Article  
Immobilization of Dibenzalacetone on TiO2 Surface and  
its Potential as Anti-UV Material  
Mokhamat Ariefin1*, Rokiy Alfanaar1  
1Department of Chemistry, University of Palangka Raya, Palangka Raya, Central Kalimantan, Indonesia  
Abstract  
Sunlight has been known to provide many benefits to human life. However, behind these benefits, there  
are some negative effects along with the destruction of the ozone layer and the environment on earth.  
One of them is exposure to ultraviolet (UV) rays which can cause several diseases such as skin cancer.  
One way to overcome this is by using sunscreen substances. In this study, dibenzalacetone  
immobilization on TiO2 has been carried out for anti-UV applications. Based on the test results using UV-  
Vis spectrometry, TiO2, and dibenzalacetone both have anti-UV properties with maximum peaks at  
wavelengths of 335 nm and 346 nm with absorbance values of 0.871 and 1.197. Immobilization of TiO2  
with dibenzalacetone gives an absorbance with a value of 1.221 at a wavelength of 329. These results  
indicate that TiO2 immobilization with dibenzalacetone provides better anti-UV A properties than TiO2  
because of the higher absorbance value.  
Keywords: dibenzalacetone, TiO2, immobilization, anti-UV  
Graphical Abstract  
*
Corresponding author  
Email addresses: mokhamatariefin@mipa.upr.ac.id  
DOI: 10.22437/chp.v7i1.26109  
Received 15 June 2023; Accepted 21 July 2023; Available online 30 July 2023  
Copyright © 2023 by Authors, Published by Chempublish Journal. This is an open access article under the CC BY License  
(https://creativecommons.org/licenses/by/4.0)  
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Chempublish Journal, 7(1) 2023, 1-7  
of UV-induced pyrimidine dimers (Figure 1)  
occurs because the skin is exposed to UV-B and  
Introduction  
UV-C rays [10]  
.
Sunlight has been utilized for a long time by  
humans in various fields such as for health,  
drying food ingredients, or just drying clothes.  
Over time and technological developments, the  
use of sunlight has also increased, such as the  
use of sunlight as an energy source or the use of  
solar cells [1]. However, behind these benefits,  
along with the times, environmental damage has  
resulted in the depletion of the ozone layer in the  
atmosphere [2]. The destruction of the ozone  
layer in the atmosphere causes the intensity of  
UV rays entering the earth to become more. The  
effects of UV light were first reported in 1983  
which showed the effects of hyperpigmentation  
[3]. This finding was supported by research  
conducted by the group of Mahmoud, et al, in  
2010 which proved that hyperpigmentation  
Figure 1. Dimer of pyridine  
Based on the dangers of mutations due to UV  
exposure, one form of prevention is the use of  
sunscreen. Sunscreen is one of the skincare  
products that can protect the skin from sun  
exposure, especially from UV rays. This product  
works by absorbing or reflecting UV rays that hit  
the protected part [11]. In addition, the use of  
sunscreen is an effective way to prevent skin  
damage that occurs due to sun exposure such as  
would occur due to UV exposure [4]  
.
UV light found in sunlight has a wavelength  
between 100-400 nm. Based on its low  
wavelength, UV light has great energy. UV light  
can be divided into several types based on its  
wavelength, namely UV-A at 320-400 nm, UV-B at  
280-320 nm, and UV-C at 100-280 nm. Rays with  
wavelengths below 200 nm are effectively  
absorbed and can be eliminated by oxygen in the  
Earth's atmosphere. UV-C has a wavelength  
below 280 nm and will be absorbed in the  
stratospheric layer [5]. However, environmental  
preventing  
sunburn,  
skin  
aging,  
collagen  
degradation, and pigmentation of the skin [12,13]  
.
Sunscreens are grouped into several types such  
as inorganic sunscreens, organic sunscreens, and  
plant-based sunscreens. Inorganic sunscreens  
are categorized as physical filters because the  
active ingredients contained in them are  
minerals, such as TiO2 [12,13]. Besides minerals,  
more than 50 types of organic material-based  
sunscreens have been developed to date. P-  
aminobenzoic acid (PABA) was the first anti-UV  
compound to be characterized as a UV-B  
absorber [12]. However, further research indicates  
that the use of PABA can cause skin irritation.  
Based on this, several alternative organic  
compounds such as cinnamates, salicylates,  
benzophenones, benzimidazoles, and other  
chromophores were developed. One of the  
damage has resulted in the inhibition of UV rays  
in the atmosphere layer becoming ineffective  
[6]  
.
Exposure to UV rays with high intensity to the  
skin for a long time will cause several losses such  
as skin redness (erythema), sunburn, or if it gets  
longer, it will cause skin cancer [7]  
.
The  
association  
between  
prolonged  
sun  
exposure and skin cancer has been widely  
studied. Epidemiologically, non-melanoma skin  
cancer is the most diagnosed type of skin cancer  
in geographical populations with high sun  
exposure [8]. However, it is not uncommon for  
melanoma skin cancer cases to occur due to high  
sun exposure [9]. DNA damage or mutation is one  
of the causes of skin cancer due to high sun  
exposure. This DNA damage can occur due to  
direct or indirect radiation. Direct DNA damage  
can occur due to the dimerization process of  
pyrimidine bases predominantly. The formation  
chromophores  
with  
an  
aromatic  
ring  
arrangement connected to a carbonyl group is  
chalcone. Several studies have reported that  
chalcone-derived compounds can absorb light in  
the UV area. In chalcone, there are two important  
absorptions, namely absorption at wavelengths  
of 220-270 nm and 340-390 nm [14]. This  
absorption occurs due to electronic transitions in  
n → π* and π → π*. This electronic transition  
shows the potential of chalcone as an anti-UV  
material. Based on research on chalcone as anti-  
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Chempublish Journal, 7(1) 2023, 1-7  
UV, analog compounds of chalcone are thought  
to have the same properties and potential. One  
of the analog compounds of chalcone is  
dibenzalacetone. Dibenzalacetone is an analog of  
chalcone with a conjugated π bond extension,  
with two aromatic rings and carbonyl groups  
total of 2 g of sodium hydroxide was dissolved in  
20 mL of water and 16 mL of ethanol. The  
solution was stirred rapidly for 15 minutes at  
room temperature. Then 25 mmol of acetone  
and 25 mmol of benzaldehyde are added to the  
mixture. After a few minutes, 25 mmol of  
benzaldehyde derivative was added and the  
mixture was left to react for a while. After that,  
the precipitate produced in the reaction was  
filtered using a Buchner funnel and washed using  
water. The precipitate obtained was then purified  
by recrystallization or separation by column  
chromatography.  
[15,16]  
.
Dibenzalacetone is an analog compound of  
chalcone which has the addition of π conjugation  
so that it will form a system of electron donors  
(D) and electron acceptors (A) with a π bridge  
connecting D and A [16]. Apart from using  
conventional methods, chalcone synthesis can  
also be carried out using irradiation assistance  
from microwave (Microwave Assisted Organic  
Immobilization dibenzalacetone on TiO2 surface  
Immobilization of dibenzalacetone is based on  
the principle of adsorption on the surface of TiO2.  
This immobilization begins with weighing  
dibenzalacetone and TiO2 in mol ratio of 2: 5.  
Dibenzalacetone dissolved in ethanol and placed  
in a closed container. In the closed container was  
inserted TiO2 solids and stirred for 48 hours. After  
48 hours, the solution was left for 12 hours to  
undergo decantation. Filtrate and solids are  
separated with filter paper where the solids will  
be dried under closed conditions from light to  
dry. The immobilized solid will be used in the next  
stage.  
Synthesis, MAOS) [17]  
.
In previous experimental studies, the use of TiO2  
as anti-UV has been used separately without  
being combined with other anti-UV materials. In  
addition, the use of chalcones as anti-UV derived  
from organic compounds has been done, but the  
compound has not been done. Therefore, in this  
research, the study of the anti-UV properties of  
dibenzalacetone  
and  
the  
effect  
of  
dibenzalacetone immobilization on TiO2 as anti-  
UV will be conducted.  
Experimental Section  
Materials  
Characterization of dibenzalacetone-TiO2 using  
FTIR  
The immobilized solid was analyzed using FT-IR  
Shimadzu from wave number 350 to 4000 cm-1.  
The characterization process was carried out at  
Department of Chemistry, Brawijaya University.  
The immobilized solid was taken with the tip of a  
spatula and crushed using KBr solids. The results  
of mixing the solids were analyzed using FT-IR to  
determine the functional groups of the solids. As  
a comparison, FT-IR characterization was also  
carried out on TiO2 and dibenzalcetone which  
had not been treated with immobilization.  
The materials used in this experiment were  
sodium hydroxide (NaOH), ethanol (C2H6O) 98%  
from Merck, distilled water, titanium oxide (TiO2),  
acetone (C3H6O) from Merck, and benzaldehyde  
(C7H6O, purity 99%) from Merck.  
Instrumentation  
Intruments used in this experiment is UV-Vis  
Spectrophotometer Jasco V760, Fourier Trnsform  
Infrared  
(FTIR)  
ATR-S  
Serial  
No.  
A224158/Shimadzu, Hotplate stirrer IKA C-MAG  
HS7 I.  
Diffuse reflectance UV study immobilizes  
dibenzalacetone-TiO2  
Procedure  
The UV Reflectance Diffuse study was conducted  
at Ma Chung University Pharmacy laboratory  
with UV-Vis Spectrophotometer Jasco V760  
Dibenzalacetone synthesis  
The synthesis procedure of dibenzalacetone  
derivatives followed the procedure performed by  
Conard and Morris with slight modifications. A  
instrumentation  
with  
solids  
mode.  
The  
wavelength used in this study was 190-900 nm.  
The immobilized solid was compacted in the  
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Chempublish Journal, 7(1) 2023, 1-7  
sample container using a manual press to avoid  
air in the solid cavity. The solid was then inserted  
in the sample holder and analyzed under dark  
conditions. The results of the DR UV study were  
used in the study of the anti-UV potential of the  
solid results of dibenzalacetone immobilization  
on the TiO2 surface.  
that can occur in either acidic or basic  
environments [18]. The use of several types of acid  
catalysts such as hydrochloric acid (HCl) or the  
use of bases such as sodium hydroxide or  
potassium hydroxide has been carried out. The  
synthesis reaction of dibenzalacetone is carried  
out through the Claisen-Schmidt condensation  
reaction by reacting benzaldehyde and acetone  
in an alkaline atmosphere. hydroxide ions from  
NaOH will react with alpha hydrogen from  
acetone to form enolate ions. The enolate ion will  
attack the electrophile side of benzaldehyde  
(carbonyl group) forming an aldol condensation  
product. The same reaction occurs twice to  
produce a yellow dibenzalacetone product. The  
Analysis of anti-UV potency of dibenzalacetone-  
TiO2  
Anti-UV potential analysis was conducted using  
the CSV file obtained from the DR UV study  
results in the previous step. The CSV file obtained  
was opened using Origin application to see the  
spectra pattern obtained. The spectra obtained  
were analyzed for the position of the absorption  
that occurred and whether it had absorption in  
the UV region. The absorption results are then  
continued by classifying them as anti-UV-A, UV-B,  
or UV-C.  
resulting  
product,  
dibenzalacetone,  
was  
obtained with a yield of 85.12%. Based on FTIR  
analysis, there is an absorption at 3053 cm-1 and  
3026 cm-1 which shows the C-H bond in the  
benzyl ring, which is reinforced by the double  
bond C=C absorption at 1446 - 1600 cm-1. Then  
there is a signal in the 1647 cm-1 region which  
shows the absorption of the C = O bond (carbonyl  
group). This absorption spectra shows the  
Results and Discussions  
Synthesis of dibenzalacetone and  
immobilized dibenzalacetone to TiO2 surface  
characteristic absorption of dibenzalacetone  
[19]  
compound  
.
The  
FTIR  
spectra  
of  
The dibenzalacetone synthesis reaction belongs  
to the category of aldol condensation reactions  
dibenzalacetone is available on Figure 2.  
Figure 2. FTIR spectra of dibenzalacetone.  
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Chempublish Journal, 7(1) 2023, 1-7  
Figure 3. Proposed immobilization mechanism of dibenzalacetone on TiO2 surface.  
The  
successful  
immobilization  
of  
maximum  
wavelength  
of  
each  
material  
dibenzalacetone was inferred from the detection  
of a distinct functional group signal in the  
immobilization outcomes. The process of  
immobilization can be attributed to electrostatic  
interactions between the positively charged Ti  
surface  
dibenzalacetone,  
associated with anti-UV properties. TiO2 used  
analyzed using a UV-Vis spectrophotometer  
showed anti-UV properties with a peak at 335 nm  
with an absorbance of 0.871. This peak is in  
accordance with previous research where TiO2 is  
a material that acts as anti-UV A[20]. TiO2 material  
is immobilized with dibenzalacetone which  
shows anti-UV-A properties with a maximum  
wavelength at 346 nm. Dibenzalacetone has a  
higher absorbance with an absorbance value of  
and  
the  
particularly  
illustrates the proposed  
electron-rich  
sites  
carbonyl  
of  
the  
groups. Figure  
3
mechanism of immobilization. The manifestation  
of dibenzalacetone on the TiO2 surface prompted  
a modification in its properties, which were  
1.197.  
The  
results  
of  
dibenzalacetone  
subsequently investigated using  
spectrophotometer.  
a
UV-Vis  
immobilization on the TiO2 surface provide anti-  
UV-A properties according to Figure 4. The  
immobilized  
material  
has  
a
maximum  
UV properties and activities as anti-UV  
wavelength of 329 nm and absorbance of 1.221  
which shows better properties than TiO2 because  
it has a higher absorbance.  
UV-Vis analysis was performed with a wavelength  
of 200-800 nm. This analysis aims to know the  
Figure 4. UV spectra of dibenzalacetone, TiO2, and dibenzalacetone immobilized on TiO2.  
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Chempublish Journal, 7(1) 2023, 1-7  
6. Appannagari, R. R. (2017). Environmental pollution  
causes and consequences: a study. North Asian  
International Research Journal of Social Science &  
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Conclusions  
Dibenzalacetone immobilization on TiO2 has  
been carried out for anti-UV applications. based  
on the test results using UV-Vis spectrometry,  
TiO2, and dibenzalacetone both have anti-UV  
properties with maximum peaks at wavelengths  
of 335 nm and 346 nm with absorbance values of  
0.871 and 1.197. Immobilization of TiO2 with  
dibenzalacetone gives an absorbance with a  
value of 1.221 at a wavelength of 329. These  
results indicate that TiO2 immobilization with  
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