Synthesis, Structure and Fluorescence of Olefin-Copper(Ⅰ) Coordination Polymers
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摘要
The organic olefin ligand 2,5-dimethyl-1-(4-vinyl-benzyl)-piperazine reacts with CuX(X = Cl, Br) to obtain two novel olefin-copper(I) coordination polymers [C_(15)H_(22)N_2Cu_2Cl_3]n(1) and [C_(15)H_(20)N_2Cu_2Br_2]n(2). There are two types of CuX warp structures that have never been seen before in the presence of methanol under solvothermal conditions. The new olefin-copper(I) coordination complex crystallizes in the monoclinic space group P21/c to obtain compounds 1 and 2. Its unique green fluorescence effect can be applied to the LED field.
The organic olefin ligand 2,5-dimethyl-1-(4-vinyl-benzyl)-piperazine reacts with CuX(X = Cl, Br) to obtain two novel olefin-copper(I) coordination polymers [C_(15)H_(22)N_2Cu_2Cl_3]n(1) and [C_(15)H_(20)N_2Cu_2Br_2]n(2). There are two types of CuX warp structures that have never been seen before in the presence of methanol under solvothermal conditions. The new olefin-copper(I) coordination complex crystallizes in the monoclinic space group P21/c to obtain compounds 1 and 2. Its unique green fluorescence effect can be applied to the LED field.
The organic olefin ligand 2,5-dimethyl-1-(4-vinyl-benzyl)-piperazine reacts with CuX(X = Cl, Br) to obtain two novel olefin-copper(I) coordination polymers [C_(15)H_(22)N_2Cu_2Cl_3]n(1) and [C_(15)H_(20)N_2Cu_2Br_2]n(2). There are two types of CuX warp structures that have never been seen before in the presence of methanol under solvothermal conditions. The new olefin-copper(I) coordination complex crystallizes in the monoclinic space group P21/c to obtain compounds 1 and 2. Its unique green fluorescence effect can be applied to the LED field.
引文
(1)Thompson,J.S.;Harlow,R.L.;Whitney,J.F.Copper(1)-olefin complexes.Support for the proposed role of copper in the ethylene effect in plants.J.Am.Chem.Sot.1983,105,3522-3527.
(2)Ye,Q.;Wang,X.S.;Zhao,H.;Xiong,R.G.Highly stable olefin-Cu(I)coordination oligomers and polymers.Chem.Soc.Rev.2005,36,208-225.
(3)Qu,Z.R.;Chen,Z.F.;Zhang,J.;Xiong,R.G.;Abrahams,B.F.;Xue,Z.L.The first highly stable homochiral olefin-copper(I)2D coordination polymer grid based on quinine as a building block.Organometallics 2003.22,2814-2816.
(4)Thompson,J.S.;Harlow,R.L.;Whitney,J.F.Copper(I)-olefin complexes.Support for the proposed role of copper in the ethylene effect in plants.J.Am.Chem.Soc.1983,105,3522-3527.
(5)Wang,W.;Zhang,L.;Xu,X.B.;Ye,Q.Formation of novel olefin-copper(I)coordination compound dependent on conformation of Olefin ligand.Inorg.Chem.Commu.2011,14,626-631.
(6)Ye,Q.;Liu,L.;Chen,Z.Q.;Sun,S.W.;Qiong,R.G.Solvothermal syntheses and physical properties of noncentrosymmetric olefin-copper(I)coordination compounds.Organometallics.2012,31,7862-7869.
(7)Maestre,L.;Sameera,W.M.C.;Díaz-Requejo,M.M..;Maseras,F.;Pérez,P.J.A general mechanism for the copper-and silver-catalyzed olefin aziridination reactions:concomitant involvement of the singlet and triplet pathways.J.Am.Chem.Soc.2013,135,1338-1348.
(8)Wang,G.X.;Xing,Z.;Chen,L.Z.;Han,G.F.Two novel olefin-copper(I)coordination polymers with DHDAB as building blocks.J.Organomet.Chem.2015,783,17-21.
(9)Ye,Q.;Hang,T.;Fu,D.W.;Qu,G.H.;Qiong,R.G.Typical ferroelectric olefin-copper(I)organometallic oligmer with flexible organic ligand.Cryst.Growth.Des.2008,8,3501-3503.
(10)Slyvka,Y.I.;Goreshnik,E.A.;Ardan,B.R.;Veryasov,G.;Morozov,D.;Mys’kiv,M.G.A new tetranuclear copper(I)complex based on allyl(5-phenyl-1,3,4-thiadiazol-2-yl)azanide ligand:synthesis and structural characterization.J.Mol.Struct.2015,1086,125-130.
(11)Li,J.;Fan,W.W.;Liu,M.;Xiao,Y.L.;Jin,Q.H.;Li,Z.H.Synthesis and structural characterization of five new copper(I)complexes with1,10-phenanthroline and 1,4-bis(diphenylphosphino)butane(dppb).J.Mol.Struct.2015,1085,235-241.
(12)Chen,J.L.;Fu,X.F.;Wang,J.Y.;Guo,Z.H.;Xiao,Y.L.;He,L.H.;Wen,H.R.A series of new emissive mononuclear copper(I)bipyridyl complexes bearing the methoxycarbonyl groups.Inorg.Chem.Commu.2015,53,88-91.
(13)Ardan,B.;Kinzhybalo,V.;Slyvka,Y.;Shyyka,O.;Luk’yanov,M.;Lis,T.;Mys’kiv,M.Ligand-forced dimerization of copper(I)-olefin complexes bearing a 1,3,4-thiadiazole core.Acta Crystallogr.2017,73,36-46.
(14)Lin,L.Z.;Zhong,Q.X.;Hong,J.T.;Chen,H.L.;Chen,W.T.Syntheses,structures,photoluminescence and semiconductor properties of two novel mercury-lanthanide complexes with a three-dimensional open framework.Inorg.Chim.Acta 2018,479,30-35
(15)Xu,Y.P.;Chen,W.T.;Yi,C.;Huang,J.G.;Zhang,D.W.;Wang,Y.F.A novel manganese complex with mixed ligands:preparation,structure,photoluminescent and semiconductive properties.J.Chem.Res.2018,42,148-152.
(16)Yi,X.G.;Zhang,Z.X.;Chen,W.T.;Lin,L.Z.;Chen,H.L.Photoluminescence and semiconductor properties of two novel lanthanidemercury compounds with one-dimensional chain-like structures.J.Solid State Chem.2018,266,16-22.
(17)Chen,L.Z.;Ji,Q.;Dan,Y.Y.Synthesis,Structure,and Luminescent and Dielectric Properties of Two Novel 1D Chains Based on a T-Shaped Tripodal Ligand 4-(4,5-Dicarboxy-1H-imidazol-2-yl)pyridine Loxide.Chin.J.Struct.Chem.2016,35,1728-1735.
(18)Chen,L.Z.;Sun,J.;Ji,Q.;Pan,Q,J.;Huang.Y.Switchable Dielectric MaterialsBased on 2-Methylimidazole.Chin.J.Struct.Chem.2017,36,329-337.
(19)Sheldrick,G.M.SHELXS-97,Program for Crystal Structure Solution.University of G?ttingen,Germany 1997.
(20)Sheldrick,G.M.SHELXL-97,Program for Crystal Structure Refinement.University of G?ttingen,Germany 1997.
(2)Ye,Q.;Wang,X.S.;Zhao,H.;Xiong,R.G.Highly stable olefin-Cu(I)coordination oligomers and polymers.Chem.Soc.Rev.2005,36,208-225.
(3)Qu,Z.R.;Chen,Z.F.;Zhang,J.;Xiong,R.G.;Abrahams,B.F.;Xue,Z.L.The first highly stable homochiral olefin-copper(I)2D coordination polymer grid based on quinine as a building block.Organometallics 2003.22,2814-2816.
(4)Thompson,J.S.;Harlow,R.L.;Whitney,J.F.Copper(I)-olefin complexes.Support for the proposed role of copper in the ethylene effect in plants.J.Am.Chem.Soc.1983,105,3522-3527.
(5)Wang,W.;Zhang,L.;Xu,X.B.;Ye,Q.Formation of novel olefin-copper(I)coordination compound dependent on conformation of Olefin ligand.Inorg.Chem.Commu.2011,14,626-631.
(6)Ye,Q.;Liu,L.;Chen,Z.Q.;Sun,S.W.;Qiong,R.G.Solvothermal syntheses and physical properties of noncentrosymmetric olefin-copper(I)coordination compounds.Organometallics.2012,31,7862-7869.
(7)Maestre,L.;Sameera,W.M.C.;Díaz-Requejo,M.M..;Maseras,F.;Pérez,P.J.A general mechanism for the copper-and silver-catalyzed olefin aziridination reactions:concomitant involvement of the singlet and triplet pathways.J.Am.Chem.Soc.2013,135,1338-1348.
(8)Wang,G.X.;Xing,Z.;Chen,L.Z.;Han,G.F.Two novel olefin-copper(I)coordination polymers with DHDAB as building blocks.J.Organomet.Chem.2015,783,17-21.
(9)Ye,Q.;Hang,T.;Fu,D.W.;Qu,G.H.;Qiong,R.G.Typical ferroelectric olefin-copper(I)organometallic oligmer with flexible organic ligand.Cryst.Growth.Des.2008,8,3501-3503.
(10)Slyvka,Y.I.;Goreshnik,E.A.;Ardan,B.R.;Veryasov,G.;Morozov,D.;Mys’kiv,M.G.A new tetranuclear copper(I)complex based on allyl(5-phenyl-1,3,4-thiadiazol-2-yl)azanide ligand:synthesis and structural characterization.J.Mol.Struct.2015,1086,125-130.
(11)Li,J.;Fan,W.W.;Liu,M.;Xiao,Y.L.;Jin,Q.H.;Li,Z.H.Synthesis and structural characterization of five new copper(I)complexes with1,10-phenanthroline and 1,4-bis(diphenylphosphino)butane(dppb).J.Mol.Struct.2015,1085,235-241.
(12)Chen,J.L.;Fu,X.F.;Wang,J.Y.;Guo,Z.H.;Xiao,Y.L.;He,L.H.;Wen,H.R.A series of new emissive mononuclear copper(I)bipyridyl complexes bearing the methoxycarbonyl groups.Inorg.Chem.Commu.2015,53,88-91.
(13)Ardan,B.;Kinzhybalo,V.;Slyvka,Y.;Shyyka,O.;Luk’yanov,M.;Lis,T.;Mys’kiv,M.Ligand-forced dimerization of copper(I)-olefin complexes bearing a 1,3,4-thiadiazole core.Acta Crystallogr.2017,73,36-46.
(14)Lin,L.Z.;Zhong,Q.X.;Hong,J.T.;Chen,H.L.;Chen,W.T.Syntheses,structures,photoluminescence and semiconductor properties of two novel mercury-lanthanide complexes with a three-dimensional open framework.Inorg.Chim.Acta 2018,479,30-35
(15)Xu,Y.P.;Chen,W.T.;Yi,C.;Huang,J.G.;Zhang,D.W.;Wang,Y.F.A novel manganese complex with mixed ligands:preparation,structure,photoluminescent and semiconductive properties.J.Chem.Res.2018,42,148-152.
(16)Yi,X.G.;Zhang,Z.X.;Chen,W.T.;Lin,L.Z.;Chen,H.L.Photoluminescence and semiconductor properties of two novel lanthanidemercury compounds with one-dimensional chain-like structures.J.Solid State Chem.2018,266,16-22.
(17)Chen,L.Z.;Ji,Q.;Dan,Y.Y.Synthesis,Structure,and Luminescent and Dielectric Properties of Two Novel 1D Chains Based on a T-Shaped Tripodal Ligand 4-(4,5-Dicarboxy-1H-imidazol-2-yl)pyridine Loxide.Chin.J.Struct.Chem.2016,35,1728-1735.
(18)Chen,L.Z.;Sun,J.;Ji,Q.;Pan,Q,J.;Huang.Y.Switchable Dielectric MaterialsBased on 2-Methylimidazole.Chin.J.Struct.Chem.2017,36,329-337.
(19)Sheldrick,G.M.SHELXS-97,Program for Crystal Structure Solution.University of G?ttingen,Germany 1997.
(20)Sheldrick,G.M.SHELXL-97,Program for Crystal Structure Refinement.University of G?ttingen,Germany 1997.