1, 2, 5, 6-Naphthalenediimide-based Conjugated Copolymers Linked by Ethynyl Units

Bing-yong Liu; Xiao-chun Yang; Cong-wu Ge; Jian-min Dou; Da-cheng Li; Xi-ke Gao

doi:10.1007/s10118-017-1988-4

Your Location：

Home >

Browse articles >

1, 2, 5, 6-Naphthalenediimide-based Conjugated Copolymers Linked by Ethynyl Units

Papers | Updated：2021-02-18

- 1, 2, 5, 6-Naphthalenediimide-based Conjugated Copolymers Linked by Ethynyl Units
- 1, 2, 5, 6-Naphthalenediimide-based Conjugated Copolymers Linked by Ethynyl Units
- Chinese Journal of Polymer Science 2017年35卷第11期页码：1342-1351
- Affiliations：
  
  a.Shandong Provincial Key Laboratory of Chemical Energy Storage and Novel Cell Technology, School of Chemical and Chemical Engineering, Liaocheng University, Liaocheng 252059, China
  b.Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
  c.Institute of BioPharmaccutical Research, Liaocheng University, Liaocheng 252059, China
- Author bio：
  
  Jian-min Dou(窦建民), E-mail:jmdou@lcu.edu.cn
  Da-cheng Li(李大成), E-mail:lidacheng62@lcu.edu.cn
  Xi-ke Gao(高希珂), E-mail:gaoxk@sioc.ac.cn
- Funds：
  
  the National Natural Science Foundation of China(21674126);the "Strategic Priority Research Program"(XDB12010100);the Shanghai Science and Technology Committee(16JC1400603);Supplementary material is available in the online version of this article at http://dx.doi.org/10.1007/s10118-017-1988-4.
- DOI：10.1007/s10118-017-1988-4
  中图分类号：
- 收稿：2017-04-17，
  
  修回：2017-5-24，
  
  录用：2017-6-1，
  
  纸质出版：2017-11-05
- Accepted：
Scan QR Code
Bing-yong Liu, Xiao-chun Yang, Cong-wu Ge, 等. 1, 2, 5, 6-Naphthalenediimide-based Conjugated Copolymers Linked by Ethynyl Units[J]. Chinese Journal of Polymer Science, 2017,35(11):1342-1351.

Bing-yong Liu, Xiao-chun Yang, Cong-wu Ge, et al. 1, 2, 5, 6-Naphthalenediimide-based Conjugated Copolymers Linked by Ethynyl Units[J]. Chinese Journal of Polymer Science, 2017, 35(11): 1342-1351.
Bing-yong Liu, Xiao-chun Yang, Cong-wu Ge, 等. 1, 2, 5, 6-Naphthalenediimide-based Conjugated Copolymers Linked by Ethynyl Units[J]. Chinese Journal of Polymer Science, 2017,35(11):1342-1351. DOI： 10.1007/s10118-017-1988-4.

Bing-yong Liu, Xiao-chun Yang, Cong-wu Ge, et al. 1, 2, 5, 6-Naphthalenediimide-based Conjugated Copolymers Linked by Ethynyl Units[J]. Chinese Journal of Polymer Science, 2017, 35(11): 1342-1351. DOI： 10.1007/s10118-017-1988-4.

摘要

Abstract

Two copolymers of

and

comprising benzothiadiazole

4-bis(dodecyloxy)-benzene units were synthesized by Sonogashira coupling polymerization based on ethynyl-linked 1

6-naphthalenediimide. Their thermal

optical

electrochemical as well as charge transport properties were studied. Bottom-gate top-contact organic field-effect transistors (OFETs) measurements of

and

thin films showed different charge transport behaviors.

displayed pure electron transport behaviors in OFETs with electron mobility up to 10

-3

·V

-1

·s

-1

while

exhibited hole transport features. The molecular structure analysis revealed that the structure of

has the acceptor-linker-acceptor' (A-L-A') characteristic

and

possesses the donor-linker-acceptor (D-L-A) structure feature. The results demonstrate that different molecular structures lead them to have distinct charge transport behaviors. In particular

the first pure electron transport copolymer in OFETs based on 1

6-naphthalenediimide is achieved.

关键词

Keywords

references

B.J. Jung , N.J. Tremblay , M.L. Yeh , H.E. Katz . Chem. Mater. , 2011 . 23 568 DOI: 10.1021/cm102296d http://doi.org/10.1021/cm102296d .

J.E. Anthony , A. Facchetti , M. Heeney , S.R. Marder , X. Zhan . Adv. Mater. , 2011 . 22 3876 .

X. Zhan , A. Facchetti , S. Barlow , T.J. Marks , M.A. Ratner , M.R. Wasielewski , S.R. Marder . Adv. Mater. , 2011 . 23 268 DOI: 10.1002/adma.v23.2 http://doi.org/10.1002/adma.v23.2 .

C. Huang , S. Barlow , S.R. Marder . J. Org. Chem. , 2011 . 76 2386 DOI: 10.1021/jo2001963 http://doi.org/10.1021/jo2001963 .

C.L. Wang , W.P. Hu , Y.Q. Liu , D.B. Zhu . Chem. Rev. , 2012 . 112 2208 DOI: 10.1021/cr100380z http://doi.org/10.1021/cr100380z .

H.E. Katz , A.J. Lovinger , J. Johnson , C. Kloc , T. Siegrist , W. Li , Y. Lin , A. Dodabalapur . Nature , 2000 . 404 478 DOI: 10.1038/35006603 http://doi.org/10.1038/35006603 .

X. Gao , C. Di , Y. Hu , X. Yang , H. Fan , F. Zhang , Y. Liu , H. Li , D. Zhu . J. Am. Chem. Soc. , 2010 . 132 3697 DOI: 10.1021/ja910667y http://doi.org/10.1021/ja910667y .

C. Piliego , D. Jarzab , G. Gigli , Z. Chen , A. Facchetti , M.A. Loi . Adv. Mater. , 2009 . 21 1573 DOI: 10.1002/adma.v21:16 http://doi.org/10.1002/adma.v21:16 .

R.P. Ortiz , H. Herrera , R. Blanco , H. Huang , A. Facchetti , T.J. Marks , Y. Zheng , J.L. Segura . J. Am. Chem. Soc. , 2010 . 132 8440 DOI: 10.1021/ja1018783 http://doi.org/10.1021/ja1018783 .

H. Yan , Z. Chen , Y. Zheng , C. Newman , J.R. Quinn , F. Dotz , M. Kastler , A. Facchetti . Nature , 2009 . 457 679 DOI: 10.1038/nature07727 http://doi.org/10.1038/nature07727 .

S. Chopin , F. Chaignon , E. Blart , F. Odobel . J. Mater. Chem. , 2007 . 17 4139 DOI: 10.1039/b704489e http://doi.org/10.1039/b704489e .

F. Chaignon , M. Falkenstrom , S. Karlsson , E. Blart , F. Odobel , L. Hammarstrom . Chem. Commun. , 2007 . 42 64 .

C. Thalacker , C. Röger , F. Würthner . J. Org. Chem. , 2006 . 71 8098 DOI: 10.1021/jo0612269 http://doi.org/10.1021/jo0612269 .

X. Zhan , Z. Tan , B. Domercq , Z. An , X. Zhang , S. Barlow , Y. Li , D. Zhu , B. Kippelen , S.R. Marder . J. Am. Chem. Soc. , 2007 . 129 7246 DOI: 10.1021/ja071760d http://doi.org/10.1021/ja071760d .

Z. Chen , Y. Zheng , H. Yan , A. Facchetti . J. Am. Chem. Soc. , 2009 . 131 8 DOI: 10.1021/ja805407g http://doi.org/10.1021/ja805407g .

M.M. Durban , P.D. Kazarinoff , C.K. Luscombe . Macromolecules , 2010 . 43 6348 DOI: 10.1021/ma100997g http://doi.org/10.1021/ma100997g .

C.J. Kudla , D. Dolfen , K.J. Schottler , J.M. Koenen , D. Breusov , S. Allard , U. Scherf . Macromolecules , 2010 . 43 7864 DOI: 10.1021/ma1014885 http://doi.org/10.1021/ma1014885 .

E. Zhou , J. Cong , Q. Wei , K. Tajima , C. Yang , K. Hashimoto . Angew. Chem. Int. Ed. , 2010 . 50 2799 .

M.S. Monika , H.G. Eliot , R.M. Christopher , L. Vincent , O. Yoann , T. Lars , V. Yana , S. Michael , S. Henning . Chem. Mater. , 2014 . 26 6796 DOI: 10.1021/cm5033578 http://doi.org/10.1021/cm5033578 .

K. Takimiya , I.O.M. Nakano . Chem. Mater. , 2014 . 26 587 DOI: 10.1021/cm4021063 http://doi.org/10.1021/cm4021063 .

C. Dou , X. Long , Z. Ding , Z. Xie , J. Liu , L. Wang . Angew. Chem. Int. Ed. , 2016 . 55 1436 DOI: 10.1002/anie.201508482 http://doi.org/10.1002/anie.201508482 .

X. Long , Z. Ding , C. Dou , J. Zhang , J. Liu , L. Wang . Adv. Mater. , 2016 . 28 6504 DOI: 10.1002/adma.201601205 http://doi.org/10.1002/adma.201601205 .

Z. Ding , X. Long , C. Dou , J. Liu , L. Wang . Chem. Sci. , 2016 . 7 6197 DOI: 10.1039/C6SC01756H http://doi.org/10.1039/C6SC01756H .

J.W. Jung , J.W. Jo , C.C. Chueh , F. Liu , W.H. Jo , T.P. Russell , A.K.Y. Jen . Adv. Mater. , 2015 . 27 3310 DOI: 10.1002/adma.v27.21 http://doi.org/10.1002/adma.v27.21 .

Y.J. Hwang , B.A. Courtright , A.S. Ferreira , S.H. Tolbert , S.A. Jenekhe . Adv. Mater. , 2015 . 27 4578 DOI: 10.1002/adma.v27.31 http://doi.org/10.1002/adma.v27.31 .

L. Gao , Z.G. Zhang , L. Xue , J. Min. , J. Zhang , Z. Wei , Y. Li . Adv. Mater. , 2016 . 28 1884 DOI: 10.1002/adma.201504629 http://doi.org/10.1002/adma.201504629 .

S. Shi , J. Yuan , G. Ding , M. Ford , K. Lu , G. Shi , J. Sun , X. Ling , Y. Li , W. Ma . Adv. Funct. Mater. , 2016 . 26 5669 DOI: 10.1002/adfm.v26.31 http://doi.org/10.1002/adfm.v26.31 .

E. Zhou , J. Cong , K. Hashimoto , K. Tajima . Adv. Mater. , 2013 . 25 6991 DOI: 10.1002/adma.v25.48 http://doi.org/10.1002/adma.v25.48 .

T.J. Hwang , G. Ren , N.M. Murari , S.A. Jenekhe . Macromolecules , 2012 . 45 9056 DOI: 10.1021/ma3020239 http://doi.org/10.1021/ma3020239 .

C. Mu , P. Liu , W. Ma , K. Jiang , J. Zhao , K. Zhang , Z. Chen , Z. Wei , Y. Yi , J. Wang , S. Yang , F. Huang , A. Facchetti , H. Ade , H. Yan . Adv. Mater. , 2014 . 26 7224 DOI: 10.1002/adma.v26.42 http://doi.org/10.1002/adma.v26.42 .

T. Kim , J.H. Kim , T.E. Kang , C. Lee , H. Kang , M. Shin , C. Wang , B. Ma , U. Jeong , T.S. Kim , B.J. Kim . Nat. Commun. , 2015 . 6 8547 DOI: 10.1038/ncomms9547 http://doi.org/10.1038/ncomms9547 .

Z. Li , X. Xu , W. Zhang , X. Meng , W. Ma , A. Yartsev , O. Inganas , M.R. Andersson , R.A. Janssen , E. Wang . J. Am. Chem. Soc. , 2016 . 138 10935 DOI: 10.1021/jacs.6b04822 http://doi.org/10.1021/jacs.6b04822 .

S.C. Chen , Q.K. Zhang , Q.D. Zheng , C.Q. Tang , C.Z. Lu . Chem. Commun. , 2012 . 48 1254 DOI: 10.1039/C2CC15733K http://doi.org/10.1039/C2CC15733K .

Z. Zhao , F.J. Zhang , X. Zhang , X.D. Yang , H.X. Li , X.K. Gao , C.A. Di , D.B. Zhu . Macromolecules , 2013 . 46 7705 DOI: 10.1021/ma4013994 http://doi.org/10.1021/ma4013994 .

Z. Zhao , Z.L. Wang , C.W. Ge , X. Zhang , X.D. Yang , X.K. Gao . Polym. Chem. , 2016 . 7 573 DOI: 10.1039/C5PY01709B http://doi.org/10.1039/C5PY01709B .

Z.J. Li , K. Feng , J. Liu , J. Mei , Y. Li , Q. Peng . J. Mater. Chem. A , 2016 . 4 7372 DOI: 10.1039/C6TA01766E http://doi.org/10.1039/C6TA01766E .

S.C. Chen , Q.D. Zheng , Q.K. Zhang , D.D. Cai , J.Y. Wang , C.Q. Tang , Polym. Sci. J. . Part A:Polym. Chem. , 2013 . 51 1999 DOI: 10.1002/pola.26580 http://doi.org/10.1002/pola.26580 .

S. Zhang , J. Liu , Y.C. Han , L.X. Wang . Macromol. Chem. Phys. , 2017 . DOI: 10.1002/macp.201600606 http://doi.org/10.1002/macp.201600606 .

U.H.F. Bunz . Chem. Rev. , 2000 . 100 1605 DOI: 10.1021/cr990257j http://doi.org/10.1021/cr990257j .

U.H.F. Bunz . Acc. Chem. Res. , 2001 . 34 998 DOI: 10.1021/ar010092c http://doi.org/10.1021/ar010092c .

S.W. Thomas , G.D. Joly , T.M. Swager . Chem. Rev. , 2007 . 107 1339 DOI: 10.1021/cr0501339 http://doi.org/10.1021/cr0501339 .

B. VanVeller , K. Miki , T.M. Swager . Org. Lett. , 2010 . 12 1292 DOI: 10.1021/ol1001768 http://doi.org/10.1021/ol1001768 .

B. Esser , T.M. Swager . Angew. Chem. Int. Ed. , 2010 . 49 8872 DOI: 10.1002/anie.v49.47 http://doi.org/10.1002/anie.v49.47 .

A. Bajaj , O.R. Miranda , R. Phillips , I.B. Kim , D.J. Jerry , U.H.F. Bunz , V.M. Rotello . J. Am. Chem. Soc. , 2009 . 132 1018 .

L.A. Bumm , J.J. Arnold , M.T. Cygan , T.D. Dunbar , T.P. Burgin , L. Jones , D.L. Allara , J.M. Tour , P.S. Weiss . Science , 1996 . 271 1705 DOI: 10.1126/science.271.5256.1705 http://doi.org/10.1126/science.271.5256.1705 .

P. Samori , V. Francke , K. Müllen , J.P. Rabe . Chem. Eur. J. , 1999 . 5 2312 DOI: 10.1002/(SICI)1521-3765(19990802)5:8<>1.0.CO;2-B http://doi.org/10.1002/(SICI)1521-3765(19990802)5:8<>1.0.CO;2-B .

P. Samori , I. Sikharulidze , V. Francke , K. Muüllen , J.P. Rabe . Nanotechnology , 1999 . 10 77 DOI: 10.1088/0957-4484/10/1/015 http://doi.org/10.1088/0957-4484/10/1/015 .

S.L. Lu , M.J. Yang , J. Luo , Y. Cao , F.L. Bai . Synthetic Met. , 2004 . 146 175 DOI: 10.1016/j.synthmet.2004.06.015 http://doi.org/10.1016/j.synthmet.2004.06.015 .

Q.H. Chu , Y. Pang . Macromolecules , 2003 . 36 3848 DOI: 10.1021/ma034028h http://doi.org/10.1021/ma034028h .

J.J. Intemann , S. Emily , E.S. Tlach , B.C. Ewan , M.D. Barnes , C.A. Bhuwalka , A. Cai , M. Shinar , J.R. Shinar , E.L. Jeffries . Macromolecules , 2012 . 45 6888 DOI: 10.1021/ma300821m http://doi.org/10.1021/ma300821m .

K.B. Woody , E.M. Henry , S. Jagtap , D.M. Collard . Macromolecules , 2011 . 44 9118 DOI: 10.1021/ma201347z http://doi.org/10.1021/ma201347z .

B.C. Popere , A.M.D. Pelle , S. Thayumanavan . Macromolecules , 2011 . 44 4767 DOI: 10.1021/ma200839q http://doi.org/10.1021/ma200839q .

S. Kola , J.H. Kim , R. Ireland , M.L. Yeh , K. Smith , W.M. Guo , H.E. Katz . ACS Macro Lett. , 2013 . 2 664 DOI: 10.1021/mz400164s http://doi.org/10.1021/mz400164s .

H.L. Dong , E.J. Wang , S.K. Yan , J.M. Zhang , C.M. Yang , N. Hiroshi , T. Keiichi , W.P. Hu . J. Phys. Chem. B , 2009 . 113 4176 DOI: 10.1021/jp811374h http://doi.org/10.1021/jp811374h .

A. Kokil , I. Shiyanovskaya , K.D. Singer , C. Weder . Synthetic Met. , 2003 . 138 513 DOI: 10.1016/S0379-6779(02)01241-9 http://doi.org/10.1016/S0379-6779(02)01241-9 .

Y.H. Hou , S.G. Yin , Y.S. Chen , A. Yua , Q. Liu , M. Yang , X.J. Wan . Macromolecules , 2008 . 41 3114 DOI: 10.1021/ma702864c http://doi.org/10.1021/ma702864c .

C. Du , W. Li , C. Li , Z. Bo . J.Polym. Sci., Part A:Polym. Chem. , 2013 . 51 383 DOI: 10.1002/pola.26396 http://doi.org/10.1002/pola.26396 .

B.S. Kim , B.W. Ma , V.R. Donuru , H.Y. Liu , J.M.J. Fréchet . Chem. Commun. , 2010 . 46 4148 DOI: 10.1039/b927350f http://doi.org/10.1039/b927350f .

G. Voskerician , C. Weder . Adv. Polym. Sci. , 2005 . 177 209 DOI: 10.1007/b101353 http://doi.org/10.1007/b101353 .

S. Debnath , S. Singh , A. Bedi , K. Krishnamoorthy , S.S. Zade . J.Polym. Sci., Part A:Polym. Chem. , 2016 . 54 1978 DOI: 10.1002/pola.v54.13 http://doi.org/10.1002/pola.v54.13 .

L.P. Anna , K. Yoosaf , H. Traboulsi , J. Mohanraj , T. Seldrum , J. Dumont , A. Minoia , R. Lazzaroni , N. Armaroli , D. Bonifazi . J. Am. Chem. Soc. , 2011 . 133 15412 DOI: 10.1021/ja2011516 http://doi.org/10.1021/ja2011516 .

Y.B. Hu , Y.K. Qin , X.K. Gao , F.J. Zhang , C.A. Di , Z. Zhao , H.X. Li , D.B. Zhu . Org. Lett. , 2012 . 14 292 DOI: 10.1021/ol203059r http://doi.org/10.1021/ol203059r .

X.J. Peng , F.L. Song , E.H. Lu , Y.N. Wang , W. Zhou , J.L. Fan , Y.L. Gao . J. Am. Chem. Soc. , 2005 . 127 4170 DOI: 10.1021/ja043413z http://doi.org/10.1021/ja043413z .

A.C. Benniston , A. Harriman , D. J. Lawrie , A. Mayeux . Phys. Chem. Chem. Phys. , 2004 . 6 51 DOI: 10.1039/B312286G http://doi.org/10.1039/B312286G .

K. Kaneda , T. Arai . Photochem. Photobiol. Sci. , 2003 . 2 402 DOI: 10.1039/B211834N http://doi.org/10.1039/B211834N .

S.A. Jenekhe , J.A. Osaheni . Science , 1994 . 265 765 DOI: 10.1126/science.265.5173.765 http://doi.org/10.1126/science.265.5173.765 .

浏览量

Downloads

CSCD

文章被引用时，请邮件提醒。

Submit

工具集

关联资源

Vapor-Induced Coating Method for Well-Aligned and Uniform Organic Semiconductor Single Crystals

Recent Progress in Donor-Acceptor Type Conjugated Polymers for Organic Field-effect Transistors

A Facile Photo-cross-linking Method for Polymer Gate Dielectrics and Their Applications in Fully Solution Processed Low Voltage Organic Field-effect Transistors on Plastic Substrate

Advances in Polymer-based Circularly Polarized Luminescent Materials

Sequence-encoded Conformation Pathways in Viscoelastic Microphase Separation of Multiblock Copolymers