Synthesis and Properties of Near-Infrared Electrochromic Polymers Containing Diketopyrrolopyrrole,Benzothiadiazole and Thiophene

doi:10.11944/j.issn.1000-0518.2018.02.170045

Chinese Journal of Applied Chemistry ›› 2018, Vol. 35 ›› Issue (2): 165-173.DOI: 10.11944/j.issn.1000-0518.2018.02.170045

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Synthesis and Properties of Near-Infrared Electrochromic Polymers Containing Diketopyrrolopyrrole,Benzothiadiazole and Thiophene

CHEN Xiuhong^a^b,HU Liuyong^a^b,QIAO Wenqiang^a^*(),WANG Zhiyuan^a^*()

^aState Key Laboratory of Polymer Physics and Chemistry,Changchun Institute of Applied Chemistry,Chinese Academy of Sciences,Changchun 130022,China
^bUniversity of Chinese Academy of Sciences,Beijing 100049,China

Received:2017-02-27 Accepted:2017-05-09 Published:2018-02-01 Online:2018-01-29
Contact: QIAO Wenqiang,WANG Zhiyuan
Supported by:
Supported by the National Natural Science Foundation of China(No.21474102, No.21474105)

Abstract

Abstract:

Donor-acceptor type polymers are new electrochromic materials which are tunable and colorfull. However, the electrochromic properties such as optical contrast and stability need to be further improved. Low band gap conjugated polymers containing diketopyrrolopyrrole(DPP), benzothiadiazole(BTZ) and thiophen (T) were synthesized and their electrochromic properties were studied. Four polymers P1~P4 were obtained by adjusting the molar ratio of the three monomers(n(DPP):n(BTZ):n(T)=1:0:1, 1.5:0.5:1, 2:1:1 and 3:2:1, respectively). The absorption and electrochromic properties of the polymers depend on the ratios of DPP, BTZ and T units in the polymers. It was found that these polymers have high optical contrast(ΔT:50%60%) and coloration efficiency(CE:300600 cm²/C) in the near-infrared region. In particular, ΔT of polymer P3 reached the high value of 63% and CE of polymer P4 was 471 cm²/C at 1550 nm. The polymers containing BTZ groups have higher optical contrast at both the near-infrared(NIR) region and the maximum absorption wavelength than that of polymer P1 in which the BTZ content is zero. Polymers containing BTZ unit shows better electrochromic stability, which is attributed to its higher oxidation potential and better electrochemical stability. It provides a new way to design high-performance electrochromic polymers.

Key words: electrochromism, donor-acceptor type polymers, spectroelectrochemistry, optical contrast, coloration efficiency, stability

CHEN Xiuhong, HU Liuyong, QIAO Wenqiang, WANG Zhiyuan. Synthesis and Properties of Near-Infrared Electrochromic Polymers Containing Diketopyrrolopyrrole,Benzothiadiazole and Thiophene[J]. Chinese Journal of Applied Chemistry, 2018, 35(2): 165-173.

References

[1]	Niklasson G A,Granqvist C G.Electrochromics for Smart Windows:Thin Films of Tungsten Oxide and Nickel Oxide, and Devices Based on These[J]. J Mater Chem,2007,17(2):127-156.
[2]	Xun S,LeClair G,Zhang J,et al. Tuning the Electrical and Optical Properties of Dinuclear Ruthenium Complexes for Near Infrared Optical Sensing[J]. Org Lett,2006,8(8):1697-1700.
[3]	Monk P M S,Mortimer R J,Rosseinsky D R. Electrochromism and Electrochromic Devices[M]. Cambridge University Press,2007:395-410.
[4]	Pochorovski I,Diederich F.Development of Redox-Switchable Resorcin[4]arene Cavitands[J]. Acc Chem Res,2014,47(7):2096-2105.
[5]	WANG Bin,WANG Xiaohong,LI Jiuming,et al.Electrochromic Properties of Hybrid Mutilayer Film Based on Pressler Type Polyoxometalate P5W30, Positive Polyelectrolyte and Graphene Oxide[J]. Chinese J Appl Chem,2017,34(2):233-241(in Chinese). 王斌,王晓红,李久明,等. 盘状多酸P5W30/阳离子聚电解质/氧化石墨烯杂化多层膜的电致变色性能[J]. 应用化学,2017,34(2):233-241.
[6]	Gunbas G E,Durmus A,Toppare L.Could Green be Greener? Novel Donor-Acceptor-Type Electrochromic Polymers:Towards Excellent Neutral Green Materials with Exceptional Transmissive Oxidized States for Completion of RGB Color Space[J]. Adv Mater,2008,20(4):691-695.
[7]	Zhang Y,Wang X,Zhang W,et al.A Single-Molecule Multicolor Electrochromic Device Generated Through Medium Engineering[J]. Light-Sci Appl,2015,4(2):249-257.
[8]	Ji L,Dai Y,Yan S,et al.A Fast Electrochromic Polymer Based on TEMPO Substituted Polytriphenylamine[J]. Sci Rep,2016,6:30068-30075.
[9]	Icli M,Pamuk M,Algi F,et al. Donor-Acceptor Polymer Electrochromes with Tunable Colors and Performance[J]. Chem Mater,2010,22(13):4034 4044.
[10]	Shi P,Amb C M,Knott E P,et al.Broadly Absorbing Black to Transmissive Switching Electrochromic Polymers[J]. Adv Mater,2010,22(44):4949-4953.
[11]	Lv X,Li W,Ouyang M,et al.Polymeric Electrochromic Materials with Donor-Acceptor Structure[J]. J Mater Chem C,2017,5(1):12-28.
[12]	Amb C M,Beaujuge P M,Reynolds J R.Spray-Processable Blue-to-Highly Transmissive Switching Polymer Electrochromes via the Donor Acceptor Approach[J]. Adv Mater,2010,22(6):724-728.
[13]	Liu X,Kong L,Zhang Y,et al.Novel Donor-acceptor Type Electrochromic Polymers Based on [1,2,5]Thiadiazolo[3,4-c]pyridine as the Acceptor Unit[J]. Int J Electrochem Sci,2016,11(1):343-358.
[14]	Patra A,Bendikov M,Chand S.Poly(3,4-ethylenedioxyselenophene) and Its Derivatives:Novel Organic Electronic Materials[J]. Acc Chem Res,2014,47(5):1465-1474.
[15]	Li W,Hendriks K H,Wienk M M,et al.Diketopyrrolopyrrole Polymers for Organic Solar Cells[J]. Acc Chem Res,2016,49(1):78-85.
[16]	Sekine C,Tsubata Y,Yamada T,et al. Recent Progress of High Performance Polymer OLED and OPV Materials for Organic Printed Electronics[J]. Sci Technol Adv Mater,2014,15(3):034203(15pp).
[17]	Kerszulis J A,Bulloch R H,Teran N B,et al.Relax:A Sterically Relaxed Donor-Acceptor Approach for Color Tuning in Broadly Absorbing, High Contrast Electrochromic Polymers[J]. Macromolecules,2016,49(17):6350-6359.
[18]	Low J Z,Neo W T,Ye Q,et al.Low Band-Gap Diketopyrrolopyrrole-Containing Polymers for Near Infrared Electrochromic and Photovoltaic Applications[J]. J Poly Sci Part A:Poly Chem,2015,53(10):1287-1295.
[19]	Capan A,Veisi H,Goren A C,et al.Concise Syntheses, Polymers, and Properties of 3-Arylthieno[3,2-b]thiophenes[J]. Macromolecules,2012,45(20):8228-8236.
[20]	Lemasson F,Berton N,Tittmann J,et al.Polymer Library Comprising Fluorene and Carbazole Homo- and Copolymers for Selective Single-Walled Carbon Nanotubes Extraction[J]. Macromolecules,2011,45(2):713-722.
[21]	Li Y,Sun B,Sonar P,et al.Solution Processable Poly(2,5-dialkyl-2,5-dihydro-3,6-di-2-thienyl-pyrrolo[3,4-c]pyrrole-1,4-dione) for Ambipolar Organic Thin Film Transistors[J]. Org Electron,2012,13(9):1606-1613.
[22]	Tourillon G,Garnier G.Structural Effect on the Electrochemical Properties of Polythiophene and Derivatives[J]. J Electroanal Chem,1984,161(1):51-58.
[23]	Sonar P,Williams L,Singh P,et al.A Benzothiadiazole End Capped Donor Acceptor Based Small Molecule for Organic Electronics[J]. Phys Chem Chem Phys,2013,15(40):17064-17069.

Synthesis and Properties of Near-Infrared Electrochromic Polymers Containing Diketopyrrolopyrrole,Benzothiadiazole and Thiophene

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