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
- Chinese Journal of Polymer Science Vol. 35, Issue 11, Pages: 1342-1351(2017)
- 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：
- DOI：10.1007/s10118-017-1988-4
  CLC：
- Received：17 April 2017，
  
  Revised：2017-5-24，
  
  Accepted：01 June 2017，
  
  Published：05 November 2017
- Accepted：
Scan QR Code
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：

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 .

Views

Downloads

CSCD

Alert me when the article has been cited

Submit

Tools

Publicity Resources

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

End-to-End Neuron-inspired Signal Transduction Using Organic Electrochemical Transistors

A Paradigm for BF3 Co-initiated Cationic Polymerization with Low Dispersity: Introducing Acetonitrile and Lowering the Reaction Temperature

Related Author

Yan-Lin Song

Lu-Jing Shao

Sheng-Nan Chen

Yu-Meng Wang

Zheng Li

Xiao-Song Shi

Hao-Ran Long

Lang Jiang

Related Institution

State Key Laboratory of Superlattices and Microstructures, Institute of Semiconductors, Chinese Academy of Sciences

Key Laboratory of Organic Solids, Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences

State Key Laboratory of Trauma, Burn and Combined Injury, Institute of Burn Research, Southwest Hospital, Army Medical University

School of Chemical Science, University of Chinese Academy of Sciences

Key Laboratory of Green Printing, Institute of Chemistry, Chinese Academy of Sciences, Research Center of Nanomaterials for Green Printing Technology, Beijing National Laboratory for Molecular Sciences (BNLMS)

⁰