N-doped ZnO as an efficient photocatalyst for thiocyanation of indoles and phenols under visible-light

Article abstract of DOI:10.1007/s43630-021-00068-0

In this study, nitrogen-doped ZnO nanorods (N–ZnO NRs) were synthesized via a very simple hydrothermal process, fully characterized, and this photocatalyst was successfully exploited in thiocyanation reactions of indoles and phenols at room temperature under visible light irradiation. Two important classes of aromatic compounds indoles, and phenols using N–ZnO NRs as photocatalyst treated with ammonium thiocyanate as thiocyanation agent formed the corresponding thiocyano compounds in good yields. Nitrogen is one of the most appropriate p-type dopants that is nontoxic, similar to the atomic radius to oxygen, and lower electronegativity and ionization energy than the O atom. Therefore, the N doping converts ZnO into the p-type ZnO semiconductor structure. This potent, simple, and versatile protocol afforded thiocyanation reactions of indole and phenols under visible light. The reactions proceeded through a radical pathway by applying air molecular oxygen as a low cost and environmentally friendly terminal oxidant. The proposed mechanism based on control experiments was thoroughly described. Graphic abstract: [Figure not available: see fulltext.]

Full text of DOI:10.1007/s43630-021-00068-0

Photochemical & Photobiological Sciences (2021) 20:903–911
https://doi.org/10.1007/s43630-021-00068-0
ORIGINAL PAPERS
N‑doped ZnO as an efcient photocatalyst for thiocyanation of indoles
and phenols under visible‑light
Mona Hosseini‑Sarvari1 · Abdollah Masoudi Sarvestani1
Received: 6 March 2021 / Accepted: 21 June 2021 / Published online: 9 July 2021
© The Author(s), under exclusive licence to European Photochemistry Association, European Society for Photobiology 2021
Abstract
In this study, nitrogen-doped ZnO nanorods (N–ZnO NRs) were synthesized via a very simple hydrothermal process, fully
characterized, and this photocatalyst was successfully exploited in thiocyanation reactions of indoles and phenols at room
temperature under visible light irradiation. Two important classes of aromatic compounds indoles, and phenols using N–
ZnO NRs as photocatalyst treated with ammonium thiocyanate as thiocyanation agent formed the corresponding thiocyano
compounds in good yields. Nitrogen is one of the most appropriate p-type dopants that is nontoxic, similar to the atomic
radius to oxygen, and lower electronegativity and ionization energy than the O atom. Therefore, the N doping converts ZnO
into the p-type ZnO semiconductor structure. This potent, simple, and versatile protocol aforded thiocyanation reactions of
indole and phenols under visible light. The reactions proceeded through a radical pathway by applying air molecular oxygen
as a low cost and environmentally friendly terminal oxidant. The proposed mechanism based on control experiments was
thoroughly described.
Graphic abstract
Keywords N-doped ZnO · Photochemistry · Green chemistry · Indole · Phenol
* Mona Hosseini-Sarvari
hossaini@shirazu.ac.ir
Extended author information available on the last page of the article
Vol.:(0123456789)
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1 Introduction
The semiconductor photocatalysis feld as a branch of pho-
tochemistry has attracted a lot of attention in recent years
due to its high potential to deliver valuable products. Indeed,
this privileged approach could successfully change the harsh
reaction conditions in milder using light as a cost-efective
source. Particularly, researchers focused on performing
photochemical reactions under visible light to meet green
chemistry principles.
ZnO is one of the most promising semiconductors due to
its unique properties such as broad bandgap, cost-efective-
ness, high electron mobility, and non-toxicity [1–3]. Studies
of ZnO hexagonal nanorod structure represent a signifcant
research area, and it is reported that one-dimensional (1D)
ZnO nanorod arrays could enhance photocatalytic efciency
[4]. One dimensional nanostructure, such as nanowires and
nanorods, ofers a higher surface-to-volume ratio compared
to nanoparticulate coatings on a fat plate [5] which increases
the photocatalytic efciency. However, unfortunately, only
UV light could activate ZnO to participate in photochemical
reactions. The efciency of photocatalysis depends upon the
harvested region of the solar spectrum by ZnO nanostruc-
tures and the lifetime of the generated electron–hole pair.
As ZnO is a wide bandgap semiconductor and its bandgap
is in the UV region, thus it can only harvest the UV region.
UV light is just 5% of the solar spectrum [6]. To improve
efciency, the frst step is to harvest a larger spectrum of
sunlight so that more electron–hole pairs can be generated.
The second step is to improve the efciency of a photon to
electron conversion. The third step is to increase the lifetime
of photogenerated electron–hole pairs. These issues could
be successfully met by doping with other additives such as
metal or non-metal ions, metal complexes, and organic dyes.
In particular, N-doping is considered to be the most suitable
p-type doping agent that has been successfully applied to
modify ZnO for use in the visible-light region [7–9].
Fig. 1 Schematic energy level diagram of N-doped ZnO for a photo-
chemical reaction
The construction of the C–S bond is a versatile trans-
formation in synthetic and medicinal chemistry due to the
biological properties of obtained sulfur compounds [13, 14].
Among the various approaches for the synthesis of organo-
sulfur compounds, the direct thiocyanation of aromatic and
heteroaromatics is most popular owing to the presence of
aryl thiocyanates in the building blocks of many biologically
active heterocycles and agrochemical compounds [15]. To
date, many methods have been developed for electrophilic
thiocyanation using thiocyanate salt in the presence of CAN,
hypervalent iodine reagents, oxone, Mn(OAc), or other oxi-
dants [16–23]. However, these methods typically sufer from
some drawbacks, such as using stoichiometric oxidants or
generating large amounts of heavy metal wastes [16–23].
In another hand, phenols can act as scavengers to trap the
photogeneration holes in the valence band of semiconduc-
tors, so the thiocyanation of phenols using semiconductors
is a challenging process requiring a suitable catalyst. In this
study, we demonstrated the efect of N-doping in photocata-
lyst properties of ZnO nanorod in thiocyanation of indoles
and phenols under visible-light irradiation.
Traditionally, among non-metal elements, N has been
considered as one of the most appropriate p-type dopants
highly thanks to its nontoxicity, abundance similar to the
atomic radius to that of O, and lower electronegativity and
ionization energy than those of the O atom. The N doping
helps to convert the n-type into the p-type ZnO semicon-
ductor structure. As the nearly similar ionic radius of N to
O, a strong contribution of mixing of its 2p orbital with 2p
orbital of O helps in the bandgap narrowing which improves
the photocatalytic activity [10, 11]. As shown in Fig. 1, with
the addition of N, an inter-band is formed between VB and
CB of ZnO, resulting in the decrease in the bandgap energy
as well as the generation of a large number of holes in VB
which converts the n-type to the p-type semiconductor [12].
2 Results and discussion
First, several N-doped ZnO with diferent content of nitro-
gen using urea as nitrogen source were synthesized based
on our previous work [24]. To evaluate the nitrogen content,
each of the synthesized catalysts was analyzed by CHNS
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Photochemical & Photobiological Sciences (2021) 20:903–911
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analysis. Accordingly from the data obtained by CHNS
analysis the weight ratios (in grams) of ZnO and urea with
0.5:1, 0.5:2, 0.5:4, and 0.5:8 ratio have 0.3%, 0.32%, 0.38%,
and 0.45% nitrogen, respectively. The obtained pink-colored
materials are shown in Fig. 2. Based on the UV–Vis dif-
fuse refectance analysis it was found that the ZnO nanorod
(NRs) with a higher content of nitrogen (0.45% N-doped)
could signifcantly improve the structure of ZnO by shifting
the absorption intensity peak in the visible region (Fig. 2).
Therefore, this material was chosen as an appropriate pho-
tocatalyst for our studies.
Zn 3d and a mixture of N 2p and O 2p states and (2) band-
gap between Zn 3d and O 2p. However, only the bandgap
between Zn 3d and the mixture of N 2p and O 2p states can
be excited by visible light.
2.1 XRD
The difractogram of the pure ZnO and 0.45% N–ZnO NRs
is shown in Fig. 4. It is observed that ZnO has a wurtzite
phase (JCPDF: 891,397) in both samples. No signifcant
peak for nitrogen is observed in N–ZnO NRs which sug-
gests the possibility of introduction of nitrogen into the
ZnO lattice without afecting the ZnO crystal structure.
However, the XRD peaks of 0.45% N–ZnO NRs are found to
be shifted to the higher ꢀ values [26]. N doping shifts the dif-
fraction peak towards a higher angle which was attributed to
the larger bond length of Zn–O than that of Zn–N [27–29].
The particle size of 0.45% N–ZnO NRs as evaluated by the
Scherrer formula is about 48.63 nm, while that of the pure
ZnO is about 49.5 nm. The reduction of particle size may be
attributed to the incorporation of nitrogen in ZnO.
The band gaps were determined by comparing the
UV–Vis DRS spectra of prepared materials. Figure 3a shows
the UV–Vis DRS of the pure and 0.45% N–ZnO NRs. While
the pure ZnO showed absorption cut of the edge at 385 nm
related to the bandgap of 3.25 eV, the nitrogen-doped ZnO
showed the absorption in the visible region (491 nm), owing
to the impurity of N 2p states [25]. The bandgap between
Zn 3d and impurity N 2p is 2.52 eV calculated by equation
Eg=1240/λmax, Eg the bandgap and λ the wavelength. Based
on these observations we can discuss two bandgaps after
nitrogen doping as shown in Fig. 3b: (1) bandgap between
2.2 FT‑IR spectrum
Figure 5 shows the FT-IR spectrums of undoped ZnO and
0.45% N–ZnO NRs in the region of 400–4000 cm−1 [30].
There is broadband at 3410 cm−1 that indicates the presence
of –OH groups of absorbed water during the preparation
process. The band arising from the bonding between Zn–O
(473 cm−1, 532 cm−1) is clearly represented. FT-IR spec-
trum shows the presence of stretching vibrational bond C–O
(1650 cm−1), C–H (1381 cm−1). In the FT-IR spectrum also
there is no peak corresponding to nitrogen which accords
well with the XRD analysis. This may be due to the low
nitrogen doping in ZnO. The intensity of stretching vibra-
tional bond of O–H (3422 cm−1), and stretching vibrational
bond C–O (1650 cm−1), C–H (1381 cm-1) peaks in 0.45%
Fig. 2 UV–Vis difuse refection absorption spectra of fve type syn-
thesized samples
Fig. 3 a UV–Vis difuse refec-
tance spectra of the pure and
0.45% N-ZnO NRs. b Proposed
band structure of nitrogen-
doped ZnO, valence band O 2p,
and a mixture of O 2p and N 2p
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Photochemical & Photobiological Sciences (2021) 20:903–911
Fig. 4 a XRD pattern of the pure ZnO and 0.45% N-ZnO NRs. b Shifts in peak position is depicted through the enlarged view of (101) peaks for
pure and 0.45% N-ZnO NRs
N–ZnO NRs lower compared to undoped ZnO. This may be
120
due to exposure to furnace heat.
100
2.3 SEM and TEM
80
We have also used the SEM to directly analyze the mor-
60
phology of the 0.45% N–ZnO NRs nanostructure. The SEM
undoped ZnO
40
image of freshly synthesized 0.45% N–ZnO NRs is shown in
Fig. 6a. The nano-rod surface morphology could be clearly
20
0.45% N-ZnONRs
seen with a wide range of sizes. To further study micro-
0
scopic morphology and structure information, the TEM
3900
3400
2900
2400
1900
1400
900
400
Wavenumber (cm-1)
analysis of 0.45% N–ZnO NRs has been also performed, as
shown in Fig. 6b.
Fig. 5 FT-IR spectrum of undoped ZnO and 0.45% N-ZnO NRs
Fig. 6 a SEM. b TEM images
0.45% N-ZnO NRs
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907
Table 1 Results of BET surface area measurements for 0.45% N-ZnO
Table 2 Model reaction using 1H-indole and ammonium thiocyanatea
NRs
BJH adsorption summary
Surface area
Pore volume
Pore Diameter Dv(d)
BET summary Surface Area
9.554 m2/g
0.072 cc/g
1.29 nm
7.823 m2/g
Entry Cat (x mg)
solvent Light
Yield %b
13
1
0.45% N-ZnO
(0.010 g)
CH3CN CFL (15 W)
2.4 BET
2
0.45% N-ZnO
CH3Cl CFL (15 W)
39
44
15
20
18
12
59
68
84
76
27
10
The specifc surface area of 0.45% N–ZnO NRs was meas-
ured by BET analysis that is shown in Table 1. The BET
surface area of 0.45% N–ZnO NRs powder was found to
be 7.823 m2/g, whereas the BJH adsorption surface area of
pores was 9.554 m2/g. The single point total pore volume
was found to be 0.072 cc/g.
(0.010 g)
3
0.45% N-ZnO
(0.010 g)
THF
CFL (15 W)
4
0.45% N-ZnO
DMSO CFL (15 W)
(0.010 g)
5
0.45% N-ZnO
(0.010 g)
DMF
EtOH
H2O
CFL (15 W)
CFL (15 W)
CFL (15 W)
In continuation of our interest in C–S bond formation,
particularly thiocyanation reaction, we frst examined the
optimal 0.45% N–ZnO NRs in thiocyanation of indoles. To
this end, the reaction of 1H-indole and ammonium thiocy-
anate was selected as a model reaction for further investi-
gations (Table 2). It was observed that solvent had a great
efect on the yield of the reaction. While no desired product
was obtained in common solvents such as EtOH, H2O, and
DMSO, in ethyl acetate the yield was improved under irra-
diation with 15 W CFL (Table 2, entry 8). Then the reaction
was carried out using diferent amounts of 0.45% N–ZnO
NRs, 3 mg of the photocatalyst was the best choice, deliver-
ing the desired product in 84% yield within 24 h (Table 2,
entry 10). The yield of the reaction reduced with ZnO
nanorod and 38% N–ZnO as photocatalyst (Table 2, entries
9 and 10), indicating the key role of N-doping in photo-
catalytic properties of ZnO. To evaluate the performance
of the photocatalyst, the model reaction was tested in the
absence of photocatalyst and only 10% yield was obtained
(Table 2, entry 13). While the reaction could not proceed in
the absence of light, blue light showed high performance for
the reaction, afording the target product in 94% yield within
16 h (Table 2, entry 18). Of note, the reaction yield signif-
cantly decreased using argon instead of oxygen atmosphere
(Table 2, entry 19).
6
0.45% N-ZnO
(0.010 g)
7
0.45% N-ZnO
(0.010 g)
8
0.45% N-ZnO
EtOAc CFL (15 W)
EtOAc CFL (15 W)
EtOAc CFL (15 W)
EtOAc CFL (15 W)
EtOAc CFL (15 W)
EtOAc CFL (15 W)
(0.010 g)
9
0.45% N-ZnO
(0.005 g)
10
11
12
0.45% N-ZnO
(0.003 g)
0.38% N-ZnO
(0.003 g)
Undoped
ZnO(0.003 g)
13
14
–
0.45% N-ZnO
EtOAc Blue LED 12 W 94
(0.003 g)
15
0.45% N-ZnO
(0.003 g)
EtOAc Green LED 12 W 38
16
0.45% N-ZnO
EtOAc Red LED 12 W
EtOAc
0
0
(0.003 g)
17
0.45% N-ZnO
(0.003 g)
–
18c
19d
0.45% N-ZnO
EtOAc Blue LED 12 W 94
EtOAc Blue LED 12 W 10
(0.003 g)
0.45% N-ZnO
(0.003 g)
As stability and reusability are the main components of
a considerable heterogeneous catalyst, we examined the
recyclability and reusability of this nano photocatalyst.
Using the optimization reaction condition, we evaluated the
catalyst activity in the thiocyanation reaction of indole with
ammonium thiocyanate. For this purpose, after each run,
the catalyst was separated by centrifugation, washed with
water and ethanol, dried, and used for the next run. The
photocatalyst was applied for four runs without any decrease
in photocatalytic activities to the preparation of the desired
aReaction conditions: 1H-indole (0.10 mmol), ammonium thiocy-
anate (0.30 mmol), 0.45% N-ZnO NRs (0.003g) in EtOAc (1 mL)
bIsolated yields
cDuring 16 h
dUnder Ar atmosphere
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Photochemical & Photobiological Sciences (2021) 20:903–911
Table 3 Thiocyanation reaction of indole derivatives
product; moreover, the XRD pattern and FT-IR spectrum of
the recovered catalyst after the last run was compared to the
fresh catalyst and no considerable change in the structure of
the photocatalyst was observed (Fig. 7).
With optimum conditions in hand, we screened the sub-
strate scope of the reaction (Table 3). In most cases, the
desired products obtained in high yields, only in the case of
2-methyl indole 1c due to steric hindrance lower yield was
observed (Tables 3, 1c).
Then we extend our work toward the thiocyanation of
phenols. In this case similar to indole the best reaction con-
ditions were obtained in EtOAc using 45% 0.45% N–ZnO
NRs at room temperature, but in longer reaction time (48 h)
(Table 4). As shown in Table 3, thiocyanation predominantly
took place at the para position of phenols. It was observed
that the reaction was sensitive to the nature of substitu-
ents, and phenols bearing electron-donating groups such as
methyl and methoxy gave higher yields (Table 4, 4d–g).
Reaction conditions: 1H-Indole (0.5 mmol), ammonium thiocyanate
(1.5 mmol), 0.45% N-ZnO NRs (15 mg), EtOAc (5 mL)
Isolated yields
92
93
94
94
4
3
2
1
To gain insight into the mechanism of the reaction several
control experiments were conducted under the optimized
conditions (Scheme 1). When the radical-trapping agent
TEMPO (2 equiv) was added to reaction mixtures under
the relevant standard conditions, no product was observed.
In addition, triethanolamine (TEA) as a scavenger to trap
the holes were examined, and no reactivity was observed
for the 0.45% N–ZnO NRs (Scheme 1). These results sug-
gested that this process was likely progressed through the
radical process.
0%
20%
40%
Yield (%)
60%
80%
100%
100
80
60
40
20
0
fresh catalyst
Based on these results we proposed a mechanism as
shown in Scheme 2. First, under visible light irradiation,
electron and hole pairs were generated between N 2p states
and the conduction band of Zn 3d. The excited electrons in
the conduction band moved to the surface and further trans-
fer to surface-adsorb oxygen, producing superoxide anion.
Subsequently, a SET process between −SCN and hole afords
·SCN. Electrophilic addition of this radical to 1a resulted in
intermediate A which oxidized to give cation intermediate
B. fnally, rearomatization of B followed by deprotonation
delivered the target product 2a.
catalyst after last run
3400
2400
1400
400
Wavenumber (cm-1)
1000
800
600
400
200
0
fresh catalyst
catalyst after last run
It should be noted that the 0.45% N–ZnO NRs photo-
catalyst could be separated and recovered conveniently by
centrifugation from the reaction mixture, and used in the
next run. Following this procedure, the catalyst was recycled
and reused efectively four times (for two model reactions,
indole, and phenol) without any decrease in photocatalytic
activities.
20
30
40
50
60
70
80
For comparison, we provide a table (Table 5) of available
visible light catalysts reports for thiocyanation of indoles
and phenols and comparing our and the previous results. As
Fig. 7 a Recyclability, b FT-IR spectrum, and c XRD pattern of the
recovered 0.45% N-ZnO NRs after four-cycle
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Photochemical & Photobiological Sciences (2021) 20:903–911
909
Table 4 Thiocyanation of phenol under visible light over 0.45% N-ZnO NRs NRs.
aReaction conditions: Phenol (0.1 mmol), ammonium thiocyanate (0.3 mmol), 0.45% N–ZnO NRs (0.003 g), solvent (1 mL)
bIsolated yields
can be seen in our work we use a heterogeneous catalyst and
also a greener solvent that are the highlight and signifcance
of the present work.
nanorod in extremely mild reaction conditions together with
moderate to good yields. Mechanistic studies confrmed
that this reaction progressed through a photoredox radical
pathway.
3 Conclusion
In summary, in this study we explored the efect of N-doping
in photochemical properties of ZnO nanorods, we have also
developed regioselective thiocyanation of various indoles
and phenols using reusable photocatalyst 0.45% N–ZnO NRs
Scheme 2 Proposed mechanism
Scheme 1 Control experiments
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Photochemical & Photobiological Sciences (2021) 20:903–911
Table 5 Thiocyanation of
indoles and phenols under
visible light irradiation over
photocatalysts using air as
oxidant at r.t
Catalyst (substrate for thiocyanation) Time (h) Solvent Irradiation
Yield
Refs
[31]
TiO2/MoS2 (indole)
Rose Bengal (indole)
ARS-TiO2 (indole)
16
18–48
20
CH3CN Visible light 14w CFL 93%
THF
THF
THF
Visible light 14 W CFL Up to 98% [32]
Blue LEDs 12w
Blue LEDs 12w
93%
92%
94%
83%
[33]
[33]
This work
This work
ARS-TiO2 (phenol)
24
0.45% N–ZnO NRs (indole)
0.45% N–ZnO NRs (phenol)
16
48
EtOAc Blue LEDs 12w
EtOAc Blue LEDs 12w
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Supplementary Information The online version contains supplemen-
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Acknowledgements This work was supported by the Shiraz University.
Author contributions The manuscript was written through the contri-
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Photochemical & Photobiological Sciences (2021) 20:903–911
911
Authors and Afliations
Mona Hosseini‑Sarvari1 · Abdollah Masoudi Sarvestani1
1
Nano Photocatalysis Lab, Department of Chemistry, Shiraz
University, Shiraz 7194684795, Islamic Republic of Iran
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