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• W3040319328 abstract "Carbon nanomaterials have drawn great attention in recent years because of their outstanding properties and widespread applications. Graphdiyne (GDY) is a two-dimensional carbon nanomaterial consisting of sp and sp2 hybridized carbon atoms. Because of the unique structure and advanced physical and chemical properties, GDY exhibits extensive potential applications in many fields, such as catalysis, electrochemical energy storage, optoelectronic devices, and biomedicine. Similar to any material, synthesis determines the future. In order to bridge the gap between reality and ideality of GDY, many methods have been developed. However, until now, there has been a lack of fully deep summarizations, analyses, and prospects regarding the synthetic methodology of GDY. Hence, we will focus on the GDY synthetic methodology in the aspect of basic acetylenic coupling reactions, controllable synthetic methods, and scale-up production. This review will give important guidance on the synthesis of GDY. Recently, various synthetic methods have been developed to synthesize graphdiyne (GDY) in the aspect of controlled layer and different morphologies. The ideal GDY should have a large crystal domain size with only one atomic layer and possess excellent mechanical, electronic, optical, and magnetic intrinsic properties. However, there is still a gap between the reality and ideality on the road to perfect GDY, which results from the synthetic challenges from the terminal alkynes coupling efficiencies, side reactions, free rotation of carbon-carbon single bond between the diacetylenic linkages, small domain size, defects, and the uncontrollability of thickness. In this review, we will summarize the advances of synthetic methodology in improving the quality and yield of GDY from the perspective of fundamental acetylenic coupling reactions. We aim to stimulate the interest of researchers working in controlled synthesis and broaden application fields of GDY. Recently, various synthetic methods have been developed to synthesize graphdiyne (GDY) in the aspect of controlled layer and different morphologies. The ideal GDY should have a large crystal domain size with only one atomic layer and possess excellent mechanical, electronic, optical, and magnetic intrinsic properties. However, there is still a gap between the reality and ideality on the road to perfect GDY, which results from the synthetic challenges from the terminal alkynes coupling efficiencies, side reactions, free rotation of carbon-carbon single bond between the diacetylenic linkages, small domain size, defects, and the uncontrollability of thickness. In this review, we will summarize the advances of synthetic methodology in improving the quality and yield of GDY from the perspective of fundamental acetylenic coupling reactions. We aim to stimulate the interest of researchers working in controlled synthesis and broaden application fields of GDY. Graphdiyne (GDY) is a kind of two-dimensional (2D) all-carbon nanomaterial with specific configuration of sp and sp2 hybridized carbon atoms. Thanks to the unique structures of diacetylenic linkages (–C≡C–C≡C–), large π-conjugated systems, and well-distributed pores, GDY presents remarkable potential applications in the fields of energy storage and transformation,1Zhang H. Xia Y. Bu H. Wang X. Zhang M. Luo Y. Zhao M. Graphdiyne: A promising anode material for lithium ion batteries with high capacity and rate capability.J. Appl. Phys. 2013; 113: 044309Crossref Scopus (117) Google Scholar, 2Tang H. Hessel C.M. Wang J. Yang N. Yu R. Zhao H. Wang D. Two-dimensional carbon leading to new photoconversion processes.Chem. Soc. Rev. 2014; 43: 4281-4299Crossref PubMed Google Scholar, 3Srinivasu K. Ghosh S.K. Graphyne and graphdiyne: promising materials for nanoelectronics and energy storage applications.J. Phys. Chem. C. 2012; 116: 5951-5956Crossref Scopus (333) Google Scholar, 4Zuo Z. Li Y. Emerging electrochemical energy applications of graphdiyne.Joule. 2019; 3: 899-903Abstract Full Text Full Text PDF Scopus (78) Google Scholar catalysis,5Wu P. Du P. Zhang H. Cai C. Graphdiyne as a metal-free catalyst for low-temperature CO oxidation.Phys. Chem. Chem. Phys. 2014; 16: 5640-5648Crossref PubMed Google Scholar, 6Huang C. Li Y. Wang N. Xue Y. Zuo Z. Liu H. Li Y. Progress in research into 2D Graphdiyne-based materials.Chem. Rev. 2018; 118: 7744-7803Crossref PubMed Scopus (371) Google Scholar, 7Ren H. Shao H. Zhang L. Guo D. Jin Q. Yu R. Wang L. Li Y. Wang Y. Zhao H. Wang D. A new graphdiyne nanosheet/Pt nanoparticle-based counter electrode material with enhanced catalytic activity for dye-sensitized solar cells.Adv. Energy Mater. 2015; 5: 1500296Crossref Scopus (140) Google Scholar, 8Qi H. 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Progress and prospects of Graphdiyne-based materials in biomedical applications.Adv. Mater. 2019; 31: e1804386Crossref PubMed Scopus (52) Google Scholar etc. Monolayer GDY is predicted to be a 2D semiconductor with a moderate band gap of 0.44–1.47 eV based on different calculation methods3Srinivasu K. Ghosh S.K. Graphyne and graphdiyne: promising materials for nanoelectronics and energy storage applications.J. Phys. Chem. C. 2012; 116: 5951-5956Crossref Scopus (333) Google Scholar,10Jiao Y. Du A. Hankel M. Zhu Z. Rudolph V. Smith S.C. Graphdiyne: a versatile nanomaterial for electronics and hydrogen purification.Chem. Commun. (Camb.). 2011; 47: 11843-11845Crossref PubMed Scopus (271) Google Scholar,13Long M. Tang L. Wang D. Li Y. Shuai Z. Electronic structure and carrier mobility in graphdiyne sheet and nanoribbons: theoretical predictions.ACS Nano. 2011; 5: 2593-2600Crossref PubMed Scopus (637) Google Scholar, 14Narita N. Nagai S. Suzuki S. Nakao K. 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Structural and electronic properties of bilayer and trilayer graphdiyne.Nanoscale. 2012; 4: 3990-3996Crossref PubMed Scopus (101) Google Scholar and an intrinsic carrier mobility of 104–105 cm2·V−1·s−1 at room temperature,13Long M. Tang L. Wang D. Li Y. Shuai Z. Electronic structure and carrier mobility in graphdiyne sheet and nanoribbons: theoretical predictions.ACS Nano. 2011; 5: 2593-2600Crossref PubMed Scopus (637) Google Scholar making it an outstanding 2D material for future electronic, optoelectronic, and spintronic applications.19Guo J. Shi R.C. Wang R. Wang Y.Z. Zhang F. Wang C. Chen H.L. Ma C.Y. Wang Z.H. Ge Y.Q. et al.Graphdiyne-polymer nanocomposite as a broadband and robust saturable absorber for ultrafast photonics.Laser Photonics Rev. 2020; 14: 1900367Crossref Scopus (35) Google Scholar Since GDY was first proposed by Haley in 1997, it has been predicted to be the most stable artificial carbon allotrope with heat formation of 18.3 kcal per g-atom C.20Haley M.M. Barand S.C. Pak J.J. Carbon networks based on dehydrobenzoannulenes. 4. Synthesis of star and trefoil graphdiyne substructures via sixfold cross-coupling of hexaiodobenzene.Angew. Chem. Int. Ed. Engl. 1997; 36: 3893-3901Crossref Scopus (327) Google Scholar Therefore, the architecture of GDY is the direction for many scientists’ efforts. Considering the unique structure and properties, much effort has been devoted to exploring the synthetic methods of single or few-layered GDY.21Gao X. Zhu Y. Yi D. Zhou J. Zhang S. Yin C. Ding F. Zhang S. Yi X. Wang J. et al.Ultrathin graphdiyne film on graphene through solution-phase van der Waals epitaxy.Sci. Adv. 2018; 4: eaat6378Crossref PubMed Scopus (93) Google Scholar, 22Matsuoka R. Sakamoto R. Hoshiko K. Sasaki S. Masunaga H. Nagashio K. Nishihara H. Crystalline graphdiyne nanosheets produced at a gas/liquid or liquid/liquid interface.J. Am. Chem. Soc. 2017; 139: 3145-3152Crossref PubMed Scopus (254) Google Scholar, 23Yin C. Li J.Q. Li T.R. Yu Y. Kong Y. Gao P. Peng H.L. Tong L.M. Zhang J. Catalyst-free synthesis of few-layer graphdiyne using a microwave-induced temperature gradient at a solid/liquid interface.Adv. Funct. Mater. 2020; 30https://doi.org/10.1002/adfm.202001396Crossref Scopus (13) Google Scholar In 2010, Li and co-workers reported the first laboratory fabrication of GDY films on copper foils using an in situ Glaser coupling reaction.24Li G. Li Y. Liu H. Guo Y. Li Y. Zhu D. Architecture of graphdiyne nanoscale films.Chem. Commun. (Camb.). 2010; 46: 3256-3258Crossref PubMed Scopus (1433) Google Scholar Mao’s group also proposed an approach of aqueous phase exfoliation to obtain damage-free and few-layered GDY with high yields.25Yan H. Yu P. Han G. Zhang Q. Gu L. Yi Y. Liu H. Li Y. Mao L. High-yield and damage-free exfoliation of layered graphdiyne in aqueous phase.Angew. Chem. Int. Ed. Engl. 2019; 58: 746-750Crossref PubMed Scopus (31) Google Scholar In the past decade, a variety of approaches have been developed to synthesize GDY with controllable layer and different morphologies, such as GDY films,21Gao X. Zhu Y. Yi D. Zhou J. Zhang S. Yin C. Ding F. Zhang S. Yi X. Wang J. et al.Ultrathin graphdiyne film on graphene through solution-phase van der Waals epitaxy.Sci. Adv. 2018; 4: eaat6378Crossref PubMed Scopus (93) Google Scholar, 22Matsuoka R. Sakamoto R. Hoshiko K. Sasaki S. Masunaga H. Nagashio K. Nishihara H. Crystalline graphdiyne nanosheets produced at a gas/liquid or liquid/liquid interface.J. Am. Chem. Soc. 2017; 139: 3145-3152Crossref PubMed Scopus (254) Google Scholar, 23Yin C. Li J.Q. Li T.R. Yu Y. Kong Y. Gao P. Peng H.L. Tong L.M. Zhang J. Catalyst-free synthesis of few-layer graphdiyne using a microwave-induced temperature gradient at a solid/liquid interface.Adv. Funct. Mater. 2020; 30https://doi.org/10.1002/adfm.202001396Crossref Scopus (13) Google Scholar, 24Li G. Li Y. Liu H. Guo Y. Li Y. Zhu D. Architecture of graphdiyne nanoscale films.Chem. Commun. (Camb.). 2010; 46: 3256-3258Crossref PubMed Scopus (1433) Google Scholar, 25Yan H. Yu P. Han G. Zhang Q. Gu L. Yi Y. Liu H. Li Y. Mao L. High-yield and damage-free exfoliation of layered graphdiyne in aqueous phase.Angew. Chem. Int. Ed. Engl. 2019; 58: 746-750Crossref PubMed Scopus (31) Google Scholar, 26Zhou J.Y. Xie Z.Q. Liu R. Gao X. Li J.Q. Xiong Y. Tong L.M. Zhang J. Liu Z.F. Synthesis of ultrathin graphdiyne film using a surface template.ACS Appl. Mater. Interfaces. 2019; 11: 2632-2637Crossref PubMed Scopus (33) Google Scholar, 27Li J. Xiong Y. Xie Z. Gao X. Zhou J. Yin C. Tong L. Chen C. Liu Z. Zhang J. Template synthesis of an ultrathin beta-graphdiyne-like film using the eglinton coupling reaction.ACS Appl. Mater. Interfaces. 2019; 11: 2734-2739Crossref PubMed Scopus (27) Google Scholar nanowalls,28Zhou J. Gao X. Liu R. Xie Z. Yang J. Zhang S. Zhang G. Liu H. Li Y. Zhang J. et al.Synthesis of graphdiyne nanowalls using acetylenic coupling reaction.J. Am. Chem. Soc. 2015; 137: 7596-7599Crossref PubMed Scopus (293) Google Scholar,29Gao X. Li J. Du R. Zhou J. Huang M.Y. Liu R. Li J. Xie Z. Wu L.Z. Liu Z. Zhang J. Direct synthesis of graphdiyne nanowalls on arbitrary substrates and its application for photoelectrochemical water splitting cell.Adv. Mater. 2017; 29: 1605308Crossref Scopus (117) Google Scholar nanoribbons,30Jia Z.Y. Li Y.J. Zuo Z.C. Liu H.B. Li D. Li Y.L. Fabrication and electroproperties of nanoribbons: carbon ene-Yne.Adv. Electron. Mater. 2017; 3: 1700133Crossref Scopus (6) Google Scholar nanosheets,22Matsuoka R. Sakamoto R. Hoshiko K. Sasaki S. Masunaga H. Nagashio K. Nishihara H. Crystalline graphdiyne nanosheets produced at a gas/liquid or liquid/liquid interface.J. Am. Chem. Soc. 2017; 139: 3145-3152Crossref PubMed Scopus (254) Google Scholar,31Shang H. Zuo Z. Li L. Wang F. Liu H. Li Y. Li Y. Ultrathin graphdiyne nanosheets grown in situ on copper nanowires and their performance as lithium-ion battery anodes.Angew. Chem. Int. Ed. Engl. 2018; 57: 774-778Crossref PubMed Scopus (147) Google Scholar nanotubes,32Li G.X. Li Y.L. Qian X.M. Liu H.B. Lin H.W. Chen N. Li Y.J. Construction of tubular molecule aggregations of graphdiyne for highly efficient field emission.J. Phys. Chem. C. 2011; 115: 2611-2615Crossref Scopus (243) Google Scholar and freestanding three-dimensional (3D) GDY.33Li J.Q. Xu J. Xie Z.Q. Gao X. Zhou J.Y. Xiong Y. Chen C.G. Zhang J. Liu Z.F. Diatomite-templated synthesis of freestanding 3D graphdiyne for energy storage and catalysis application.Adv. Mater. 2018; 30: e1800548Crossref PubMed Scopus (74) Google Scholar Despite tremendous progress in the synthesis of highly ordered GDY, there is a gap between reality and ideality due to some intrinsic synthetic problems and challenges (Figure 1).34Zhou J.Y. Li J.Q. Liu Z.F. Zhang J. Exploring approaches for the synthesis of few-layered graphdiyne.Adv. Mater. 2019; 31: e1803758Crossref PubMed Scopus (26) Google Scholar As mentioned above, the ideal GDY should have a large crystal domain with one atomic layer and possess excellent mechanical, electronic, optical, and magnetic properties.35Gao X. Liu H. Wang D. Zhang J. Graphdiyne: synthesis, properties, and applications.Chem. Soc. Rev. 2019; 48: 908-936Crossref PubMed Google Scholar,36Li Y. Xu L. Liu H. Li Y. Graphdiyne and graphyne: from theoretical predictions to practical construction.Chem. Soc. Rev. 2014; 43: 2572-2586Crossref PubMed Scopus (611) Google Scholar Nevertheless, the performances of as-synthesized GDY are not the same as the theoretical prediction, due to the polycrystalline or amorphous nature of GDY. Therefore, the preparation of ideal GDY, especially the single crystal monolayered GDY, is an urgent issue. In 2009, Sakamoto et al. discussed the synthetic approaches and issues of GDY-based 2D polymers.37Sakamoto J. van Heijst J. Lukin O. Schlüter A.D. Two-dimensional polymers: just a dream of synthetic chemists?.Angew. Chem. Int. Ed. Engl. 2009; 48: 1030-1069Crossref PubMed Scopus (555) Google Scholar The unprotected terminal alkyne compounds with high chemical sensitivity are considered as a disadvantage to the ideal GDY. In the process of reactions, because of the multiple intramolecular cyclization and numerous bonds that should be formed at the right place, the number of bond-formations may be limited for hexaethynylbenzene (HEB). Besides, the flexibility of the main skeleton could lead to a 3D geometry in the growth steps. In this respect, a number of challenges are worthwhile mentioned combining theories and experiments: (1) the terminal alkyne coupling efficiencies of monomer, HEB, are difficult to be equivalent to coupling reaction of phenylacetylene under the same reaction conditions; (2) the side reactions, such as oxidative addition, cyclotrimerization, and reductive elimination coupling reactions, appear and affect crystallinity of GDY because of the high activity of the monomers;38Li X. Zhang H. Chi L. On-surface synthesis of Graphyne-based nanostructures.Adv. Mater. 2019; 31: e1804087Crossref PubMed Scopus (22) Google Scholar (3) the free rotation of carbon-carbon single bond between the diacetylenic linkages lead to unordered structure;37Sakamoto J. van Heijst J. Lukin O. Schlüter A.D. Two-dimensional polymers: just a dream of synthetic chemists?.Angew. Chem. Int. Ed. Engl. 2009; 48: 1030-1069Crossref PubMed Scopus (555) Google Scholar (4) small domain size and defects influence the properties of GDY; and (5) the thickness is difficult to be controlled because of the interaction between GDY layers. The differences between “real GDY” and “ideal GDY” lead to the gap. In order to bridge the gap, rational design of synthetic methods could be an efficient solution. Recently, there have been comprehensive reviews on the intrinsic properties, synthesis, functionalization, and potential applications of GDY.4Zuo Z. Li Y. Emerging electrochemical energy applications of graphdiyne.Joule. 2019; 3: 899-903Abstract Full Text Full Text PDF Scopus (78) Google Scholar,6Huang C. Li Y. Wang N. Xue Y. Zuo Z. Liu H. Li Y. Progress in research into 2D Graphdiyne-based materials.Chem. Rev. 2018; 118: 7744-7803Crossref PubMed Scopus (371) Google Scholar,12Liu J. Chen C. Zhao Y. Progress and prospects of Graphdiyne-based materials in biomedical applications.Adv. Mater. 2019; 31: e1804386Crossref PubMed Scopus (52) Google Scholar,34Zhou J.Y. Li J.Q. Liu Z.F. Zhang J. Exploring approaches for the synthesis of few-layered graphdiyne.Adv. Mater. 2019; 31: e1803758Crossref PubMed Scopus (26) Google Scholar, 35Gao X. Liu H. Wang D. Zhang J. Graphdiyne: synthesis, properties, and applications.Chem. Soc. Rev. 2019; 48: 908-936Crossref PubMed Google Scholar, 36Li Y. Xu L. Liu H. Li Y. Graphdiyne and graphyne: from theoretical predictions to practical construction.Chem. Soc. Rev. 2014; 43: 2572-2586Crossref PubMed Scopus (611) Google Scholar,39Yu H. Xue Y. Li Y. Graphdiyne and its assembly architectures: synthesis, functionalization, and applications.Adv. Mater. 2019; 31: e1803101Crossref PubMed Scopus (83) Google Scholar,40Sakamoto R. Fukui N. Maeda H. Matsuoka R. Toyoda R. Nishihara H. The accelerating world of Graphdiynes.Adv. Mater. 2019; 31: e1804211Crossref PubMed Scopus (43) Google Scholar Nevertheless, the challenges from the point of view of synthetic methodology of GDY have not been fully addressed. Deep reviews about how to bridge the gap between “real GDY” and “ideal GDY” are scarce. In this review, we will overview the advances of synthetic methodology in improving the quality and yield of GDY from the perspective of fundamental acetylenic coupling reactions. Glaser coupling catalyzed by Cu(Ι) was proposed first, and the subsequent three coupling reactions modified the catalyst systems. In the Glaser-Hay coupling reaction, an organic base was added to improve solubility of the Cu catalyst complex. Cu(II) acetate was applied to the Eglinton coupling reaction, which was carried out by a radical mechanism at room temperature. The utilization of alkynylsilane precursor could improve the stability of monomers in the alkynylsilane reaction. In addition, we highlight several strategies in wet chemical route, including catalyst, monomer, and interface-confined synthetic methods. Subsequently, we give in-depth insights into large-scale synthetic methods of highly ordered GDY by controlling the surface area of substrate, utilizing the solid-liquid interface, and employing graphene as an epitaxy template. Finally, we put forward the prospects for future developments in the synthesis and applications of GDY. We hope that this review would provide an overall analysis of challenges regarding the developed synthetic methods and guide the researchers toward issues that should be taken into consideration in future synthesis of GDY. GDY is a kind of polymeric network comprising sp and sp2 hybridized carbon atoms. Hence, the synthesis of GDY could be inspired from the organic molecules as building blocks that connect with each other via chemical bonds. GDY would be realized through the chemical reactions of appropriate precursors theoretically. As proposed by Haley et al., GDY substructures were realized via Cu-mediated acetylenic coupling reactions based on terminal alkynes or their derivatives.20Haley M.M. Barand S.C. Pak J.J. Carbon networks based on dehydrobenzoannulenes. 4. Synthesis of star and trefoil graphdiyne substructures via sixfold cross-coupling of hexaiodobenzene.Angew. Chem. Int. Ed. Engl. 1997; 36: 3893-3901Crossref Scopus (327) Google Scholar,41Haley M.M. Bell M.L. English J.J. Johnson C.A. Weakley T.J.R. Versatile synthetic route to and DSC analysis of Dehydrobenzoannulenes: crystal structure of a heretofore inaccessible [20] annulene derivative.J. Am. Chem. Soc. 1997; 119: 2956-2957Crossref Scopus (123) Google Scholar,42Marsden J.A. Haley M.M. Carbon networks based on dehydrobenzoannulenes. 5. Extension of two-dimensional conjugation in graphdiyne nanoarchitectures.J. Org. Chem. 2005; 70: 10213-10226Crossref PubMed Scopus (162) Google Scholar For conjugated alkynyl groups, Pb-catalyzed Sonogashira coupling reaction based on alkynyl halides could be applied,43Sonogashira K. Tohda Y. Hagihara N. A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines.Tetrahedron Lett. 1975; 16: 4467-4470Crossref Scopus (5153) Google Scholar and the controlled oligotrimerization of cyclic polyynes would also lead to the macromolecular networks for GDY.44Diederich F. Rubin Y. Synthetic approaches toward molecular and polymeric carbon allotropes.Angew. Chem. Int. Ed. Engl. 1992; 31: 1101-1123Crossref Scopus (528) Google Scholar Whereas, more stable precursors and more valid catalyst systems make Cu-mediated acetylenic coupling reactions stand out as more promising approaches for GDY’s synthesis. Until now, four types of Cu-mediated coupling reactions, including Glaser coupling, Glaser-Hay coupling, Eglinton coupling, and alkynylsilane coupling, were conventionally applied in the fabrication of GDY, as concluded in Figure 2A. Understanding of the fundamental catalytic systems and mechanisms of the coupling reactions is critical for developing high-efficient coupling approaches for GDY. The observation of acetylenic coupling reaction and that phenylacetylene catalyzed by Cu(I) salt in the alkaline solvent underwent the formation of Cu(I) phenylacetyl intermediate and subsequent oxidative dimerization was first reported by Glaser.45Glaser C. Beiträge zur Kenntniss des Acetenylbenzols.Ber. Dtsch. Chem. Ges. 1869; 2: 422-424Crossref Google Scholar Mechanisms for the classical acetylenic coupling reactions are demonstrated in Figure 2B. As for the Glaser coupling, a speculation of dinuclear-copper-acetylide-complex-mediated oxidized coupling mechanism proposed by Bohlmann et al. was widely accepted.46Bohlmann F.S.H. Schönowsky H. Inhoffen E. Grau G. Polyacetylenverbindungen, LII. über den mechanismus der oxydativen dimerisierung von acetylenverbindungen.Chem. Ber. 1964; 97: 794-800Crossref Scopus (112) Google Scholar,47Klappenberger F. Zhang Y.Q. Björk J. Klyatskaya S. Ruben M. Barth J.V. On-surface synthesis of carbon-based scaffolds and nanomaterials using terminal alkynes.Acc. Chem. Res. 2015; 48: 2140-2150Crossref PubMed Scopus (132) Google Scholar While the monomer of phenylacetylene was utilized in the Glaser coupling, its conversion and yield could reach more than 90%, indicating a high selectivity.48Li Y.N. Wang J.L. He L.N. Copper(II) chloride-catalyzed Glaser oxidative coupling reaction in polyethylene glycol.Tetrahedron Lett. 2011; 52: 3485-3488Crossref Scopus (60) Google Scholar Aiming at the synthesis of stable GDY networks, Li and co-workers designed HEB as the monomer and carried out a modified in situ Glaser coupling reaction in the alkaline pyridine solvent.24Li G. Li Y. Liu H. Guo Y. Li Y. Zhu D. Architecture of graphdiyne nanoscale films.Chem. Commun. (Camb.). 2010; 46: 3256-3258Crossref PubMed Scopus (1433) Google Scholar They exploited the Cu foil as both the catalyst and planar substrate tactfully since Cu would be oxidized to copper ions in the presence of a basic solvent. The planar Cu surface plays an important catalytic role in the polymerization and drives the synthesis of flat GDY films. Referring to this designing concept, GDY nanotubes32Li G.X. Li Y.L. Qian X.M. Liu H.B. Lin H.W. Chen N. Li Y.J. Construction of tubular molecule aggregations of graphdiyne for highly efficient field emission.J. Phys. Chem. C. 2011; 115: 2611-2615Crossref Scopus (243) Google Scholar and strip arrays49Wang S.S. Liu H.B. Kan X.N. Wang L. Chen Y.H. Su B. Li Y.L. Jiang L. Superlyophilicity-facilitated synthesis reaction at the microscale: ordered graphdiyne stripe arrays.Small. 2017; 13: 1602265Crossref Scopus (44) Google Scholar could also be synthesized. This Cu foil-assisted coupling reaction opened up a way for the emerging GDY nanomaterials. However, a full understanding of the formation mechanism and explicit component characterizations are lacking. Based on the acetylenic coupling reactions, several curial evolutions on the controllable preparation of GDY have been made. For the first time, Liu’s group reported a feasible synthetic route of GDY nanowalls via a modified Glaser-Hay coupling reaction,28Zhou J. Gao X. Liu R. Xie Z. Yang J. Zhang S. Zhang G. Liu H. Li Y. Zhang J. et al.Synthesis of graphdiyne nanowalls using acetylenic coupling reaction.J. Am. Chem. Soc. 2015; 137: 7596-7599Crossref PubMed Scopus (293) Google Scholar whose reaction conditions were demonstrated in Table 1. The Glaser-Hay coupling was derived from the Glaser reaction and achieved an important improvement under the application of a catalytic amount of bidentate ligand N, N, N′, N′-tetramethylethylenediamine (TMEDA).50Hay A.S. Oxidative coupling of acetylenes. II 1.J. Org. Chem. 1962; 27: 3320-3321Crossref Scopus (897) Google Scholar The coupling reaction rate was considerably faster ascribed to the enhanced solubility of Cu-TMEDA complex, which experienced further oxidative coupling with O2. According to the coupling mechanism based on DFT calculation proposed by Fomine et al., Cu(I)/Cu(Ⅲ)/Cu(Ⅱ)/Cu(I) catalytic cycle was involved for Glaser-Hay coupling and the dominant step was the dioxygen activation of Cu(I) complex for Cu(Ⅲ) complex (Figure 2C).51Fomina L. Vazquez B. Tkatchouk E. Fomine S. The Glaser reaction mechanism. A DFT study.Tetrahedron. 2002; 58: 6741-6747Crossref Scopus (80) Google Scholar Glaser-Hay coupling reaction with a more active catalyst system could be applied in diverse organic solvents and lower temperatures. Therefore, the reaction temperature and time in the modified Glaser-Hay coupling reactions on the copper foil are relatively lower than those of modified Glaser coupling. Glaser-Hay-coupling-reaction-induced GDY nanowalls with highly conjugated electronic structure and uniform sharp character are considered to have excellent roles in the field-emission application area,28Zhou J. Gao X. Liu R. Xie Z. Yang J. Zhang S. Zhang G. Liu H. Li Y. Zhang J. et al.Synthesis of graphdiyne nanowalls using acetylenic coupling reaction.J. Am. Chem. Soc. 2015; 137: 7596-7599Crossref PubMed Scopus (293) Google Scholar meanwhile their nanoporous networks and the abundant active sites are promising in the construction of high-performance catalysts.52Li J. Gao X. Li Z.Z. Wang J. Zhu L. Yin C. Wang Y. Li X.B. Liu Z.F. Zhang J. et al.Superhydrophilic graphdiyne accelerates interfacial mass/electron transportation to boost electrocatalytic and photoelectrocatalytic water oxidation activity.Adv. Funct. Mater. 2019; 29: 1808079Crossref Scopus (47) Google ScholarTable 1Reaction Conditions and Promising Application Fields of the Fundamental Acetylenic Coupling Reactions for GDYReactionsPrecursorCatalytic SystemTemperatureApplicationsModified Glaser couplingHEBCu, pyridine60°Cfield-emission;32Li G.X. Li Y.L. Qian X.M. Liu H.B. Lin H.W. Chen N. Li Y.J. Construction of tubular molecule aggregations of graphdiyne for highly efficient field emission.J. Phys. Chem. C. 2011; 115: 2611-2615Crossref Scopus (243) Google Scholar energy storage;53Shang H. Zuo Z. Yu L. Wang F. He F. Li Y. Low-temperature growth of all-carbon graphdiyne on a silicon anode for high-performance lithium-ion batteries.Adv. Mater. 2018; 30: e1801459Crossref PubMed Scopus (153) Google Scholar electroanalysis and electrochemistry54Guo S. Yan H. Wu F. Zhao L. Yu P. Liu H. Li Y. Mao L. Graphdiyne as electrode material: tuning electronic state and surface chemistry for improved electrode reactivity.Anal. Chem. 2017; 89: 13008-13015Crossref PubMed Scopus (40) Google Scholar,55Guo S. Yu P. Li W. Yi Y. Wu F. Mao L. Electron hopping by interfacing semiconducting graphdiyne nanosheets and redox molecules for selective electrocatalysis.J. Am. Chem. Soc. 2020; 142: 2074-2082Crossref PubMed Scopus (17) Google ScholarModified Glaser-Hay couplingHEBCu, TMEAD, pyridine50°Cfield-emission;28Zhou J. Gao X. Liu R. Xie Z. Yang J. Zhang S. Zhang G. Liu H. Li Y. 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• W3040319328 created "2020-07-10" @default.
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• W3040319328 date "2020-08-01" @default.
• W3040319328 modified "2023-10-18" @default.
• W3040319328 title "Bridging the Gap between Reality and Ideality of Graphdiyne: The Advances of Synthetic Methodology" @default.
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• W3040319328 doi "https://doi.org/10.1016/j.chempr.2020.06.011" @default.

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