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Cite this paper: Vietnam J. Chem., 2021, 59(2), 203-210 Article
DOI: 10.1002/vjch.202000200

TD-DFT benchmark for UV-Vis spectra of coumarin derivatives

Mai Van Bay1,2, Nguyen Khoa Hien3, Phan Thi Diem Tran3, Nguyen Tran Kim Tuyen4,
Doan Thi Yen Oanh5, Pham Cam Nam6*, Duong Tuan Quang1*
1
University of Education, Hue University, 34 Le Loi, Hue City, Thua Thien Hue 49000, Viet Nam
2
The University of Danang- University of Science and Education, 41 Le Duan, Hai Chau, Da Nang City
50000, Viet Nam
3
Mientrung Institute for Scientific Research, Vietnam Academy of Science and Technology, 312 Huynh Thuc
Khang, Phu Hoa, Hue City, Thua Thien Hue 49000, Viet Nam
4
Kontum Community College, 704 Phan Dinh Phung, Kon Tum City, Kon Tum 60000, Viet Nam
5
Publishing House for Science and Technology, Vietnam Academy of Science and Technology, 18 Hoang
Quoc Viet, Cau Giay, Hanoi 10000, Viet Nam
6
The University of Danang - University of Science and Technology, 41 Le Duan, Hai Chau, Da Nang City
50000, Viet Nam
Submitted December 9, 2020; Accepted December 30, 2020

Abstract
The predictive performances for maximum absorption wavelength of the PBE, BP86, PBE0, B3LYP, M06, M06-
2X, CAM-B3LYP, LC-wPBE, APDF, wB97XD, and PW6B9D3 functionals have been benchmarked through
comparison of maximum absorption wavelength values between calculation and experiment of 21 coumarin derivatives.
For the results obtained from direct calculation by these functionals, the predictive performance decreases gradually in
the following order: B3LYP > APDF > M06 > PW6B9D3 > PBE0 > BP86 > PBE > M06-2X > CAM-B3LYP >
wB97XD > LC-wPBE. B3LYP functional gives the best predictive performance, with the smallest value of the mean
absolute error (MAE = 15 nm) and the root mean square deviation (RMSD=19 nm). When using the results obtained
through correction based on the linear correlation, the predictive performance decreases gradually in the following
order: M06-2X > PBE0, M06, PW6B9D3 > B3LYP, APDF > CAM-B3LYP, LC-wPBE, wB97XD > PBE and BP86.
M06-2X functional gives the best predictive performance, with the smallest values of MAE fix (7 nm) and RMSDfix
(9nm). The correction is very necessary because the values of the corrected maximum absorption wavelengths are
closer to the experimental maximum absorption wavelengths. The values of MAE fix and RMSDfix are much smaller than
those of MAE and RMSD.
Keywords. DFT, TD-DFT, UV-Vis, coumarin, benchmark.

1. INTRODUCTION and fluorescence spectra is necessary in order to

Coumarins are from the benzoryrone family, an
important class of phytochemicals. Over 1300
different coumarin derivatives have been identified,
including natural and synthetic derivatives.[1]
Coumarin derivatives are widely used in medicine,
food, and industry.[2] In particular, many
applications are based on the outstanding optical
properties of coumarin derivatives such as dyes,
color indicators, sunscreens, organic light-emitting
diodes, fluorescent markers, and fluorescence
sensors[3-6] Therefore, the prediction of the optical
properties of coumarin derivatives such as UV-Vis
provide a scientific basis for the design and
development of new materials from
thesederivatives.[3,7,8]
Based on methods of electronic structure theory
for studying the electron excited states, theoretical
calculations allow predicting quite accurately optical
properties of molecules. Some recent publications
show that the UV-Vis spectra of some large organic
molecules are predictable with high accuracy and
reasonable computing costs by using the time-
dependent density functional theory (TD-DFT)
method. Therefore, TD-DFT is the current popular
method for calculation of the electron excited states

203 Wiley Online Library © 2021 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH

Vietnam Journal of Chemistry
of large molecules[9-13] So far, many DFT methods
(pure, hybrid, long-range-corrected, dispersion
corrected, etc.) have been developed.[14] However,
accurate prediction of UV-Vis spectra using DFT
methods depends on the structure of molecules.
Therefore, it is necessary to choose suitable DFT
functional for each group of compounds to get the
accurate calculation results.[15,16] Denis Jacquemin et
al. used 29 DFT functionals to predict the UV-Vis
spectra of about 500 compounds including bio-
organic molecules and dyes. The obtained results
were compared with the previous theoretical
calculations or experimental measurements. The
results show that the predictive performance of the
DFT functionals strongly depends on the molecular
structure of organic compounds. For example, PBE0
and LC-ωPBE(20) give very good results in
predicting the UV-Vis spectra of many neutral
organic dyes but are completely inconsistent with
cyanine-like derivatives.[17] Azzam Charaf-Eddin et
al used the six hybrid functionals, including B3LYP,
PBE0, M06, M06-2X, CAM-B3LYP and LC-PBE
Figure 1: Coumarin derivatives for this investigation
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Duong Tuan Quang et al.
for calculation of the UV-Vis spectra of 20
conjugated organic compounds in solvent.[18] The
results show that B3LYP functional gives the
smallest mean signed error (MSE) and mean
unsigned error (MUE) for the position of absorption
peaks, but is not the most efficient in terms of root
mean square deviation (RMSD) or largest standard
deviation (SD). Meanwhile, M06-2X functional
provides the most appropriate results with the
experiment for the band shapes corresponding to the
absorption spectra of conjugated compounds.[18] So
far, some studies, but not many, have been
successful in using TD-DFT method to calculate the
UV-Vis spectra of coumarin derivatives.[19,20]
In this work, the predictive performances of the
PBE, BP86, PBE0, B3LYP, M06, M06-2X, CAM-
B3LYP, LC-wPBE; APDF, wB97XD, and
PW6B9D3 functionals for maximum absorption
wavelength of 21 coumarin derivatives (figure 1) are
benchmarked through comparison of maximum
absorption wavelength values between calculation
and experiment.
204
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Vietnam Journal of Chemistry TD-DFT benchmark for UV-Vis spectra of…

2. COMPUTATIONAL METHODS root mean square error, RMSE) are frequently used
to evaluate the performance of these models.[24] The
In this study, the optimized geometry of all mean signed error (MSE) (or average signed
molecules in the ground state is carried out by using difference, MSD) is also used for the purpose of
density functional theory (DFT) at the PBE0/6- examining the direction of the errors.[14,25] In
311++G(d,p) level of theory.[15] Here, it should be addition, the linear correlation relationship between
emphasized that the PBE0 density functional has the experimental and the calculated values of the
been evaluated to accurately predict the geometrical maximum absorption wavelength is also used to
structure of most of the organic molecules in the evaluate the method's predicted performance.[26]
ground states.[21] The UV-Vis spectra of coumarin Then, the corrected calculated maximum absorption
derivatives are carried out by using time-dependent wavelength is also determined based on the
density functional theory (TD-DFT)[9,10] at the X/6- linear correlation equations between and
311++G(d,p) level of theory, where X: PBE, BP86, . The predictive performance of DFT
PBE0, B3LYP, M06, M06-2X, CAM-B3LYP, LC- functionals is once again evaluated through
wPBE; APDF, wB97XD and PW6B9D3. The comparison between values of and .[14,25]
polarizable continuum model (PCM) is applied for
3. RESULTS AND DISCUSSION
all DFT and TD-DFT calculations, with the solvent
used in the calculations being the same as that used 3.1. TD-DFT benchmark based on comparison
in the experiment.[22] All calculations are performed between the and
using Gaussian 16 Revision A.03 program.[23]
The predictive performance of DFT functionals The results of calculation of maximum absorption
for maximum absorption wavelength of coumarin wavelength of 21 coumarin derivatives using 11
derivatives is benchmarked through comparison DFT functionals, difference between the calculated
between the calculated maximum absorption maximum absorption wavelength and the
wavelength ( ) and experimental maximum experimental maximum absorption wavelength
absorption wavelength ( ). In this case, both the (Δλmax), and statistical analysis data of MAE,
mean absolute error (MAE) (or mean unsigned error, RMSM, and MSE are presented in table 1 and
MUE), and root mean square deviation (RMSD) (or figure 2.

70 62

45 49
50 43
Error relative to experiment (nm)

29 30 29 29
30 23 21 22
20
15
10

-10
-12
-22 -20 -19 -21
-30

-50 -42 -45 -49

MSE MAE
-70 -62
Figure 2: Graph of MSE and MAE values by DFT functionals based on comparison between the and
of coumarin derivatives

© 2021 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 205
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Vietnam Journal of Chemistry Duong Tuan Quang et al.

Table 1: Results of comparison between the and of coumarin derivatives

Δλmax = - (nm)
Compound CAM- LC- PW6B9
PBE BP86 PBE0 B3LYP M06 M06-2X APDF wB97XD [Ref]
B3LYP wPBE D3
M1 6 6 -26 -19 -20 -39 -36 -48 -24 -38 -25 326 [27]
M2 30 30 1 7 6 -11 -9 -19 3 -10 2 280 [27]
M3 22 21 -24 -15 -21 -41 -41 -56 -21 -43 -22 351 [27]
M4 25 25 -28 -17 -25 -52 -50 -70 -24 -54 -27 384 [27]
M5 46 46 -8 3 -4 -28 -26 -42 -5 -29 -7 360 [27]
M6 23 22 -15 -8 -11 -31 -29 -42 -13 -31 -14 324 [27]
M7 17 16 -20 -13 -16 -35 -33 -45 -18 -35 -19 355 [27]
M8 50 49 -13 -2 -13 -39 -39 -59 -9 -43 -13 370 [27]
M9 50 49 -15 -4 -16 -42 -43 -63 -11 -47 -15 376 [27]
M10 46 45 -16 -5 -16 -42 -43 -64 -14 -47 -16 400 [27]
M11 39 38 -22 -11 -22 -46 -47 -64 -18 -50 -21 373 [27]
M12 16 17 -38 -27 -37 -63 -66 -88 -35 -70 -38 459 [27]
M13 25 25 -37 -25 -37 -59 -61 -79 -33 -65 -36 436 [27]
M14 36 37 -23 -11 -21 -50 -52 -75 -19 -57 -23 436 [27]
M15 32 32 -28 -17 -26 -52 -55 -75 -25 -59 -28 408 [27]
M16 4 4 -46 -36 -45 -64 -66 -81 -43 -69 -44 420 [27]
M17 63 63 -11 3 -11 -43 -44 -65 -7 -49 -11 376 [27]
M18 34 34 3 10 11 3 -57 -67 5 -59 3 278 [27]
M19 53 52 -3 6 0 -27 -25 -41 0 -26 -3 340 [27]
M20 -5 -6 -50 -41 -48 -66 -68 -83 -47 -71 -48 445 [27]
M21 0 0 -46 -37 -44 -62 -64 -81 -43 -68 -44 436 [27]
MSE 29 29 -22 -12 -20 -42 -45 -62 -19 -49 -21
MAE 30 29 23 15 21 43 45 62 20 49 22
RMSD 34 34 27 19 25 46 48 65 24 51 26

The calculation results show that the DFT
functionals used to predict the maximum absorption
wavelength of coumarin derivatives can be divided
into three groups with different performance. The
best performing group includes 5 functionals, sorted
in descending order B3LYP (MAE = 15, RMSD =
19) > APDF (MAE = 20, RMSD = 24) > M06
(MAE = 21, RMSD = 25) > PW6B9D3 (MAE = 22,
RMSD = 26) > PBE0 (MAE = 23, RMSD = 27).
The average performing group includes 2
functionals, sorted in descending order BP86 (MAE
= 29, RSMSD = 34) > PBE (MAE = 30, RMSD =
34). The worst performing group includes 4
functionals, sorted in descending order M06-2X
(MAE = 43, RMSD = 46) > CAM-B3LYP (MAE =
45, RMSD = 48) > wB97XD (MAE = 49, RMSD =
51) > LC-wPBE (MAE = 62, RMSD = 65).
In this study, B3LYP and PBE0 belong to the
group of functionals that give the best predictive
performance of the maximum absorption
wavelength, consistent with previous
publications.[14,25] B3LYP functional gives better
performance than PBE0 functional for coumarin
derivatives, whereas in some previous studies, PBE0
functional gave better performance than B3LYP
functional for other derivatives.[14,25] This indicates
that it is necessary to choose right functionals for
each compound. The studied results also show that
there is no difference between MAE and RMSD
when using them for these model evaluation studies.
When considering the direction of the errors,
PBE and BP86 functionals give values of
systematically higher than the values of .
Meanwhile, the remaining functionals give values of
systematically smaller than the values of
. The results indicate that the values of λmax
systematically obey the order of PBE > BP86 >
B3LYP > APDF > M06 > PW6B9D3 > PBE0 >
M06-2X > CAM-B3LYP > wB97XD > LC-wPBE.
3.2. TD-DFT benchmark based on comparison
between the ( ) and ( )
The results of the linear correlation analysis between
experimental maximum absorption wavelength and
calculated maximum absorption wavelength are
shown in figure 3. The results show that all the DFT
functionals used above yield a very good linear
correlation between and . The evidence is

© 2021 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 206

Vietnam Journal of Chemistry
that the linear correlation coefficient (R) ranges from
0.932 to 0.982, sorted in descending order
corresponding to the functionals as follows: M06-2X
(R = 0.982) > PW6B9D3 (R = 0.979) > M06 (R =
0.977) > PBE0 (R = 0.976) > APDF (R = 0.975) >
B3LYP (R = 0.971) > CAM-B3LYP (R = 0.967) >
LC-wPBE (R = 0.9654) > wB97XD (R = 0.9649) >
BP86 (R = 0.933) > PBE (R = 0.932). Thus, if it is
based on MAE and RMSE (obtained from
comparison between and ), M06-2X
belongs to the group of functionals with the worst
predictive performance (with the largest error), but
from linear correlation analysis, M06-2X belongs to
the group of functionals with the best predictive
performance (with the largest linear correlation
coefficient). When considering the direction of the
errors, the PBE and BP86 functionals result in all the
points on the graph as being below a line with the
Figure 3: Diagrams of linear correlation between the
The calculation results show that the MAEfix
values decrease from 33.8 % (B3LYP) to 84.6 %
(LC-wPBE) compared to those without correction,
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TD-DFT benchmark for UV-Vis spectra of…
equation y = x. Meanwhile, the remaining
functionals result in all the points on the graph as
being above a line with the equation y = x. This
shows that whole recommended DFT functionals
give the calculated maximum absorption wavelength
systematically larger, or smaller than the
experimental maximum absorption wavelength.
On the basis of the linear relationship between
experimental maximum absorption wavelengths and
calculated maximum absorption wavelengths (figure
3), the calculated maximum absorption wavelengths
can be determined according to the equations in
table 2. The calculated differences between the
corrected calculated maximum absorption
wavelengths and experimental maximum absorption
wavelengths ∆ and statistical analysis data of
MAE, RMSM, and MSE are presented in table 3 and
figure 4.
and
the RMSDfix values decrease from 37.1 % (B3LYP)
to 79.8 % (M06-2X) compared to those without
correction. The values of MAEfix and RMSDfix obey
207
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Vietnam Journal of Chemistry Duong Tuan Quang et al.

a M06-2X (MAEfix = 7, RMSDfix = 9) < PBE0, M06, maximum absorption wavelength of coumarin
PW6B9D3 (MAEfix = 9, RMSDfix = 11) < B3LYP, derivatives. These results show the importance of
APDF (MAEfix = 10, RMSDfix = 12) < CAM- correcting the calculated results for the maximum
B3LYP, LC-wPBE, wB97XD (MAEfix = 10, absorption wavelength of coumarin derivatives by
RMSDfix = 13) < PBE, BP86 (MAEfix = 15, RMSDfix TD-DFT, in order to obtain the values of corrected
= 19) order. These results indicate that M06-2X maximum absorption wavelength that are closer to
functional gives the best predictive performance for experimental maximum absorption wavelengths.

Table 2: Equations for calculation of according to of DFT functionals

Functionals Equations
PBE - 17.802
BP86 - 16.424
PBE0 - 66.822
B3LYP - 59.939
M06 - 89.388
M06-2X - 93.783
CAM-B3LYP - 24.851
LC-wPBE - 31.871
APDF - 65.196
wB97XD - 28.301
PW6B9D3 - 69.671

70 62
Error relative to experiment (nm)

MAE without fixing MAE with linear fixing

60
45 49
50 43
40
30 29
30 23 21 22
20
20 15 15 15
9 10 9 7 10 10 9 10 9
10
0

Figure 4: Graph of MAE values with/without linear fixing

4. CONCLUSION between and . For the results obtained

from direct calculation by functionals, B3LYP
The predictive performances of the PBE, BP86, functional gives the best predictive performance of
PBE0, B3LYP, M06, M06-2X, CAM-B3LYP, LC- the maximum absorption wavelengths, with the
wPBE; APDF, wB97XD, and PW6B9D3 smallest values of MAE and RMSD. However,
functionals for maximum absorption wavelength when using the results obtained through correction
have been benchmarked through comparison of based on the linear correlation between the
maximum absorption wavelength values between experimental maximum absorption wavelengths and
calculation and experiment of 21 coumarin the calculated maximum absorption wavelengths,
derivatives. The results show that all the DFT the M06-2X functional gives the best predictive
functionals yield a very good linear correlation performance, with the smallest values of MAEfix and

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RMSDfix. This correction is very necessary because maximum absorption wavelengths. The values of
the values of the corrected maximum absorption MAEfix and RMSDfix are much smaller than MAE
wavelengths are closer to the experimental and RMSD.

Table 3: Results of comparison between the and of coumarin derivatives

= - (nm)

CAM-B3LYP

PW6B9D3
LC-wPBE

wB97XD
M06-2X
B3LYP

APDF
Compounds

PBE0
BP86

M06
PBE

M1 -21 -21 -18 -18 -16 -16 0 3 -18 1 -18

M2 4 4 4 4 4 4 23 27 4 25 4
M3 -6 -7 -9 -8 -10 -9 0 0 -9 1 -8
M4 -4 -4 -6 -4 -5 -11 -4 -8 -5 -5 -5
M5 17 17 13 15 15 13 20 21 13 20 14
M6 -4 -5 -5 -5 -5 -6 9 10 -5 9 -4
M7 -11 -12 -3 -5 -2 1 10 16 -4 11 -3
M8 20 20 9 11 7 2 6 2 11 5 9
M9 20 20 9 10 4 0 3 -2 10 2 8
M10 16 15 13 13 12 9 8 4 12 7 12
M11 10 9 -1 1 -4 -7 -3 -4 0 -3 -1
M12 -15 -14 1 -1 2 4 -8 -9 -1 -7 0
M13 -6 -5 -4 -4 -5 0 -7 -4 -3 -7 -3
M14 5 6 14 13 16 13 4 1 14 3 13
M15 2 2 0 0 1 -1 -5 -8 0 -6 -1
M16 -26 -25 -19 -20 -20 -13 -16 -12 -20 -15 -18
M17 33 33 14 18 11 -2 1 -4 15 -1 13
M18 7 8 6 7 10 23 -35 -36 6 -36 5
M19 24 24 14 14 14 6 17 16 15 19 13
M20 -35 -36 -18 -21 -16 -6 -13 -7 -19 -12 -16
M21 -30 -30 -15 -18 -14 -4 -10 -7 -16 -10 -14
MSEfix 0 0 0 0 0 0 0 0 0 0 0
MAEfix 15 15 9 10 9 7 10 10 10 10 9
RMSDfix 19 19 11 12 11 9 13 13 12 13 11

Acknowledgment. This research was funded by the
Vietnam National Foundation for Science and
Technology Development (NAFOSTED) under grant
number 104.06-2017.51 (Duong Tuan Quang).
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Corresponding authors: Duong Tuan Quang
University of Education, Hue University
34 Le Loi, Hue City, Thua Thien Hue 49000, Viet Nam
E-mail: duongtuanquang@gmail.com.
Pham Cam Nam
The University of Danang - University of Science and Education
41 Le Duan, Hai Chau, Da Nang City 50000, Viet Nam
E-mail: pcnam@dut.udn.vn.
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