Preparation of N-Graphdiyne Nanosheets at Liquid ... - ACS Publications

Subscriber access provided by UNIV OF DURHAM

Preparation of N-Graphdiyne Nanosheets at Liquid/ liquid Interface for Photocatalytic NADH Regeneration Qingyan Pan, Hui Liu, Yingjie Zhao, Siqi Chen, Bo Xue, Xiao-Nan Kan, Xiaowen Huang, Jian Liu, and Zhibo Li ACS Appl. Mater. Interfaces, Just Accepted Manuscript • DOI: 10.1021/acsami.8b03311 • Publication Date (Web): 12 Apr 2018 Downloaded from http://pubs.acs.org on April 12, 2018

Just Accepted “Just Accepted” manuscripts have been peer-reviewed and accepted for publication. They are posted online prior to technical editing, formatting for publication and author proofing. The American Chemical Society provides “Just Accepted” as a service to the research community to expedite the dissemination of scientific material as soon as possible after acceptance. “Just Accepted” manuscripts appear in full in PDF format accompanied by an HTML abstract. “Just Accepted” manuscripts have been fully peer reviewed, but should not be considered the official version of record. They are citable by the Digital Object Identifier (DOI®). “Just Accepted” is an optional service offered to authors. Therefore, the “Just Accepted” Web site may not include all articles that will be published in the journal. After a manuscript is technically edited and formatted, it will be removed from the “Just Accepted” Web site and published as an ASAP article. Note that technical editing may introduce minor changes to the manuscript text and/or graphics which could affect content, and all legal disclaimers and ethical guidelines that apply to the journal pertain. ACS cannot be held responsible for errors or consequences arising from the use of information contained in these “Just Accepted” manuscripts.

is published by the American Chemical Society. 1155 Sixteenth Street N.W., Washington, DC 20036 Published by American Chemical Society. Copyright © American Chemical Society. However, no copyright claim is made to original U.S. Government works, or works produced by employees of any Commonwealth realm Crown government in the course of their duties.

Page 1 of 17 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

ACS Applied Materials & Interfaces

Preparation of N-Graphdiyne Nanosheets at Liquid/liquid Interface for Photocatalytic NADH Regeneration Qingyan Pan,†‡ Hui Liu,†‡ Yingjie Zhao,†* Siqi Chen,† Bo Xue,† Xiaonan Kan,† Xiaowen Huang,† Jian Liu,§* and Zhibo Li†* †

Key Laboratory of Biobased Polymer Materials, Shandong Provincial Education Department;

School of Polymer Science and Engineering, Qingdao University of Science and Technology, Qingdao 266042, China §

College of Materials Science and Engineering, Qingdao University of Science and Technology,

Qingdao 266042, China [*] Corresponding Authors: [email protected], [email protected], [email protected] [‡] These authors contributed equally to this work. KEYWORDS: N-graphdiyne; nanosheets; interfacial synthesis; NADH; photocatalysis.

ACS Paragon Plus Environment

1

ACS Applied Materials & Interfaces 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

Page 2 of 17

ABSTRACT: Two-dimensional (2D) N-graphdiyne (N-GDY) nanosheets containing different number of N were synthesized by polymerization of triazine, pyrazine and pyridine based monomers at liquid/liquid interface. The configurations and nanostructures of N-GDY were well characterized. The wettability changed to more hydrophilic as the N contents increased. The collected N-GDY was further employed as metal-free photocatalyst for NADH regeneration. The catalytic performance was related with the N content in the graphdiyne. The N3-GDY demonstrated the best activity. This strategy provided a new promising platform of design unique 2D N-GDY with tunable performance in bio-related catalysis. Graphdiyne, as a typical 2D material has attracted broad interests since it was first synthesized in 2010 by Li and co-workers.1-4 This all-carbon 2D material bearing both sp2 and sp-carbon has already shown great potential in photovoltaic devices, high capacity and long-life lithium storage, as well as catalysts due to its excellent semiconductor property.5-7 Several explorations have been made for the chemical synthesis of GDY with different morphologies, including films, nanotubes, nanowires and nanowalls.8-10 Inspired by the numerous studies on the N-doped carbon materials, the heteroatom doped-GDY is greatly appealing and promising as a new 2D material. The electronic structure of GDY can be regulated by the heteroatom doping, which may further improve the semiconducting characteristics such as the

conductivity, mobility, band-gap and

charge separation efficiency. This provides opportunities to optimize the device performance and catalytic activity. It has been experimentally demonstrated that heteroatom-doped GDY structures are excellent metal-free electrocatalysts for the ORR and highly efficient lithium storage material.11-14 However, the heteroatom doped-GDY has not yet been investigated deeply. Most of the studies are based on the modification of the bulk material, which could be considered as “topdown” strategy.11-13, 15 This doped strategy suffered from structure manipulation and precision


2

Page 3 of 17 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


control of doping elements. Considering the unique structure of GDY, the heteroatom could be introduced based on the monomer design prior to polymerization which goes through a “bottomup” preparation process.16-19 Different from other carbon materials, the unique structures and the diversity of the monomers of graphdiyne can lead to well-defined heteroatom-doped GDYs with good controllability. The heteroatom contents and doping configurations could be precisely controlled to recognize the active role of heteroatoms.17 Moreover, the electronic structure of GDY could be modulated by the types of doping heteroatoms and concentrations, which may further improve its catalytic activity. Theoretical calculations have proved that N doping could lead to high degrees of positive charge on the carbon atoms adjacent to the N atoms, thereby facilitating electron movement from the anode to promote the ORR.12 Artificial photosynthesis is the imitation of natural photosynthesis, which provides an efficient way to use solar energy for synthesis of organic matters, in which one of the key step is the coenzyme regeneration (NADH/NADPH). In the light-independent reaction, with the newly formed NAD(P)H, the specific enzyme captures and converts CO2 into three-carbon sugars, which are later combined to form sucrose and starch. All the photosynthetic reactions are catalyzed by enzyme. The artificial mimic of enzyme by light driven enzymatic catalysis is very promising for delicate synthesis of drug intermediate and expensive chemicals. The cofactor NADH regeneration was well established through a photocatalytic route in the literature.20-23 However, metal-free photocatalyst is relatively rare.24, 25 Given the unique structure of heteroatom doped GDY, we here attempted to use N-GDY for regeneration of NADH. Three monomers based on triazine, pyrazine and pyridine were polymerized at the liquid/liquid interface to generate well-defined N-GDYs with different N-doping configurations, N-contents, and micropores, respectively, which was controlled


3


Page 4 of 17

by the monomer structure and compositions. Afterwards, the N-GDYs were explored as photocatalyst for NADH regeneration and showed good performance.

Figure 1. Schematic illustration of the liquid/liquid interface preparation of N-GDYs from the corresponding monomers and photocatalytic NADH regeneration in the presence of [Cp*Rh(bpy)(H)]+ in aqueous solution. The detailed experimental procedures of the interfacial synthesis of the N-GDYs were described in the Supporting Information (SI). Three precursors including 2, 3, 4, 5, 6-pentaethynylpyridine, 2, 3, 5, 6-tetraethynyl pyrazine and 2, 4, 6-triethynyl-1, 3, 5-triazine with the increased number of N atoms were predesigned and synthesized for the interfacial polymerization. 10 mL CH2Cl2 solution of monomer (0.1 mM) and 10 mL H2O solution of Cu(AcO)2 (0.05 mg/mL) and pyridine (0.05 M) were separately loaded to form two phases at room temperature. In the presence of Cu2+ as catalyst, the polymerization occurred at the liquid/liquid interface to form well-defined N-doped GDY thin films. The corresponding samples were named as N1-GDY, N2-GDY and N3-GDY, respectively. Considering the instability of the monomers, all the experiments were performed in a home-made dry box filled with Argon gas (SI). Compared with the classical GDY synthesis on the surface of copper foil, the liquid/liquid interfacial synthesis is simple, economical, eco-friendly and transferrable. The obtained films with average thickness from 12 nm to 23 nm could be well-


4

Page 5 of 17 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


dispersed in common solvent for further characterizations. Ideally, the nitrogen content of the N1, 2, 3-GDY which are estimated to be 7.2%, 16.3% and 28.0% can be tuned by the structure of corresponding monomers. Hence, the great advantage of interfacial synthesis is that it allows precise control on the configuration of the N-GDY by the monomer design. With the increase of N atom instead of the acetylenic group, the wettability, pore size, and electronic property such like the band gap of the N-GDY could be tuned to influence the semiconductors properties. Therefore, the catalytic performance in terms of photocatalytic NADH regeneration yield might be influenced by the structure of N-GDYs (Figure 1).

Figure 2. Morphological characterizations of N1-GDY, N2-GDY and N3-GDY. (a) proposed structure; (b) TEM; (c) SEM and (d) AFM images of N1-GDY; (e), (f), (g), (h) and (i), (j), (k), (l) are for N2-GDY and N3-GDY, respectively. The morphologies of the N-GDYs are presented in Figure 2. Three N-GDYs show similar film structures from the transmission electron microscope (TEM) (Figure 2b, f, j) and scanning electron microscopy (SEM) images (Figure 2c, g, k). These results suggest that the morphologies of the as-


5


Page 6 of 17

prepared GDYs all formed large 2D sheets, which confirmed the advantage of interfacial synthesis strategy. These results also indicated that the film morphologies are not influenced by the number of acetylenic groups and the N-doping contents. The films are uniform and in average continuous. This suggests that the N-doping doesn’t affect the material morphology but probably the electronic structure and other intrinsic properties. Atomic force microscopy (AFM) measurements demonstrate that the average thicknesses of N1-GDY, N2-GDY and N3-GDY are 12 nm, 20 nm and 23 nm, respectively. Thickness data were extracted from 30 positions of different nanosheets with a deviation < 2nm. Apparently, the thickness of N-GDY nanosheets increased with the N content, which is probably due to enhancement of the Van der Waals force between layer and layer with the increase of the N content.

Figure 3. (a) XPS survey spectra of N-GDYs; (b), (c) and (d) are XPS C 1s spectra of N1-GDY, N2-GDY and N3-GDY, respectively; e) Raman spectra of N-GDYs. XPS was applied to charagerize the elemental composition of N-GDYs. As shown in Figure 3a, the N-GDYs films are mainly composed of carbon, nitrogen, oxygen and silicon. Distinct N characteristic peaks were observed over 400 eV. Further analysis of the high resolution C 1s


6

Page 7 of 17 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


spectra of N-GDYs was shown in Figure 3b, c, d. The peaks can be mainly deconvoluted and assigned into C=C (sp2), C≡C (sp), C=N (sp2), respectively. Note that some C-O and C=O species are also detected in all the three cases, which might be introduced by the reaction between terminal alkyne and oxygen. For sample N1-GDY, the C≡C (sp), C=N (sp2), C=C (sp2), C–O and C=O peaks were located at 284.8, 285.6, 284.4, 286.4 and 287.9 eV, respectively, while the corresponding peaks are located at 284.8, 285.7, 284.2, 286.6 and 288.0 eV, respectively, for N2GDY. Note that there are no C=C (sp2) peak existing in the N3-GDY given even distribution of the N in the benzene group. The corresponding C≡C (sp), C=N (sp2), C–O and C=O peaks were found at 284.7, 285.3, 286.8 and 288.5 eV, respectively. The area ratios of the different hybridized carbon atoms are in agreement with the chemical composition of the N-GDYs, confirming GDY features benzene rings linked through diacetylenic linkages. As a powerful technique to characterize carbon materials and evaluate the quality and uniformity of them, Raman spectroscopy was applied to characterize the obtained N-GDY nanosheets (Figure 3e). All of the three N-GDYs exhibit two prominent peaks attributed to the G and D bands, corresponding to the E2g stretching vibration mode and the breathing vibration of sp2 carbon domains in aromatic rings. Furthermore, the peaks at 2180-2210 cm−1 were attributed to the vibration of the diacetylenic linkages, indicating the successful coupling reaction between acetylenic terminal. XPS and Raman spectra demonstrated the unambiguous configuration of the N-GDYs. FT-IR spectrum of N-GDYs showing typical C=N heterocycle stretches in the 1000-1600 cm-1 spectral range, while the weak peak at 2260 cm-1 was typical C≡C stretches (Figure S10). The broad absorption of N-GDYS was observed from 200 to around 800 nm which is in agreement with the reported GDYs (Figure S9).26


7


Page 8 of 17

Figure 4．Experimental results of the NADH regeneration rates in three systems: a) N1-GDY, b) N2-GDY and c) N3-GDY; (d) Comparison of the regeneration rates of the three systems; Static contact angles of (e) N1-GDY; (f) N2-GDY and (g) N3-GDY on Si substrate. Cofactor NADH is found in all living system as the biological form of hydrogen. In metabolism, NADH/NAD+ is involved in dehydrogenase redox reactions, carrying electrons from one reaction to another. Maintaining the complete cycle between NAD+ and NADH is extremely important for the dehydrogenase enzymatic reactions. The NADH regeneration was well established by semiconductor photocatalysis with [Cp*Rh(bpy)(H)]+ acting as electron mediator and hydride transfer agent and TEOA as an electron donor. The enzymatic active 1,4-NADH among various NADH isomers (1,2- or 1,6-NADH) and dimers (NAD2) can be selectively regenerated in the presence of [Cp*Rh(bpy)(H)]+ by taking two electrons and one proton from the excited semiconductor and stereoselectively transferring them to NAD+.27 The GDYs obtained by interfacial synthesis is very promising for such applications. Due to the unique N-doped molecular


8

Page 9 of 17 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


configuration and well-defined nanosheet morphology, the GDYs nanosheets can be well dispersed in the aqueous solution. With as low as 200 µg/mL concentration of GDYs, the NADH can be regenerated under light illumination and the NADH regeneration yield can be measured by monitoring the characteristic 340 nm absorbance using the UV-vis spectrophotometer. The blank reactions without N-GDY or [Cp*Rh(bpy)(H)]+ were performed as illustrated in Figure S4 and Figure S5 in SI. Without N-GDY or [Cp*Rh(bpy)(H)]+, the NADH cannot be regenerated under identical light illumination period. This suggested the determined role of N-GDYs in the lightdriven NADH regeneration process. Herein, under white light illumination, NADH regeneration yields for N3-GDY get to 35% in three hours. The favorable energy level of the conduction band renders the electron from the excited N-GDYs to the Rh complex and further to NAD+ (Figure 1). The NADH regeneration profiles were illustrated in Figure 4. However, further increasing the GDYs concentration above 200 µg/ml in the reaction solution doesn’t help increase the NADH regeneration yield probably due to the light shielding effect (Figure S6). It was found that the N content in the N-GDY affects the performance of NADH regeneration yield. For N1-GDY and N2-GDY, the NADH yields were not as good as that of N3-GDY. Part of the reason was ascribed to the wettability difference of the N-GDYs.28, 29 As the N contents increased from N1-GDY to N3-GDY, the wettability changed to more hydrophilic, as demonstrated by the decreasing of the static contact angles (81.3°, 67.7°and 50.7°for N1-GDY, N2-GDY and N3-GDY) in Figure 4e-g. Higher hydrophilicity ensures the well contact between aqueous solution with the catalyst surface and facilitates the catalytic reaction for NADH regeneration. Mott-Schottky plots were included in Figure S16. The flat-band potentials of N1, N2, and N3-GDYs obtained from the Mott-Schottky plots are -1.28, -1.43, and -1.73 V versus Ag/AgCl, respectively. N3-GDY possessed the most negative potential among three GDYs.


9


Page 10 of 17

Higher hydrophilicity and more negative conduction band potential might partly account for the higher NADH regeneration performance for N3-GDY. Other affecting factors are also under investigation to further improve the performance. Although the regeneration yield is not as high as that reported in the literature,30 the result is still promising considering the low concentration of the catalyst and metal-free property of GDYs. Due to the facile functionalization of the GDY monomer and post-processing of N-GDYs, further improving the NADH regeneration yield is feasible. Interfacial synthesis has been successfully applied to prepare a series of 2D N-GDY nanosheets. Through the monomers design, the structures and N-content of the obtained N-GDY are tunable and controllable. The obtained N-GDY nanosheets with thickness from 12-23 nm can be well dispersed in aqueous solution. For demonstration application, the N-GDYs were applied in the light-driven NADH regeneration coupling with the [Cp*Rh(bpy)(H)]+ as the electron and proton transfer agent. The activity of N-GDYs for NADH regeneration were found to be related with the N content in the monomers. As the N contents increased from N1 to N3, the activity was enhanced and reached to 35% for N3-GDY. This was probably ascribed to the increased hydrophilicity related to the higher N contents. Further exploring the mechanism and improving the performance are currently under investigation. The current work sheds light on the performance through the monomer design and N doping. The metal-free property renders the N-GDYs promising platform for bioinspired application. The enzymatic reaction coupled with in-situ NADH regeneration could be realized with light as the only input energy on such metal-free photocatalysts. ASSOCIATED CONTENT


10

Page 11 of 17 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


Supporting Information. The following files are available free of charge via the Internet on the ACS publications website at http://pubs.acs.org. General experimental procedures for synthesis process of N-GDYs at liquid/liquid interface and details for NADH regeneration are presented. Results of control experiments: NADH regeneration without N-GDY or [Cp*Rh(bpy)(H)]+. NADH regeneration yields with different N-GDYs concentrations. High resolution N 1s spectra of N-GDYs on HMDS modified SiO2/Si (100), picture of the glove-box and photograph of the liquid/liquid interfacial synthetic procedure.

AUTHOR INFORMATION

Corresponding Author *Yingjie Zhao, Email: [email protected] *Jian Liu, Email: [email protected] *Zhibo Li, Email: [email protected] Author Contributions Q. P. did the synthesis and characterization of N-GDYs. H, L. did the NADH regeneration part, J. L., Z. L. and Y. Z. directed the study. Funding Sources National Natural Science Foundation of China. National Young Thousand Talents Program. Shandong Provincial Natural Science Foundation, China.


11


Page 12 of 17

Notes The authors declare no competing financial interest. ACKNOWLEDGEMENT The work was supported by the National Natural Science Foundation of China (21604046), the National Young Thousand Talents Program, Shandong Provincial Natural Science Foundation, China (ZR2016XJ004, ZR2018MB018). REFERENCES (1) Li, G. X.; Li, Y. L.; Liu, H. B.; Guo, Y. B.; Li, Y. J.; Zhu, D. B., Architecture of graphdiyne nanoscale films. Chem. Commun. 2010, 46, 3256-3258. (2) Li, Y. J.; Xu, L.; Liu, H. B.; Li, Y. L., Graphdiyne and graphyne: from theoretical predictions to practical construction. Chem. Soc. Rev. 2014, 43, 2572-2586. (3) Jia, Z.; Li, Y.; Zuo, Z.; Liu, H.; Huang, C.; Li, Y., Synthesis and Properties of 2D Carbon— Graphdiyne. Acc. Chem. Res. 2017, 50, 2470-2478. (4) Chen, Y.; Huibiao, L.; Li, Y., Progress and prospect of two dimensional carbon graphdiyne. Chin. Sci. Bull. 2016, 61, 2901–2912. (5) Kuang, C.; Tang, G.; Jiu, T.; Yang, H.; Liu, H.; Li, B.; Luo, W.; Li, X.; Zhang, W.; Lu, F.; Fang, J.; Li, Y., Highly Efficient Electron Transport Obtained by Doping PCBM with Graphdiyne in Planar-Heterojunction Perovskite Solar Cells. Nano Letters 2015, 15, 2756-2762. (6) Zhang, S. L.; Du, H. P.; He, J. J.; Huang, C. S.; Liu, H. B.; Cui, G. L.; Li, Y. L., NitrogenDoped Graphdiyne Applied for Lithium-Ion Storage. ACS Appl. Mater. Interfaces 2016, 8, 84678473.


12

Page 13 of 17 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


(7) Huang, C.-S.; Li , Y.-L., Structure of 2D graphdiyne and its application in energy fields. Acta Phys. -Chim. Sin. 2016, 32, 1314-1329. (8) Li, G.; Li, Y.; Qian, X.; Liu, H.; Lin, H.; Chen, N.; Li, Y., Construction of Tubular Molecule Aggregations of Graphdiyne for Highly Efficient Field Emission. J. Phys. Chem. C 2011, 115, 2611-2615. (9) Qian, X.; Ning, Z.; Li, Y.; Liu, H.; Ouyang, C.; Chen, Q.; Li, Y., Construction of graphdiyne nanowires with high-conductivity and mobility. Dalton Trans. 2012, 41, 730-733. (10) Zhou, J.; Gao, X.; Liu, R.; Xie, Z.; Yang, J.; Zhang, S.; Zhang, G.; Liu, H.; Li, Y.; Zhang, J.; Liu, Z., Synthesis of Graphdiyne Nanowalls Using Acetylenic Coupling Reaction. J. Am. Chem. Soc. 2015, 137, 7596-7599. (11) Zhang, S.; Cai, Y.; He, H.; Zhang, Y.; Liu, R.; Cao, H.; Wang, M.; Liu, J.; Zhang, G.; Li, Y.; Liu, H.; Li, B., Heteroatom doped graphdiyne as efficient metal-free electrocatalyst for oxygen reduction reaction in alkaline medium. J. Mater. Chem. A 2016, 4, 4738-4744. (12) Liu, R.; Liu, H.; Li, Y.; Yi, Y.; Shang, X.; Zhang, S.; Yu, X.; Zhang, S.; Cao, H.; Zhang, G., Nitrogen-doped graphdiyne as a metal-free catalyst for high-performance oxygen reduction reactions. Nanoscale 2014, 6, 11336-11343. (13) Lv, Q.; Si, W.; Yang, Z.; Wang, N.; Tu, Z.; Yi, Y.; Huang, C.; Jiang, L.; Zhang, M.; He, J.; Long, Y., Nitrogen-Doped Porous Graphdiyne: A Highly Efficient Metal-Free Electrocatalyst for Oxygen Reduction Reaction. ACS Appl. Mater. Interfaces 2017, 9, 29744-29752. (14) Yongjun, L.; Yuliang, L., Chemical Modification and Functionalization of Graphdiyne. Acta Phys. -Chim. Sin. 2018, 1-9.


13


Page 14 of 17

(15) Du, H.; Zhang, Z.; He, J.; Cui, Z.; Chai, J.; Ma, J.; Yang, Z.; Huang, C.; Cui, G., A Delicately Designed Sulfide Graphdiyne Compatible Cathode for High-Performance Lithium/Magnesium– Sulfur Batteries. Small 2017, 13, 1702277. (16) Wang, N.; He, J.; Tu, Z.; Yang, Z.; Zhao, F.; Li, X.; Huang, C.; Wang, K.; Jiu, T.; Yi, Y.; Li, Y., Synthesis of Chlorine-Substituted Graphdiyne and Applications for Lithium-Ion Storage. Angew. Chem. Int. Ed. 2017, 56, 10740-10745. (17) Shang, H.; Zuo, Z. C.; Zheng, H. Y.; Li, K.; Tu, Z. Y.; Yi, Y. P.; Liu, H. B.; Li, Y. J.; Li, Y. L., N-doped graphdiyne for high-performance electrochemical electrodes. Nano Energy 2018, 44, 144-154. (18) He, J. J.; Wang, N.; Cui, Z. L.; Du, H. P.; Fu, L.; Huang, C. S.; Yang, Z.; Shen, X. Y.; Yi, Y. P.; Tu, Z. Y.; Li, Y. L., Hydrogen substituted graphdiyne as carbon-rich flexible electrode for lithium and sodium ion batteries. Nat. Commun. 2017, 8, 1172. (19) Kan, X.; Ban, Y.; Wu, C.; Pan, Q.; Liu, H.; Song, J.; Zuo, Z.; Li, Z.; Zhao, Y., Interfacial Synthesis of Conjugated Two-Dimensional N-Graphdiyne. ACS Appl. Mater. Interfaces 2018, 10, 53-58. (20) Ryu, J.; Lee, S. H.; Nam, D. H.; Park, C. B., Rational Design and Engineering of QuantumDot-Sensitized TiO2 Nanotube Arrays for Artificial Photosynthesis. Adv. Mater. 2011, 23, 18831888. (21) Yadav, R. K.; Oh, G. H.; Park, N.-J.; Kumar, A.; Kong, K.-j.; Baeg, J.-O., Highly Selective Solar-Driven Methanol from CO2 by a Photocatalyst/Biocatalyst Integrated System. J. Am. Chem. Soc. 2014, 136, 16728-16731.


14

Page 15 of 17 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


(22) Liu, J.; Cazelles, R.; Chen, Z. P.; Zhou, H.; Galarneau, A.; Antonietti, M., The bioinspired construction of an ordered carbon nitride array for photocatalytic mediated enzymatic reduction. Phys. Chem. Chem. Phys. 2014, 16, 14699-14705. (23) Wang, X.; Saba, T.; Yiu, H. H. P.; Howe, R. F.; Anderson, J. A.; Shi, J., Cofactor NAD(P)H Regeneration Inspired by Heterogeneous Pathways. Chem 2017, 2, 621-654. (24) Liu, J.; Antonietti, M., Bio-inspired NADH regeneration by carbon nitride photocatalysis using diatom templates. Energy Environ. Sci. 2013, 6, 1486-1493. (25) Huang, X.; Liu, J.; Yang, Q.; Liu, Y.; Zhu, Y.; Li, T.; Tsang, Y. H.; Zhang, X., Microfluidic chip-based one-step fabrication of an artificial photosystem I for photocatalytic cofactor regeneration. RSC Adv. 2016, 6, 101974-101980. (26) Liu, R.; Gao, X.; Zhou, J.; Xu, H.; Li, Z.; Zhang, S.; Xie, Z.; Zhang, J.; Liu, Z., Chemical Vapor Deposition Growth of Linked Carbon Monolayers with Acetylenic Scaffoldings on Silver Foil. Adv. Mater. 2017, 29, 1604665. (27) Hollmann, F.; Witholt, B.; Schmid, A., [Cp∗Rh(bpy)(H2O)]2+: a versatile tool for efficient and non-enzymatic regeneration of nicotinamide and flavin coenzymes. J. Mol. Catal. B: Enzym. 2002, 19-20, 167-176. (28) Hong, G.; Han, Y.; Schutzius, T. M.; Wang, Y.; Pan, Y.; Hu, M.; Jie, J.; Sharma, C. S.; Müller, U.; Poulikakos, D., On the Mechanism of Hydrophilicity of Graphene. Nano Letters 2016, 16, 4447-4453. (29) Tian, T.; Lin, S.; Li, S.; Zhao, L.; Santos, E. J. G.; Shih, C.-J., Doping-Driven Wettability of Two-Dimensional Materials: A Multiscale Theory. Langmuir 2017, 33, 12827-12837.


15


Page 16 of 17

(30) Liu, J.; Huang, J.; Zhou, H.; Antonietti, M., Uniform Graphitic Carbon Nitride Nanorod for Efficient Photocatalytic Hydrogen Evolution and Sustained Photoenzymatic Catalysis. ACS Appl. Mater. Interfaces 2014, 6, 8434-8440.


16

Page 17 of 17 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


Table of Contents


17

Preparation of N-Graphdiyne Nanosheets at Liquid ... - ACS Publications

Recommend Documents