Abstract: The tetraphenylethene-based monomer 1-(4-butenyloxy)phenyl-1,2,2-triphenylethylene (TPE-BE) with aggregation-induced emission (AIE) characteristic was synthesized.And then,hydrophilic polymer P1 and hydrophobic polymer P2 were prepared by the copolymerization of a small amount of TPE-BE with acrylamide and acrylic acid,and with styrene through free radical solution polymerization,respectively.The structures and fluorescence properties of P1 and P2 were studied by IR and fluorescence spectra.The effect of hydrophilicity and hydrophobicity of P1 and P2 on the fluorescence behaviors was discussed.The results indicated that P1 was non-emissive in water but the emission was gradually enhanced with the addition of tetrahydrofuran (THF).However,P2 was non-emissive in both water and THF/H2O mixtures.These data indicated that the hydrophilicity/hydrophobicity of polymers can affect the fluorescence properties.However,P1 and P2 both demonstrated strong emission in the solid states,showing aggregation-induced emission (AIE) activities.In addition,SEM study demonstrated that P2 can form microspheres in THF/water mixtures as the water content was above 30%.New AIE polymers with diverse structures and functionalities can be expected to be prepared by tuning the kinds of comonomers.
赵秋丽, 卞洁鹏, 杨庆浩, 后振中. 自由基聚合制备聚集诱导发光聚合物[J]. 化工新型材料, 2019, 47(7): 154-158.
Zhao Qiuli, Bian Jiepeng, Yang Qinghao, Hou Zhenzhong. Synthesis of the polymer with AIE characteristic by radical polymerazation. New Chemical Materials, 2019, 47(7): 154-158.
Hong Y N,Lam J W Y,Tang B Z.Aggregation-induced emission[J].Chemical Society Reviews,2011,40(11):5361-5388.
[2]
Zhao Q L,Li K,Chen S J,et al.Aggregation-induced red-NIR emission organic nanoparticles as effective and photostable fluorescent probes for bioimaging[J].Journal of Materials Chemistry,2012,22(30):15128-15135.
[3]
Mei J,Leung N L C,Kwok R T K,et al.Aggregation-induced emission:together we shine,united we soar[J].Chemical Reviews,2015,115(21):11718-11940.
[4]
Wang Z K,Nie J Y,Qin W,et al.Gelation process visualized by aggregation-induced emission fluorogens[J].Nature Communications,2016,7:12033-12040.
[5]
Wang Y J,Shi Y,Wang Z Y,et al.A red to near-IR fluorogen:aggregation-induced emission,large stokes shift,high solid efficiency and application in cell-imaging[J].Chemistry-A European Journal,2016,22(28):9784-9791.
[6]
Zhao Q L,Sun J Z.Red and near infrared emission materials with AIE characteristics[J].Journal of Materials Chemistry C,2016,4(45):10588-10609.
[7]
Hu R R,Leung N L C,Tang B Z.AIE macromolecules:syntheses,structures and functionalities[J].Chemical Society Reviews,2014,43(13):4494-4562.
[8]
Qin A,Lam J W Y,Tang B Z.Luminogenic polymers with aggregation-induced emission characteristics[J].Progress in Polymer Science,2012,37(1):182-209.
Gu P Y,Lu C J,Hu Z J,et al.The AIEE effect and two-photon absorption (TPA) enhancement induced by polymerization:synthesis of a monomer with ICT and AIE effects and its homopolymer by ATRP and a study of their photophysical properties[J].Journal of Materials Chemistry C,2013,1(14):2599-2606.
[13]
Tang L,Jin J K,Qin A J,et al.A fluorescent thermometer operating in aggregation-induced emission mechanism:probing thermal transitions of PNIPAM in water[J].Chemical Communications,2009(33):4974-4976.
[14]
Lu H G,Su F Y,Mei Q,et al.A series of poly[N-(2-hydroxypropyl)methacrylamide] copolymers with anthracene-derived fluorophores showing aggregation-induced emission properties for bioimaging[J].Journal of Polymer Science Part A:Polymmer Chemistry,2012,50(5):890-899.
[15]
Shen X,Shi Y,Peng B,et al.Fluorescent polymeric micelles with tetraphenylethylene moieties and their application for the selective detection of glucose[J].Macromolecular Bioscience,2012,12(11):1583-1590.
[16]
Zhang X Y,Zhang X Q,Yang B,et al.Polymerizable aggregation-induced emission dye-based fluorescent nanoparticles for cell imaging applications[J].Polymer Chemistry,2014,5(2):356-360.
[17]
Wang K,Zhang X Y,Zhang X Q,et al.Red fluorescent cross-linked glycopolymer nanoparticles based on aggregation induced emission dyes for cell imaging[J].Polymer Chemistry,2015,6(8):1360-1366.