self‐assembled pdinh supramolecular system for photocatalysis under … · 2019. 12. 17. ·...

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Photocatalysis under Visible Light

Di Liu , Jun Wang , Xiaojuan Bai , Ruilong Zong , and Yongfa Zhu *

Dr. D. Liu, Dr. J. Wang, Dr. R. L. Zong, Prof. Y. F. Zhu Department of Chemistry Tsinghua University 100084 , Beijing , P. R. ChinaE-mail: [email protected] Prof. Y. F. Zhu Collaborative Innovation Center for Regional Environmental Quality Tsinghua University Beijing 100084 , P. R. China Dr. X. J. Bai Academy of State Administration of Grain 100037 Beijing , P. R. China

DOI: 10.1002/adma.201601168

non-substituents at the parent skeleton (PDINH), show intrinsic insolubility in most common organic solvents, [ 15 ] leading to a great challenge for self-assembly of PDI. So far, only special solvents such as concentrated sulfuric acid or m-cresol [ 32 ] were reported to enable PDINH solublility. Ji et al. reported the fab-rication of PDINH nanowire assemblies using gas-phase phys-ical vapor deposition. [ 33 ] Self-assembly of PDINH nanobelts was successfully achieved by Yao’s group through oxidation of perylenediimide dianion precursors. [ 34 ] However, simple and economic methods for controlled formation of PDINH self-assemblies are still faced with great challenges.

Herein, we successfully fabricated supramolecule-engi-neered PDINH nanoassemblies consisting of purely organic small-PDINH molecule building blocks through non-covalent interactions using a rapid and simple solution dispersion method. This self-assembled PDINH supramolecular system exhibits band-like electronic structures with certain bandwidths for valence and conduction bands, and shows excellent photo-catalytic activity for degradation of phenol and splitting water for O 2 evolution under visible light irradiation. Systemic studies on the electronic energy level structure, intermolecular packing arrangement within the self-assembled PDINH supramolecular system, and photocatalytic performance have been carried out.

The self-assembled PDINH supramolecular system was fabricated through a simple and economic method of “rapid solution dispersion” reported by Zang and co-workers [ 35 ] which can be described as rapid dispersion of the dissolved PDI mol-ecules from a “good” solvent into a “poor” solvent, where the originally dissolved molecules have limited solubility, and then self-assembly of the molecules through non-covalent inter-actions leads to its solid-state precipitating out. In this work, we chose concentrated sulfuric acid as the “good” solvent for commercial PDINH, and water as the “poor” solvent. Self-assembled PDINHs with interesting morphology evolution can be easily obtained through varying adding volume of H 2 O (see Figure S1, Supporting Information), indicating better struc-tural fl exibility and morphology tunability compared with the conducting polymers. The optimized sample of PDINH 100 was named as self-assembled PDINH supramolecular system in the following part. The mass percent of each element in commer-cial PDINH and self-assembled PDINH supramolecular system almost shows the same value similar to the theoretical value based on the elemental analysis (Table S1, Supporting Informa-tion), indicating that the self-assembled PDINH supramolecular system indeed retains the same composition as the commercial PDINH. As shown in Figure 1 C, the self-assembled PDINH supramolecular system exhibits the willow leaf-like shape with a width of ≈200–300 nm and a length of ≈2–10 µm, whereas the commercial PDINH shows thick-rod structure (Figure S1, Supporting Information). The height profi le of atomic force

Organic materials have many merits compared to inorganic materials, such as chemically tunable electronic and optical properties, diverse structural fl exibility, low cost, and a wealth of element resources supplement. Hence, organocatalysts have attracted the interests of many researchers during the last dec-ades. However, organocatalysts have mainly been based on two types of organic materials: organometallic complexes, [ 1 ] in which the metallic composition may limit their practical applications due to high cost, potential toxicity, and poor sus-tainability; or covalent organic polymers, including commonly reported carbon nitride, [ 2,3 ] triazine/hydrazone-based carbon nitrides, [ 4–7 ] and some covalent organic polymers based on poly( p -phenylene), [ 8,9 ] poly(phenyleneethinylene), [ 10 ] poly(diphenylbutadiyne), [ 11 ] poly(azomethine), [ 12 ] and carbazolic frame-works. [ 13 ] However, non-covalent self-assembly supramolecular systems composed of purely organic molecules alone, working as a photocatalyst with wide visible-light responses has not been reported. PDI (perylene-3,4,9,10-tetracarboxylic diimide) stands out among n-type organic semiconductors due to its excellent thermal/photo-stability, high electron affi nity, and charge carrier mobilities. [ 14,15 ] Due to the unique optical and electronic properties of PDI, recently, various applications have been investigated, [ 16,17 ] such as fl uorescence switches, [ 18 ] sen-sors, [ 19,20 ] organic fi eld-effect transistors (OFETs), [ 21–23 ] light harvesting materials, [ 24,25 ] light emitting diodes, [ 26 ] and solar cells. [ 27–29 ] However, some of these above applications of PDI mainly focus on the isolated PDI molecule (i.e., monomeric PDI), the application in photocatalysis using self-assembled nanostructures of PDI has been rarely reported. Recently, Zang and co-workers gained enhanced hydrogen production activity under visible-light irradiation through in situ deposition of TiO 2 layers and/or a co-catalyst (Pt) on 1D self-assembled nanofi bers of PDI derivatives. [ 30 ] By the incorporation of PDI into a metal–organic polymer Zn-PDI, Duan’s group revealed that Zn-PDI was highly photoactive in oxidation of benzyl alcohols and amines. [ 31 ] PDIs, especially for commercially available PDI with

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microscopy (AFM) over the willow leaf-like structure of self-assembled PDINH supramolecular system indicates a single sheet thickness of 5–8 nm (Figure S2, Supporting Information). Based on small-PDINH molecule building block with non-sub-stitute groups (unmodifi ed PDI), PDINH assembled products reported by other groups [ 33,34 ] also show lamellar structures. The lamellar structure of the nanoassemblies suggests both the formation of linear tape-like hydrogen-bonded strands and the existence of tight π–π packing of the PDINH molecules due to the small size of PDINH molecule.

The FT-IR spectrum of the self-assembled perylene-3,4,9,10-tetracarboxylic diimide(PDINH) supramolecular system is almost the same as that of commercial PDINH. It was reported that formation of N H⋅⋅⋅O hydrogen bonds between the imide hydrogen atoms and the carbonyl oxygen atoms would lead the stretching vibrations of N H and C O to lower wave-numbers. [ 36 ] Hereby, stretching frequencies at υ(N H) = 3153, 3034 cm −1 and υ(C O) = 1662 cm −1 in this FT-IR spectrum (Figure S3, Supporting Information) indicate that intermolec-ular hydrogen bonds form between N H and C O groups in both commercial PDINH and self-assembled PDINH supra-molecular systems. Such hydrogen bond interactions together with intermolecular π–π stacking interactions are proposed to infl uence the arrangement of PDINH molecules in self-assem-bled PDINH supramolecular system and stabilize the PDINH nanoassemblies.

XRD patterns of commercial PDINH and self-assembled PDINH supramolecular system are provided in Figure S4 (Sup-porting Information). It can be seen that, increased regularity

was gained after the assembly process, leading to long-range ordered structure and enhanced crystallization property for the self-assembled PDINH supramolecular system in comparison with commercial PDINH. From observation of Figure 1 A, XRD peaks corresponding to typical π–π stacking distance between the PDINH perylene skeletons with d -spacing of 3.2–3.7 Å emerged. 3.27 Å can be attributed to closely co-facial π–π stacking distance, whereas 3.57 Å should correspond to dis-tances of π–π stacking interaction between PDINH molecules adopting twisted arrangements. The nominal length between two adjacent H-bonded PDI at the longitudinal direction is reported to be 1.402 nm, and the width of the PDI molecule is reported to be 0.92 nm. [ 37 ] As a result, the fi rst strong (020) peak [ 38 ] in Figure 1 A ( d -spacing of 7.35 Å) can be assigned to half of PDINH molecule length at the longitudinal direction. [ 33 ] The diffraction peak ( d -spacing of 4.46 Å) can be attributed to half of PDINH molecular length at the transversal direction, [ 37 ] while two peaks emerged at high diffraction angles ( d -spacing of 2.21 and 1.97 Å) can be assigned to lengths of hydrogen-bond [ 39 ] or edge-to-edge distances between two adjacent PDINH molecules at the longitudinal and transversal directions. The structure of self-assembled PDINH supramolecular system was further investigated through HRTEM analysis. The HRTEM picture shows the lattice fringes of the willow leaf-like plate from its top view, as shown in Figure S5A (Supporting Infor-mation), revealing parallel rows of PDINH π-stacks with 3.7 Å typical stack-spacing in the longitudinal direction of nanoplate. This also suggests that the PDINH molecules are oriented with their π–π stacking direction parallel to the longitudinal

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Figure 1. A) XRD peaks of self-assembled PDINH supramolecular system; B) UV–vis absorption spectra of non-aggregated form (PDINH dissolved in H 2 SO 4 ) and aggregated form (PDINH aggregation dispersed in water or coated onto a quartz glass); C) TEM image of self-assembled PDINH supra-molecular system (left) and schematic diagram showing the intermolecular arrangement within the nanoplate and a mimetic packing model revealing the size of a single PDINH molecule and the π–π stacking distance, respectively (right).

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assembled PDINH supramolecular system which underwent air drying under room temperature, the product which under-went oven drying at 60 °C (Figure S5B, Supporting Informa-tion) shows clearer lattice fringes, among which the clear d -spacing of 2.40 Å can be attributed to the lattice spacing for (002) planes, indicating a higher crystallinity. [ 40 ]

Strong π–π stacking interactions in the self-assembled PDINH supramolecular system can be revealed from obser-vation of absorption spectra. Distinct change in absorption spectra appeared after monomeric PDINH molecules self-assembling into the supramolecular system (solid state), dem-onstrating great variation in optical and electronic properties of self-assembled PDINH supramolecular system. As shown in Figure 1 B, the spectrum of PDINH dissolved in H 2 SO 4 exhibited typically three pronounced peaks between 650 and 450 nm which correspond to the 0→0, 0→1, and 0→2 elec-tronic transitions of monomeric PDINH molecules, respec-tively. [ 15 ] However, blue-shift of the maximum absorption and a loss of fi ne curve structure for the aggregated form can be seen, demonstrating that strong π–π stacks (H-aggregate) between PDINH molecules in the self-assembled PDINH supramolec-ular system exist. [ 41,42 ] Hereby, the willow leaf-like plate of the self-assembled PDINH supramolecular system is comprised of parallel stacks of PDINH with stacking space of 3.2–3.7 Å between two adjacent PDINH molecular planes through face-to-face organization, and interconnect with adjacent PDINH molecule in an edge-to-edge way through hydrogen bonds to provide a closely intertwined supramolecular structure, as dis-played in Figure 1 C. Actually, the parallel stacks of PDINH molecules within the self-assembled PDINH supramolecular system accordingly account for its photocatalytic activity dis-cussed in the following part.

The self-assembled PDINH supramolecular system can be used as a visible-light active photocatalyst for photodegradation over different kinds of pollutants and photocatalytic water oxi-dation. First, to distinguish the contribution of adsorption and photodegradation to the overall decreased amount of phenol, the adsorption ability on the targeted pollutant (phenol) was also investigated, as shown in Figure S6 (Supporting Informa-tion). It was found that the adsorption quantity of phenol by self-assembled PDINH supramolecular system was very low (less than 5% of the original amount of phenol), which can be ignored as compared with photodegradation. Figure S7 (Supporting Information) reveals a trend of fi rst increase and then decrease of the photocatalytic rate constants of the as-synthesized PDINHs nanoassemblies when increasing adding “poor” solvent. PDINH 100 , that is self-assembled PDINH supra-molecular system, shows the best photodegradation perfor-mance over phenol. To further confi rm the photodegradation ability of self-assembled PDINH supramolecular system, blank and control experiments were performed (details are provided in the Supporting Information) and the results reveal that intermediate products of photocatalytic degradation of phenol are attributed to hydroquinol, p -benzoquinone/catechol, and bi-phenol. Analysis of the in situ active species during the photocatalytic reaction can be obtained through the trapping experiments. And by using DMPO (5,5-dimethyl-1-pyrroline N -oxide), TEMP (2,2,6,6-tetramethyl-1-piperidine), and TEMPO

(2,2,6,6-tetramethylpiperidine-1-oxyl) as spin probes, con-tents of •− O 2 , •OH, 1 O 2 , and photo-generated electrons can be detected through ESR (electron paramagnetic resonance) technique. Then, measurements on the active species shown in the Supporting Information (Figures S10 and S11, Sup-porting Information) reveal that main active species including •− O 2 , 1 O 2 , photo-generated holes and electrons can be produced by self-assembled PDINH supramolecular system under visible light irradiation and were expected to govern the photocatalytic process. Most importantly, the self-assembled PDINH supra-molecular system exhibits superior photodegradation perfor-mance to other reported visible-light active photocatalysts such as g-C 3 N 4 , [ 2 ] BiOBr, [ 43 ] and Bi 2 WO 6 , [ 44 ] as shown in Figure 2 C. The self-assembled PDINH supramolecular system also proved to be photoactive in the degradation of cationic dye (methylene blue/MB, Rhodamin B/RhB), anionic dyes (methyl orange/MO), and phenolic compounds (bisphenol A/BPA), as shown in Figure 2 A,B. Through comparison of the rate constants k , the self-assembled PDINH supramolecular system was found to possess greater removal ability for MB and RhB (cationic dyes), which can be attributed to its strong adsorption ability of MB and RhB with the help of the negative surface electric prop-erty revealed by zeta potential measurement (Table S2, Sup-porting Information). It is worth noting that the photocatalyst (50 mg) also exhibits visible-light activity ( λ > 420 nm) for water splitting only in the presence of an electron acceptor (0.1 M AgNO 3 ). The amount of O 2 adds up to 1.29 µmol after 10 h of reaction. There is no oxygen generated after 10 h of reaction in the blank test (visible-light irradiation of AgNO 3 solution (0.1 M , 100 mL in the absence of photocatalyst)), confi rming the activity of self-assembled PDINH supramolecular system for oxygen evolution. For further comparison, the O 2 evolution system of carbon nitride under visible light ( λ > 420 nm) irra-diation has been conducted, as shown below and in Figure 2 D. It can be seen that, the as-prepared g-C 3 N 4 shows no oxygen evolution activity, which may be associated with its structure of electronic energy band. At the same time, three types of electron acceptors (AgNO 3 , Fe(NO 3 ) 3 , and Na 2 S 2 O 8 ) have been adopted in the O 2 evolution system with 50 mg catalyst of self-assembled PDINH supramolecular system under visible light ( λ > 420 nm) irradiation. The results shown in Figure S12 (Sup-porting Information) indicate that the attempt at replacing Ag + with Fe 3+ failed to further improve the evolution amount of O 2 . Other electron sacrifi cial reagent such as Na 2 S 2 O 8 showed a low activity for O 2 evolution. Although the present result of O 2 evolution is still low, further optimization for the O 2 evolution system is in progress.

Investigation into the factors infl uencing the photocatalytic activity of self-assembled PDINH supramolecular system is essential. The fl uorescence of the self-assembled PDINH supra-molecular system was almost entirely quenched as shown in Figure 2 E, suggesting low recombination probability of photo-induced carriers in PDINH aggregation. Strong π–π stacking interactions normally generate non-emitting crystal phase due to the forbidden low-energy excitonic transition. [ 15 ] As a result, fl uorescence quenching of the self-assembled PDINH supramo-lecular system also provides a clear confi rmation of the existence of strong π-electron coupling between the assembled PDINH molecules, consistent with the result of UV–vis absorption

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spectra. At the same time, the self-assembled PDINH supramo-lecular system exhibits higher photocurrent response than com-mercial PDINH under irradiation of visible light, suggesting a great separation and transport ability of photocarriers, as shown in Figure 2 F. Optical absorption capacity of the self-assembled PDINH supramolecular system was found to play a key role in its photocatalytic performance. In this work, wavelength-dependent photodegradation results show that the photodeg-radation rate constants ( k ) can be related to optical absorption as a function of wavelength (Figure 2 G). The trends of phenol

degradation rates of the self-assembled PDINH supramolecular system along with the wavelengths (red line) match well with its optical absorption curve (black line), indicating that the optical absorption may contribute a lot to its photodegradation per-formance. In addition, self-assembled PDINH supramolecular system shows higher photocatalytic activity under visible light than that under UV light irradiation. Even under the irradia-tion using 650 ± 15 nm visible light, the self-assembled PDINH supramolecular system exhibits considerable photocatalytic activity (Figure 2 G), revealing an extended spectral response

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Figure 2. A) Photodegradation performance on various probe pollutants by using self-assembled PDINH supramolecular system under visible light irradiation ( λ > 420 nm); B) Degradation rate constants k calculated from (A); C) Comparison of different photocatalysts for photodegradation of phenol under visible light irradiation; D) Oxygen evolution from water by self-assembled PDINH supramolecular system and g-C 3 N 4 in the presence of an electron acceptor (0.1 M AgNO 3 ) under the visible light ( λ > 420 nm); E) Fluorescence spectra of non-aggregated form (PDINH dissolved in H 2 SO 4 ) and aggregated form (PDINH aggregation dispersed in water or coated onto a quartz glass); F) Photocurrents of self-assembled PDINH supramolecular system and commercial PDINH under visible light irradiation ( λ > 420 nm); G) Absorbance and degradation rate constants k of self-assembled PDINH supramolecular system as a function of wavelength, the degradation rate constant k were calculated from wavelength-dependent photodegradation results under irradiation with band-pass fi lters.


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even to the infrared region. Previous reports proposed that larger distances between PDI molecules result in less electron transfer due to the larger Δ G ° for charge separation and weaker electronic coupling between the two molecules. [ 19 ] However, in our work, the self-assembled PDINH supramolecular system is expected to exhibit closely π-packed structure due to non-sub-stituents at the NH group. Recently, Sprick’ group found that increased exciton dissociation yields can be gained in polymers consisting of extended planarized units through decreasing the coulomb binding energy for dissociating electron–hole pairs. [ 45 ] Hence, integrating the above discussions, the strong cofacial π–π stacking of PDINH molecules along the long axis of its nanoplate would enable effective long-range band-like π-electron delocalization, [ 46 ] resulting in an enhancement of electronic coupling [ 39 ] and charge mobility. [ 47,48 ]

Band-like electronic energy level structure similar to inor-ganic semiconductor due to orbital overlaps between PDINH-molecular units can be obtained by the self-assembled PDINH supramolecular system. Monomeric PDINH molecules own discrete HOMO and LUMO levels, whereas π-stacked PDINH assemblies were reported to have band-like electronic structures with certain bandwidths for valence and con-duction bands based on the intermolec-ular transfer integrals of the HOMOs and LUMOs. [ 49 ] Further experimental results are provided here by pronounced discrete energy level characteristic of fl uorescence spectros-copy (Figure 2 E) and UV–vis absorption spectra (Figure 1 B) for monomeric PDINH, whereas broad UV–vis absorption spectra are observed for self-assembled PDINH supra-molecular system owning extended intermo-lecular π-stacking. Previous report reveals that theoretical HOMO and LUMO levels of monomeric non-substituted PDINH is −6.11 and −3.58 eV, which are equivalent to +1.61 and −0.92 eV versus NHE, respectively. [ 50 ] In this work, the electronic energy level struc-ture of self-assembled PDINH supramolec-ular system was investigated by combining Mott–Schottky (MS) measurements with

X-ray photoemission spectroscopy (XPS) valence band spectra. The fl at-band potential obtained from the χ intercepts of the linear region in MS plots was found to be −0.194 V versus SCE ( Figure 3 A). It was reported that the conduction bands of n-type semiconductors are normally 0.1−0.2 eV deeper than the fl at-band potential. [ 51 ] Herein, the voltage differences between CB value and the fl at potential value are set to be 0.1 eV, and thus the bottom of the conduction band is estimated to be −0.049 eV versus NHE, which is more positive than the LUMO level (−0.92 eV) of monomeric PDINH. The XPS valence band spec-trum of self-assembled PDINH supramolecular system reveals the VB position at about 2.20 eV (Figure 3 B). In general, sche-matic diagram revealing the electronic energy level structure of self-assembled PDINH supramolecular system and mechanism of photocatalytic reaction was depicted in Scheme 1 . Deeper VB position (+2.20 eV) gives rise to thermodynamic driving force of self-assembled PDINH supramolecular system for O 2 evolution. Upon visible light irradiation, photo-generated elec-trons prefer to migrate along the long-range transport pathway

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Figure 3. A) Mott–Schottky plots and B) XPS valence band spectra of the self-assembled PDINH supramolecular system.

Scheme 1. Schematic illustration of the electronic energy level structure of the self-assembled PDINH supramolecular system and mechanism of photocatalytic reaction of the self-assem-bled PDINH supramolecular system under visible light irradiation ( λ > 420 nm).


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through charge delocalization, while holes can easily spread out over self-assembled PDINH supramolecular system with nanoscale thickness to catch pollutants or oxide water, leading to effective spatial charge separation.

In conclusion, we successfully constructed a self-assembled PDINH supramolecular system via non-covalent interactions based on a simple and economic method from solution. Most importantly, this purely organic PDINH supramolecular system is found to be an effective visible-light photocatalyst for the photodegradation of pollutants and even split water for oxygen evolution in the absence of co-catalyst. The band-like electronic energy level structure of the PDINH supramolecular system originating from orbital overlaps between PDINH molecular units and long-range conjugated π-delocalization within the self-assembled PDINH supramolecular system mainly contrib-utes to its remarkable photocatalytic properties. Our fi ndings will pave the way forward for photocatalysis based on self-assembled supramolecular systems.

Supporting Information Supporting Information is available from the Wiley Online Library or from the author.

Acknowledgements This work was partly supported by National Basic Research Program of China (2013CB632403), National High Technology Research and Development Program of China (2012AA062701), and Chinese National Science Foundation (21437003, and 21373121).

Received: February 29, 2016 Revised: April 29, 2016

Published online: June 16, 2016

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