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Pillar[5]arene based conjugated macrocycle polymers with unique photocatalytic selectivity
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Hui Qianga, b, Tao Chenb, c, Zhuo Wangd, Wenqian Lib, c, Yunzhe Guob, c, Jie Yangd, Xueshun Jiaa, Hui Yangb, Weibo Hub, *, Ke Wenb, d, *
Chinese Chemical Letters | 2020, 31(12) : 3225 - 3229
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Chinese Chemical Letters | 2020, 31(12): 3225-3229
• Communication •
Pillar[5]arene based conjugated macrocycle polymers with unique photocatalytic selectivity
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Hui Qianga, b, Tao Chenb, c, Zhuo Wangd, Wenqian Lib, c, Yunzhe Guob, c, Jie Yangd, Xueshun Jiaa, Hui Yangb, Weibo Hub, *, Ke Wenb, d, *
Affiliations
  • a College of Science, Shanghai University, Shanghai 200444, China
  • b Shanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai 201210, China
  • c University of Chinese Academy of Sciences, Beijing 100049, China
  • d School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China
Published: 2020-12-15 doi: 10.1016/j.cclet.2020.04.020
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The development of heterogeneous catalysts with substrate shape, size or electronic constitution selectivity is a huge challenge in photocatalysis. Reported herein is a host-guest interaction strategy to endow photocatalysts with special selectivity. By adjusting the precursors, conjugated macrocycle polymers (CMPs) with pillar[5]arene struts (CMP-1 and CMP-2) and a corresponding non-pillar[5]arene-contained conjugated organic polymer (COP-1) were prepared and the photocatalytic activities toward sulfide derivatives were investigated. The sulfides showed similar conversions when COP-1 was used as a photocatalyst, but exhibited significant differences when it turned to the CMPs. Remarkably, the conversion yield of S-1 achieved near 18 folds over the one of S-2 when CMP-2 was used as a catalyst. Mechanism studies confirmed that the "host-guest" effect of pillar[5]arene struts in CMPs was the main cause of the difference. The present work establishes CMPs as novel heterogeneous photocatalysts with substrate selectivity, and such a method will inspire the researchers concerning preparation of heterogeneous catalysts with excellent selectivity.

Heterogeneous photocatalysis  /  Selectivity  /  Host-guest  /  Pillar[5]arene  /  Sulfide
Hui Qiang, Tao Chen, Zhuo Wang, Wenqian Li, Yunzhe Guo, Jie Yang, Xueshun Jia, Hui Yang, Weibo Hu, Ke Wen. Pillar[5]arene based conjugated macrocycle polymers with unique photocatalytic selectivity[J]. Chinese Chemical Letters, 2020 , 31 (12) : 3225 -3229 . DOI: 10.1016/j.cclet.2020.04.020
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To alleviate energy crisis, design and preparation of photocatalysts which can efficiently convert solar energy into chemical energy have drawn increasing interests in recent years [1-7]. Various photocatalytic systems, including inorganic semiconductor, organic semiconductor [8, 9], and metal-organic complex [10-12] have been intensely developed. Among them, organic semiconductors [13-18], such as conjugated organic polymers (COPs)[19-23], possessing advantages of facilely tailored functionality, thermal stability, recyclability and environmental friendliness, have gained much attention recently. Indeed, excellent photocatalytic activity has been achieved by some functional COPs [24-31], but substrate selective photocatalysis have rarely been reported. As such, strategies which enable photocatalysts with substrate shape, size or electronic constitution selectivity are very welcome.
Enzymatic reactions possess highly substrates selectivity, which is partially due to their binding specificity [28, 32-36]. Similar to enzymatic reactions, interactions between the reactant molecules and the catalysts is an important process for a heterogeneous photocatalysis. Hence, once selective adsorption occurred, substrates selective photocatalysis could be achieved. It is well-known that macrocyclic hosts could bind guest molecules selectively [37-42]. For example, pillar[5]arenes tend to include linear chain molecules into their cavities [43-46], and the binding constants vary with different functional groups of the linear chain molecules [47]. Recent studies have indicated that solid materials with macrocyclic host motifs could adsorb specific molecules [48-60]. Therefore, developing conjugated macrocycle polymer (CMPs)[61] photocatalysts, a class of organic semiconductors possessing macrocyclic host motifs, might be a feasible way to endow photocatalysts with special substrate selectivity.
Herein, we report a type of conjugated macrocycle polymers with pillar[5]arene struts (CMP-1 [61] and CMP-2) for selective photocatalytic oxidation of sulfides. A corresponding nonpillar[5]arene-containing conjugated organic polymer (COP-1) was also prepared for comparison. Electron spin resonance (ESR) studies indicated that the CMPs and COP-1 all possessed the abilities to convert O2 or H2O to active oxygen species (·OH or 1O2) under visible light irradiation to initiate the oxidation of sulfides.COP-1 showed similar photocatalytic activity toward the oxidation of sulfides with different substituents. CMP-1 and CMP-2 were found to exhibit much higher activity toward a guest-like sulfide than a non-guest-like one. The influence of the host-guest nature of the pillar[5]arene struts in the CMPs on the photocatalytic oxidation of the guest-like sulfide was confirmed by competitive experiments.
The CMPs and COP-1 were prepared according to literature reports (Scheme 1) (details are deposited in Supporting information) [61, 62]. The formation of the polymers was first characterized by Fourier transform infrared spectroscopy (FTIR). The disappearance of the C-H stretching band around 3250 cm-1 of the alkynes and the trifluoromethane sulfonate group at 931 cm-1 of pillar[4]-arene[1]1, 4-phenylenebistriflate indicated total consumption of the starting materials (Figs. S1a-c in Supporting information). 13C cross-polarization magic-angle spinning (CP-MAS) NMR analysis provided further evidence for the formation of the polymers. Both CMP-1 and CMP-2 showed clear signals at ~30, ~55, ~90 and ~170 ppm, which could be assigned to the carbons of methoxy, methylene of the pillar[5]arene moiety, and carbons of the C≡C and triazine C=N units, respectively (Fig. 1d and Fig. S1d in Supporting information). Similarly, in the (CP-MAS) NMR spectra of COP-1, the signals at ~170 ppm assigned to triazine C=N units and ~90 ppm assigned to C≡C units were observable (Fig. 1d).
Scanning electron microscopy (SEM) was used to study the morphologies of the polymers. Irregular particles with different sizes for the as-synthesized conjugated polymers of CMP-1 and COP-1 could be observed in the SEM images, and the particles were inclined to be independent with each other (Figs. 1a and b). Interconnected particles could be found in CMP-2 (Fig. S1e in Supporting information). Brunauer-Emmett-Teller (BET) surface areas were calculated from N2 adsorption/desorption isotherm at 77 K. CMP-1 and CMP-2 exhibited type-II iso-thermal curve, and the BET areas were only 23.67 m2/g and 8.56 m2/g respectively. The low BET areas of CMP-1 and CMP-2 were speculated to be related the non-porous structure of pillar[5]arene, which could also be found in some previous reports [47]. COP-1 exhibited type-IV isothermal curve with hysteresis loop at high absolute pressure value which indicated complex micro-mesoporous structure and the BET areas was 482.63 m2/g. The pore volume of COP-1 was 0.12 cm3/g, while the ones of CMP-1 and CMP-2 were only 0.007 cm3/g and 0.0012 cm3/g respectively. The pore size distributions of polymers were calculated by nonlocal density functional theory (NLDFT) method (Figs. S2c and d in Supporting information). Thermogravimetric analysis (TGA) revealed that the polymers were stable at 300 ℃ (Fig. S2b in Supporting information). UV-vis diffuse reflectance (DRS) spectra showed that the absorption bands of the polymers extended to the visible light region (Fig. 1c), indicating the possible use of the polymers as photocatalysts under visible light irradiation.
Photocatalytic performances of the polymers toward the oxidation of sulfides with different substituents were investigated. The experiments were carried out at room temperature, with a 200 W blue LED lamp (420–460 nm) as light source, using open vessels under air, with photo-irradiated time for 10 h, 20 h and 30 h. The conversion yields of the sulfides were calculated by a 1H NMR spectroscopic method [63], using the formula of Conv. (%)(SO-1 or SO-2) = Integration b/Integration [(a + b + c)] × 100% and Conv. (%) (SF-1 or SF-2) = Integration c/Integration [(a + b + c)] × 100%, where "a", "b", "c" stand for the integrated peak area of characteristic H of sulfides, sulfoxides, and sulfones in the corresponding 1H NMR spectra, respectively (details in Supporting information). The conversion yields of the sulfides with photo-irradiated time of 10 h, 20 h and 30 h were shown in Table 1. With the photo-irradiated time increased from 10 h to 30 h, the conversion yield of S-2 to the corresponding sulfoxide (SO-2) catalyzed by both pillar[5]arene-based CMPs kept lower than 10%, while the conversion yield of S-1 to SO-1 increased with the increase of irradiation time and finally reached 80% in 30 h irradiation (Figs. S26-S39 in Supporting information). The conversion yields of S-2 and S-1 to their corresponding sulfoxides catalyzed by COP-1 increased with the irradiation time and reached 93% and 92%, respectively, in 30 h irradiation. The substrate selectivity was examined for pillar[5]arene-based CMPs catalysts as well as COP-1. It can be found that when COP-1 was used as a catalyst, both sulfides (S-1 and S-2) showed similar conversion yields after 30 h irradiation (92% and 93%). However, when catalyst CMP-1 was used, the conversion yields of S-1 and S-2 exhibited significant difference. The conversion yield of S-1 to SO-1 was 80%, but S-2 to SO-2 was only 10%. The conversion yield ratio for S-1:S-2 was 8:1. Similar phenomenon could be found in the case of catalyst CMP-2, with the conversion yields of S-1 to SO-1 and S-2 to SO-2 being 53% and 3%, respectively, and a conversion yield ratio for S-1:S-2 was nearly 18:1. Prolonged irradiation time after 30 h did not increase the conversion yields of the products.CMP-1 showed a higher photocatalytic activity than CMP-2, which might result from the triazine units of CMP-1 that cause better electron-hole separation. Interestingly, in the cases of CMP-1 and CMP-2, the conversion yields of S-1 and S-2 seemed to be proportional to the binding strength of pillar[5]arene toward the sulfides. As reported before, pillar[5]arenes can effectively bind linear dinitriles with the binding constant (Ka) of 104 L/mol for hexanedinitrile in CDCl3 [46-47, 64]. Phenyl group is too larger to be included by the pillar[5]arene cavity [43, 47].
To confirm the presumption that the host-guest interaction induced catalytic difference in the CMPs photocatalytic systems, corresponding oligomers of the CMPs and COP-1 (O-CMP-1, O-CMP-2 and O-COP-1) were prepared and 1H NMR experiments were conducted (Fig. 2a and Figs. S3a and b in Supporting information). Upon addition of O-CMP-1 to the CDCl3 solution of S-1, upfield shift and broadening for the proton signal of S-1 was observed, suggesting the existence of host-guest interaction between S-1 and the pillar[5]arene moieties of O-CMP-1. Such a change was not observed in the 1H NMR spectrum of S-1 upon addition of O-COP-1, indicating no interaction existed between S-1 and O-COP-1. In the case of S-2, no change could be observed in its 1H NMR spectrum upon addition of both O-CMP-1 and O-COP-1(Fig. S3b), implying no interaction existed between S-2 and O-CMP-1 (O-COP-1). Similarly, host-guest interaction can be observed in the 1H NMR spectrum of S-1 and O-CMP-2, but not in the 1H NMR spectrum of S-2 and O-CMP-2.
Competitive experiments were used to evaluate the host-guest effect of pillar[5]arenes on the photocatalytic oxidation of S-1(Fig. 2b). Butanenitrile (BN), a well-known guest molecule for pillar[5]arenes [65, 66], was used as a competitive guest molecule to bind the pillar[5]arene struts, weakening the interaction of the CMPs and S-1. As expected, by introducing excess BN into the system of CMP-1 and S-1, a remarkable change was observed in the conversion yield of S-1, dropping from 80% to 18%. Similar phenomenon can be found in CMP-2 involved photocatalytic system. However, under the same reaction conditions, no obvious change was observed in the conversion yield of S-1 when COP-1 was used as a photocatalyst. Therefore, we could concluded that the host-guest interaction of pillar[5]arene moieties in the CMPs with the substrate was vital to catalytic performance of the CMPs.
Electron spin resonance (ESR) was used to explore the photocatalytic mechanism of the polymers on oxidation of sulfides under visible light. In an O2 saturated toluene solution, with 5, 5-dimethyl-1-pyrroline N-oxide (DMPO) as the probe, the polymers all displayed clear four-line spectra of DMPO–·OH adducts after blue light irradiation, and the corresponding signal intensity increased with the irradiation time, indicating that all the polymers could generate OH under visible light irradiation. By changing the spin trap matter from DMPO to 2, 2, 6, 6-tetramethylpiperidinyloxyl (TEMPO), three-line spectra, which were the characteristic signal for the spin adduct formed by TEMPO and 1O2, were observed in the systems (Figs. S4a-d in Supporting information), indicating that the polymers could generate 1O2 under visible light irradiation. OH and 1O2 are all reactive oxygen species which can attack the S group in the oxidation reaction of sulfides.
As OH either originated from the solvent H2O or desolved O2, ESR spectra in N2 saturated CH3CN/H2O were examined. Except the CMP-2/DMPO system, clear four-line spectra of DMPO–OH adducts were detected in the systems of COP-1/DMPO and CMP-1/DMPO after blue light irradiation, indicating that COP-1 and CMP-1 could efficiently convert H2O to OH under visible light irradiation (Figs. S4e-g in Supporting information). Photocatalytic performance of all the polymers in the oxidation of S-1 and S-2 under N2 atmosphere were assessed (Table 2). The result showed that except CMP-2, CMP-1 and COP-1 possessed certain catalytic activity under N2 atmosphere toward the oxidation of sulfides, but the conversion yields were relatively lower than the ones in the air. The results were consistent with the ESR, indicating COP-1 and CMP-1 could photocatalytically convert H2O to OH to oxidize the sulfides to sulfoxides.
Based on the above observations, a mechanism for CMP-1 (COP-1) involved photocatalytic oxidation reaction was proposed. Under light irradiation, electron-hole pairs are generated in the polymers which activate H2O or solvated O2 to produce active oxygen species, the active oxygen species can subsequently oxidize the sulfides to their corresponding sulfoxides. Accessibility of the active oxygen species to the sulfide substrates is crucial to catalytic efficiency. In the system of CMP-1, pillar[5]arene motifs tend to bind guest-like sulfide substrates and increase the availability of activated oxygen species to the bonded sulfides. Consequently, the oxidation rate of guest-like sulfide (S-1) is accelerated. In the system of COP-1, no selective binding exists, and therefore similar photocatalytic activities of COP-1 toward both sulfides were observed.
In summary, we have demonstrated a host-guest interaction strategy to endow photocatalysts with special selectivity. By adopting conjugated macrocycle polymers with pillar[5]arene struts (CMP-1 and CMP-2), enhanced oxidation efficiency of the guest-like substrate (S-1) over non-guest-like substrate (S-2) was observed. Mechanism studies confirmed that the "host-guest" nature of pillar[5]arene struts in the CMPs was the main cause of the difference. The present work will open up new opportunities in design of highly efficient organic semiconductor catalysts with reactant selectivity. Related work is ongoing in our lab.
Declaration of competing interest
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The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
Acknowledgments
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This work is sponsored by Shanghai Sailing Program (No. 19YF1452900), National Key Research and Development Program of China (No. 2017YFA0206500), Science and Technology Commission of Shanghai Municipality (No. 18DZ1100403) and the National Natural Science Foundation of China (No. 21871281).
Appendix A. Supplementary data
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Supplementary material related to this article can be found, in the online version, at doi:https://doi.org/10.1016/j.cclet.2020.04.020.
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doi: 10.1016/j.cclet.2020.04.020
  • Receive Date：2020-03-04
  • Online Date：2026-01-31
  • Published：2020-12-15
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  • Received：2020-03-04
  • Revised：2020-03-27
  • Accepted：2020-04-09
Affiliations
    a College of Science, Shanghai University, Shanghai 200444, China
    b Shanghai Advanced Research Institute, Chinese Academy of Sciences, Shanghai 201210, China
    c University of Chinese Academy of Sciences, Beijing 100049, China
    d School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China
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表12种不同金属材料的力学参数
科
Family		 属数
Number of
genus		 种数
Number of
species		 占总种数比例
Percentage of
total species (%)		 属
Genus		 种数
Number of
species		 占总种数比例
Percentage of total
species (%)
鹅膏菌科Amanitaceae 2 11 5.26 鹅膏菌属 Amanita 10 4.78
小菇科 Mycenaceae 2 12 5.74 丝盖伞属 Inocybe 5 2.39
多孔菌科 Polyporaceae 8 14 6.70 蜡蘑属 Laccaria 5 2.39
红菇科 Russulaceae 3 23 11.00 小皮伞属 Marasmius 6 2.87
小菇属 Mycena 11 5.26
光柄菇属 Pluteus 5 2.39
红菇属 Russula 17 8.13
栓菌属 Trametes 5 2.39
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