Synthesis and Mechanofluorochromic Property of Dicyanodistyrylbenzene Derivative

Xiang-jian CAO; Xin-xiao ZUO; Zhen-gong MENG; Zhen-qiang YU

doi:10.37188/CJL.20210129

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Synthesis and Mechanofluorochromic Property of Dicyanodistyrylbenzene Derivative

Synthesis and Properties of Materials | 更新时间：2021-07-22

- Synthesis and Mechanofluorochromic Property of Dicyanodistyrylbenzene Derivative
  增强出版
- Chinese Journal of Luminescence Vol. 42, Issue 7, Pages: 976-983(2021)
- 作者机构：
  
  1.天津大学　化工学院，天津　　300350
  2.深圳大学　化学与环境工程学院，广东　深圳　 518071
- 作者简介：
- 基金信息：
  
  National Natural Science Foundation of China(21875143);Innovation Research Foundation of Shenzhen(JCYJ20180507182229597);Natural Science Foundation of Guangdong Province(2016A030312002)
- DOI：10.37188/CJL.20210129
  CLC： O482.31
- Published：01 July 2021，
  
  Received：08 April 2021，
  
  Revised：28 April 2021，
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Xiang-jian CAO, Xin-xiao ZUO, Zhen-gong MENG, et al. Synthesis and Mechanofluorochromic Property of Dicyanodistyrylbenzene Derivative. [J]. Chinese Journal of Luminescence 42(7):976-983(2021)
DOI：

Xiang-jian CAO, Xin-xiao ZUO, Zhen-gong MENG, et al. Synthesis and Mechanofluorochromic Property of Dicyanodistyrylbenzene Derivative. [J]. Chinese Journal of Luminescence 42(7):976-983(2021) DOI： 10.37188/CJL.20210129.

摘要

力致变色荧光材料具有机械力刺激响应的性能，在压敏传感等领域有着广阔的应用前景。本文制备了一种具有聚集诱导发光效应的二氰基二苯乙烯基苯衍生物(DCS-Bn)，采用高分辨质谱对其化学结构进行了表征。通过吸收光谱和荧光发射光谱研究了DCS-Bn的光物理性质，并使用差示扫描量热仪和X射线粉末衍射仪考察了其聚集态结构。实验结果表明，DCS-Bn在溶液和固体状态均具有较强的发光性能。并且，基于DCS-Bn独特的棒状分子结构及“晶态-非晶态”的聚集态结构变化，该材料具有力致发光变色性质。采用溶剂熏蒸或者加热处理，DCS-Bn荧光颜色又能恢复，在可重复书写荧光材料等领域具有潜在应用价值。

Abstract

Mechanochromic luminescent materials have potential applications in pressure sensitive sensing due to their mechanical response properties. In this paper

a dicyanodistyrylbenzene(DCS) derivative(DCS-Bn) with aggregation-induced emission(AIE) property was synthesized

and its molecular structure was characterized by high-resolution mass spectra. The photophysical properties of DCS-Bn were studied by absorption spectra and fluorescence emission spectra. Furthermore

the aggregation structures of DCS-Bn were measured by differential scanning calorimetry and X-ray diffraction experiment. The results revealed that DCS-Bn has high efficiency luminescence both in solution and solid state. DCS-Bn has the mechanofluorochromic property due to its unique rod molecular structure and the changes of aggregated structures(crystalline or amorphous state). The fluorescence emission color can recover to pristine state through solvent fuming or heating treatment

thus

DCS-Bn has potential application value in the fields of rewritable fluorescent materials.

关键词

聚集诱导发光二氰基二苯乙烯基苯高荧光量子产率聚集态结构力致发光变色

Keywords

aggregation-induced emissiondicyanodistyrylbenzenehigh fluorescence quantum yieldaggregation structuresmechanofluorochromic

references

WANG Y W, LI H X, WANG D, et al. Inorganic-organic nanocomposites based on aggregation-induced emission luminogens [J].Adv. Funct. Mater., 2021, 31(7): 2006952.

MARTÍNEZ-ABADÍA M, GIMÉNEZ R, ROS M B. Self-assembled α-cyanostilbenes for advanced functional materials [J].Adv. Mater., 2018, 30(5): 1704161-1-9.

王嘉慧, 曾晓璇, 吴玥, 等. 具有pH响应性能的聚集诱导发光材料制备与表征 [J].发光学报, 2021, 42(3): 311-318.

WANG J H, ZENG X X, WU Y, et al. Synthesis and characterization of pH-responsive material with aggregation-induced emission property [J].Chin. J. Lumin., 2021, 42(3): 311-318. (in Chinese)

LEMMER U, HEUN S, MAHRT R F, et al. Aggregate fluorescence in conjugated polymers [J].Chem. Phys. Lett., 1995, 240(4): 373-378.

陆红波, 张超, 吴少君, 等. 发光液晶材料的合成及发光特性研究 [J].发光学报, 2015, 36(11): 1227-1232.

LU H B, ZHANG C, WU S J, et al. Synthesis and photoluminescence property of luminescent liquid crystal material [J].Chin. J. Lumin., 2015, 36(11): 1227-1232. (in Chinese)

LUO J D, XIE Z L, LAM J W Y, et al. Aggregation-induced emission of 1-methyl-1, 2, 3, 4, 5-pentaphenylsilole [J].Chem. Commun., 2001, (18): 1740-1741.

MEI J, LEUNG N L C, KWOK R T K, et al. Aggregation-induced emission:together we shine, united we soar! [J].Chem. Rev., 2015, 115(21): 11718-11940.

LI J, WANG J X, LI H X, et al. Supramolecular materials based on AIE luminogens (AIEgens):construction and applications [J].Chem. Soc. Rev., 2020, 49(4): 1144-1172.

赵阳, 曾雨婷, 任相魁. 四苯基乙烯室温发光液体材料的制备与表征 [J].化学工业与工程, 2020, 37(5): 1-6.

ZHAO Y, ZENG Y T, REN X K. Preparation and characterization of a new tetraphenylethylene derivative as room-temperature luminescent liquid material [J].Chem. Ind. Eng., 2020, 37(5): 1-6. (in Chinese)

WU Y, YOU L H, YU Z Q, et al. Rational design of circularly polarized luminescent aggregation-induced emission luminogens (AIEgens):promoting the dissymmetry factor and emission efficiency synchronously [J].ACS Mater. Lett., 2020, 2(5): 505-510.

LU H B, WU S J, ZHANG C, et al. Photoluminescence intensity and polarization modulation of a light emitting liquid crystal via reversible isomerization of an α-cyanostilbenic derivative [J].Dyes Pigments, 2016, 128: 289-295.

YOON S J, KIM J H, KIM K S, et al. Mesomorphic organization and thermochromic luminescence of dicyanodistyrylbenzene- based phasmidic molecular disks:uniaxially aligned hexagonal columnar liquid crystals at room temperature with enhanced fluorescence emission and semiconductivity [J].Adv. Funct. Mater., 2012, 22(1): 61-69.

WANG X X, DING Z Y, MA Y, et al. Multi-stimuli responsive supramolecular gels based on a D-π-A structural cyanostilbene derivative with aggregation induced emission properties [J].Soft Matter, 2019, 15(7): 1658-1665.

KUNZELMAN J, KINAMI M, CRENSHAW B R, et al. Oligo(p-phenylene vinylene)s as a “new” class of piezochromic fluorophores [J].Adv. Mater., 2008, 20(1): 119-122.

KIM D Y, KOO J, LIM S I, et al. Solid-state light emission controlled by tuning the hierarchical superstructure of self-assembled luminogens [J].Adv. Funct. Mater., 2018, 28(14): 1707075-1-8.

SAGARA Y, KUBO K, NAKAMURA T, et al. Temperature-dependent mechanochromic behavior of mechanoresponsive luminescent compounds [J].Chem. Mater., 2017, 29(3): 1273-1278.

毛文纲, 陈康, 欧阳密, 等. 基于苯乙烯腈结构的可逆力致变色化合物的合成及性能 [J].化学学报, 2013, 71(4): 613-618.

MAO W G, CHEN K, OUYANG M, et al. Synthesis and characterization of new cyanostilbene-based compound exhibiting reversible mechanochromism [J].Acta Chim. Sinica, 2013, 71(4): 613-618. (in Chinese)

BHAUMIK S K, PATRA Y S, BANERJEE S. High affinity heparin detection by multivalent supramolecular polymers through aggregation induced emission [J].Chem. Commun., 2020, 56(66): 9541-9544.

MU B, ZHAO Y, LI X, et al. Enhanced conductivity and thermochromic luminescence in hydrogen bond-stabilized columnar liquid crystals [J].ACS Appl. Mater. Interfaces, 2020, 12(8): 9637-9645.

MAN Z W, LV Z, XU Z Z, et al. Highly sensitive and easily recoverable excitonic piezochromic fluorescent materials for haptic sensors and anti-counterfeiting applications [J].Adv. Funct. Mater., 2020, 30(17): 2000105-1-8.

HUITOREL B, BENITO Q, FARGUES A, et al. Mechanochromic luminescence and liquid crystallinity of molecular copper clusters [J].Chem. Mater., 2016, 28(22): 8190-8200.

HAN T, LIU L J, WANG D, et al. Mechanochromic fluorescent polymers enabled by AIE processes [J].Macromol. Rapid Commun., 2021, 42(1): 2000311-1-14.

李爱森, 王金凤, 李振. 分子堆积——影响固态有机小分子力响应发光行为的关键因素 [J].发光学报, 2021, 42(3): 283-295.

LI A S, WANG J F, LI Z. Molecular stacking——key factor in mechanical-responsive luminescent behaviors of solid organic small molecules [J].Chin. J. Lumin., 2021, 42(3): 283-295. (in Chinese)

WANG C, LI Z. Molecular conformation and packing:their critical roles in the emission performance of mechanochromic fluorescence materials [J].Mater. Chem. Front., 2017, 1(11): 2174-2194.

YANG J, CHI Z G, ZHU W H, et al. Aggregation-induced emission:a coming-of-age ceremony at the age of eighteen [J].Sci. China Chem., 2019, 62(9): 1090-1098.

ZHAO J, CHI Z H, ZHANG Y, et al. Recent progress in the mechanofluorochromism of cyanoethylene derivatives with aggregation-induced emission [J].J. Mater. Chem. C, 2018, 6(24): 6327-6353.

CHI Z G, ZHANG X Q, XU B J, et al. Recent advances in organic mechanofluorochromic materials [J].Chem. Soc. Rev., 2012, 41(10): 3878-3896.

彭邦银, 许适当, 池振国, 等. 压致变色聚集诱导发光材料 [J].化学进展, 2013, 25(11): 1805-1820.

PENG B Y, XU S D, CHI Z G, et al. Piezochromic aggregation-induced emission materials [J].Prog. Chem., 2013, 25(11): 1805-1820. (in Chinese)

WU H W, CHEN Z, CHI W J, et al. Structural engineering of luminogens with high emission efficiency both in solution and in the solid state [J].Angew. Chem. Int. Ed., 2019, 58(33): 11419-11423.

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School of Chemical Engineering and Technology， State Key Laboratory of Chemical Engineering， Tianjin University

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