Visible Light-induced Photoluminescence of a Zinc(Ⅱ) Complex of N-methyl-4,4-bipyridinium Cation
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摘要
Compounds with visible-light-induced photoluminescence are particularly attractive in acting as the emitting components of light-emitting diodes and fluorescent probes for biological applications. A new complex [Zn(NCS)_3(MQ)](MQ~+ = N-methyl-4,4?-bipyridinium) with an isolated molecular structure has been hydrothermally synthesized and characterized by single-crystal X-ray diffraction, elemental analysis, IR spectroscopy and solid-state photoluminescent determination. Crystal data: C_(14)H_(11)N_5S_3Zn, M_r = 410.83, monoclinic, space group P2_1/c, a = 8.809(5), b = 13.138(7), c = 15.580(9) ?, b = 104.433(10)°, V = 1746.2(17) ?~3, Z = 4, D–c = 1.563 g×cm~3, μ = 1.769 mm~(–1), F(000) = 832, the final R = 0.0376 and wR = 0.1243 for 2850 observed reflections with I > 2s(I). In the crystal structure, the zinc atom is tetrahedrally coordinated by one MQ+ ligand and three NCS– groups to yield a tetrahedral configuration. The bond length of Zn–NMQ is clearly shorter than those found in reported Zn(Ⅱ) complexes of 4,4?-bipy. The isolated units are joined by C–H···S interactions to generate a 2D hydrogen-bonding network. This compound displays visible light-induced photoluminescence, which originates from both intraligand charge-transfer of the MQ+ ligand and NCS~–→MQ~+ charge-transfer according to a density of states(DOS) calculation. Moreover, its emission band shows a clear blue shift compared with those of halide compounds.
Compounds with visible-light-induced photoluminescence are particularly attractive in acting as the emitting components of light-emitting diodes and fluorescent probes for biological applications. A new complex [Zn(NCS)_3(MQ)](MQ~+ = N-methyl-4,4?-bipyridinium) with an isolated molecular structure has been hydrothermally synthesized and characterized by single-crystal X-ray diffraction, elemental analysis, IR spectroscopy and solid-state photoluminescent determination. Crystal data: C_(14)H_(11)N_5S_3Zn, M_r = 410.83, monoclinic, space group P2_1/c, a = 8.809(5), b = 13.138(7), c = 15.580(9) ?, b = 104.433(10)°, V = 1746.2(17) ?~3, Z = 4, D–c = 1.563 g×cm~3, μ = 1.769 mm~(–1), F(000) = 832, the final R = 0.0376 and wR = 0.1243 for 2850 observed reflections with I > 2s(I). In the crystal structure, the zinc atom is tetrahedrally coordinated by one MQ+ ligand and three NCS– groups to yield a tetrahedral configuration. The bond length of Zn–NMQ is clearly shorter than those found in reported Zn(Ⅱ) complexes of 4,4?-bipy. The isolated units are joined by C–H···S interactions to generate a 2D hydrogen-bonding network. This compound displays visible light-induced photoluminescence, which originates from both intraligand charge-transfer of the MQ+ ligand and NCS~–→MQ~+ charge-transfer according to a density of states(DOS) calculation. Moreover, its emission band shows a clear blue shift compared with those of halide compounds.
Compounds with visible-light-induced photoluminescence are particularly attractive in acting as the emitting components of light-emitting diodes and fluorescent probes for biological applications. A new complex [Zn(NCS)_3(MQ)](MQ~+ = N-methyl-4,4?-bipyridinium) with an isolated molecular structure has been hydrothermally synthesized and characterized by single-crystal X-ray diffraction, elemental analysis, IR spectroscopy and solid-state photoluminescent determination. Crystal data: C_(14)H_(11)N_5S_3Zn, M_r = 410.83, monoclinic, space group P2_1/c, a = 8.809(5), b = 13.138(7), c = 15.580(9) ?, b = 104.433(10)°, V = 1746.2(17) ?~3, Z = 4, D–c = 1.563 g×cm~3, μ = 1.769 mm~(–1), F(000) = 832, the final R = 0.0376 and wR = 0.1243 for 2850 observed reflections with I > 2s(I). In the crystal structure, the zinc atom is tetrahedrally coordinated by one MQ+ ligand and three NCS– groups to yield a tetrahedral configuration. The bond length of Zn–NMQ is clearly shorter than those found in reported Zn(Ⅱ) complexes of 4,4?-bipy. The isolated units are joined by C–H···S interactions to generate a 2D hydrogen-bonding network. This compound displays visible light-induced photoluminescence, which originates from both intraligand charge-transfer of the MQ+ ligand and NCS~–→MQ~+ charge-transfer according to a density of states(DOS) calculation. Moreover, its emission band shows a clear blue shift compared with those of halide compounds.
引文
(1)(1)Zhao,C.C.;Ni,W.W.;Yu,M.M.;Cui,A.L.;Kou,H.Z.Hydrothermal synthesis of a 2-(2-pyridyl)imidazole derivative and its copper(II)and zinc(II)complexes.Trans.Met.Chem.2008,33,861-866.
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(5)Waldhr,E.;Kaim,W.;Olabe,J.A.;Slep,L.D.;Fiedler,J.The mpz+/mpz·pair as organic analogue of the NO+/NO·ligand redox system(mpz=N-methylpyrazinium).A combined electrochemical and spectroscopic study(UV/Vis/NIR,IR,EPR)of complexes[(mpz)M(CN)5]2-/3-(M=Fe,Ru,Os).Inorg.Chem.1997,36,2969-2974.
(6)Yang,C.;Wang,M.S.;Xu,Z.N.;Chen,F.;Liu,G.N.;Xu,G.;Guo,G.C.;Huang,J.S.Crystal structures and photoluminescence of the Zn(II)and Cd(II)complexes of N-methylpyrazinium obtained by a less hazardous approach.Inorg.Chem.Commun.2010,13,326-329.
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(9)Berger,S.;Klein,A.;Kaim,W.;Fiedler,J.Variable reduction sequences for axial(L)and chelate ligands(N∧N)in rhenium(I)complexes[(N∧N)Re(CO)3(L)]n.Inorg.Chem.1998,37,5664-5671.
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(11)Bates,W.D.;Chen,P.;Bignozzi,C.A.;Schoonover,J.R.;Meyer,T.J.Resonance Raman spectroscopy of ruthenium(II)and osmium(II)polypyridyl complexes containing the N-methyl-4,4?-bipyridinium radical(MQ·)as a ligand:evidence for a M(dπ).fwdarw.MQ·(π*)metal-to-ligand charge transfer(MLCT)transition.Inorg.Chem.1995,34,6215-6217.
(12)Lv,X.Y.;Wang,M.S.;Yang,C.;Wang,G.E.;Wang,S.H.;Lin,R.G.;Guo,G.C.Photochromic metal complexes of N-methyl-4,4′-bipyridinium:mechanism and influence of halogen atoms.Inorg.Chem.2012,51,4015-4019.
(13)Coe,B.J.;Chamberlain,M.C.;Essex-Lopresti,J.P.;Gaines,S.;Jeffery,J.C.;Houbrechts,S.;Persoons,A.Large molecular quadratic hyperpolarizabilities in donor/acceptor-substituted trans-tetraammineruthenium(II)complexes.Inorg.Chem.1997,36,3284-3292.
(14)Coe,B.J.;Harries,J.L.;Allelberghs,I.;Persoons,A.;Jeffery,J.C.;Rees,L.H.;Gelbrich,T.;Hursthouse,M.B.Tuning of charge-transfer absorption and molecular quadratic non-linear optical properties in ruthenium(II)ammine complexes.J.Chem.Soc.,Dalton Trans.1999,3617-3625.
(15)Coe,B.J.;Beyer,T.;Jeffery,J.C.;Coles,S.J.;Gelbrich,T.;Hursthouse,M.B.;Light,M.E.spectroscopic,electrochemical and structural study of polarizable,dipolar ruthenium(II)arsine complexes as models for chromophores with large quadratic non-linear optical response.J.Chem.Soc.,Dalton Trans.2000,797-803.
(16)Lu,W.;Chan,M.C.W.;Cheung,K.K.;Che,C.M.π-πInteractions in organometallic systems.Crystal structures and spectroscopic properties of luminescent mono-,bi-,and trinuclear trans-cyclometalated platinum(II)complexes derived from 2,6-diphenylpyridine.Organometallics 2001,20,2477-2486.
(17)Busby,M.;Liard,D.J.;Motevalli,M.;Toms,H.;Jr.A.V.Molecular structures of electron-transfer active complexes[Re(XQ+)(CO)3(NN)]2+(XQ+=N-Me-4,4?-bipyridinium or N-Ph-4,4?-bipyridinium;NN=bpy,4,4?-Me2-2,2?-bpy or N,N?-bis-isopropyl-1,4-diazabutadiene)in the solid state and solution:an X-ray and NOESY NMR study.Inorg.Chim.Acta 2004,357,167-176.
(18)Coe,B.J.;Harries,J.L.;Helliwell,M.;Jones,L.A.;Allelberghs,I.;Clays,K.;Brunschwig,B.S.;Harris,J.A.;Garín,J.;Ouduna,J.Pentacyanoiron(II)as an electron donor group for nonlinear optics:medium-responsive properties and comparisons with related pentaammineruthenium(II)complexes.J.Am.Chem.Soc.2006,128,12192-12204.
(19)Chen,W.T.;Liu,D.S.;Ying,S.M.;Chen,H.L.;Xu,Y.P.ZnCl3(4-methyl-4,4?-bipyridinium)with 4-methyl-4,4?-bipyridinium generated in situ:synthesis,structure and photoluminescence.Inorg.Chem.Commun.2008,11,1212-1214.
(20)Shen,Y.;Walters,K.A.;Abboud,K.;Schanze,K.S.Intramolecular charge transfer in pyridinium-substituted Ru-polypyridine complexes.Inorg.Chim.Acta 2000,300-302.
(21)Xie,R.J.;Hirosaki,N.;Sakuma,K.;Yamamoto,Y.;Mitomo,M.Eu2+-doped Ca-α-SiAlON:a yellow phosphor for white light-emitting diodes.Appl.Phys.Lett.2004,84,5404-5406.
(22)Qian,F.;Zhang,C.;Zhang,Y.;He,W.;Gao,X.;Hu,P.;Guo,Z.Visible light excitable Zn2+fluorescent sensor derived from an intramolecular charge transfer fluorophore and its in vitro and in vivo application.J.Am.Chem.Soc.2009,131,1460-1468.
(23)Yang,C.;Wang,M.S.;Cai,L.Z;Jiang,X.M.;Wu,M.F.;Guo,G.C.;Huang,J.S.Crystal structures and visible-light excited photoluminescence of N-methyl-4,4?-bipyridinium chloride and its Zn(II)and Cd(II)complexes.Inorg.Chem.Commun.2010,13,1021-1024.
(24)Rigaku.CrystalClear Version 1.3.5,Rigaku Corporation 2002.
(25)Siemens,SHELXTLTM Version 5 Reference Manual,Siemens Energy&Automation Inc.,Madison,Wisconsin,USA 1994.
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(28)Wang,M.S.;Guo,S.P.;Li,Y.;Cai,L.Z.;Zou,J.P.;Xu,G.;Zhou,W.W.;Zheng,F.K.;Guo,G.C.A direct white-light-emitting metal-organic framework with tunable yellow-to-white photoluminescence by variation of excitation light.J.Am.Chem.Soc.2009,131,13572-13573.
(29)Hamann,D.R.;Schluter,M.;Chiang,C.Norm-conserving pseudopotentials.Phys.Rev.Lett.1979,43,1494-1497.
(30)Sampanthar,J.T.;Vittal,J.J.Syntheses and crystal structures of the dimer[{Zn(SPh)2(bpy)}2(μ-bpy)]and two forms of the zigzag co-ordination polymer[{Zn(SPh)2(μ-bpy)}n](bpy=4,4?-bipyridyl).J.Chem.Soc.,Dalton Trans.1999,1993-1998.
(31)Lian,Z.X.;Cai,J.;Chen,C.H.A series of metal-organic frameworks constructed with arenesulfonates and 4,4?-bipy ligands.Polyhedron 2007,26,2647-2654.
(32)Aoki,K.;Yamazaki,H.;Adeyemo,A.Metal ion interactions with vitamin B1.Crystal structures of Zn(thiamine)(SCN)3 having a metal-base bond and Cd(thiamine)(SCN)3 having a metal-hydroxyethyl bond.Inorg.Chim.Acta 1991,180,117-124.
(33)Lee,S.H.;Kim,S.H.;Kim,P.G.;Kim,C.;Kim,Y.Bis(2,6-dimethylpyrazine-κN4)diiodidozinc(II).Acta Crystallogr.E 2008,64,511.
(34)Bhosekar,G.;Je?,I.;Lehnert,N.;N?ther,C.Synthesis,crystal structure and thermal reactivity of[ZnX2(2-chloropyrazine)](X=Cl,Br,I)coordination compounds.Eur.J.Inorg.Chem.2008,605-611.
(2)Geoffroy,L.G.Topics in stereochemistry:topics in inorganic and organometallic stereochemistry.Top.Stereochem.1981,12,155-215.
(3)McCleverty,J.A.Chemistry of nitric oxide relevant to biology.Chem.Rev.2004,104,403-418.
(4)Kaim,W.;Matheis,W.Kopplung zwischen polypyridinruthenium(II)-und methylviologen-einheiten inπ-konjugierten hybridsystemen.Chem.Ber.1990,123,1323-1325.
(5)Waldhr,E.;Kaim,W.;Olabe,J.A.;Slep,L.D.;Fiedler,J.The mpz+/mpz·pair as organic analogue of the NO+/NO·ligand redox system(mpz=N-methylpyrazinium).A combined electrochemical and spectroscopic study(UV/Vis/NIR,IR,EPR)of complexes[(mpz)M(CN)5]2-/3-(M=Fe,Ru,Os).Inorg.Chem.1997,36,2969-2974.
(6)Yang,C.;Wang,M.S.;Xu,Z.N.;Chen,F.;Liu,G.N.;Xu,G.;Guo,G.C.;Huang,J.S.Crystal structures and photoluminescence of the Zn(II)and Cd(II)complexes of N-methylpyrazinium obtained by a less hazardous approach.Inorg.Chem.Commun.2010,13,326-329.
(7)Coe,B.J.;Harris,J.A.;Asselberghs,I.;Persoons,A.;Jeffery,J.C.;Rees,L.H.;Gelbrich,T.;Hursthouse,M.B.Tuning of charge-transfer absorption and molecular quadratic non-linear optical properties in ruthenium(II)ammine complexes.J.Chem.Soc.,Dalton Trans.1999,3617-3625.
(8)Abe,M.;Sasaki,Y.;Yamada,Y.;Tsukahara,K.;Yano,S.;Yamaguchi,T.;Tominaga,M.;Taniguchi,I.;Ito,T.Oxo-centered mixed-ligand triruthenium complexes having redox-active N-methyl-4,4?-bipyridinium ions(mbpy+).Reversible multistep electrochemical properties of[RuIII2RuII(μ3-O)(μ-CH3CO2)6(mbpy+)2(CO)]2+and[RuIII3(μ3-O)(μ-CH3CO2)6(mbpy+)2(L)]3+(L=H2O and N-heterocyclic ligands).Inorg.Chem.1996,35,6724-6734.
(9)Berger,S.;Klein,A.;Kaim,W.;Fiedler,J.Variable reduction sequences for axial(L)and chelate ligands(N∧N)in rhenium(I)complexes[(N∧N)Re(CO)3(L)]n.Inorg.Chem.1998,37,5664-5671.
(10)Schoonover,J.R.;Chen,P.;Bates,W.D.;Dyer,R.B.;Meyer,T.J.Application of transient resonance Raman spectroscopy to the structure of a photoinduced electron-transfer intermediate.Inorg.Chem.1994,33,793-797.
(11)Bates,W.D.;Chen,P.;Bignozzi,C.A.;Schoonover,J.R.;Meyer,T.J.Resonance Raman spectroscopy of ruthenium(II)and osmium(II)polypyridyl complexes containing the N-methyl-4,4?-bipyridinium radical(MQ·)as a ligand:evidence for a M(dπ).fwdarw.MQ·(π*)metal-to-ligand charge transfer(MLCT)transition.Inorg.Chem.1995,34,6215-6217.
(12)Lv,X.Y.;Wang,M.S.;Yang,C.;Wang,G.E.;Wang,S.H.;Lin,R.G.;Guo,G.C.Photochromic metal complexes of N-methyl-4,4′-bipyridinium:mechanism and influence of halogen atoms.Inorg.Chem.2012,51,4015-4019.
(13)Coe,B.J.;Chamberlain,M.C.;Essex-Lopresti,J.P.;Gaines,S.;Jeffery,J.C.;Houbrechts,S.;Persoons,A.Large molecular quadratic hyperpolarizabilities in donor/acceptor-substituted trans-tetraammineruthenium(II)complexes.Inorg.Chem.1997,36,3284-3292.
(14)Coe,B.J.;Harries,J.L.;Allelberghs,I.;Persoons,A.;Jeffery,J.C.;Rees,L.H.;Gelbrich,T.;Hursthouse,M.B.Tuning of charge-transfer absorption and molecular quadratic non-linear optical properties in ruthenium(II)ammine complexes.J.Chem.Soc.,Dalton Trans.1999,3617-3625.
(15)Coe,B.J.;Beyer,T.;Jeffery,J.C.;Coles,S.J.;Gelbrich,T.;Hursthouse,M.B.;Light,M.E.spectroscopic,electrochemical and structural study of polarizable,dipolar ruthenium(II)arsine complexes as models for chromophores with large quadratic non-linear optical response.J.Chem.Soc.,Dalton Trans.2000,797-803.
(16)Lu,W.;Chan,M.C.W.;Cheung,K.K.;Che,C.M.π-πInteractions in organometallic systems.Crystal structures and spectroscopic properties of luminescent mono-,bi-,and trinuclear trans-cyclometalated platinum(II)complexes derived from 2,6-diphenylpyridine.Organometallics 2001,20,2477-2486.
(17)Busby,M.;Liard,D.J.;Motevalli,M.;Toms,H.;Jr.A.V.Molecular structures of electron-transfer active complexes[Re(XQ+)(CO)3(NN)]2+(XQ+=N-Me-4,4?-bipyridinium or N-Ph-4,4?-bipyridinium;NN=bpy,4,4?-Me2-2,2?-bpy or N,N?-bis-isopropyl-1,4-diazabutadiene)in the solid state and solution:an X-ray and NOESY NMR study.Inorg.Chim.Acta 2004,357,167-176.
(18)Coe,B.J.;Harries,J.L.;Helliwell,M.;Jones,L.A.;Allelberghs,I.;Clays,K.;Brunschwig,B.S.;Harris,J.A.;Garín,J.;Ouduna,J.Pentacyanoiron(II)as an electron donor group for nonlinear optics:medium-responsive properties and comparisons with related pentaammineruthenium(II)complexes.J.Am.Chem.Soc.2006,128,12192-12204.
(19)Chen,W.T.;Liu,D.S.;Ying,S.M.;Chen,H.L.;Xu,Y.P.ZnCl3(4-methyl-4,4?-bipyridinium)with 4-methyl-4,4?-bipyridinium generated in situ:synthesis,structure and photoluminescence.Inorg.Chem.Commun.2008,11,1212-1214.
(20)Shen,Y.;Walters,K.A.;Abboud,K.;Schanze,K.S.Intramolecular charge transfer in pyridinium-substituted Ru-polypyridine complexes.Inorg.Chim.Acta 2000,300-302.
(21)Xie,R.J.;Hirosaki,N.;Sakuma,K.;Yamamoto,Y.;Mitomo,M.Eu2+-doped Ca-α-SiAlON:a yellow phosphor for white light-emitting diodes.Appl.Phys.Lett.2004,84,5404-5406.
(22)Qian,F.;Zhang,C.;Zhang,Y.;He,W.;Gao,X.;Hu,P.;Guo,Z.Visible light excitable Zn2+fluorescent sensor derived from an intramolecular charge transfer fluorophore and its in vitro and in vivo application.J.Am.Chem.Soc.2009,131,1460-1468.
(23)Yang,C.;Wang,M.S.;Cai,L.Z;Jiang,X.M.;Wu,M.F.;Guo,G.C.;Huang,J.S.Crystal structures and visible-light excited photoluminescence of N-methyl-4,4?-bipyridinium chloride and its Zn(II)and Cd(II)complexes.Inorg.Chem.Commun.2010,13,1021-1024.
(24)Rigaku.CrystalClear Version 1.3.5,Rigaku Corporation 2002.
(25)Siemens,SHELXTLTM Version 5 Reference Manual,Siemens Energy&Automation Inc.,Madison,Wisconsin,USA 1994.
(26)Segall,M.;Linda,P.;Probert,M.;Pickard,C.;Hasnip,P.;Clark,S.;Payne,M.Materials Studio CASTEP,Version 2.2 Accelrys:San Diego,CA2002.
(27)Segall,M.;Linda,P.;Probert,M.;Pickard,C.;Hasnip,P.;Clark,S.;Payne,M.First-principles simulation:ideas,illustrations and the CASTEPcode.J.Phys.:Condens.Matter 2002,14,2717-2744.
(28)Wang,M.S.;Guo,S.P.;Li,Y.;Cai,L.Z.;Zou,J.P.;Xu,G.;Zhou,W.W.;Zheng,F.K.;Guo,G.C.A direct white-light-emitting metal-organic framework with tunable yellow-to-white photoluminescence by variation of excitation light.J.Am.Chem.Soc.2009,131,13572-13573.
(29)Hamann,D.R.;Schluter,M.;Chiang,C.Norm-conserving pseudopotentials.Phys.Rev.Lett.1979,43,1494-1497.
(30)Sampanthar,J.T.;Vittal,J.J.Syntheses and crystal structures of the dimer[{Zn(SPh)2(bpy)}2(μ-bpy)]and two forms of the zigzag co-ordination polymer[{Zn(SPh)2(μ-bpy)}n](bpy=4,4?-bipyridyl).J.Chem.Soc.,Dalton Trans.1999,1993-1998.
(31)Lian,Z.X.;Cai,J.;Chen,C.H.A series of metal-organic frameworks constructed with arenesulfonates and 4,4?-bipy ligands.Polyhedron 2007,26,2647-2654.
(32)Aoki,K.;Yamazaki,H.;Adeyemo,A.Metal ion interactions with vitamin B1.Crystal structures of Zn(thiamine)(SCN)3 having a metal-base bond and Cd(thiamine)(SCN)3 having a metal-hydroxyethyl bond.Inorg.Chim.Acta 1991,180,117-124.
(33)Lee,S.H.;Kim,S.H.;Kim,P.G.;Kim,C.;Kim,Y.Bis(2,6-dimethylpyrazine-κN4)diiodidozinc(II).Acta Crystallogr.E 2008,64,511.
(34)Bhosekar,G.;Je?,I.;Lehnert,N.;N?ther,C.Synthesis,crystal structure and thermal reactivity of[ZnX2(2-chloropyrazine)](X=Cl,Br,I)coordination compounds.Eur.J.Inorg.Chem.2008,605-611.