摘要
五芳基取代环戊二烯衍生物是一类具有聚集诱导荧光性质的化合物,但相应的研究比较少.为了研究不同推拉电子能力的取代基以及取代位置对聚集诱导荧光性质的影响和拓展其在化学传感器、生物探针等方面的应用,我们合成了不同芳香取代基的五芳基取代环戊二烯及其衍生物,并对其进行了紫外吸收、荧光光谱、荧光量子产率、单晶分析等方面的测试表征,重点研究了其聚集诱导荧光性质.
Pentaarylated cyclopentcyclodienes have aggregation-induced emission(AIE) characteristics and can be easily derivatized, but are rarely studied. In order to examine the effect of the electronic properties and the position of the substituents on AIE properties, an expedient method for the synthesis of a series of pentaarylated cyclopentadiene derivatives was developed, and their UV-Vis, fluorescence spectra, fluorescence quantum yields as well as the XRD structures of single crystals were investigated. The AIE properties of pentaarylated cyclopentadiene derivatives were studied in detail.
引文
[1]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.2001,18,1740.
[2]Mao,W.-G.;Chen,K.;Ouyang,M.;Sun,J.-W.;Zhou,Y.-B.;Wang,Y.-S.;Song,Q.-B.;Zhang,C.Chin.J.Org.Chem.2014,34,161(in Chinese).(毛文纲,陈康,欧阳密,孙璟玮,周永兵,王永胜,宋庆宝,张诚,有机化学,2014,34,161.)
[3]Guan,C.-F.;Qian,Y.Chin.J.Org.Chem.2014,34,537(in Chinese).(管成飞,钱鹰,有机化学,2014,34,537.)
[4]Birks,J.B.Rep.Prog.Phys.1975,38,903.
[5]Hong,Y.-N.;Lam,J.W.Y.;Tang,B.-Z.Chem.Soc.Rev.2011,40,5361.
[6]Mei,J.;Hong,Y.-N.;Lam,J.W.Y.;Qin,A.-J.;Tang,Y.-H.;Tang,B.-Z.Adv.Mater.2014,26,5429.
[7](a)Zhao,Z.-J.;Chan,C.Y.K.;Chen,S.-M.;Deng,C.-M.;Lam,J.W.Y.;Jim,C.K.W.;Hong,Y.-N.;Lu,P.;Chang,Z.-F.;Chen,X.-P.;Lu,P.;Kwok,H.-S.;Qiu,H.-Y.;Tang,B.-Z.J.Mater.Chem.2012,22,4527.(b)Huang,J.;Yang,X.;Wang,J.-Y.;Zhong,C.;Wang,L.;Qin,J.-G.;Li,Z.J.Mater.Chem.2012,22,2478.
[8](a)Mei,J.;Tong,J.-Q.;Wang,J.;Qin,A.-J.;Sun,J.-Z.;Tang,B.-Z.J.Mater.Chem.2012,22,17063.(b)Mei,J.;Wang,Y.-J.;Tong,J.-Q.;Wang,J.;Qin,A.-J.;Sun,J.-Z.;Tang,B.-Z.Chem.Eur.J.2013,19,612.(c)Anariba,F.;Chng,L.L.;Abdullah,N.S.;Tay,F.E.H.J.Mater.Chem.2012,22,19303.(d)Yu,Y.;Feng,C.;Hong,Y.-N.;Liu,J.-Z.;Chen,S.-J.;Ng,K.M.;Luo,K.-Q.;Tang,B.-Z.Adv.Mater.2011,23,3298.
[9]Li,H.-Y.;Zhang,X.-Q.;Zhang,X.-Y.;Yang,B.;Wei,Y.Colloids Surf.,B 2014,121,347.
[10]Chen,X.-J.;Shen,X.-Y.;Guan,E.-J.;Liu,Y.;Qin,A.-J.;Sun,J.-Z.;Tang,B.-Z.Chem.Commun.2013,49,1503.
[11](a)Franklin,A.;Chng,L.-L.;Nur,S.A.;Francis,T.J.Mater.Chem.2012,22,19303.(b)Tong,H.;Hong,Y.;Dong,Y.;Haeussler,M.;Li,Z.;Lam,J.W.Y.;Dong,Y.;Sung,H.H.Y.;Williams,I.D.;Tang,B.-Z.J.Phys.Chem.B.2007,111,11817.
[12]Chen,L.;Jiang,Y.-B.;Nie,H.;Lu,P.;Sung,H.-H.Y.;Williams,I.D.;Kwok,H.-S.;Huang,F.;Qin,A.-J.;Zhao,Z.-J.;Tang,B.-Z.Adv.Funct.Mater.2014,24,3621.
[13](a)Wang,M.;Zhang,D.-Q.;Zhang,G.-X.;Zhu,D.-B.Chem.Commun.2008,37,4469.(b)Huang,J.;Wang,M.;Zhou,Y.-Y.;Weng,X.-C.;Shuai,L.;Zhou,X.;Zhang,D.-Q.Bioorg.Med.Chem.2009,17,7743.(c)Liu,Z.-T.;Xue,W.-X.;Cai,Z.-X.;Zhang,G.-X.;Zhang,D.-Q.J.Mater.Chem.2011,21,14487.
[14]Tang,B.-Z.;Zhan,X.-W.;Yu,G.;Lee,P.P.S.;Liu,Y.-Q.;Zhu,D.-B.J.Mater.Chem.2001,11,2974.
[15]Yu,G.;Yin,S.-W.;Liu,Y.-Q.;Chen,J.-S.;Xu,X.-J.;Sun,X.-B.;Ma,D.-G.;Zhan,X.-W.;Peng,Q.;Shuai,Z.-G.;Tang,B.-Z.;Zhu,D.-B.;Fang,W.-H.;Luo,Y.J.Am.Chem.Soc.2005,127,6335.
[16](a)Zhang,X.-D.;Ye,J.-W.;Xu,L.-F.;Yang,L.-J.;Deng,D.;Ning,G.-L.J.Lumin.2013,139,28.(b)Gu,X.-G.;Yao,J.-J.;Zhang,G.-X.;Yan,Y.-L.;Zhang,C.;Peng,Q.;Liao,Q.;Wu,Y.-S.;Xu,Z.-Z.;Zhao,Y.-S.;Fu,H.-B.;Zhang,D.-Q.Adv.Funct.Mater.2012,22,4862.(c)Wu,Y.-T.;Kuo,M.-Y.;Chang,Y.-T.;Shin,C.-C.;Wu,T.-C.;Tai,C.-C.;Cheng,T.-H.;Liu,W.-S.Angew.Chem.,Int.Ed.2008,47,9891.(d)Chen,Z.;Zhang,J.;Song,M.;Yin,J.;Yu,G.-A.;Liu,S.-H.Chem.Commun.2015,51,326.
[17]Anariba,F.;Chng,L.L.;Abdullah,N.S.;Tay,F.E.H.J.Mater.Chem.2012,22,19303.
[18]Dyker,G.;Heiermann,J.;Miura,M.;Inoh,J.I.;Pivsa-Art,S.;Satoh,T.;Nomura,M.Chem.-Eur J.2000,18,3426.
[19]Kanthak,M.;Muth,E.;Dyker,G.Eur.J.Org.Chem.2010,31,6084.
[20](a)Feng,X.-A.;Tong,B.;Shen,J.-B.;Shi,J.-B.;Han,T.-Y.;Chen,L.;Zhi,J.-G.;Lu,P.;Ma,Y.-G.;Dong,Y.-P.J.Phys.Chem.B 2010,114,16731.(b)Ouyang,M.;Yu,C.-H.;Zhang,Y.-J.;Hu,B.;Lu,X.-J.;Sun,J.-W.;Zhang,C.Acta.Phys.-Chim.Sin.2012,28,2944(in Chinese).(欧阳密,俞春辉,张玉建,胡彬,吕晓静,孙璟玮,张诚,物理化学学报,2012,28,2944.)(c)Tang,H.-Y.;Zeng,Y.;Li,Y.-Y.;Chen,J.-P.;Li,Y.Acta Chim.Sinica 2011,69,2241(in Chinese).(唐海云,曾毅,李迎迎,陈金平,李嫕,化学学报,2011,6,2241.)
[21]Yan,D.-P.;Yang,H.-J.;Meng,Q.-Y.;Lin,H.-Y.;Wei,M.Adv Funct.Mater.2014,24,587.
[22]Chi,Z.-G.;Zhang,X.-Q.;Xu,B.-J.;Zhou,X.;Ma,C.P.;Zhang,Y.;Liu,S.-W.;Xu,J.-R.Chem.Soc.Rev.2012,41,3878.
[23]Dong,Y.-J.;Xu,B.;Zhang,J.-B.;Tan,X.;Wang,L.-J.;Chen,J.-L.;Lv,H.-G.;Wen,S.-P.;Li,B.;Ye,L.;Zou,B.;Tian,W.-J.Angew.Chem.,Int.Ed.2012,51,10782.
[24]Cai,R.-R.;Huang,M.-M.;Cui,X.-L.;Zhang,J.-Y.;Du,C.-X.;Wu,Y.-S.;Wu,Y.J.RSC Adv.2013,3,13140.
[25]Chen,X.-P.;Li,X.-H.;Wang,N.-N.;Jin,J.-S.;Lu,P.;Wang,Y.-G.Eur.J.Org.Chem.2012,4380.