Synthesis and Characterization of Novel Chalcone with good Nonlinear Optical Properties

Abstract

In this combined experimental and theoretical research, we report the synthesis, characterization, and quantum chemical investigation of optical and electrical properties of novel chalcone. The properties were studied using density functional theory method at the B3LYP, PBE0, BVP86, HCTH, and MPW1PW91 functionals. The relationship between the nonlinear optical properties and the energy gap has been taken into account. High total first hyperpolarizability tot up to 4230.65 a.u. and low energy gap E g less than 2.60 eV closed to the experimental one have been obtained. The properties have extensively discussed the structure-property relationship to provide appropriate information for the design of novel chalcone-based materials for nonlinear optical applications. The new study urges researchers to focus on the future advancement of nonlinear optics. Graphical Abstract

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Chemistry Africa
https://doi.org/10.1007/s42250-024-01143-6
ORIGINAL ARTICLE
Synthesis andCharacterization ofNovel Chalcone withgood
Nonlinear Optical Properties
AbdelmadjidBenmohammed1,2· DjebarHadji3,4 · YounesMouchaal5,6· AyadaDjafri1
Received: 8 July 2024 / Accepted: 11 November 2024
© The Tunisian Chemical Society and Springer Nature Switzerland AG 2024
Abstract
In this combined experimental and theoretical research, we report the synthesis, characterization, and quantum chemical
investigation of optical and electrical properties of novel chalcone. The properties were studied using density functional
theory method at the B3LYP, PBE0, BVP86, HCTH, and MPW1PW91 functionals. The relationship between the nonlinear
optical properties and the energy gap has been taken into account. High total first hyperpolarizability
𝛽tot
up to 4230.65 a.u.
and low energy gap
Eg
less than 2.60eV closed to the experimental one have been obtained. The properties have extensively
discussed the structure-property relationship to provide appropriate information for the design of novel chalcone-based
materials for nonlinear optical applications. The new study urges researchers to focus on the future advancement of nonlinear
optics.
Graphical Abstract
Keywords Chalcone· Polarizability· Nonlinear Optics· Charge Transfer
* Djebar Hadji
hadji120780@yahoo.fr; djeber.hadji@univ-saida.dz
1 Laboratoire de Synthèse Organique Appliquée (LSOA),
Département de Chimie, Faculté des Sciences Exactes
et Appliquées, Université Oran1 Ahmed Ben Bella, El
M’naouer, BP 1524, Oran, Algérie
2 Department ofChemistry, Faculty ofExact Sciences,
University ofMascara, 29000Mascara, Algeria
3 Department ofChemistry, Faculty ofSciences, University
ofSaida – Dr. Moulay Tahar, 20000Saida, Algeria
4 Modeling andCalculation Methods Laboratory, University
ofSaida – Dr. Moulay Tahar, 20000Saïda, Algeria
5 Department ofPhysics, Faculty ofExact Sciences, University
ofMascara, Mascara, Algeria
6 Laboratory ofThin Films Physics andMaterials
forElectronics (LPCMME), Université Oran1 Ahmed Ben
Bella, El M’naouer, BP1524Oran, Algérie

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1 Introduction
Chalcones are a class of compounds obtained from natu-
ral or synthetic sources that are precursors of flavonoid
biosynthesis [1]. Several strategies have been used for the
synthesis of chalcones [2]. The condensation of aromatic
aldehydes with acetophenones results in chalcones [3].
Chalcones have been explored because of their multiple
properties as different biologically active heterocycles
that can be prepared from chalcones such as pyridines,
pyrimidines and pyrazoles [4]. Studies have shown that
chalcones possess some biological activities such as
anticancer, anti-inflammatory, antioxidant, anti-HIV-1,
anti-plasmodial, anti-bacterial and anti-fungal [5]. New
synthesized chalcone derivatives have shown many inter-
esting pharmacological activities, including antibacterial
[6], and antifungal [7]. Studies showed that chalcones can
serve as important anticancer drug candidates [8]. Also,
chalcone could serve as a precursor for the functionali-
zation of exocyclic conjugated chalcone compounds [9].
Organic materials that have nonlinear optical (NLO) prop-
erties have been the main focus of various studies due to
their utilization in optoelectronics and optical data pro-
cessing [10–12]. Chalcones with π-conjugated structures
as well as donor and acceptor groups are widely studied
compounds and represent NLO properties that can be sig-
nificantly increased by increasing the capacity of donor
and acceptor substituents related to the conjugate system
[13, 14]. Among the different types of organic materials,
chalcone derivatives representing the D-π-A configuration
are considered promising NLO materials [15, 16]. In this
new investigation, the main aim was to synthesize and
analyze the linear and nonlinear optical properties of the
novel (E)−3-(2,4-dimethoxyphenyl)−1-(4-fluorophenyl)
prop-2-en-1-one (DMPFP) chalcone. Five density func-
tional theory (DFT) levels (
B3LYP
, PBE0, BVP86,
HCTH, and MPW1PW91) have performed in this study.
The correlation between the
𝛽HRS
and
𝛽∕∕
is taken into
account. Also, the correlation between the hyperpolariz-
ability
𝛽tot
and the band gap of the DMPFP chalcone. A
detailed analysis of the frontier molecular orbital energies
EHOMO
and
ELUMO
and their nature were also discussed in
this study. These orbitals gives valuable insights into the
structure and reactivity of systems [17–20], and predicts
the most reactive position in conjugated systems [21, 22].
Molecules with a significant
Eg
are stable and exhibiting
high chemical hardness [23, 24].
2 Materials andInstrumentations
The compounds used in the syntheses of the DMPFP chal-
cone were purchased from Aldrich and used without puri-
fication. Melting point was determined on the Büchi B-540
apparatus and is uncorrected. The IR spectra were taken on
a Perkin-Elmer series II analyzer. The optical measurements
were carried using Perkin-Elmer Lambda 950 UV-vis-NIR.
The optical transmission was observed in 300 to 1100nm.
1H-NMR were recorded on the BRUKER AC 300P spec-
trometer and 13C-NMR spectra on BRUKER AC 300 P
spectrometer in d6-DMSO. We performed thin-layer chro-
matography using silica gel Merck 60F-254.
Synthesis of the DMPFP The 4-fluoroacetophenone (1.38g,
0.01 mol) and a 2,4-dimethoxybenzaldehyde (1.66g,
0.01mol) were dissolved in the ethanol (30ml). We added
20% NaOH (5ml) to the solution dropwise while vigorously
stirring. We stirred the mixture for 24h at 25°C. We suc-
cessively filtered and washed the resultant crude products
with distilled water, and then dried and recrystallized the
compound from ethanol (Scheme1).
2.1 The DMPFP
White solid, Yield 85%, mp 122°C; FT-IR (ATR, νmax.
cm−l): 3072 (Ar-H), 1663 (C = O), 1583 (-CH = CH-), 514
(C-F). 1H-NMR (300MHz, d6-DMSO, δ (ppm): 8.20 (dd,
2H, J = 9.0Hz, J = 5.67Hz, Ar-H), 8.0 (d, 1H, J = 15.34Hz,
-CH = CH-), 7.93 (d, 1H, J = 8.71Hz, Ar-H), 7.76 (d, 1H,
J = 15.34Hz, -CH = CH-), 7.41 (t, 2H, J = 9.3 Hz, Ar-H),
3.86 (s, 3H,
−OCH3
), 6.64 (m, 2H, Ar-H), 3.92 (s, 3H,
−OCH3
).13C-NMR (75MHz, d6-DMSO,δ (ppm)): 188.14
(C = O), 167, 163.70, 160.50, 139.41 (CH = CH), 135.20,
131.77, 130.64, 119.21 (CH = CH), 116.34, 116.03, 106.86,
98.76, 56.31 (
−OCH3
), 56.02 (
−OCH3
).
Scheme1 Synthetic scheme of the DMPFP chalcone

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3 Results andDiscussion
3.1 IR Spectral Analysis
The DMPFP IR spectrum was recorded in the solid state
using the ATR technique. The DMPFP absorbance spectrum
is presented in Fig.1.
The wavenumber domain of 3000–3120 cm−1 was
reported for CH stretching modes [25]. The CH of the
DMPFP modes is obtained in 3016 –3008 cm−1 regions.
The vibrational stretching modes CH for the DMPFP are
observed at 2937 –2844 cm−1. The DMPFP IR spectrum
showed unique peak at 1635 cm−1 attributable to stretching
vibration mode of C = O [26]. These C = O vibrations are
dependent on the strength of double bond and lone pair of
oxygen atom [27]. However, the C = C stretching vibration
in conjugation with C = O shows the vibration at 1600 cm−1
for the DMPFP. The DMPFP shows C-F stretching vibration
recorded at 514 cm−1.
4 Nuclear Magnetic Resonance Spectra
Analysis
The DMPFP 1H-NMR spectrum is illustrated in Figs.2 and
3. The NMR analysis of the DMPFP was taken by dissolv-
ing the sample in d6-DMSO with TMS as an internal stand-
ard. The NMR spectrum confirms the DMPFP chalcone
formation. The proton Hα appears as a doublet (δ 7.76 and
j = 15.34) represent the hydrogen atom available next to the
C = O in t he 1H-NMR spectra [28]. Another doublet at δ 8.0
with j = 15.34 representing the adjacent H atom Hβ. These
Fig. 1 IR spectrum of DMPFP chalcone
Fig. 2 1H-NMR spectrum of the DMPFP chalcone

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values correspond to the double-bond trans that is generally
appeared in natural chalcones [29].
The δ value of Hα and Hβ is slightly shifted; this is due
to the conjugation effect with the aromatic rings and C = O
[30]. The two aromatic ring protons appear in five different
positions 8.2, 8.0, 7.76, 7.41, and 6.6 as a doublet of dou-
blets, doublet, triplet and multiplet. In the DMPFP 13C-NMR
spectrum (Fig.3), the C = O chemical shift appeared at 188,
relative to other carbon atoms due to environmental factor
and increased electronegativity of the oxygen atom [31]. The
methyl group was appeared at δ 56.31 and δ 56.02.
5 Optical Properties
The optical property measurements were performed using
a UV-vis Perkin-Elmer Lambda 950 UV-Vis-NIR spectro-
photometer. The equipment operates at a scanning speed of
60nm/min. The interval between 200 and 800nm was set
for the measurement acquisition of the optical absorbance
of the DMPFP chalcone. Figure4 shows the variation of
the square of the product of the absorption coefficient and
the incident photon energy (
𝛼
hν)2 as a function of the latter
specific to the DMPFP chalcone. The DMPFP optical gap
Fig. 3 13C- NMR of the DMPFP chalcone
Fig. 4 (
𝛼
hν)² of the DMPFP chalcone as a function of the energy of
the incident photons

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is estimated using their linear absorption data by the Tauc
relationship [32].
Where
𝛼
, h, ν and
Eg
are the absorption, plank constant,
frequency of the incident photons, and the energy gap,
respectively. The
𝛼
is obtained as:
The extrapolation of Eq.(1) shown in Fig.4 allows us
to deduce the value of the band gap energy. The
Eg
of the
thin layers of DMPFP is 3.05eV. The DMPFP chalcone
has a lower optical band-gap compared to other active NLO
chalcones found in the literature [15, 33, 34]. The
Eg
value
proposes that the DMPFP is in the range of powerful pho-
tovoltaic compounds, and could be applied in various solar
cell applications [28].
5.1 Linear andNonlinear Optical Results
5.1.1 Computational Methods
Geometrical optimization of the DMPFP chalcone
(Fig.5) was performed at the B3LYP functional using the
6–311 + G** basis set. The B3LYP [35], PBE0 [36, 37],
BVP86 [38–40], HCTH [41], and MPW1PW91 [42] lev-
els were used to calculate the dipole moment
𝜇tot
, polar-
izability anisotropy
Δ𝛼
, mean polarizability
𝛼
, total static
first hyperpolarizability
𝛽tot
, HRS first hyperpolarizability
𝛽HRS
, EFISHG
𝛽∕∕
, and the depolarization ratios DR. The
B3LYP level allows for appropriate predictions of structures
and electronic properties [43, 44]. Compared to many DFT
functionals, this level has been found to perform well for
organic systems [45, 46].
The total µ was calculated using
𝜇x
,
𝜇y
, and
𝜇z
contribu-
tions as:
(1)
𝛼hν =(h𝜈−Eg)
(2)
𝛼
=(
1
t
)log (
1
T)
⟨𝛼⟩
was calculated from
𝛼xx
,
𝛼yy
, and
𝛼zz
components as:
and
Δ𝛼
as:
For
𝛽
, using the
𝛽xxx
,
𝛽xyy
,
𝛽xzz
,
𝛽yyy
,
𝛽yxx
,
𝛽yzz
,
𝛽zzz
,
𝛽zxx
, and
𝛽zzz
contributions, we calculate the
𝛽tot
as:
with
and
All theoretical calculations are conducted using Gaussian
09 [47]. The GaussView 5.1 [48] was used for the structure
visualization. The 6–311 + G** [49–52] was used for all
parameter calculations. The
𝛽∕∕
response is projected along
the
𝜇
-axis given by:
(3)
𝜇
=
√(
𝜇2
x+𝜇2
y+𝜇2
z
)
(4)
⟨
𝛼
⟩
=
1
3�
i=x,y,z𝛼
ii
(5)

𝛼

=
1
3
𝛼xx +𝛼yy +𝛼zz

(6)
Δ
𝛼=

1
2
𝛼xx −𝛼yy

2+

𝛼xx −𝛼zz

2+

𝛼yy −𝛼zz

2

(7)
𝛽
tot =
√
𝛽x
2+𝛽y
2+𝛽z
2
(8)
𝛽x=𝛽xxx +𝛽xyy +𝛽xzz
(9)
𝛽y=𝛽yyy +𝛽yxx +𝛽yzz
(10)
𝛽z=𝛽zzz +𝛽zxx +𝛽zzz
Fig. 5 Optimized structure of the DMPFP chalcone at the B3LYP
level
Fig. 6
𝜇
of the DMPFP chalcone calculated using five levels at the
6–311 + G(d, p) basis set

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|
|� �
𝜇|
|
,
𝜇i
,
𝛽i
are the norm of
𝜇
, the ith components of the
𝜇
vector, and the ith components of the
𝛽
vector, respectively.
The
𝛽HRS
was defined by the sum of the
⟨𝛽2
ZZZ ⟩
and
⟨𝛽2
ZXX ⟩
as:
and the DR was defined by the ratio of the
⟨
𝛽
2
ZZZ ⟩
and
⟨
𝛽
2
ZXX ⟩
as:
(11)
𝛽∕∕(−
2
ω
;
ω
,
ω)=
1
5∑
i
𝜇i
|
| 
𝜇|
|
∑
j
(
𝛽ijj +𝛽jij +𝛽jji
)
=
3
5∑
i
𝜇i𝛽i
|
| 
𝜇|
|
(12)
𝛽HRS
=
⟨
𝛽
2
HRS⟩
=
⟨
𝛽
2
ZZZ ⟩
+
⟨
𝛽
2
ZXX ⟩
The detailed
⟨𝛽2
ZZZ ⟩
and
⟨𝛽2
XZZ ⟩
can be find in Ref [53]. :
(13)
DR
=
I
2ω
VV
I2ω
HV
=
⟨
𝛽
2
ZZZ
⟩
⟨
𝛽2
ZXX ⟩
(14)
⟨𝛽
2
ZZZ ⟩=
1
7
∑x,y,z
𝜁≠𝜂𝛽
2
𝜁𝜁𝜁 +
4
35
∑x,y,z
𝜁≠𝜂𝛽
2
𝜁𝜁𝜂
+2
35 ∑x,y,z
𝜁≠𝜂𝛽𝜁𝜁𝜁 𝛽𝜁𝜂𝜂 +4
35 ∑x,y,z
𝜁≠𝜂𝛽𝜂𝜁𝜁 𝛽𝜁𝜁𝜂
+4
35 ∑x,y,z
𝜁≠𝜂𝛽𝜁𝜁𝜁 𝛽𝜂𝜂𝜁 +1
35 ∑x,y,z
𝜁≠𝜂𝛽2
𝜂𝜁𝜁
+4
105 ∑x,y,z
𝜁≠𝜂≠𝜀𝛽𝜁𝜁𝜂 𝛽𝜂𝜀𝜀 +1
105 ∑x,y,z
𝜁≠𝜂≠𝜀𝛽𝜂𝜁𝜁 𝛽𝜂𝜀𝜀
+4
105 ∑x,y,z
𝜁≠𝜂≠𝜀𝛽𝜁𝜁𝜂𝛽𝜀𝜀𝜂
+2
105 ∑
x,y,z
𝜁≠𝜂≠𝜀
𝛽2
𝜁𝜂𝜀
+4
105 ∑
x,y,z
𝜁≠𝜂≠𝜀
𝛽𝜁𝜂𝜀 𝛽𝜂𝜁𝜀
Table 1 µ (D),
∣𝛼∣
,
⟨𝛼⟩
,
𝛽tot
,
𝛽∕∕
, and
𝛽HRS
(a.u.) of the DMPFP chalcone calculated at five levels using the 6–311 + G** basis set
a [54] Results for the 2,3,4,4’-tetramethoxychalcone obtained at the CAM-B3LYP level
b [55] Results for similar chalcone obtained at the B3LYP level
c [56] Results for similar strutures calculated at the PBE0 level
𝝁
⟨
𝛼
⟩
|𝜶|
𝜷∕∕
𝜷𝐭𝐨𝐭
𝜷𝐇
<
𝐄𝐦𝐩𝐡𝐚𝐬𝐢𝐬𝐓𝐲𝐩𝐞=ε𝐈𝐭𝐚𝐥𝐢𝐜ε
>
𝐑
<
∕𝐄𝐦𝐩𝐡𝐚𝐬𝐢𝐬
>
𝐒
(DR)
B3LYP 6.60 236.93 175.21 –2045.21 3433.25 1562.36 (3.21)
PBE0 6.70 249.40 197.26 –2516.32 4230.65 1905.48 (3.04)
BVP86
HCTH
6.72
6.68
248.86
246.93
196.84
194.42
–2488.25
–2486.58
4182.58
4178.58
1887.98 (3.11)
1882.84 (3.20)
MPW1PW91 6.60 232.57 171.26 –1395.31 3263.41 1483.65 (3.84)
5.19a217.00c
262.00c
3583.18a
1597.99b
Fig. 7
𝜇
vector of the DMPFP
chalcone

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The detailed expressions of
⟨
𝛽
2
ZZZ ⟩
and
⟨
𝛽
2
XZZ ⟩
was listed
in Ref [53].
6 Dipole Moment
The
𝜇tot
and their contributions are calculated for the
DMPFP chalcone using the B3LYP, PBE0, BVP86,
HCTH, and MPW1PW91 functionals (Table1 and Fig.6).
The
𝜇
contributions of the DMPFP novel chalcone clearly
show the direction of charge transfer in the chalcone.
The contributions µx and µy are the majority (Fig.7).
High
𝜇tot
values have ranged between 6.60 and 6.70 D for
the DMPFP. The B3LYP and MPW1PW91 give close µ
values; the difference does not exceed 2.85% in the case of
PBE0, BVP86, and HCTH functionals.
The presence of the double bond between the
𝛼
and
𝛽
-car-
bon of the C = O influenced the
𝜇
in DMPFP chalcone. In the
C = O functional group, the oxygen atom pulls the electron
density towards itself, creating a
𝜇
with a negative charge on
O and a partial positive charge on C. Also, the high
𝜇
values
can be explained by the presence of a F and two
−OCH3
on
both aryl rings as a strong electron-withdrawing group [57]
and two
−OCH3
as an electron-donating groups. Like our
DMPFP chalcone, and according to Salim etal. [58], the
presence of the fluorine (F) atom as an electron-attractor
group increases the
𝜇
values of pyrazoline analogues. Our
DMPFP chalcone gets a high
𝜇
value compared to those
in the 2,3,4,4’-tetramethoxychalcone [54] obtained at the
CAM-B3LYP functional.
6.1 Polarizability
The B3LYP, PBE0, BVP86, HCTH, and MPW1PW91
𝛼
results of our DMPFP chalcone are presented in Table I and
Fig.8.
⟨𝛼⟩
and
|𝛼|
values have varied from 232.57 to 249.40
a.u, and for 171.26 to –197.26 a.u., respectively. The PBE0
and MPW1PW91 showed the high and the lowest
⟨𝛼⟩
and
|𝛼|
values, respectively. The
𝛼
results show that
⟨𝛼⟩
is depends
on the DMPFP volume and
|𝛼|
the DMPFP structure. The
(15)
⟨
𝛽2
XZZ ⟩=
1
35
�
x,y,z
𝜁𝛽2
𝜁𝜁𝜁 +
4
105
�
x,y,z
𝜁≠𝜂𝛽𝜁𝜁𝜁 𝛽𝜁𝜂𝜂 −
2
35
�
x,y,z
𝜁≠𝜂𝛽𝜁𝜁𝜁𝛽𝜂𝜂𝜁 +
8
105
�
x,y,z
𝜁≠𝜂𝛽2
𝜁𝜁𝜂
+3
35 �x,y,z
𝜁≠𝜂𝛽2
𝜁𝜂𝜂 −2
35 �x,y,z
𝜁≠𝜂𝛽𝜁𝜁𝜂𝛽𝜂𝜁𝜁 +1
35 �x,y,z
𝜁≠𝜂𝛽𝜁𝜂𝜂 𝛽𝜁 𝜀𝜀
−2
105 �x,y,z
𝜁≠𝜂≠𝜀𝛽𝜁𝜁𝜂 𝛽𝜂𝜀𝜀
+2
35 �
x,y,z
𝜁≠𝜂≠𝜀𝛽2
𝜁𝜂𝜀 −2
105 �
x,y,z
𝜁≠𝜂≠𝜀𝛽𝜁𝜂𝜀 𝛽𝜂𝜁 𝜀
similar
𝛼
evolution has been achieved in several studies
[59–69].
The
𝛼
ordering follows:
⟨
𝛼
⟩
MPW1PW91 <
⟨
𝛼
⟩
B3LYP <
⟨
𝛼
⟩
HCTH <
⟨
𝛼
⟩
BVP86 <
⟨
𝛼
⟩
PBE0
�
𝛼�
MPW1PW91
<�𝛼�
B3LYP
<�𝛼�
HCTH
<�𝛼�
BVP86
<�𝛼�
PBE0
Authors [54] proposed new metabolite chalcones with
⟨𝛼⟩
value between 37 × 10−24 and 53.5 × 10−24 esu, which are
quite similar to those of the DMPFP. The authors showed
that the structural effect of the substitution of HC = CH by
H2C–CH2 acts decreasing
⟨𝛼⟩
. In the same task, Muhammad
Fig. 8
⟨𝛼⟩
and
|𝛼|
of the DMPFP chalcone calculated at five levels
using the 6–311 + G(d, p) basis set

Chemistry Africa
Fig. 9
𝛽HRS
and
𝛽∕∕
of the
DMPFP chalcone calculated
using five functionals
Fig. 10
𝛽tot
vs.
Eg
of the DMPFP chalcone determined at five levels Fig. 11 The DMPFP chalcone orientation during calculations

Chemistry Africa
etal. [56] were synthesized similar chalcones with
⟨𝛼⟩
between 217.00 and 262.00 a.u., respectively, close to our
⟨𝛼⟩
for the DMPFP.
6.2 First Hyperpolarizability
The five DFT (B3LYP, PBE0, BVP86, HCTH, and
MPW1PW91) results of the hyperpolarizability (
𝛽tot
,
𝛽HRS
,
𝛽∕∕
and DR) are presented in Table1, Figs.9, and10
The high
𝛽∕∕
,
𝛽tot
, and
𝛽HRS
are − 1395.31, 4230.65, and
1905.48 a.u., respectively, using the MPW1PW91 and PBE0
levels. The obtained
𝛽
components show that the
𝛽x
are the
majority (Fig.11).
For the
𝛽∕∕
, the MPW1PW91 gives high values, whereas,
for the
𝛽tot
and
𝛽HRS
, the PBE0 gives the highest values.
The results in Table1 and Fig.9 state opposite variations
between the
𝛽HRS
and
𝛽∕∕
and a direct relationship between
the
𝛽HRS
and
𝛽tot
. Studies confirmed the same relationship
[65, 68–80]. The DMPFP chalcone has a high
𝛽tot
value
compared with those of chalcones [56] attached with
−OCH3
at the ortho, meta, and para phenyl positions.
The DMPFP chalcone has also high
𝛽tot
values compared
with those of some biotransformed chalcones using the
endophytic fungus Aspergillus flavus and 2,3,4,4’-tetrameth-
oxychalcone [54, 55] obtained at the CAM-B3LYP and
B3LYP levels, respectively. Like our DMPFP chalcone, a
recent study [56] showed that the suitability of chalcone
derivative for NLO applications. The results show that the
DR values calculated at the B3LYP, PBE0, BVP86, HCTH,
and MPW1PW91 of the DMPFP chalcone are almost close
to 3. These DR values, in combination with the chemical
topology of the DMPFP chalcone, are concurring with the
typical
Cs
the molecular point group of the DMPFP. The
Cs
point group symmetry is well marked by the presence
of a single
𝜎
plane of symmetry (a planar structure) for the
DMPFP.
6.3 FMOs Analysis
The determination of both FMOs and their energy
Eg
it is
a crucial tools in experimental and theoretical chemistry.
The calculated EHOMO, ELUMO, and
Eg
at the B3LYP, PBE0,
BVP86, HCTH, and MPW1PW91 levels are presented in
Table2 and Fig.10.
Eg
values of the DMPFP ranged from
2.60 to 4.38eV. The BVP86, PBE0, and HCTH functionals
give the lowest
Eg
values. Their values are 2.60, 2.64, and
2.68eV, respectively. These functionals give close
Eg
values
to the experimental ones obtained using linear absorption
data from the Tauc relationship. The PBE0 provides reli-
able
Eg
results for similar chalcones [16], their calculated
Eg
values range from 3 to 4eV. The obtained
Eg
values of the
DMPFP chalcone are lower compared to similar chalcones
[15, 34, 81]. We note that the B3LYP functional gives a high
Eg
value not far from what was experimentally observed
using linear absorption data. The difference does not exceed
23%. A recent study shows that the B3LYP level gives excel-
lent
Eg
values for similar chalcones [82].
The FMO isosurfaces HOMO and LUMO (Fig.12) of our
DMPFP chalcone are formed by px and py atomic orbitals,
Table 2
EHOMO
,
Eg
, (eV) and
𝛽tot
(a.u.) of the DMPFP chalcone
obtained at five levels
E HOMO E LUMO
E𝐠
𝜷𝐭𝐨𝐭
B3LYP –6.32 –2.30 4.02 3433.25
PBE0 –5.25 –2.61 2.64 4230.65
BVP86 –5.24 –2.64 2.60 4182.58
HCTH –5.42 –2.74 2.68 4178.58
MPW1PW91
Exp
–6.26 –1.88 4.38
3.05
3263.41
Fig. 12 FMOs and their
Eg
(eV) of the DMPFP chalcone estimated at
five DFT levels

Chemistry Africa
which show there
𝜋
-nature. The HOMO is localized on the
cinnamoyl group on the side of the two
−OCH3
. The LUMO
is delocalized over all the conjugated backbone and also
touches the F atom. The same distribution was shown by
Xue etal. [83] for similar chalcones and by Fathimunnisa
etal. [84] in the biphenyl-based difluorochalcones. The rela-
tively small
Eg
obtained at the BVP86, PBE0, and HCTH
approaches as well as high dipole moment, contribute to
strong hyperpolarizability values.
7 Conclusion
In this study, we have reported for the first time the synthesis
and characterization of the novel DMPFP chalcone using IR,
1H-NMR, 13C-NMR, and UV-vis. The energy gap measured
for DMPFP thin film is found to be 3.05eV, which confirms
that the studied DMPFP chalcone is embeddable in organic
solar cells. At the five B3LYP, PBE0, BVP86, HCTH, and
MPW1PW91 in combination with the 6–311 + G** basis
set, a computational investigation is performed to study in
detail the
𝜇
,
⟨𝛼⟩
,
|𝛼|
,
𝛽HRS
,
𝛽∕∕
, and DR as well as the
Eg
of the DMPFP. The results show that the novel DMPFP
chalcone gets low
Eg
obtained at the PBE0, BVP86, and
HCTH functionals and possesses excellent
𝛽
responses. In
addition to the direct link between the
𝛽HRS
and
𝛽tot
, we
also indicate the opposite variations between the
𝛽HRS
and
𝛽∕∕
. An opposite relationship has been acquired between the
𝛽tot
and
Eg
. This combined study of the DMPFP chalcone
with high NLO responses will direct numerous scientists to
utilise computational data for the rational design of novel
chalcone-based materials with potential applications in non-
linear optics and photovoltaic cells [85–89].
Supplementary Information The online version contains supplemen-
tary material available at https:// doi. org/ 10. 1007/ s42250- 024- 01143-6.
Acknowledgements This investigation was supported by the Alge-
rian Ministry of Higher Education and Scientific Research as well
as the directorate general for scientific research and technological
development.
Authors Contribution Abdelmadjid Benmohammed: investigation,
conceptualization, methodology, visualization, writing- reviewing and
editing.Djebar Hadji: data curation, writing-original draft preparation,
visualization, investigation, software, validation, supervision.Younes
Mouchaal: conceptualization, methodology, writing-reviewing and
editing.Ayada Djafri: conceptualization, methodology, writing-
reviewing and editing.
Funding Not applicable.
Data Availability The authors confirm that the data supporting the
findings of this study are available within the article [and/or] its sup-
plementary materials.
Declarations
Conflict of interest The authors declare that they have no conflict of
interest.
Ethical Approval Not applicable.
Informed Consent Not applicable.
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