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Covalent Organic Frameworks
Transformation of Covalent Organic Frameworks from
N-Acylhydrazone to Oxadiazole Linkages for Smooth Electron
Transfer in Photocatalysis
Shuailong Yang, Haowei Lv, Hong Zhong, Daqiang Yuan, Xinchen Wang, and Ruihu Wang*
Abstract: Covalent organic frameworks (COFs) are regarded
as new platforms for solar-to-chemical energy conversion due
to their tailor-made functions and pre-designable structures.
Their intrinsic reversibility and the high polarization of
organic linkages inevitably result in poor chemical stability
and weak optoelectronic properties. Herein, one N-acylhydra-
zone-linked COF (H-COF) was converted into a stable and
π-conjugated oxadiazole-linked COF via post-oxidative cycli-
zation. Both chemical stability and π-electron delocalization
throughout the reticular framework are significantly im-
proved, leading to a high hydrogen evolution rate of
2615 μmol g 1 h 1 upon visible light irradiation, which is over
four times higher than that of H-COF. This work provides a
facile protocol for the fabrication of π-conjugated COFs and
the modulation of photophysical properties for photocatalytic
application.
Covalent organic frameworks (COFs) are one class of
promising crystalline porous materials owing to their large
surface area, well-defined porosity and tailor-made
functions.[1–3] The structural superiorities of COFs offer
tremendous potential for diverse applications in gas adsorp-
tion, catalysis, energy storage and optoelectronics.[4–7] It is
widely accepted that the functionality of COFs comes from
the building blocks, while the stability is attributed to the
covalent linkages.[8–10] The flexible synthetic strategy of
COFs allows for reversible formation of covalent bonds
between task-specific building blocks by following basic
principles of reticular chemistry and dynamic covalent
[*] S. Yang, H. Lv, H. Zhong, Prof. D. Yuan, Prof. R. Wang
State Key Laboratory of Structural Chemistry, Fujian Institute of
Research on the Structure of Matter, Chinese Academy of Sciences
Fuzhou
Fujian 350002 (China)
S. Yang, Prof. R. Wang
School of Chemical Engineering and Technology
Hebei University of Technology
Tianjin, 300130 (China)
E-mail: ruihu@fjirsm.ac.cn
Prof. X. Wang
State Key Laboratory of Photocatalysis on Energy and Environment
College of Chemistry
Fuzhou, Fujian 350108 (China)
S. Yang, Prof. R. Wang
University of Chinese Academy of Sciences
Beijing, 100049 (China)
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How to cite: Angew. Chem. Int. Ed. 2022, 61, e202115655
International Edition: doi.org/10.1002/anie.202115655
German Edition: doi.org/10.1002/ange.202115655
chemistry.[11, 12] However, the intrinsic reversibility and high
polarization of organic linkages could lead to insufficient
chemical stability and discontinuous π-electron delocaliza-
tion throughout host frameworks.[12, 13] For example, typical
imine-linked COFs usually undergo hydrolysis under acidic
conditions or exchange with amines owing to the reversible
nature of the imine linkage, while the strong polarization
nature of the C=N bond is inferior in π-electron delocaliza-
tion between the linked building units.[14] Considerable
efforts have been made to explore new chemistry to
construct highly stable and fully conjugated COFs.[15–17] A
prevalent method is the combination of a reversible imine-
forming reaction with an irreversible post-synthetic modifi-
cation reaction that confers stability.[18] The two-step strat-
egy could convert the imine bond into more stable aromatic
linkages, such as oxazole, thiazole and quinolone.[13, 19]
Despite great advances in the aromatic conversion of the
imine-linked COFs, the synthesis of chemically stable COFs
from other linkages into new aromatic units remains
challenging.
N-acylhydrazone is another type of promising linkage in
COFs.[20, 21] N-acylhydrazone-linked COFs are relatively
stable when compared with their imine-linked counterparts,
but significant loss in crystallinity and an obvious decrease
in catalytic activity are still observed when the reticular
frameworks are employed in heterogeneous catalysis.[22] The
oxidative cyclization of N-acylhydrazone is known to be one
of the feasible routes for the synthesis of 1,3,4-oxadiazole
derivatives.[23] The resultant oxadiazole motifs have attracted
considerable interest in the field of material science and
pharmaceutical chemistry primarily due to their unique
optoelectronic performance and biological properties.[24, 25]
However, rapid formation of the oxadiazole ring by
irreversible oxidation minimizes the reverse reaction. The
crystalline oxadiazole-based polymers remain largely unex-
plored despite the fact that the oxadiazole-based amorphous
materials have been widely applied.[26] It is of paramount
importance from both academic and industrial viewpoints to
construct oxadiazole-linked COFs. Starting from N-acylhy-
drazone-linked COFs will be one feasible solution to bypass
crystallization problems encountered in irreversible forma-
tion of the oxadiazole unit.
As a proof-of-concept study, herein, we report the
synthesis of an irreversible oxadiazole-linked COF (ODA-
COF) achieved by post-oxidative cyclization of the rever-
sible hydrazone linkage. ODA-COF maintains its topology,
crystallinity and the porosity of the hydrazone-linked COF
© 2021 Wiley-VCH GmbH

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(H-COF) with concomitant enhancement of the chemical
stability and π-electron delocalization. As a result of the
irreversible formation of an aromatic oxadiazole linkage
throughout the host framework, ODA-COF shows superior
photocatalytic H2 evolution activity of 2615 μmol g 1 h 1
upon visible light irradiation, which significantly outper-
forms that of H-COF under identical conditions.
The synthesis of ODA-COF followed a two-step reac-
tion sequence of Schiff-base reaction and irreversible
oxidative cyclization (Figure 1). The reversible condensation
reaction between 2,5-diethoxyterephthalohydrazide and
1,3,5-triformylbenzene in mesitylene/dioxane and acetic acid
gave rise to H-COF. Subsequent oxidative cyclization of the
N-acylhydrazone linkage in H-COF into the aromatic
oxadiazole unit by Cu(CF3SO3)2 in DMF generated ODA-
COF. The inductively coupled plasma atom emission
spectrometry (ICP-AES) measurement shows that the
content of Cu residual in ODA-COF is as low as
0.023 mmol g 1.
The conversion of N-acylhydrazone into the oxadiazole
linkage was monitored by Fourier-transform infrared
(FTIR), solid-state 13C NMR and X-ray photoelectron
spectroscopy (XPS) spectra. In the FTIR spectrum of H-
COF, the C=N and C=O stretching vibration peaks of the
N-acylhydrazone linkage occur at 1625 and 1670 cm 1,
respectively. These characteristic peaks disappear in the
FTIR spectrum of ODA-COF, new peaks at 1655 and
1611 cm 1 correspond to C=N, while the peaks at 1230 and
950 cm 1 are assigned to C O C and oxadiazole, respec-
tively (Figure 2a).[27, 28] These results support the oxidative
cyclization of the N-acylhydrazone linkage into the oxadia-
zole unit. In the solid-state 13C NMR spectrum of ODA-
COF, the characteristic carbonyl peak of N-acylhydrazone
Figure 1. a) Model reaction between benzoyl hydrazine and benzaldehyde to form the hydrazone-based compound and subsequent conversion into
the oxadiazole-based compound by the oxidative cyclization. b) The scheme for the synthesis of H-COF and ODA-COF.
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at 160 ppm disappears, and a new peak of for the oxadiazole
carbon is observed at 158 ppm (Figure 2b). The assignment
of these signals has been corroborated by comparing with
those of the molecular counterpart (Figure S1). The high-
resolution N 1s XPS spectrum of H-COF presents the
binding energy peaks at 400.5 and 399.8 eV, corresponding
to the amide and imine groups, respectively (Figure 2c).[21]
However, there is only one peak of the oxadiazole ring at
399.3 eV for ODA-COF. The binding energy peaks at 533.1
and 532.4 eV in the deconvoluted O 1s XPS spectra of H-
COF and ODA-COF are assigned to the carbonyl of N-
acylhydrazone and the C O C of oxadiazole, respectively
(Figure 2d).[27, 28] These observations provide overwhelming
evidence for the successful conversion of H-COF to ODA-
COF.
The crystalline structures of H-COF and ODA-COF
were verified by powder X-ray diffraction (XRD) measure-
ments. ODA-COF retains good crystallinity after the post-
cyclization reaction of H-COF. The intense diffraction peak
of the (100) reflection slightly shifts from 3.4° in H-COF to
3.6° in ODA-COF (Figure 2e), which originates from the
reduction in pore size caused by the oxidative cyclization of
the N-acylhydrazone linkage.[12] The simulation of XRD
patterns reveals that both ODA-COF and H-COF display
the eclipsed structure (Figure S2, S3); they crystallize in
hexagonal space group P3 (Table S1–S4). ODA-COF fea-
tures a porous hexagonal structure (Figure 2f). The Pawley
refinements of the experimental patterns provide the unit
cell parameters of H-COF (a = b = 30.01 Å and c = 3.82 Å
with the residual factors of Rwp = 1.6 % and Rp = 1.24 %)
and ODA-COF (a = b = 30.05 Å and c = 3.82 Å with the
residual factors of Rwp = 7.68 % and Rp = 5.75 %).
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Figure 2. Characterization of H-COF and ODA-COF: a) FTIR spectra. b) Solid-state 13C NMR spectra and the signals assignment (the inset).
c) High-resolution N 1s XPS spectra. d) High-resolution O 1s XPS spectra. e) XRD patterns. f) Top and side views for AA stacking model of ODA-
COF. g) The nitrogen adsorption–desorption isotherms for H-COF and ODA-COF. Chemical stability of h) ODA-COF and i) H-COF after treatment
under various conditions for 24 h.
The permanent porosities of H-COF and ODA-COF
were assessed by nitrogen adsorption/desorption measure-
ments at 77 K (Figure 2g). Both of them exhibit rapid
nitrogen uptake at very low relative pressure. The Bruna-
uer–Emmett–Teller (BET) specific surface areas of H-COF
and ODA-COF are calculated to be 770 and 650 m2 g 1,
respectively. The slight loss in specific surface area of ODA-
COF is attributed to the decrease in pore size after chemical
transformation, which is consistent with their pore-size
distribution calculated using non-local density functional
theory model (Figure S4). Scanning/transmission electron
microscopy (SEM/TEM) images show that H-COF and
ODA-COF possess wire-shaped morphology consisting of
tiny particles (Figure S5, S6).
The effects for the formation of the oxadiazole linkage
on thermal and chemical stability of the resultant COFs
were initially evaluated. Thermogravimetric analysis (TGA)
curves show that H-COF and ODA-COF are stable before
300 °C under a nitrogen atmosphere (Figure S7), but ODA-
COF exhibits superior chemical stability under harsh
conditions over H-COF. When ODA-COF was immersed in
hydrochloric acid (HCl, 12 M), trifluoroacetic acid (TFA),
sodium borohydride (NaBH4. 0.26 M in CH3OH) and
aqueous sodium hydroxide (NaOH, 10 M) solutions for 24 h,
XRD patterns of the resultant samples showed no obvious
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variation (Figure 2h). The porosity of ODA-COF is also
retained, but the BET specific surface area is decreased
(Figure S8). In sharp contrast, typical diffraction peaks of H-
COF disappear after the same treatment owing to the loss of
crystallinity (Figure 2i).
The conversion of the N-acylhyrdrazone linkage into the
aromatic oxadiazole unit markedly influences their photo-
physical performance. The UV/Visible diffuse-reflectance
spectrum (UV/Vis DRS) of ODA-COF exhibits a broad
absorption band in the visible and near infrared region. The
obvious redshift of the absorption band edge at 612 nm is
observed when compared with that of 436 nm in H-COF
(Figure 3a), which indicates the enhanced π-electron deloc-
alization after the conversion of the N-acylhydrazone to
oxadiazole linkage. The bright yellow color of ODA-COF
further shows that ODA-COF could absorb a wide range of
low-energy light when compared with the pale yellow color
of H-COF. The optical band gap of ODA-COF is estimated
by Tauc plots to be 2.00 eV, which is much smaller than that
of 2.80 eV for H-COF (Figure S9). To further illustrate the
effect of the linkage conversion on band structure, density
functional theory (DFT) calculations were performed. The
calculated band gaps narrow from H-COF (2.2 eV) to
ODA-COF (1.7 eV, Figure S10), indicative of the increase
of the intrinsic carrier concentration in ODA-COF,[29, 30]
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Figure 3. Characterization of H-COF and ODA-COF: a) UV/Vis DRS and optical images (the inset). b) Band structure diagram. c) Steady-state PL
spectra. d) EPR spectra in the dark and visible-light illumination. e) Transient photocurrents under visible light irradiation. f) EIS Nyquist plots.
g) The plots for photocatalytic H2 evolution under visible light irradiation (� 420 nm). h) Photocatalytic H2 production of ODA-COF upon
irradiation with monochromatic light. i) Cyclic measurements of ODA-COF catalytic system with each run for 4 h.

which is consistent with the experiment results. These
observations have demonstrated that the oxadiazole linkage
is efficient in narrowing the band gap, enhancing the light-
harvesting capability and transmitting π-conjugation over
the reticular framework. Mott–Schottky measurements show
that H-COF and ODA-COF are n-type semiconductors
(Figure S11). The flatband potentials of H-COF and ODA-
COF are determined to be 0.90 and 0.85 V vs. Ag/AgCl,
respectively, corresponding to 0.70 and 0.65 vs. normal
hydrogen electrode (NHE), respectively (Figure 3b). The
energy levels show that both ODA-COF and H-COF could
meet thermodynamic conditions for photocatalytic hydrogen
evolution and other solar-to-chemical energy conversion.[31]
To understand the advantages of the oxadiazole linkage
in photoelectron separation and transfer, the steady-state
photoluminescence (PL) spectra of H-COF and ODA-COF
were explored. ODA-COF emits light centered at 615 nm
upon excitation at 375 nm (Figure 3c), which is significantly
attenuated when compared with that of 470 nm in H-COF.
The obvious redshift of the emission peak is in accordance
with the band gap narrowing identified from UV/Vis DRS.
The time-resolved PL decay spectroscopy show that the
average PL lifetime of ODA-COF (0.6 ns) is clearly shorter
than that of 0.9 ns in H-COF (Figure S12). The electron
paramagnetic resonance (EPR) spectroscopy of ODA-COF
exhibits a paramagnetic absorption signal with a g value of
2.0055. The signal is intensified upon visible light
illumination.[32, 33] In sharp contrast, no apparent EPR signal
is observed for H-COF either in the dark or upon visible
light irradiation (Figure 3d). The transient photocurrent
experiments indicate that both H-COF and ODA-COF
possess rapid photocurrent response and good reproducibil-
ity under visible light irradiation (Figure 3e). The photo-
current density of ODA-COF is much higher than that of H-
COF. In their electrochemical impedance spectroscopy
(EIS), the Nyquist curve of ODA-COF exhibits a smaller
semicycle arc radius than that of H-COF (Figure 3f),
suggesting lower interfacial charge transfer resistance in
ODA-COF. These results demonstrate that the conversion
from the irreversible N-acylhydrazone linkage to the
oxadiazole unit extends the π-conjugated system of COFs.
Therefore, ODA-COF could promote π-electron delocaliza-

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tion throughout the reticular framework and inhibit the
recombination of the photogenerated charge carriers. Strong
π-electron delocalization together with high chemical stabil-
ity endow ODA-COF with great promise for photocatalytic
application in visible-light-driven reactions.
The photocatalytic H2 generation was selected to exam-
ine photocatalytic performance of H-COF and ODA-COF.
The reaction was performed under visible-light irradiation
(300 W Xe lamp, λ � 420 nm) with Pt as the cocatalyst and
triethanolamine (TEOA) as the electron donor. As ex-
pected, the photocatalytic activity is significantly enhanced
after the conversion of the N-acylhydrazone into the
oxadiazole linkage. As shown in Figure 3g, the H2 evolution
rate for ODA-COF is 2615 μmol g 1 h 1, while H-COF
presents much lower efficiency with a H2 production rate of
609 μmol g 1 h 1 under the same conditions, which is less
than one fourth those in ODA-COF. Notably, the H2
production rate for ODA-COF is only 205 μmol g 1 h 1 in
the absence of Pt cocatalyst. The light-wavelength depend-
ency examination shows that ODA-COF could utilize a
broad range of visible light, the H2 evolution rate under
monochromatic light irradiation at 420, 450 and 550 nm is
800, 790 and 200 μmol g 1 h 1, respectively (Figure 3h). The
apparent quantum efficiency (AQE) for H2 evolution at
420 nm is calculated to be 0.42 %. The catalytic system
possesses superior robustness and durability in photocata-
lytic H2 evolution. No significant decrement of photo-
catalytic activity is observed after consecutive reaction for
four runs with each run of 4 h (Figure 3i). The FTIR
spectrum and XRD pattern of the recovered ODA-COF
(post-ODA-COF) are almost identical with that of the as-
synthesized sample (Figure S13). The high activity and
durability validate the superiority of the conversion from N-
acylhydrazone-linked COFs to oxadiazole-linked COFs.
In conclusion, we have successfully fabricated an oxadia-
zole-linked COF through post-synthetic modification of the
N-acylhydrazone linkage. This new two-step synthetic strat-
egy allows for the maintenance of crystallinity and periodic
frameworks. The extended π-electron delocalization and the
improved chemical stability by the formation of irreversible
oxadiazole units inhibit recombination of the photogener-
ated charge carriers and facilitate the electron transfer,
resulting in significantly improved photocatalytic hydrogen
generation performance when compared with that of the N-
acylhydrazone-linked counterpart. This work provides new
protocols to prepare oxadiazole-linked COFs and enhance
photophysical performance, which contributes to the design
and development of new COF-based photocatalytic systems
for solar-to-chemical conversion.
Acknowledgements
This work was supported by National Natural Science
Foundation of China (21975259, 22075286 and 21673241),
and Innovation Academy for Green Manufacture of Chinese
Academy of Sciences (IAGM2020C17).
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Conflict of Interest
The authors declare no conflict of interest.
Data Availability Statement
The data that support the findings of this study are available
from the corresponding author upon reasonable request.
Keywords: Charge Transfer · Covalent Organic Frameworks ·
Hydrogen Generation · Oxadiazole · Photocatalysis
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Manuscript received: November 17, 2021
Accepted manuscript online: December 28, 2021
Version of record online: January 12, 2022
© 2021 Wiley-VCH GmbH