyclopropylamine,
assembling a layered organic-inorganic hybrid dielectric phase transition compound ([C3H5NH3]2[CdCl4], CPA) which displays
remarkable switchable dielectric response induced by order-disorder transformation of organic moiety. More specifically,
the dielectric constant of CPA can be tuned between high- and low-dielectric states at ~273 K, which discloses its potential
application in switchable dielectric field. In addition, theoretical analysis of electronic band structure suggests that CPA
exhibit direct-band-gap with the value of 5.20 eV. This solid-state structural phase transition triggered by ordering of three-
membered ring organic amine should be the first report, which highlights a new potential strategy to design switchable
dielectric materials.
studies have been focused on the applications of such materials.
Among them, cyclic organic amines have recently been
considered as the most promising candidates for designing
1. Introduction
Dielectric phase transition materials that can switch their
dielectric constants between the low and high states under
external temperature stimuli, have been receiving
extraordinary interest in the past few years because of their
potential application in the field of information storage, data
communication, signal processing and memory devices, etc.1-4
As the dielectric constant ε (ε = ε′ − iε″, where ε″ and ε′ are the
imaginary and real parts, respectively) is closely related to the
degree of electric polarizability of a material, the dipolar
motions play an important part in dielectric phase transition.5
From the microscopic point of view, this tunable dielectric
permittivity comes from the reorientation transformation of
structural components between dynamic (motional) and static
(frozen) states, corresponding to a high-temperature phase
(HTP) and low-temperature phase (LTP), respectively, which can
be achieved by a structural phase transition.6-8
phase transition materials. For instance, Xiong et al. used
cyclopentylamine assembled an ABX3 type ferroelectric phase
transition compound, [C5H9NH3][CdCl3], whose dielectric
constant changes from 10 to 70 (f = 100 kHz) induced by the
structural transition of its flexible organic ring building blocks.12
In addition, we have reported a layered perovskite-type
ferroelectric making use of the reaction of cyclohexylamine and
PbBr2, [C6H12NH3][PbBr4], which exhibits excellent dielectric
switchable property (the values of ε′ show the changes from 20
to 400 at the frequency of 100 kHz).13 More recently, two
above-room-temperature dielectric switchable materials were
fabricated adopting seven-membered heterocyclic organic
amine.14-15 Introducing cyclic organic amine has been
considered as an effective strategy for designing dielectric
switchable devices. That is, cyclic organic amines are emerging
as excellent building blocks to design OIHPT compounds, which
might be attributed to its flexible cyclic structure. Numerous
researches have been reported in the study on synthesis OIHPT
materials based on five-, six- and seven-membered heterocycle
organic amine.16-23 Nevertheless, this kind of phase transition
compound synthesised containing three-membered ring
organic amines, such as cyclopropylamine, has never been
reported.
Organic-inorganic hybrid phase transition (OIHPT) materials
combine the outstanding merits of organic and inorganic
components. The organic parts provide the possibility of
dynamic behaviours, while inorganic framework offer
thermostability.9-11 Under this circumstance, considerable
a.State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the
Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, China.
b.University of Chinese Academy of Sciences, Beijing 10049, China.
Inspired by such results, we have tried to adopt three-membered
ring organic amines for assembling novel OIHPT materials and
successfully achieved an OIHPT compound, [C3H5NH3]2[CdCl4] (CPA,
*E-mail: sunzhihua@fjirsm.ac.cn; jhluo@fjirsm.ac.cn
† Electronic Supplementary Information (ESI) available: CIF file; simulated and
experimental XRD patterns; TG-DSC curves; ultraviolet-Vis diffuse reflectance
spectrometry; selected bond lengths and angles; CCDC 1827265–1827266. For ESI
and crystallographic data see DOI: 10.1039/x0xx00000x
+
where C3H5NH3 is cyclopropylamine), which features the two-
dimension layered perovskite framework constructed by corner-
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sharing CdCl6 octahedra. In particular, CPA displays remarkable Single-crystal X-ray diffractions were performed onViaewBArrtuickleeOrnlDin8e
dielectric switchable responses caused by structural phase transition Quesr/Venture diffractometer with Mo Kα rDaOdiIa: t1i0o.1n0(3λ9/=C80T.7C703A5)17aBt
at Tc = 273 K, which is attributed to the order-disordering of its different temperatures (100 K and 290 K). All of crystal data were
organic cyclic building blocks. That is, introducing three-membered performed by the Crystalclear software package (Rigaku, 2005).
ring organic amines could assemble organic-inorganic hybrid Crystal structure of CPA were processed by the direct method and
dielectric phase transition compound, which highlights a new then refined by the full-matrix least-squares refinements on F2,
effective strategy to design switchable dielectric materials. To the which use the SHELXLTL software package. Non-H atoms were
best of our knowledge, this should be the first report on the solid- refined anisotropically according to all reflections with I > 2σ (I) and
state structural phase transition triggered by ordering of three- all of hydrogen atoms were obtained geometrically.
membered ring organic amine.
2.7 Computational methods
2. Experimental section
First-principles density function theory (DFT) calculations were
performed by the plane-wave pseudopotential method
implemented in the Cambridge Sequential Total Energy Package
(CASTEP) software package The exchange-correlation potential was
2.1 Synthesis
All starting reagents and solvents used in experiment are of high
purity (AR grade) without any further purification. First of all,
cadmium chloride (CdCl2) salts were prepared by the reaction of
cadmium carbonate (1.72g, 0.01 mol) with excessive hydrochloric
acid (20 ml) in a cold bath. After stirring for 10minutes, add
appropriate cyclopropylamine (1.14g, 0.02 mol) to the bath. Then,
heat the mixed solution for 10 minutes to dissolve the sediment
thoroughly. Compound CPA was easily obtained by means of
temperature lowering method with the temperature lowing rate of
3 °C/day from saturated solution.
calculated using Perdew-Burke-Ernzerhof for solids (PBEsol)
functional within the generalized gradient approximation (GGA). The
interactions between the ionic cores and the electrons were
described by the norm-conserving pseudopotential. The following
orbital electrons were treated as valence electrons: Cd 4d10 5s2 4p6;
Cl 3s2 3p5; C 2s2 2p2; N 2s22p3 and H 1s1. The numbers of plane waves
included in the basis sets were determined by a cut-off energy 670
eV. The other parameters and convergent criteria were the default
values of CASTEP code.
3. Results and discussion
2.2 Podwer X-ray Diffraction (PXRD)
PXRD patterns data were collected in a Mini Flex 600 powder X-ray
diffractometer in the 2θ range of 5-45º with a step of 0.02.
2.3 Thermal measurements
Differential scanning calorimetry (DSC) and specific heat (Cp) analyses
were recorded using a NETZSCH DSC 200 F3 instrument. The
crystalline powder was put into aluminum crucible with the cooling
and heating rates of
5 K/min under nitrogen atmosphere.
Thermogravimetric-differential scanning calorimetry (TG-DSC)
analysis was carried out on a Netzsch STA 449C unit within the
temperature of 300–1150 K with a heating rate of 10 K min-1.
Fig.1 Temperature-dependent (a) DSC and (b) Cp curves of CPA
.
Single crystals of CPA were obtained adopting the solution-
processed method and the powder X-ray diffraction (PXRD)
patterns match well with simulated data confirm its phase
purity (Fig. S1). Reversible phase transition of CPA was
demonstrated by differential scanning calorimetry (DSC) and
specific heat (Cp) measurements. As depicted in Fig. 1, DSC curve
exhibits an endothermic/exothermic peak in the heating/cooling
mode at 274.5 K/269.5 K. The large thermal hysteresis (5 K) and
steep peak-like anomalies disclose the occurrence of first-order
phase transition in CPA. This result also resembles other
inorganic–organic hybrid phase transition compounds based on
various cyclic organic amines as shown in Table. S1. Moreover,
the entropy change calculated to be 5.67 J/mol K according to
the equation ΔS = ΔH/Tc. As a result, the value of N calculated to
be 1.98 on the basis of Boltzmann equation (ΔS = Rln 푁) and
such large value of N indicates CPA undergoes a typical order-
2.4 Dielectric measurements
Pressed-powder pellets covered by silver conducting glue were used
to measure dielectric constant of compound CPA on a Tonghui
TH2828A analyzer. The cooling/heating rate is 10 K/min with the
frequencies of 200/300 kHz, respectively.
2.5 Ultraviolet-visible Spectrometry
Ultraviolet–visible diffuse reflectance spectrometry was performed
on a PerkinElmer Lambda 950 UV-vis-IR spectrophotometer.
2.6 Single-crystal X-ray diffraction
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disorder structural phase transition.24 Furthermore, the CdCl6 octahedra displays a slight distortion, which can be deduced
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DOI: 10.1039/C8TC03517B
environmental stability was confirmed by PXRD analysis. Fig. S2 from the disparity of Cl-Cd-Cl bond angles and Cd-Cl bond lengths
discloses that CPA possesses outstanding phase stability, which
will be beneficial to its potential application. Besides, the TG-
DSC curve shows that CPA can thermally stable up to 500 K without
any thermal decomposition (Fig. S3), which indicates it could
satisfy the general working condition of crystal device.
(Table S5 and Table S6).
Fig.4 (a) The calculated band-gap and (b) partial density of states of
CPA.
Fig. 2 Packing view of the unit cell viewed along b-axis at LTP. Red
imaginary lines represent the N-H···Cl hydrogen bonds.
Based on such a layered structure, we calculated the electronic
band structure and partial density of states (PDOS) adopting density
functional theory to gain further insights into the electronic
properties of CPA. As the Fig. 4a displays, both maximum of valence
and the minimum of conduction are coherently located at Z point,
which indicates CPA as a direct band-gap material. In addition, the
calculated band-gap of CPA is 5.20 eV, which matches well with
ultraviolet-visible diffuse reflectance spectrometry result (Fig. S4)
and comparable to other analogues, for instance, (CH3NH3)2CdCl4
with a band-gap of 5.29 eV.25 Furthermore, it is obvious that Cd 5s
orbit dominates the conduction band minimum while Cl 3p orbit
offers the valence band maximum (Fig. 4b). That is, the energy band-
gap of CPA comes from the 2D inorganic framework.
Fig. 3 Packing view of the unit cell viewed along c-axis at HTP. Red
imaginary lines represent the N-H···Cl hydrogen bonds.
In order to further study the mechanism of phase transition of
CPA, variable-temperature single-crystal X-ray diffraction were
performed at 100 K (LTP) and 280 K (HTP), respectively and
the basic crystal structure data are listed in Table S2. From the
view of packing structure, as depicted in Fig. 2 and Fig.3, the
metal-halide CdCl6 octahedra that share four bridging corners
with the adjacent octahedra spread along the bc plane at LTP (or
ac plane at HTP), and thus construct a two-dimension (2D)
+
inorganic perovskite framework. The C3H5NH3 cations are
situated between two inorganic-layers and bonded to CdCl6
octahedra through N−H··Cl hydrogen bonds (Table S3 and
Table S4). In addition, it is quite clear that the metal-halide
Fig.5 Top: Asymmetric unit of CPA in (a) LTP (100 K) and (b)
HTP (280 K). Bottom: the order-disorder transformation of
cyclopropylamine.
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From the crystallographic point of view, CPA crystallizes in
the monoclinic space group at LTP, P21/c, with cell parameters
of a = 11.9475(7), b = 7.2805(4), c = 7.6597(5) Å, β = 108.539°, Z
= 2 and V = 631.69(7) Å3. However, with the temperature rising
above phase transition point, CPA transforms to an
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DOI: 10.1039/C8TC03517B
orthorhombic system
(space group, Cmca) with the cell
parameters of a = 7.5746(7), b = 22.852(2), c = 7.5728(6) Å, Z =
4 and V = 1310.8(2) Å3. That is, the unit volume of CPA is
approximately doubled from LTP to HTP. Such remarkable changes
in cell parameters confirm the occurrence of phase transition of
CPA from another perspective, which is in accordance well with
DSC and Cp results. From the microscopic point of view, the
+
asymmetric unit of CPA is made up of one protonated C3H5NH3
cation and one-half [CdCl4]2- at LTP, but contains one-half
protonated C3H5NH3+ cation and a quarter of [CdCl4]2- at HTP, as
shown in the Fig. 5. The considerable difference for CPA
between LTP and HTP is the organic cations become disordered
at high temperature phase induced by thermal effect. As is vividly
described in the bottom of Fig. 5, all the atoms of C3H5NH3+ are
in an order state at LTP. Particularly, three carbon-atoms (C1,
C2 and C3) determine a plane and the nitrogen-atom (N1) is
situated on the side of the coplane. More narrowly, the value of
N1-C1-C2 band angle is 119.2° as well as the N1-C1-C3 band
angle measured to be 117.5°. On the contrary, at HTP, the
atoms of C1, C2 and N1 still remain ordered while the C3 atom
becomes sternly disordered with adopting two equivalent
disordered positions. In addition, the N1 atom almost lie in the
plane determined by the atoms of C1, C2 and C3.
More specifically, the N1-C1-C2 and N1-C1-C3 band angles
become to be 169.2° and 128.2°, respectively, which could be
another evidence for the occurrence of phase transition.
Fig.7 Temperature-dependent dielectric constants of CPA
performed on the cooling mode at the frequency of 200/300
kHz.
Such microcosmic structural changes will bright macroscopic
abrupt anomalies of physical properties in the vicinity of phase
transition.29-30 As the physical properties (for instance, dielectric
property) of OIHPT materials are highly sensitive to external stimuli
such as pressure, temperature and magnetic fields, temperature-
dependent complex dielectric permittivities of CPA was performed
in the cooling mode to explore dielectric switchable responses
induced by structural phase transition. As shown in Fig. 7, the
real part of permittivity remain almost unchanged until Tc upon
cooling. Subsequently, the value of dielectric constant
declined sharply while the temperature approaches to 269.5 K.
In detail, the values of ε′ decreases from 12.3 to 10.6 at the
frequency of 200 kHz. Therefore, the temperature-dependent
dielectric constant curve is split into two different regimes,
corresponding to high- and low-dielectric states, respectively.
That is, the dielectric responses of CPA can be tuned or switched
between two different dielectric states. This result indicates that
CPA might be a splendid candidate for designing molecular-based
dielectric switchable device.
4. Conclusions
In summary, we used the three-membered ring organic amines
to construct a new 2D layered OIHPT compound CPA, which
undergoes a solid-state phase transition around 273 K induced
by the order-disorder transformation of cyclopropylamine. In
detail, the dielectric constant of CPA can be tuned between
high- and low-dielectric states in the vicinity of the phase
transition point, which indicates its potential as a switchable
dielectric material. Besides, theoretical analysis of electronic
band structure suggests that CPA exhibit direct-band-gap with
the value of 5.20 eV. Our work highlight a new potential strategy
to design dielectric phase transition materials.
Fig.6 Symmetry transformation of CPA during the phase transition.
From the viewpoint of symmetry breaking, as the temperature
goes down, crystallographic symmetry of CPA transformed from
mmm to 2/m point group. Accordingly, symmetric elements
decrease by half from eight (E, C2, 2퐶2ˊ , i, σh, 2σν) to four (E, i, C2,
σh), corresponding well with Landau phase transition theory (Fig.
6).26--28
Conflicts of interest
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26 K. Aizu, J. Phys. Soc. Jpn., 1969, 27, 387.
There are no conflicts to declare
View Article Online
27 P. P. Shi , Y. Y. Tang , P. F. Li , W. Q. Liao , Z. Wang , Q. Ye and
R. G. Xiong, Chem. Soc. Rev., 2016, 45, D38O1I:11.0.1039/C8TC03517B
28 K. Aizu, K. Phys. Rev. B: Solid State, 1970, 2, 754
Acknowledgements
29 S. Horike, S. Shimomura and S. Kitagawa, Nat. Chem, 2009, 1,
695.
This work is supported by NSFC (21622108, 21525104,
21601188, and 51502290), the NSF of Fujian Province
(2015J05040), the Strategic Priority Research Program of the
Chinese Academy of Sciences (XDB20000000), the Youth
Innovation Promotion of CAS (2014262).
30 S. Horiuchi and Y. Tokura, Nat. Mater, 2008, 7, 357.
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Journal of Materials Chemistry C
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We used Cyclopropylamine to assemble a layered inorganic-organic hybrid phase transition compound, which
displays remarkable switchable dielectric response. To the best of our knowledge, this should be the first report on the
solid-state structural phase transition triggered by three-membered ring organic amine.