聚集诱导发光特性解决了传统有机分子在固态或高浓度状态荧光淬灭问题,从而扩展了荧光材料的应用范围。近年来,四苯乙烯及其衍生物作为经典聚集诱导分子被广泛用于材料科学和生物医学领域。有机力致发光材料作为一种独特的发光现象已在生物成像、防伪加密和新型光源等领域被广泛研究。聚集诱导效应和力致荧光响应模式结合,增强了材料的机械力致特性,并为其在刺激响应性材料、智能开关等方面提供了新思路。总结了近年来四苯乙烯衍生物在有机力致发光材料中的研究进展,并展望了其发展趋势。
The aggregation-induced luminescence characteristics have solved the problem of fluorescence quenching of traditional organic molecules in the solid state or high-concentration state,thereby expanding its application range.In recent years,tetraphenylethylene and its derivatives as classical aggregation-inducing emission molecules have been widely used in the fields of materials and biomedical science.As a unique luminescence phenomenon,organic mechanoluminescence materials are applied for biological imaging,anti-counterfeiting and encryption,and new light sources.The combination of aggregation-inducing effect and force-induced fluorescence response mode enhances the mechanical force-induced properties,which providing new insights in stimuli-responsive materials and smart switches.This paper summarized the research progress of tetraphenylethylene derivatives in organic photoluminescent materials and discussed its development trend.
[1] Feng A,Smet P F.A review of mechanoluminescence in inorganic solids:compounds,mechanisms,models and applications[J].Materials,2018,11(4):484.
[2] Chi Z,Zhang X,Xu B,et al.Recent advances in organic mechanofluorochromic materials[J].Chemical Society Reviews,2012,41(10):3878-3896.
[3] Zhao J,Chi Z,Zhang Y,et al.Recent progress in the mechanofluorochromism of cyanoethylene derivatives with aggregation-induced emission[J].Journal of Materials Chemistry C,2018,6(24):6327-6353.
[4] 常凯,李倩倩,李振.力致发光现象及其应用研究进展[J].有机化学,2020,40(11):3656-3671.
[5] Luo J,Xie Z,Lam J W Y,et al.Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole[J].Chemical Communications,2001,18:1740-1741.
[6] Feng H T,Yuan Y X,Xiong J B,et al.Macrocycles and cages based on tetraphenylethylene with aggregation-induced emission effect[J].Chemical Society Reviews,2018,47(19):7452-7476.
[7] Hong Y,Lam J W Y,Tang B Z.Aggregation-induced emission:phenomenon,mechanism and applications[J].Chemical Communications,2009,(29):4332-4353.
[8] Xu Y,Xu R,Wang Z,et al.Recent advances in luminescent materials for super-resolution imaging via stimulated emission depletion nanoscopy[J].Chemical Society Reviews,2021,50:667-690.
[9] 罗海媛,郑捷,梁水妹,等.四苯乙烯衍生物在有机电致发光材料中的研究进展,化工新型材料,2016,44:14-16.
[10] 李亚雯,敖宛彤,金慧琳,等.四苯乙烯衍生物与大环主体在主客体相互作用下的聚集诱导发光,化学进展,2019,31(1):121-133.
[11] Shen X Y,Wang Y J,Zhao E,et al.Effects of substitution with donor-acceptor groups on the properties of tetraphenylethene trimer:aggregation-induced emission,solvatochromism,and mechanochromism[J].The Journal of Physical Chemistry C,2013,117(14):7334-7347.
[12] Ma Y,Zhang Y,Kong L,et al.Mechanoresponsive material of AIE-active 1,4-dihydropyrrolo [3,2-b] pyrrole luminophores bearing tetraphenylethylene group with rewritable data storage[J].Molecules,2018,23(12):3255.
[13] Ma C P Zhang X,Yang Y,et al.Effect of alkyl length dependent crystallinity for the mechanofluorochromic feature of alkyl phenothiazinyl tetraphenylethenyl acrylonitrile derivatives[J].Journal of Materials Chemistry C,2016,4(21):4786-4791.
[14] Wang Y,Cheng D,Zhou H,et al.Tetraphenylethene-containing cruciform luminophores with aggregation-induced emission and mechanoresponsive behavior[J].Dyes and Pigments,2019,170:107606.
[15] Li W B,Luo W J,Li K X,et al.Aggregation-induced phosphorescence and mechanochromic luminescence of a tetraphenylethene-based gold(I) isocyanide complex[J].Chinese Chemical Letters,2017,28(6):1300-1305.
[16] Jadhav T,Choi J M,Dhokale B,et al.Effect of end groups on mechanochromism and electroluminescence in tetraphenylethylene substituted phenanthroimidazoles[J].The Journal of Physical Chemistry C,2016,120(33):18487-18495.
[17] Jadhav T,Choi J M,Shinde J,et al.Mechanochromism and electroluminescence in positional isomers of tetraphenylethylene substituted phenanthroimidazoles[J].Journal of Materials Chemistry C,2017,5(24):6014-6020.
[18] Jadhav T,Dhokale B,Misra R.Effect of the cyano group on solid state photophysical behavior of tetraphenylethene substituted benzothiadiazoles[J].Journal of Materials Chemistry C,2015,3(35):9063-9068.
[19] Zhang S,Huang Y,Kong L,et al.Aggregation-induced emission-active tetraphenylethylene derivatives containing arylimidazole unit for reversible mechanofluorochromism and selective detection of picric acid[J].Dyes and Pigments,2020,181:108574.
[20] Liu W,Wang Y T,Ge G,et al.Design,synthesis,photophysical properties and intrinsic mechanism of two difluoroboron β-diketonate complexes with TPE and N-alkyl pyrrole units[J].Dyes and Pigments,2019,171:107704.
[21] Ma Z,Wang Z,Meng X,et al.A mechanochromic single crystal:turning two color changes into a tricolored switch[J].Angewandte Chemie International Edition,2016,55(2):519-522.
[22] Gao H,Xu D,Liu X L,et al.Tetraphenylethene-based β-diketonate boron complex:efficient aggregation-induced emission and high contrast mechanofluorochromism[J].Dyes and Pigments,2017,139:157-165.
[23] Jadhav T,Dhokale B,Misra R.Aggregation induced emission and mechanochromism in tetraphenylethene substituted pyrazabole[J].RSC Advances,2015,5(83):68187-68191.
[24] Xu B,He J,Mu Y,et al.Very bright mechanoluminescence and remarkable mechanochromism using a tetraphenylethene derivative with aggregation-induced emission[J].Chemical Science,2015,6(5):3236-3241.
[25] Yin Y,Chen Z,Fan C,et al.1,8-Naphthalimide-based highly emissive luminophors with various mechanofluorochromism and aggregation-induced characteristics[J].ACS Omega,2019,4(10):14324-14332.
[26] Umar S,Jha A K,Purohit D,et al.A tetraphenylethene-naphthyridine-based AIEgen TPEN with dual mechanochromic and chemosensing properties[J].The Journal of Organic Chemistry,2017,82(9):4766-4773.
[27] Qi Q,Qian J,Tan X,et al.Remarkable turn-on and color-tuned piezochromic luminescence:mechanically switching intramolecular charge transfer in molecular crystals[J].Advanced Functional Materials,2015,25(26):4005-4010.
[28] Liu L,Su X,Yu Q,et al.Photoacid-spiropyran exhibits different mechanofluorochromism before and after modification of tetraphenylethene under grinding and hydrostatic pressure[J].The Journal of Physical Chemistry C,2019,123(41):25366-25372.
[29] Jia J H,Zhao H.A multi-responsive AIE-active tetraphenylethylene-functioned salicylaldehyde-based schiff base for reversible mechanofluorochromism and Zn2+ and CO2-3 detection[J].Organic Electronics,2019,73:55-61.
[30] Khan F,Ekbote A,Misra R.Reversible mechanochromism and aggregation induced enhanced emission in phenothiazine substituted tetraphenylethylene[J].New Journal of Chemistry,2019,43(41):16156-16163.
[31] Ma X,Hu L,Han X,et al.Vinylpyridine-and vinylnitrobenzene-coating tetraphenylethenes:aggregation-induced emission (AIE) behavior and mechanochromic property[J].Chinese Chemical Letters,2018,29(10):1489-1492.
[32] Ramachandran E,Dhamodharan R.Tetrakis (trialkylsilylethynylphenyl) ethenes:mechanofluorochromism arising from steric considerations with an unusual crystal structure[J].Journal of Materials Chemistry C,2017,5(40):10469-10476.
[33] Lu Z,Lu S,Cheng Y,et al.Synthesis of isoniazid-substituted tetraphenylethylene stereoisomers with dramatic differences on aggregate morphologies,optical and mechanocharomic properties[J].Journal of Photochemistry and Photobiology A:Chemistry,2020,392:112357.
基金资助
陕西省技术创新引导专项(2022QFY09-09),陕西省自然科学基金项目S2018-JC-QN-0631);陕西省教育厅专项科研计划项目(20JK0473,17JK0017);农业农村部富硒产品开发与质量控制重点实验室开放课题(Se-2020C04);国家级大学生创新创业训练计划(S202011397021);陕西省大学生创新创业训练计划(S202011397042)。
PDF
