Crystal Structure, One-and Two-photon Excited Fluorescence and Bioimaging of a D-π-A Structural Triphenylamine Derivative
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摘要
An electron donor-π-bridge-electron acceptor(D-π-A) optical functional organic compound comprising a triphenylamine moiety as the electron donor and pyridine moiety as the electron acceptor was synthesized. The structure of the compound was solved by single-crystal X-ray diffraction analysis. It crystallizes in monoclinic, space group P21, with a = 9.753(5), b = 8.815(5), c = 25.554(5) ?, β = 96.315(5)°, V = 2184(2) ?~3, Z = 2, D_c = 1.136 g/m~3, F(000) = 792, Μr = 746.92, μ = 0.069 mm~(-1), the final R = 0.0658 and wR = 0.1730 for 6790 observed reflections with I > 2(I). Study of nonlinear optical properties shows that the compound exhibits excellent two-photon excited fluorescence with the two-photon absorption cross-section value of 116 GM. The structure-property relationship was researched in detail through X-ray crystallography and quantum chemical calculation. Result of living cell imaging experiment shows its potential in fluorescence microscopy bioimaging.
An electron donor-π-bridge-electron acceptor(D-π-A) optical functional organic compound comprising a triphenylamine moiety as the electron donor and pyridine moiety as the electron acceptor was synthesized. The structure of the compound was solved by single-crystal X-ray diffraction analysis. It crystallizes in monoclinic, space group P21, with a = 9.753(5), b = 8.815(5), c = 25.554(5) ?, β = 96.315(5)°, V = 2184(2) ?~3, Z = 2, D_c = 1.136 g/m~3, F(000) = 792, Μr = 746.92, μ = 0.069 mm~(-1), the final R = 0.0658 and wR = 0.1730 for 6790 observed reflections with I > 2(I). Study of nonlinear optical properties shows that the compound exhibits excellent two-photon excited fluorescence with the two-photon absorption cross-section value of 116 GM. The structure-property relationship was researched in detail through X-ray crystallography and quantum chemical calculation. Result of living cell imaging experiment shows its potential in fluorescence microscopy bioimaging.
An electron donor-π-bridge-electron acceptor(D-π-A) optical functional organic compound comprising a triphenylamine moiety as the electron donor and pyridine moiety as the electron acceptor was synthesized. The structure of the compound was solved by single-crystal X-ray diffraction analysis. It crystallizes in monoclinic, space group P21, with a = 9.753(5), b = 8.815(5), c = 25.554(5) ?, β = 96.315(5)°, V = 2184(2) ?~3, Z = 2, D_c = 1.136 g/m~3, F(000) = 792, Μr = 746.92, μ = 0.069 mm~(-1), the final R = 0.0658 and wR = 0.1730 for 6790 observed reflections with I > 2(I). Study of nonlinear optical properties shows that the compound exhibits excellent two-photon excited fluorescence with the two-photon absorption cross-section value of 116 GM. The structure-property relationship was researched in detail through X-ray crystallography and quantum chemical calculation. Result of living cell imaging experiment shows its potential in fluorescence microscopy bioimaging.
引文
(1)Denk,W.;Strickler,J.H.;Webb,W.W.Two-photon laser scanning fluorescence microscopy.Science 1990,248,73-76.
(2)Jin,F.;Xu,D.L.;Zhou,H.P.;Wu,J.Y.;Tian,Y.P.New conjugated organic dyes with various electron donors:one-and two-photon excited fluorescence,and bioimaging.Dyes.Pigm.2014,109,42-53.
(3)Liu,X.;Sun,Y.M.;Zhang,Y.H.;Miao,F.;Wang,G.C.;Wong,W.Y.A 2,7-carbazole-based dicationic salt for fluorescence detection of nucleic acids and two-photon fluorescence imaging of RNA in nucleoli and cytoplasm.Org.Biomol.Chem.2011,9,3615-3618.
(4)Jin,F.;Rong,Z.K.;Guo,X.J.;Ma,M.Y.;Lv,J.J.;Zhang,L.;Liao,R.B.;Liu,Y.;Tao,D.L.;Tian,Y.P.Novel D-π-A-π-D structural2,2′-bipyridine derivatives with different electron donors:structure,one-and two-photon excited fluorescence and bioimaging.Dyes.Pigm.2018,150,174-180.
(5)Chen,S.Y.;Zhao,M.;Su,J.;Zhang,Q.;Tian,X.H.;Li,S.L.;Zhou,H.P.;Wu,J.Y.;Tian,Y.P.Two novel two-photon excited fluorescent pHprobes based on the A-π-D-π-A system for intracellular pH mapping.Dyes.Pigm.2017,136,807-816.
(6)Qian,L.H.;Li,L.;Yao,S.Q.Two-photon small molecule enzymetic probes.Acc.Chem.Res.2016,49,626-634.
(7)Li,L.;Zhang,C.W.;Chen,G.Y.J.;Zhu,B.;Chai,C.;Xu,Q.H.;Tan,E.K.;Zhu,Q.;Lim,K.L.;Yao,S.Q.A sensitive two-photon probe to selectively detect monoamine oxidase B activity in parkinson’s disease models.Nat.Commun.2014,5,3276-3285.
(8)Li,L.;Zhang,C.W.;Ge,J.;Qian,L.;Chai,B.H.;Zhu,Q.;Lee,J.S.;Lim,K.L.;Yao,S.Q.A small-molecule probe for selective profiling and imaging of monoamine oxidase B activities in models of parkinson’s disease.Angew.Chem.Int.Ed.2015,54,10821-10825.
(9)Huang,Y.;Qiu,F.;Shen,L.Y.;Chen,D.;Su,Y.;Yan,D.Y.Combining two-photon-activated fluorescence resonance energy transfer and near-infrared photothermal effect of unimolecular micelles for enhanced photodynamic therapy.ACS Nano.2016,10,10489-10499.
(10)Dvornikov,A.;Walker,E.;Rentzepis,P.Two-photon three-dimensional optical storage memory.J.Phys.Chem.A 2009,113,13633-13644.
(11)Kannan,R.;He,G.S.;Yuan,L.X.;Xu,F.M.;Prasad,P.N.;Dombroskie,A.G.;Reinhardt,B.A.;Baur,J.W.;Vaia,R.A.;Tan,L.S.Diphenylaminofluorene-based two-photon-absorbing chromophores with variousπ-electron acceptors.Chem.Mater.2001,13,1896-1904.
(12)Jin,F.;Pan,C.Y.;Zhang,W.X.;Sun,L.;Hu,X.Y.;Liao,R.B.;Tao,D.L.Enhanced two-photon excited fluorescence of mercury complexes with a conjugated ligand:effect of the central metal ion.J.Lumin.2016,172,264-269.
(13)Jin,F.;Shu,W.C.;Yu,X.P.;Zhang,Y.;Sun,L.;Liu,Y.;Zhou,H.P.;Tao,D.L.;Tian,Y.P.Crystal structures,two-photon excited fluorescence and bioimaging of Zn(II)complexes based on an extended 2,2'-bipyridine ligand.Dyes.Pigm.2015,121,379-384.
(14)Li,D.D.;Sun,X.S.;Wang,M.M.;Yu,H.;Zhou,H.P.;Wu,J.Y.;Tian,Y.P.Novel colorimetric detection probe for copper(II)ions based on triphenylamine mixed-valence chromophores bearing prodigious two-photon absorption activity.Sens.Actuators B 2015,220,1006-1016.
(15)Jin,F.;Lu,T.Q.;Wang,P.;Rong,Z.K.;Wu,X.Q.;Qiao,L.Y.;Liu,Y.;Liao,R.B.;Tao,D.L.Crystal structures,two-photon excited fluorescence and bioimaging of Zn(II)complexes based on D-π-A structural triphenylamine derivative.J.Lumin.2017,192,1127-1132.
(16)Gao,Y.H.;Wu,J.Y.;Zhou,H.P.;Yang,J.X.;Jin,B.K.;Tian,Y.P.A sulfur-terminal Zn(II)complex and its two-photon microscopy biological imaging application.J.Am.Chem.Soc.2009,131,5208-5213.
(17)Wang,H.;Tian,X.H.;Du,W.;Zhang,Q.;Guan,L.J.;Wu,J.Y.;Tian,Y.P.A two-photon fluorescent RNA probe screened from a series of oxime-functionalized 2,2?:6?,2??-terpyridine ZnX2(X=Cl,Br,I)complexes.J.Mater.Chem.B 2016,4,4818-4825.
(18)Liu,J.;Zhu,Y.Z.;Tian,X.H.;Li,F.;Wu,J.Y.;Tian,Y.P.Synthesis,crystal structures of a series of novel 2,2?:6?,2??-terpyridine derivatives:the influences of substituents on their photophysical properties and intracellular acid organelle targeting.Dyes.Pigm.2016,128,149-157.
(19)Xu,C.;Webb,W.W.Measurement of two-photon excitation cross sections of molecular fluorophores with data from 690 to 1050 nm.J.Opt.Soc.Am.B 1996,13,481-91.
(20)Sheldrick,G.M.SHELXS-97 and SHELXL-97.Programs for Solution and Refinement of Crystal Structure.University of G?ttingen,Germany1997.
(21)Frisch,M.J.;Trucks,G.W.;Schlegel,H.B.;Scuseria,G.E.;Robb,M.A.;Cheeseman,J.R.;Scalmani,G.;Barone,V.;Mennucci,B.;Petersson,G.A.;Nakatsuji,H.;Caricato,M.;Li,X.;Hratchian,H.P.;Izmaylov,A.F.;Bloino,J.;Zheng,G.;Sonnenberg,J.L.;Hada,M.;Ehara,M.;Toyota,K.;Fukuda,R.;Hasegawa,J.;Ishida,M.;Nakajima,T.;Honda,Y.;Kitao,O.;Nakai,H.;Vreven,T.;Montgomery,J.A.Jr.;Peralta,J.E.;Ogliaro,F.;Bearpark,M.;Heyd,J.J.;Brothers,E.;Kudin,K.N.;Staroverov,V.N.;Kobayashi,R.;Normand,J.;Raghavachari,K.;Rendell,A.;Burant,J.C.;Iyengar,S.S.;Tomasi,J.;Cossi,M.;Rega,N.;Millam,J.M.;Klene,M.;Knox,J.E.;Cross,J.B.;Bakken,V.;Adamo,C.;Jaramillo,J.;Gomperts,R.;Stratmann,R.E.;Yazyev,O.;Austin,A.J.;Cammi,R.;Pomelli,C.;Ochterski,J.W.;Martin,R.L.;Morokuma,K.;Zakrzewski,V.G.;Voth,G.A.;Salvador,P.;Dannenberg,J.J.;Dapprich,S.;Daniels,A.D.;Farkas,?.;Foresman,J.B.;Ortiz,J.V.;Cioslowski,J.;Fox,D.J.Gaussian 09,Revision A.02.Gaussian,Inc.Pittsburgh 2009.
(22)Jin,F.;Hao,F.Y.;Ma,J.L.;Wu,J.Y.;Tian,Y.P.Synthesis,crystal structure and spectral properties of a novel Co(II)complex containing imidazole derivative.Chin.J.Struct.Chem.2006,25,1303-1308.
(23)Zheng,Z.;Zhang,Q.;Yu,Z.P.;Yang,M.D.;Zhou,H.P.;Wu,J.Y.;Tian,Y.P.Four new two-photon absorbing imidazo[4,5-f]1,10-phenanthroline dye derivatives with different dipole moment orientation based on different groups:synthesis,optical characterization and bioimaging.J.Mater.Chem.C 2013,1,822-830.
(24)Xu,C.;Zipfel,W.;Shear,J.B.;Williams,R.M.;Webb,W.W.Multiphoton fluorescence excitation:new spectral windows for biological nonlinear microscopy.Proc.Natl.Acad.Sci.USA 1996,93,10763-10768.
(2)Jin,F.;Xu,D.L.;Zhou,H.P.;Wu,J.Y.;Tian,Y.P.New conjugated organic dyes with various electron donors:one-and two-photon excited fluorescence,and bioimaging.Dyes.Pigm.2014,109,42-53.
(3)Liu,X.;Sun,Y.M.;Zhang,Y.H.;Miao,F.;Wang,G.C.;Wong,W.Y.A 2,7-carbazole-based dicationic salt for fluorescence detection of nucleic acids and two-photon fluorescence imaging of RNA in nucleoli and cytoplasm.Org.Biomol.Chem.2011,9,3615-3618.
(4)Jin,F.;Rong,Z.K.;Guo,X.J.;Ma,M.Y.;Lv,J.J.;Zhang,L.;Liao,R.B.;Liu,Y.;Tao,D.L.;Tian,Y.P.Novel D-π-A-π-D structural2,2′-bipyridine derivatives with different electron donors:structure,one-and two-photon excited fluorescence and bioimaging.Dyes.Pigm.2018,150,174-180.
(5)Chen,S.Y.;Zhao,M.;Su,J.;Zhang,Q.;Tian,X.H.;Li,S.L.;Zhou,H.P.;Wu,J.Y.;Tian,Y.P.Two novel two-photon excited fluorescent pHprobes based on the A-π-D-π-A system for intracellular pH mapping.Dyes.Pigm.2017,136,807-816.
(6)Qian,L.H.;Li,L.;Yao,S.Q.Two-photon small molecule enzymetic probes.Acc.Chem.Res.2016,49,626-634.
(7)Li,L.;Zhang,C.W.;Chen,G.Y.J.;Zhu,B.;Chai,C.;Xu,Q.H.;Tan,E.K.;Zhu,Q.;Lim,K.L.;Yao,S.Q.A sensitive two-photon probe to selectively detect monoamine oxidase B activity in parkinson’s disease models.Nat.Commun.2014,5,3276-3285.
(8)Li,L.;Zhang,C.W.;Ge,J.;Qian,L.;Chai,B.H.;Zhu,Q.;Lee,J.S.;Lim,K.L.;Yao,S.Q.A small-molecule probe for selective profiling and imaging of monoamine oxidase B activities in models of parkinson’s disease.Angew.Chem.Int.Ed.2015,54,10821-10825.
(9)Huang,Y.;Qiu,F.;Shen,L.Y.;Chen,D.;Su,Y.;Yan,D.Y.Combining two-photon-activated fluorescence resonance energy transfer and near-infrared photothermal effect of unimolecular micelles for enhanced photodynamic therapy.ACS Nano.2016,10,10489-10499.
(10)Dvornikov,A.;Walker,E.;Rentzepis,P.Two-photon three-dimensional optical storage memory.J.Phys.Chem.A 2009,113,13633-13644.
(11)Kannan,R.;He,G.S.;Yuan,L.X.;Xu,F.M.;Prasad,P.N.;Dombroskie,A.G.;Reinhardt,B.A.;Baur,J.W.;Vaia,R.A.;Tan,L.S.Diphenylaminofluorene-based two-photon-absorbing chromophores with variousπ-electron acceptors.Chem.Mater.2001,13,1896-1904.
(12)Jin,F.;Pan,C.Y.;Zhang,W.X.;Sun,L.;Hu,X.Y.;Liao,R.B.;Tao,D.L.Enhanced two-photon excited fluorescence of mercury complexes with a conjugated ligand:effect of the central metal ion.J.Lumin.2016,172,264-269.
(13)Jin,F.;Shu,W.C.;Yu,X.P.;Zhang,Y.;Sun,L.;Liu,Y.;Zhou,H.P.;Tao,D.L.;Tian,Y.P.Crystal structures,two-photon excited fluorescence and bioimaging of Zn(II)complexes based on an extended 2,2'-bipyridine ligand.Dyes.Pigm.2015,121,379-384.
(14)Li,D.D.;Sun,X.S.;Wang,M.M.;Yu,H.;Zhou,H.P.;Wu,J.Y.;Tian,Y.P.Novel colorimetric detection probe for copper(II)ions based on triphenylamine mixed-valence chromophores bearing prodigious two-photon absorption activity.Sens.Actuators B 2015,220,1006-1016.
(15)Jin,F.;Lu,T.Q.;Wang,P.;Rong,Z.K.;Wu,X.Q.;Qiao,L.Y.;Liu,Y.;Liao,R.B.;Tao,D.L.Crystal structures,two-photon excited fluorescence and bioimaging of Zn(II)complexes based on D-π-A structural triphenylamine derivative.J.Lumin.2017,192,1127-1132.
(16)Gao,Y.H.;Wu,J.Y.;Zhou,H.P.;Yang,J.X.;Jin,B.K.;Tian,Y.P.A sulfur-terminal Zn(II)complex and its two-photon microscopy biological imaging application.J.Am.Chem.Soc.2009,131,5208-5213.
(17)Wang,H.;Tian,X.H.;Du,W.;Zhang,Q.;Guan,L.J.;Wu,J.Y.;Tian,Y.P.A two-photon fluorescent RNA probe screened from a series of oxime-functionalized 2,2?:6?,2??-terpyridine ZnX2(X=Cl,Br,I)complexes.J.Mater.Chem.B 2016,4,4818-4825.
(18)Liu,J.;Zhu,Y.Z.;Tian,X.H.;Li,F.;Wu,J.Y.;Tian,Y.P.Synthesis,crystal structures of a series of novel 2,2?:6?,2??-terpyridine derivatives:the influences of substituents on their photophysical properties and intracellular acid organelle targeting.Dyes.Pigm.2016,128,149-157.
(19)Xu,C.;Webb,W.W.Measurement of two-photon excitation cross sections of molecular fluorophores with data from 690 to 1050 nm.J.Opt.Soc.Am.B 1996,13,481-91.
(20)Sheldrick,G.M.SHELXS-97 and SHELXL-97.Programs for Solution and Refinement of Crystal Structure.University of G?ttingen,Germany1997.
(21)Frisch,M.J.;Trucks,G.W.;Schlegel,H.B.;Scuseria,G.E.;Robb,M.A.;Cheeseman,J.R.;Scalmani,G.;Barone,V.;Mennucci,B.;Petersson,G.A.;Nakatsuji,H.;Caricato,M.;Li,X.;Hratchian,H.P.;Izmaylov,A.F.;Bloino,J.;Zheng,G.;Sonnenberg,J.L.;Hada,M.;Ehara,M.;Toyota,K.;Fukuda,R.;Hasegawa,J.;Ishida,M.;Nakajima,T.;Honda,Y.;Kitao,O.;Nakai,H.;Vreven,T.;Montgomery,J.A.Jr.;Peralta,J.E.;Ogliaro,F.;Bearpark,M.;Heyd,J.J.;Brothers,E.;Kudin,K.N.;Staroverov,V.N.;Kobayashi,R.;Normand,J.;Raghavachari,K.;Rendell,A.;Burant,J.C.;Iyengar,S.S.;Tomasi,J.;Cossi,M.;Rega,N.;Millam,J.M.;Klene,M.;Knox,J.E.;Cross,J.B.;Bakken,V.;Adamo,C.;Jaramillo,J.;Gomperts,R.;Stratmann,R.E.;Yazyev,O.;Austin,A.J.;Cammi,R.;Pomelli,C.;Ochterski,J.W.;Martin,R.L.;Morokuma,K.;Zakrzewski,V.G.;Voth,G.A.;Salvador,P.;Dannenberg,J.J.;Dapprich,S.;Daniels,A.D.;Farkas,?.;Foresman,J.B.;Ortiz,J.V.;Cioslowski,J.;Fox,D.J.Gaussian 09,Revision A.02.Gaussian,Inc.Pittsburgh 2009.
(22)Jin,F.;Hao,F.Y.;Ma,J.L.;Wu,J.Y.;Tian,Y.P.Synthesis,crystal structure and spectral properties of a novel Co(II)complex containing imidazole derivative.Chin.J.Struct.Chem.2006,25,1303-1308.
(23)Zheng,Z.;Zhang,Q.;Yu,Z.P.;Yang,M.D.;Zhou,H.P.;Wu,J.Y.;Tian,Y.P.Four new two-photon absorbing imidazo[4,5-f]1,10-phenanthroline dye derivatives with different dipole moment orientation based on different groups:synthesis,optical characterization and bioimaging.J.Mater.Chem.C 2013,1,822-830.
(24)Xu,C.;Zipfel,W.;Shear,J.B.;Williams,R.M.;Webb,W.W.Multiphoton fluorescence excitation:new spectral windows for biological nonlinear microscopy.Proc.Natl.Acad.Sci.USA 1996,93,10763-10768.