An AEE-active Polymer Containing Tetraphenylethene and 9, 10-Distyrylanthracene Moieties with Remarkable Mechanochromism

Jun-ru Chen; Juan Zhao; Bing-jia Xu; Zhi-yong Yang; Si-wei Liu; Jia-rui Xu; Yi Zhang; Yuan-chun Wu; Po-yen Lv; Zhen-guo Chi

doi:10.1007/s10118-017-1894-9

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An AEE-active Polymer Containing Tetraphenylethene and 9, 10-Distyrylanthracene Moieties with Remarkable Mechanochromism

Papers | Updated：2021-02-18

- An AEE-active Polymer Containing Tetraphenylethene and 9, 10-Distyrylanthracene Moieties with Remarkable Mechanochromism
- Chinese Journal of Polymer Science Vol. 35, Issue 2, Pages: 282-292(2017)
- Affiliations：
  
  a.Key Laboratory for Polymeric Composite & Functional Materials of Ministry of Education, Guangdong Provincial Key Laboratory for High Performance Polymer-based Composites, Guangdong Engineering Technology Research Center for High-performance Organic and Polymer Photoelectric Functional Films, State Key Laboratory of Optoelectronic Material and Technologies, School of Chemistry, Sun Yat-sen University, Guangzhou 510275, China
  b.Shenzhen China Star Optoelectronics Technology Co., Ltd, Shenzhen 518107, China
- Author bio：
  
  Zhi-yong Yang (杨志涌), E-mail:yangzhy29@mail.sysu.edu.cn
  Yi Zhang (张艺), E-mail:ceszy@mail.sysu.edu.cn
  Zhen-guo Chi (池振国), E-mail:chizhg@mail.sysu.edu.cn
- Funds：
- DOI：10.1007/s10118-017-1894-9
  CLC：
- Received：29 September 2016，
  
  Revised：2016-10-24，
  
  Accepted：25 October 2016，
  
  Published：2017-02
- Accepted：
Scan QR Code
Jun-ru Chen, Juan Zhao, Bing-jia Xu, et al. An AEE-active Polymer Containing Tetraphenylethene and 9, 10-Distyrylanthracene Moieties with Remarkable Mechanochromism[J]. Chinese Journal of Polymer Science, 2017, 35(2): 282-292.
DOI：

Jun-ru Chen, Juan Zhao, Bing-jia Xu, et al. An AEE-active Polymer Containing Tetraphenylethene and 9, 10-Distyrylanthracene Moieties with Remarkable Mechanochromism[J]. Chinese Journal of Polymer Science, 2017, 35(2): 282-292. DOI： 10.1007/s10118-017-1894-9.

摘要

Abstract

A polymer (poly (9

10-anthracenevinylene-

alt

-4

4'-(9

9-bis (4-(4'-(1

2'-triphenylvinyl) phenoxy) butyl)-9

-fluorene-2

7-diyl) dibenzaldehyde)

) was successfully synthesized through the Wittig-Horner reaction by employing fluorene and 9

10-distyrylanthracene moieties as building blocks for backbone and tetraphenylethenes as pendant groups. Photophysical and thermal properties of the resulting polymeric emitter were fully characterized by ultraviolet-visible (UV-Vis) absorption and photoluminescence (PL) spectra

thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). While

emits an orange-light centered at 567 nm in dilute tetrahydrofuran (THF) solution

the solid powder of the polymer exhibits strong yellow emission peaked at 541 nm. It is also found that the as-synthesized polymer shows unique property of aggregation-enhanced emission (AEE). In addition

possesses high thermal stability with a decomposition temperature (

) of 430℃ and high morphological stability with a glass transition temperature (

) of 171℃. Under the stimulus of mechanical force

the emission of

can be changed from yellow to red (Δ

max

=61 nm)

showing a remarkable mechanochromism. The results from XRD analysis suggest that such mechanochromic phenomenonof

is probably caused by the destruction of crystalline structure

which leads to the conformational planarization of the distyrylanthracene moieties forming by the polymerization and the increase of molecular conjugation of the backbone.

关键词

Keywords

references

Z.G. Chi , X.Q. Zhang , B.J. Xu , X. Zhou , C.P. Ma , Y. Zhang , S.W. Liu , J.R. Xu . Chem. Soc. Rev. , 2012 . 41 ( 10 ): 3878 DOI: 10.1039/c2cs35016e http://doi.org/10.1039/c2cs35016e .

Y.Y. Gong , Y.Q. Tan , J. Liu , P. Lu , C.F. Feng , W.Z. Yuan , Y.W. Lu , J.Z. Sun , G.F. He , Y.M. Zhang . Chem. Commun. , 2013 . 49 ( 38 ): 4009 DOI: 10.1039/c3cc39243k http://doi.org/10.1039/c3cc39243k .

P. Gautam , R. Maragani , S.M. Mobin , R. Misra . RSC Adv. , 2014 . 4 ( 94 ): 52526 DOI: 10.1039/C4RA09921D http://doi.org/10.1039/C4RA09921D .

S.K. Park , I. Cho , J. Gierschner , J.H. Kim , J.H. Kim , J.E. Kwon , O.K. Kwon , D.R. Whang , J.H. Park , B.K. An . Angew. Chem. , 2016 . 128 ( 1 ): 211 DOI: 10.1002/ange.201508210 http://doi.org/10.1002/ange.201508210 .

J. Wu , Y.Y. Cheng , J.B. Lan , D. Wu , S.Y. Qian , L.P. Yan , Z. He , X.Y. Li , K. Wang , B. Zou , J.S. You . J. Am. Chem. Soc. , 2016 . DOI: 10.1021/jacs.6b03890 http://doi.org/10.1021/jacs.6b03890 .

S.S. Zeng , D.Y. Zhang , W.H. Huang , Z.F. Wang , S.G. Freire , X.Y. Yu , A.T. Smith , E.Y. Huang , H. Nguon , L.Y. Sun . Nat. Commun. , 2016 . 7 1 .

Y. Sagara , T. Kato . Nat. Chem. , 2009 . 1 ( 8 ): 605 DOI: 10.1038/nchem.411 http://doi.org/10.1038/nchem.411 .

J. Mei , N.L.C. Leung , R.T.K. Kwok , J.W.Y. Lam , B.Z. Tang . Chem. Rev. , 2015 . 115 ( 21 ): 11718 DOI: 10.1021/acs.chemrev.5b00263 http://doi.org/10.1021/acs.chemrev.5b00263 .

Y. Sagara , T. Mutai , I. Yoshikawa , K. Araki . J. Am. Chem. Soc. , 2007 . 129 ( 6 ): 1520 DOI: 10.1021/ja0677362 http://doi.org/10.1021/ja0677362 .

W.Z. Yuan , Y.Q. Tan , Y.Y. Gong , P. Lu , J.W.Y. Lam , X.Y. Shen , C.F. Feng , H.H.Y. Sung , Y.W. Lu , I.D. Williams . Adv. Mater. , 2013 . 25 ( 20 ): 2837 DOI: 10.1002/adma.201205043 http://doi.org/10.1002/adma.201205043 .

J. Yang , J. Huang , Q.Q. Li , Z. Li . J. Mater. Chem. C , 2016 . 4 ( 14 ): 2663 DOI: 10.1039/C5TC03262H http://doi.org/10.1039/C5TC03262H .

Q.Q. Li , Z. Li . Sci. China Chem. , 2015 . 58 ( 12 ): 1800 DOI: 10.1007/s11426-015-5517-4 http://doi.org/10.1007/s11426-015-5517-4 .

H.Y. Li , X.Q. Zhang , Z.G. Chi , B.J. Xu , W. Zhou , S.W. Liu , Y. Zhang , J.R. Xu . Org. Lett. , 2011 . 13 ( 4 ): 556 DOI: 10.1021/ol102872x http://doi.org/10.1021/ol102872x .

B.J. Xu , Z.G. Chi , J.Y. Zhang , X.Q. Zhang , H.Y. Li , X.F. Li , S.W. Liu , Y. Zhang , J.R. Xu . Chem. Asian J. , 2011 . 6 ( 6 ): 1470 DOI: 10.1002/asia.v6.6 http://doi.org/10.1002/asia.v6.6 .

Y.J. Dong , B. Xu , J.B. Zhang , X. Tan , L.J. Wang , J.L. Chen , H.G. Lv , S.P. Wen , B. Li , L. Ye . Angew. Chem. Int. Ed. , 2012 . 51 ( 43 ): 10782 DOI: 10.1002/anie.v51.43 http://doi.org/10.1002/anie.v51.43 .

R. Misra , T. Jadhav , B. Dhokale , S.M. Mobin . Chem. Commun. , 2014 . 50 ( 65 ): 9076 DOI: 10.1039/C4CC02824D http://doi.org/10.1039/C4CC02824D .

J. Wang , J. Mei , R.R. Hu , J.Z. Sun , A.J. Qin , B.Z. Tang . J. Am. Chem. Soc. , 2012 . 134 ( 24 ): 9956 DOI: 10.1021/ja208883h http://doi.org/10.1021/ja208883h .

N. Zhao , Z.Y. Yang , J.W.Y. Lam , H.H.Y. Sung , N. Xie , S.J. Chen , H.M. Su , M. Gao , I.D. Williams , K.S. Wong . Chem. Commun. , 2012 . 48 ( 69 ): 8637 DOI: 10.1039/c2cc33780k http://doi.org/10.1039/c2cc33780k .

J.Q. Tong , Y.J. Wang , J. Mei , J. Wang , A.J. Qin , J.Z. Sun , B.Z. Tang . Chem. Eur. J. , 2014 . 20 ( 16 ): 4461 http://onlinelibrary.wiley.com/doi/10.1002/chem.201202969/full http://onlinelibrary.wiley.com/doi/10.1002/chem.201202969/full , .

J.B. Zhang , J.L. Chen , B. Xu , L.J. Wang , S.Q. Ma , Y.J. Dong , B. Li , L. Ye , W.J. Tian . Chem. Commun. , 2013 . 49 ( 37 ): 3878 DOI: 10.1039/c3cc41171k http://doi.org/10.1039/c3cc41171k .

Q.K. Qi , Y.F. Liu , X.F. Fang , Y.M. Zhang , P. Chen , Y. Wang , B. Yang , B. Xu , W.J. Tian , S.X.A. Zhang . RSC Adv. , 2013 . 3 ( 21 ): 7996 DOI: 10.1039/c3ra40734a http://doi.org/10.1039/c3ra40734a .

H.J. Kim , D.R. Whang , J. Gierschner , C.H. Lee , S.Y. Park . Angew. Chem. Int. Ed. , 2015 . 54 ( 14 ): 4330 DOI: 10.1002/anie.201411568 http://doi.org/10.1002/anie.201411568 .

Z.Y. Ma , M.J. Teng , Z.J. Wang , S. Yang , X.R. Jia . Angew. Chem. Int. Ed. , 2013 . 52 ( 47 ): 12268 DOI: 10.1002/anie.201306503 http://doi.org/10.1002/anie.201306503 .

Y. Gong , Y. Zhang , W.Z. Yuan , J.Z. Sun , Y. Zhang . J. Phys. Chem. C , 2014 . 118 ( 20 ): 10998 DOI: 10.1021/jp500556p http://doi.org/10.1021/jp500556p .

L. Wang , K. Wang , B. Zou , K. Ye , H. Zhang , Y. Wang . Adv. Mater. , 2015 . 27 ( 18 ): 2918 DOI: 10.1002/adma.v27.18 http://doi.org/10.1002/adma.v27.18 .

Z. Mao , Z.Y. Yang , Y.X. Mu , Y. Zhang , Y.F. Wang , Z.G. Chi , C.C. Lo , S.W. Liu , L. Alan , J.R. Xu . Angew. Chem. Int. Ed. , 2015 . 54 ( 21 ): 6270 DOI: 10.1002/anie.201500426 http://doi.org/10.1002/anie.201500426 .

B.J. Xu , Y.X. Mu , Z. Mao , Z.L. Xie , H.Z. Wu , Y. Zhang , C.J. Jin , Z.G. Chi , S.W. Liu , J.R. Xu , Y.C. Wu , P.Y. Lu , L. Alan , R.B. Martin . Chem. Sci. , 2016 . 7 ( 3 ): 2201 DOI: 10.1039/C5SC04155D http://doi.org/10.1039/C5SC04155D .

R.R. Hu , N.L.C. Leung , B.B. Tang . Chem. Soc. Rev. , 2014 . 43 ( 13 ): 4494 DOI: 10.1039/c4cs00044g http://doi.org/10.1039/c4cs00044g .

F. Ciardelli , G. Ruggeribc , A. Pucci . Chem. Soc. Rev. , 2013 . 42 ( 3 ): 857 DOI: 10.1039/C2CS35414D http://doi.org/10.1039/C2CS35414D .

R.T. K. Kwok , C.W.T. Leung , J.W.Y. Lam , B.B. Tang . Chem. Soc. Rev. , 2015 . 44 ( 13 ): 4228 DOI: 10.1039/C4CS00325J http://doi.org/10.1039/C4CS00325J .

X.Q. Zhang , Z.G. Chi , H.Y. Li , B.J. Xu , X.F. Li , W. Zhou , S.W. Liu , Y. Zhang , J.R. Xu . Chem. Asian J. , 2011 . 6 ( 3 ): 808 DOI: 10.1002/asia.201000802 http://doi.org/10.1002/asia.201000802 .

Z.K. Wang , S.J. Chen , J.W.Y. Lam , W. Qin , R.T.K. Kwok , N. Xie , Q.L. Hu , B.Z. Tang . J. Am. Chem. Soc. , 2013 . 135 ( 22 ): 8238 DOI: 10.1021/ja312581r http://doi.org/10.1021/ja312581r .

H. Tong , Y.N. Hong , Y.Q. Dong , H. Matthias , W.Y. Jacky , Z. Li , Z.F. Guo , Z.H. Guo , B.Z. Tang . Chem. Commun. , 2006 . ( 35 ): 3705 DOI: 10.1039/B608425G http://doi.org/10.1039/B608425G .

M. Chen , L.Z. Li , H. Nie , J.Q. Tong , L.L. Yan , B. Xu , J.Z. Sun , W.J. Tian , Z.J. Zhao , A.J. Qin . Chem. Sci. , 2015 . 6 ( 3 ): 1932 DOI: 10.1039/C4SC03365E http://doi.org/10.1039/C4SC03365E .

B.J. Xu , J.J. He , Y.X. Mu , Q.Z. Zhu , S.K. Wu , Y.F. Wang , Y. Zhang , C.J. Jin , C.C. Lo , Z.G. Chi . Chem. Sci. , 2015 . 6 ( 5 ): 3236 DOI: 10.1039/C5SC00466G http://doi.org/10.1039/C5SC00466G .

B.J. Xu , J.J. He , Y. Liu , B. Xu , Q.Z. Zhu , M.Y. Xie , Z.B. Zheng , Z.G. Chi , W.J. Tian , C.J. Jin . J. Mater. Chem. C , 2014 . 2 ( 17 ): 3416 DOI: 10.1039/c3tc32052a http://doi.org/10.1039/c3tc32052a .

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