Microwave-assisted One-pot Three-component Polymerization of Alkynes, Aldehydes and Amines toward Amino-functionalized Optoelectronic Polymers

Tao Jia; Nan-nan Zheng; Wan-qing Cai; Jie Zhang; Lei Ying; Fei Huang; Yong Cao

doi:10.1007/s10118-017-1890-0

Your Location：

Home >

Browse articles >

Microwave-assisted One-pot Three-component Polymerization of Alkynes, Aldehydes and Amines toward Amino-functionalized Optoelectronic Polymers

Papers | Updated：2021-02-18

- Microwave-assisted One-pot Three-component Polymerization of Alkynes, Aldehydes and Amines toward Amino-functionalized Optoelectronic Polymers
- Chinese Journal of Polymer Science Vol. 35, Issue 2, Pages: 269-281(2017)
- Affiliations：
  
  Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640, China
- Author bio：
  
  Fei Huang (黄飞), E-mail:msfhuang@scut.edu.cn
- Funds：
- DOI：10.1007/s10118-017-1890-0
  CLC：
- Received：30 September 2016，
  
  Revised：2016-11-2，
  
  Accepted：03 November 2016，
  
  Published：2017-02
- Accepted：
Scan QR Code
Tao Jia, Nan-nan Zheng, Wan-qing Cai, et al. Microwave-assisted One-pot Three-component Polymerization of Alkynes, Aldehydes and Amines toward Amino-functionalized Optoelectronic Polymers[J]. Chinese Journal of Polymer Science, 2017, 35(2): 269-281.
DOI：

Tao Jia, Nan-nan Zheng, Wan-qing Cai, et al. Microwave-assisted One-pot Three-component Polymerization of Alkynes, Aldehydes and Amines toward Amino-functionalized Optoelectronic Polymers[J]. Chinese Journal of Polymer Science, 2017, 35(2): 269-281. DOI： 10.1007/s10118-017-1890-0.

摘要

Abstract

We present a microwave-assisted one-pot polymerization with three-components of alkynes

aldehydes and amines for the synthesis of new amino-functionalized optoelectronic polymers. The polymerization of diynes (

)

dialdehydes (

and

) and dibenzylamine catalyzed by InCl

was carried out smoothly within 1 h under microwave radiation

yielding four soluble polymers with high molecular weights. The resulting polymers

and

could be easily dissolved in alcohol and thus utilized as the cathode interlayer for polymer solar cells (PSCs). Compared with the control device

the PSCs with

and

as the cathode interlayer and PTB7-Th:PC

BM as the photoactive layer exhibited significantly higher power conversion efficiencies (PCEs) of 9.49% and 9.16%

respectively. These results suggest that this polycoupling reaction is an efficient approach to construct three-component polymers for the practical applications.

关键词

Keywords

references

E. Ruijter , R. Scheffelaar , R.V.A. Orru , Chem. Angew. . Int. Ed. , 2011 . 50 6234 DOI: 10.1002/anie.201006515 http://doi.org/10.1002/anie.201006515 .

A. Domling , I. Ugi , Chem. Angew. . Int. Ed. , 2000 . 39 3168 http://onlinelibrary.wiley.com/doi/10.1002/chin.200039265/full http://onlinelibrary.wiley.com/doi/10.1002/chin.200039265/full , .

R. Kakuchi , Chem. Angew. . Int. Ed. , 2014 . 53 46 DOI: 10.1002/anie.v53.1 http://doi.org/10.1002/anie.v53.1 .

B.H. Rotstein , S. Zaretsky , V. Rai , A.K. Yudin . Chem. Rev. , 2014 . 114 8323 DOI: 10.1021/cr400615v http://doi.org/10.1021/cr400615v .

D.M. D'Souza , T.J.J. Mueller . Chem. Soc. Rev. , 2007 . 36 1095 DOI: 10.1039/B608235C http://doi.org/10.1039/B608235C .

A.R. Siamaki , M. Sakalauskas , B.A. Arndtsen , Chem. Angew. . Int. Ed. , 2011 . 50 6552 DOI: 10.1002/anie.v50.29 http://doi.org/10.1002/anie.v50.29 .

B.B. Toure , D.G. Hall . Chem. Rev. , 2009 . 109 4439 DOI: 10.1021/cr800296p http://doi.org/10.1021/cr800296p .

M. Teiber , T.J.J. Mueller . Chem. Commun. , 2012 . 48 2080 DOI: 10.1039/c2cc17548g http://doi.org/10.1039/c2cc17548g .

Y. Zhang , P. Li , M. Wang , L. Wang . J. Org. Chem. , 2009 . 74 4364 DOI: 10.1021/jo900507v http://doi.org/10.1021/jo900507v .

N. Thanh Binh , T. Minh Quan , L. Ermolenko , A. Al-Mourabit . Org. Lett. , 2014 . 16 310 DOI: 10.1021/ol403345e http://doi.org/10.1021/ol403345e .

R. Dhawan , R.D. Dghaym , B.A. Arndtsen . J. Am. Chem. Soc. , 2003 . 125 1474 DOI: 10.1021/ja027474d http://doi.org/10.1021/ja027474d .

J.G. Rudick , Sci. J. Polym. . Part A:Polym. Chem. , 2013 . 51 3985 DOI: 10.1002/pola.26808 http://doi.org/10.1002/pola.26808 .

G. Frapper , C. Bachmann , Y. Gu , R.C. de Sousa , F. Jerome . Phys. Chem. Chem. Phys. , 2011 . 13 628 DOI: 10.1039/B927015A http://doi.org/10.1039/B927015A .

R. Kakuchi , P. Theato . ACS Macro Lett. , 2013 . 2 419 DOI: 10.1021/mz400144q http://doi.org/10.1021/mz400144q .

H. Kim , T.L. Choi . ACS Macro Lett. , 2014 . 3 791 DOI: 10.1021/mz5003239 http://doi.org/10.1021/mz5003239 .

E. Ihara , Y. Hara , T. Itoh , K. Inoue . Macromolecules , 2011 . 44 5955 DOI: 10.1021/ma201037p http://doi.org/10.1021/ma201037p .

W. Li , X. Wu , Z. Zhao , A. Qin , R. Hu , B.Z. Tang . Macromolecules , 2015 . 48 7747 DOI: 10.1021/acs.macromol.5b02193 http://doi.org/10.1021/acs.macromol.5b02193 .

Y. Liu , M. Gao , J.W.Y. Lam , R. Hu , B.Z. Tang . Macromolecules , 2014 . 47 4908 DOI: 10.1021/ma501477w http://doi.org/10.1021/ma501477w .

Z. Zhang , Y.Z. You , D.C. Wu , C.Y. Hong . Macromolecules , 2015 . 48 3414 DOI: 10.1021/acs.macromol.5b00463 http://doi.org/10.1021/acs.macromol.5b00463 .

C. Zheng , H. Deng , Z. Zhao , A. Qin , R. Hu , B.Z. Tang . Macromolecules , 2015 . 48 1941 DOI: 10.1021/acs.macromol.5b00175 http://doi.org/10.1021/acs.macromol.5b00175 .

O. Kreye , C. Trefzger , A. Sehlinger , M.A.R. Meier . Macromol. Chem. Phys. , 2014 . 215 2207 DOI: 10.1002/macp.v215.22 http://doi.org/10.1002/macp.v215.22 .

L. Yang , Z. Zhang , B. Cheng , Y. You , D. Wu , C. Hong . Sci. China Chem. , 2015 . 58 1734 DOI: 10.1007/s11426-015-5448-0 http://doi.org/10.1007/s11426-015-5448-0 .

O. Kreye , T. Toth , M.A.R. Meier . J. Am. Chem. Soc. , 2011 . 133 1790 DOI: 10.1021/ja1113003 http://doi.org/10.1021/ja1113003 .

I.H. Lee , H. Kim , T.L. Choi . J. Am. Chem. Soc. , 2013 . 135 3760 DOI: 10.1021/ja312592e http://doi.org/10.1021/ja312592e .

H. Deng , R. Hu , E. Zhao , C.Y.K. Chan , J.W.Y. Lam , B.Z. Tang . Macromolecules , 2014 . 47 4920 DOI: 10.1021/ma501190g http://doi.org/10.1021/ma501190g .

C.J. Li , C. Wei . Chem. Commun. , 2002 . 268 http://www.ncbi.nlm.nih.gov/pubmed/12010027 http://www.ncbi.nlm.nih.gov/pubmed/12010027 , .

C.Y.K. Chan , N.W. Tseng , J.W.Y. Lam , J. Liu , R.T.K. Kwok , B.Z. Tang . Macromolecules , 2013 . 46 3246 DOI: 10.1021/ma4005346 http://doi.org/10.1021/ma4005346 .

E. Chauveau , C. Marestin , R. Mercier . Polymer , 2014 . 55 6435 DOI: 10.1016/j.polymer.2014.10.042 http://doi.org/10.1016/j.polymer.2014.10.042 .

H.M. Hugel . Molecules , 2009 . 14 4936 DOI: 10.3390/molecules14124936 http://doi.org/10.3390/molecules14124936 .

F. Huang , H.B. Wu , D. Wang , W. Yang , Y. Cao . Chem. Mater. , 2004 . 16 708 DOI: 10.1021/cm034650o http://doi.org/10.1021/cm034650o .

J. Wang , K. Lin , K. Zhang , X.F. Jiang , K. Mahmood , L. Ying , F. Huang , Y. Cao . Adv. Energy Mater. , 2016 . 6 http://onlinelibrary.wiley.com/doi/10.1002/aenm.201670065/full http://onlinelibrary.wiley.com/doi/10.1002/aenm.201670065/full , .

J. Lu , W. Cai , G. Zhang , S. Liu , L. Ying , F. Huang . Acta Chimica Sinica , 2015 . 73 1153 DOI: 10.6023/A15080546 http://doi.org/10.6023/A15080546 .

Y. Zhu , S. Guang , H. Xu , X. Su , X. Liu . J. Mater. Chem. C , 2013 . 1 5277 DOI: 10.1039/c3tc30597j http://doi.org/10.1039/c3tc30597j .

Q. Xu , L. An , M. Yu , S. Wang . Macromol. Rapid Commun. , 2008 . 29 390 DOI: 10.1002/(ISSN)1521-3927 http://doi.org/10.1002/(ISSN)1521-3927 .

T. Bura , R. Ziessel . Tetrahedron Lett. , 2010 . 51 2875 DOI: 10.1016/j.tetlet.2010.03.095 http://doi.org/10.1016/j.tetlet.2010.03.095 .

J.R. Sommer , A.H. Shelton , A. Parthasarathy , I. Ghiviriga , J.R. Reynolds , K.S. Schanze . Chem. Mater. , 2011 . 23 5296 DOI: 10.1021/cm202241e http://doi.org/10.1021/cm202241e .

J. Fang , B.H. Wallikewitz , F. Gao , G. Tu , C. Muller , G. Pace , R.H. Friend , W.T. Huck . J. Am. Chem. Soc. , 2011 . 133 683 DOI: 10.1021/ja108541z http://doi.org/10.1021/ja108541z .

Y. Xing , C. Sun , H.L. Yip , G.C. Bazan , F. Huang , Y. Cao . Nano Energy , 2016 . 26 7 DOI: 10.1016/j.nanoen.2016.04.057 http://doi.org/10.1016/j.nanoen.2016.04.057 .

Z.H. Wu , C. Sun , S. Dong , X.F. Jiang , S.P. Wu , H.B. Wu , H.L. Yip , F. Huang , Y. Cao . J. Am. Chem. Soc. , 2016 . 138 2004 DOI: 10.1021/jacs.5b12664 http://doi.org/10.1021/jacs.5b12664 .

Views

Downloads

CSCD

Alert me when the article has been cited

Submit

Tools

Publicity Resources

End-group and Side-chain Dual-engineering of Selenium-fused Acceptors for 20.08% Efficiency Polymer Solar Cells with Low Energy Loss

A Simple Building Block with Noncovalently Conformational Locks towards Constructing Low-Cost and High-Performance Nonfused Ring Electron Acceptors

ZnO Surface Passivation with Glucose Enables Simultaneously Improving Efficiency and Stability of Inverted Polymer: Non-fullerene Solar Cells

Advances in Polymer-based Circularly Polarized Luminescent Materials

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

Related Author

Wen-Yan Su

Hao-Yu Su

Xu-Min Zhou

Kai Xiang

Chen-Yang Dong

Teng-Fei Li

Shu-Juan Liu

Tao Sun

Related Institution

College of Polymer Science and Engineering, National Key Laboratory of Advanced Polymer Materials, Sichuan University

College of Materials and Energy, Guang’an Institute of Technology, Guang’an

School of Materials Science and Engineering, Shaanxi Normal University

Xi’an Key Laboratory of Liquid Crystal and Organic Photovoltaic Materials, Xi’an Modern Chemistry Research Institute

State Key Laboratory of Mechanical Behavior of Materials, Xi’an Jiaotong University

⁰