基于1,3,5-三嗪的具有力致变色性质的聚集诱导荧光化合物的合成及性能
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摘要
以1,3,5-三嗪为核,四苯基乙烯为端基,合成了两种新型的星状结构分子2,4,6-三(4-(1,2,2-三苯基乙烯基)苯基)-1,3,5-三嗪(TTPE-Tr)和2,4,6-三(4-(1,2,2-三苯基乙烯基)-4-联苯基)-1,3,5-三嗪(TTPE-Ph-Tr),并利用核磁共振(NMR)、离子化质谱(MALDI-MS)及元素分析等对其进行了结构表征.通过混合溶剂四氢呋喃(THF)/水析出实验显示,化合物TTPE-Tr和TTPE-Ph-Tr在纯THF溶剂中无荧光,而在THF/水混合溶剂中,当水体积分数增加时呈现荧光增强现象.通过紫外-可见(UV-Vis)光谱、荧光(PL)光谱、扫描电子显微镜(SEM)证实荧光量子效率的提高是由于分子内电子旋转受限(RIR)导致的.同时发现化合物TTPE-Tr具有力致变色性质,简单的研磨使其发光颜色(蓝绿光到黄绿光)及发光强度(ΦF,24.4%到14.7%)发生了明显的改变.UV-Vis光谱、PL光谱、X射线衍射(XRD)、荧光寿命和荧光量子效率等测试结果显示,这种现象是由于力刺激改变了TTPE-Tr的分子堆积形式导致的.热分析结果显示化合物TTPE-Tr和TTPE-Ph-Tr的热分解温度分别为464和385°C,具有良好的热稳定性.
Two star-shaped molecules consisting of a 1,3,5-triazine core with peripheral tetraphenylethylene moieties,2,4,6-tris(4-(1,2,2-triphenylvinyl)phenyl)-1,3,5-triazine(TTPE-Tr)and 2,4,6-tris(4-(1,2,2-triphenylvinyl)- [1,1-biphenyl]-4-yl)-1,3,5-triazine(TTPE-Ph-Tr),have been synthesized.These compounds were characterized by nuclear magnetic resonance spectroscopy(NMR),matrix assisted laser desorption/ionization-mass spectrometry(MALDI-MS)and elemental analysis.Both compounds exhibited aggregation-induced emission enhancement(AIEE)properties during addition of water to their tetrahydrofuran(THF)solutions. Results from UV-Vis spectroscopy,photoluminescence(PL)spectroscopy,and scanning electron microscopy(SEM)demonstrated that the restricted intra-molecular bond rotation(RIR)reduced non-radiative transitions in these compounds in the aggregated state,resulting in the fluorescence quantum yields(Φ F )increase.TTPE-Tr was also found to display mechanofluorochromic behavior.This compound,a blue-green powder(Φ F =24.4%,λ em =508 nm),exhibited relatively weak yellow/green emission(Φ F =14.7%,λ em =517 nm)upon grinding.The phase transition process responsible for this mechanochromism was confirmed by PL spectroscopy,X-ray diffraction(XRD)and time-resolved fluorescence spectroscopy. Thermal analysis of TTPE-Tr and TTPE-Ph-Tr showed that these compounds possess excellent thermal stability,with decomposition temperatures of 464 and 385°C,respectively.
Two star-shaped molecules consisting of a 1,3,5-triazine core with peripheral tetraphenylethylene moieties,2,4,6-tris(4-(1,2,2-triphenylvinyl)phenyl)-1,3,5-triazine(TTPE-Tr)and 2,4,6-tris(4-(1,2,2-triphenylvinyl)- [1,1-biphenyl]-4-yl)-1,3,5-triazine(TTPE-Ph-Tr),have been synthesized.These compounds were characterized by nuclear magnetic resonance spectroscopy(NMR),matrix assisted laser desorption/ionization-mass spectrometry(MALDI-MS)and elemental analysis.Both compounds exhibited aggregation-induced emission enhancement(AIEE)properties during addition of water to their tetrahydrofuran(THF)solutions. Results from UV-Vis spectroscopy,photoluminescence(PL)spectroscopy,and scanning electron microscopy(SEM)demonstrated that the restricted intra-molecular bond rotation(RIR)reduced non-radiative transitions in these compounds in the aggregated state,resulting in the fluorescence quantum yields(Φ F )increase.TTPE-Tr was also found to display mechanofluorochromic behavior.This compound,a blue-green powder(Φ F =24.4%,λ em =508 nm),exhibited relatively weak yellow/green emission(Φ F =14.7%,λ em =517 nm)upon grinding.The phase transition process responsible for this mechanochromism was confirmed by PL spectroscopy,X-ray diffraction(XRD)and time-resolved fluorescence spectroscopy. Thermal analysis of TTPE-Tr and TTPE-Ph-Tr showed that these compounds possess excellent thermal stability,with decomposition temperatures of 464 and 385°C,respectively.
引文
(1)Hong,Y.N.;Lam,J.W.Y.;Tang,B.Z.Chem.Commun.2009,4332.
(2)Fan,X.;Sun,J.L.;Wang,F.Z.;Chu,Z.Z.;Wang,P.;Dong,Y.Q.;Hu,R.;Tang,B.Z.;Zou,D.C.Chem.Commun.2008,2989.
(3)Xie,Z.Q.;Yang,B.;Li,F.;Cheng,G.;Liu,L.L.;Yang,G.D.;Xu,H.;Ye,L.;Hanif,M.;Liu,S.Y.;Ma,D.G.;Ma,Y.G.J.Am.Chem.Soc.2005,127,14152.doi:10.1021/ja054661d
(4)Würthner,F.;Sens,R.;Etzbach,K.H.;Seybold,G.Angew.Chem.Int.Edit.1999,38,1649.
(5)Oelkrug,D.;Tompert,A.;Gierschner,J.;Egelhaaf,H.J.;Hanack,M.;Hohloch,M.;Steinhuber,E.J.Phys.Chem.B1998,102,1902.doi:10.1021/jp973225d
(6)Xia,W.S.;Schmehl,R.H.;Li,C.J.Chem.Commun.2000,695.
(7)Tang,B.Z.;Zhan,X.W.;Yu,G.;Lee,P.;Liu,Y.Q.;Zhu,D.B.J.Mater.Chem.2001,11,2974.doi:10.1039/b102221k
(8)Luo,J.D.;Xie,Z.L.;Lam,J.W.Y.;Cheng,L.;Chen,H.Y.;Qiu,C.F.;Kwok,H.S.;Zhan,X.W.;Liu,Y.Q.;Zhu,D.B.;Tang,B.Z.Chem.Commun.2001,1740.
(9)An,B.K.;Kwon,S.K.;Park,S.Y.J.Am.Chem.Soc.2002,124,14410.doi:10.1021/ja0269082
(10)Chen,J.W.;Law,C.C.W.;Lam,J.W.Y.;Dong,Y.P.;Lo,S.M.F.;Williams,I.D.;Zhu,D.B.;Tang,B.Z.Chem.Mater.2003,15,1535.doi:10.1021/cm021715z
(11)Li,Z.;Dong,Y.Q.;Mi,B.X.;Tang,Y.H.;Hussler,M.;Tong,H.;Dong,Y.P.;Lam,J.W.Y.;Ren,Y.;Sung,H.H.Y.;Wong,K.S.;Gao,P.;Williams,I.D.;Kwok,H.S.;Tang,B.Z.J.Phys.Chem.B2005,109,10061.doi:10.1021/jp0503462
(12)Yu,W.;Li,Y.G.;Wang,T.Y.;Liu,M.H.;Li,Z.S.Acta Phys.-Chim.Sin.2008,24,1535.[于微,李远刚,王天宇,刘鸣华,李占双.物理化学学报,2008,24,1535.]doi:10.1016/S1872-1508(08)60062-5
(13)Liu,Y.;Deng,C.M.;Tang,L.;Qin,A.J.;Hu,R.R.;Sun,J.Z.;Tang,B.Z.J.Am.Chem.Soc.2011,133,660.doi:10.1021/ja107086y
(14)Zhao,Z.J.;Chen,S.M.;Shen,X.Y.;Mahtab,F.;Yu,Y.;Lu,P.;Lam,J.W.Y.;Kwok,H.S.;Tang,B.Z.Chem.Commun.2010,46,686.doi:10.1039/b915271g
(15)Zhao,Z.J.;Chen,S.M.;Lam,J.W.Y.;Lu,P.;Zhong,Y.C.;Wong,K.S.;Kwok,H.S.;Tang,B.Z.Chem.Commun.2010,46,2221.doi:10.1039/b921451h
(16)Cheng,K.H.;Zhong,Y.C.;Xie,B.Y.;Dong,Y.Q.;Hong,Y.N.;Sun,J.Z.;Tang,B.Z.;Wong,K.S.J.Phys.Chem.C2008,112,17507.doi:10.1021/jp805158b
(17)Zhang,Y.J.;Sun,J.W.;Bian,G.F.;Chen,Y.Y.;Ouyang,M.;Hu,B.;Zhang,C.Photochem.Photobiol.Sci.2012,11,1414.doi:10.1039/c2pp05404c.
(18)Jenekhe,S.A.;Osaheni,J.A.Science1994,265,765.doi:10.1126/science.265.5173.765
(19)Friend,R.H.;Gymer,R.W.;Holmes,A.B.;Burroughes,J.H.;Marks,R.N.;Talini,C.;Bradley,D.D.C.;Dos Santos,D.A.;Bredas,J.L.;Logdlund,M.;Salaneck,W.R.Nature1999,397,121.doi:10.1038/16393
(20)Li,Y.P.;Li,F.;Zhang,H.Y.;Xie,Z.Q.;Xie,W.J.;Xu,H.;Li,B.;Shen,F.Z.;Ye,L.;Hanif,M.;Ma,D.G.;Ma,Y.G.Chem.Commun.2007,231.
(21)Xie,Z.Q.;Yang,B.;Xie,W.J.;Liu,L.L.;Shen,F.Z.;Wang,H.;Yang,X.Y.;Wang,Z.M.;Li,Y.P.;Muddasir,H.;Yang,G.D.;Ye,L.;Ma,Y.G.J.Phys.Chem.B2006,110,20993.doi:10.1021/jp064069q
(22)Lwe,C.;Weder,C.Adv.Mater.2002,14,1625.doi:10.1002/1521-4095(20021118)14:22<1625::AID-ADMA1625>3.0.CO;2-Q
(23)Kunzelman,J.;Kinami,M.;Crenshaw,B.R.;Protasiewicz,J.D.;Weder,C.Adv.Mater.2008,20,119.
(24)Crenshaw,B.R.;Burnworth,M.;Khariwala,D.;Hiltner,A.;Mather,P.T.;Simha,R.;Weder,C.Macromolecules2007,40,2400.doi:10.1021/ma062936j
(25)Papaefstathiou,G.S.;Zhong,Z.;Geng,L.;MacGillivray,L.R.J.Am.Chem.Soc.2004,126,9158.doi:10.1021/ja047819n
(26)Ren,S.J.;Zeng,D.L.;Zhong,H.L.;Wang,Y.C.;Qian,S.X.;Fang,Q.J.Phys.Chem.B2010,114,10374.doi:10.1021/jp104710y
(27)Hu,B.;Ouyang,M.;Zhang Y.J.;Xiang,W.Q.;Zhang,C.Chem.J.Chin.Univ.2012,33,82.[胡彬,欧阳密,张玉建,项文勤,张诚.高等学校化学学报,2012,33,82.]
(28)Dong,Y.Q.;Lam,J.W.Y.;Qin,A.J.;Liu,J.Z.;Li,Z.;Tang,B.Z.Appl.Phys.Lett.2007,91,011111.doi:10.1063/1.2753723
(29)Zhang,X.Q.;Chi,Z.G.;Xu,B.J.;Zhou,W.;Zhang,Y.;Xu,J.R.Chem-Asian J.2011,6,808.doi:10.1002/asia.201000802
(2)Fan,X.;Sun,J.L.;Wang,F.Z.;Chu,Z.Z.;Wang,P.;Dong,Y.Q.;Hu,R.;Tang,B.Z.;Zou,D.C.Chem.Commun.2008,2989.
(3)Xie,Z.Q.;Yang,B.;Li,F.;Cheng,G.;Liu,L.L.;Yang,G.D.;Xu,H.;Ye,L.;Hanif,M.;Liu,S.Y.;Ma,D.G.;Ma,Y.G.J.Am.Chem.Soc.2005,127,14152.doi:10.1021/ja054661d
(4)Würthner,F.;Sens,R.;Etzbach,K.H.;Seybold,G.Angew.Chem.Int.Edit.1999,38,1649.
(5)Oelkrug,D.;Tompert,A.;Gierschner,J.;Egelhaaf,H.J.;Hanack,M.;Hohloch,M.;Steinhuber,E.J.Phys.Chem.B1998,102,1902.doi:10.1021/jp973225d
(6)Xia,W.S.;Schmehl,R.H.;Li,C.J.Chem.Commun.2000,695.
(7)Tang,B.Z.;Zhan,X.W.;Yu,G.;Lee,P.;Liu,Y.Q.;Zhu,D.B.J.Mater.Chem.2001,11,2974.doi:10.1039/b102221k
(8)Luo,J.D.;Xie,Z.L.;Lam,J.W.Y.;Cheng,L.;Chen,H.Y.;Qiu,C.F.;Kwok,H.S.;Zhan,X.W.;Liu,Y.Q.;Zhu,D.B.;Tang,B.Z.Chem.Commun.2001,1740.
(9)An,B.K.;Kwon,S.K.;Park,S.Y.J.Am.Chem.Soc.2002,124,14410.doi:10.1021/ja0269082
(10)Chen,J.W.;Law,C.C.W.;Lam,J.W.Y.;Dong,Y.P.;Lo,S.M.F.;Williams,I.D.;Zhu,D.B.;Tang,B.Z.Chem.Mater.2003,15,1535.doi:10.1021/cm021715z
(11)Li,Z.;Dong,Y.Q.;Mi,B.X.;Tang,Y.H.;Hussler,M.;Tong,H.;Dong,Y.P.;Lam,J.W.Y.;Ren,Y.;Sung,H.H.Y.;Wong,K.S.;Gao,P.;Williams,I.D.;Kwok,H.S.;Tang,B.Z.J.Phys.Chem.B2005,109,10061.doi:10.1021/jp0503462
(12)Yu,W.;Li,Y.G.;Wang,T.Y.;Liu,M.H.;Li,Z.S.Acta Phys.-Chim.Sin.2008,24,1535.[于微,李远刚,王天宇,刘鸣华,李占双.物理化学学报,2008,24,1535.]doi:10.1016/S1872-1508(08)60062-5
(13)Liu,Y.;Deng,C.M.;Tang,L.;Qin,A.J.;Hu,R.R.;Sun,J.Z.;Tang,B.Z.J.Am.Chem.Soc.2011,133,660.doi:10.1021/ja107086y
(14)Zhao,Z.J.;Chen,S.M.;Shen,X.Y.;Mahtab,F.;Yu,Y.;Lu,P.;Lam,J.W.Y.;Kwok,H.S.;Tang,B.Z.Chem.Commun.2010,46,686.doi:10.1039/b915271g
(15)Zhao,Z.J.;Chen,S.M.;Lam,J.W.Y.;Lu,P.;Zhong,Y.C.;Wong,K.S.;Kwok,H.S.;Tang,B.Z.Chem.Commun.2010,46,2221.doi:10.1039/b921451h
(16)Cheng,K.H.;Zhong,Y.C.;Xie,B.Y.;Dong,Y.Q.;Hong,Y.N.;Sun,J.Z.;Tang,B.Z.;Wong,K.S.J.Phys.Chem.C2008,112,17507.doi:10.1021/jp805158b
(17)Zhang,Y.J.;Sun,J.W.;Bian,G.F.;Chen,Y.Y.;Ouyang,M.;Hu,B.;Zhang,C.Photochem.Photobiol.Sci.2012,11,1414.doi:10.1039/c2pp05404c.
(18)Jenekhe,S.A.;Osaheni,J.A.Science1994,265,765.doi:10.1126/science.265.5173.765
(19)Friend,R.H.;Gymer,R.W.;Holmes,A.B.;Burroughes,J.H.;Marks,R.N.;Talini,C.;Bradley,D.D.C.;Dos Santos,D.A.;Bredas,J.L.;Logdlund,M.;Salaneck,W.R.Nature1999,397,121.doi:10.1038/16393
(20)Li,Y.P.;Li,F.;Zhang,H.Y.;Xie,Z.Q.;Xie,W.J.;Xu,H.;Li,B.;Shen,F.Z.;Ye,L.;Hanif,M.;Ma,D.G.;Ma,Y.G.Chem.Commun.2007,231.
(21)Xie,Z.Q.;Yang,B.;Xie,W.J.;Liu,L.L.;Shen,F.Z.;Wang,H.;Yang,X.Y.;Wang,Z.M.;Li,Y.P.;Muddasir,H.;Yang,G.D.;Ye,L.;Ma,Y.G.J.Phys.Chem.B2006,110,20993.doi:10.1021/jp064069q
(22)Lwe,C.;Weder,C.Adv.Mater.2002,14,1625.doi:10.1002/1521-4095(20021118)14:22<1625::AID-ADMA1625>3.0.CO;2-Q
(23)Kunzelman,J.;Kinami,M.;Crenshaw,B.R.;Protasiewicz,J.D.;Weder,C.Adv.Mater.2008,20,119.
(24)Crenshaw,B.R.;Burnworth,M.;Khariwala,D.;Hiltner,A.;Mather,P.T.;Simha,R.;Weder,C.Macromolecules2007,40,2400.doi:10.1021/ma062936j
(25)Papaefstathiou,G.S.;Zhong,Z.;Geng,L.;MacGillivray,L.R.J.Am.Chem.Soc.2004,126,9158.doi:10.1021/ja047819n
(26)Ren,S.J.;Zeng,D.L.;Zhong,H.L.;Wang,Y.C.;Qian,S.X.;Fang,Q.J.Phys.Chem.B2010,114,10374.doi:10.1021/jp104710y
(27)Hu,B.;Ouyang,M.;Zhang Y.J.;Xiang,W.Q.;Zhang,C.Chem.J.Chin.Univ.2012,33,82.[胡彬,欧阳密,张玉建,项文勤,张诚.高等学校化学学报,2012,33,82.]
(28)Dong,Y.Q.;Lam,J.W.Y.;Qin,A.J.;Liu,J.Z.;Li,Z.;Tang,B.Z.Appl.Phys.Lett.2007,91,011111.doi:10.1063/1.2753723
(29)Zhang,X.Q.;Chi,Z.G.;Xu,B.J.;Zhou,W.;Zhang,Y.;Xu,J.R.Chem-Asian J.2011,6,808.doi:10.1002/asia.201000802