Skip to main content
Disciplines
Automotive Business IT + Informatics Construction + Real Estate Electrical Engineering + Electronics Energy + Sustainability Insurance + Risk Finance + Banking Management + Leadership Marketing + Sales Mechanical Engineering + Materials
Events
DE
EN
Books
Journals
Topic Page
Marketing
Start single access now
Access for companies
EXTENDED SEARCH
Log in
Top
Journal of Materials Science
Published in: Journal of Materials Science 17/2015

01-09-2015 | Original Paper

Red-to-black electrochromism of 4,9-dihydro-s-indaceno[1,2-b:5,6-b’]dithiophene-embedded conjugated polymers

Authors: Ching Mui Cho, Qun Ye, Wei Teng Neo, Tingting Lin, Jing Song, Xuehong Lu, Jianwei Xu

Published in: Journal of Materials Science | Issue 17/2015

Log in

Activate our intelligent search to find suitable subject content or patents.

search-config
loading …

Abstract

A series of 4,9-dihydro-s-indaceno[1,2-b:5,6-b′]dithiophene-based conjugated polymers with 3,4-bis(dodecyloxy)thiophene, 3,3-bis((dodecyloxy)methyl)-3,4-dihydro-2H-thieno[3,4-b] [1, 4] dioxepine and 3,4-ethylenedioxythiophene as co-monomers were synthesized via Stille coupling reaction in more than 50 % yields. These polymers possess relatively high number-average molecular weights of 14,900–21,000 g mol−1 and exhibit good solubility in common organic solvents. The physical and electrochemical properties of these polymers were studied, and the polymers showed optical bandgap between 2.04 and 2.08 eV. Electrochromic devices showed a rare and reversible colour change between dark red at neutral state and black at oxidized state with optical switching contrast ratios of up to 50 % at λ max and 90 % at 1500 nm in the visible and NIR regions, respectively.

Graphical abstract

4,9-dihydro-s-indaceno[1,2-b:5,6-b’]dithiophene-based conjugated polymers showing rare and reversible colour change between dark red at neutral state and black at oxidized state were synthesized via Stille coupling. These polymers possess high optical contrast in both the visible and NIR regions.
previous article Process investigating and modelling for the self-polymerization of toluene diisocyanate (TDI)-based polyurethane prepolymer
next article Facile synthesis and photocatalytic performance of Mg2SnO4/SnO2 heterostructures

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

inform now

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

inform now
Appendix
Available only for authorised users
Literature
1.
Cheng Y-J, Yang S-H, Hsu C-S (2009) Synthesis of conjugated polymers for organic solar cell applications. Chem Rev 109(11):5868–5923CrossRef
2.
Duan CH, Huang F, Cao Y (2012) Recent development of push-pull conjugated polymers for bulk-heterojunction photovoltaics: rational design and fine tailoring of molecular structures. J Mater Chem 22(21):10416–10434CrossRef
3.
Guenes S, Neugebauer H, Sariciftci NS (2007) Conjugated polymer-based organic solar cells. Chem Rev 107(4):1324–1338CrossRef
4.
Boudreault P-LT, Najari A, Leclerc M (2011) Processable low-bandgap polymers for photovoltaic applications. Chem Mater 23(3):456–469CrossRef
5.
Kulkarni AP, Tonzola CJ, Babel A, Jenekhe SA (2004) Electron transport materials for organic light-emitting diodes. Chem Mater 16(23):4556–4573CrossRef
6.
Bernius MT, Inbasekaran M, O’Brien J, Wu WS (2000) Progress with light-emitting polymers. Adv Mater 12(23):1737–1750CrossRef
7.
Kamtekar KT, Monkman AP, Bryce MR (2010) Recent advances in white organic light-emitting materials and devices (WOLEDs). Adv Mater 22(5):572–582CrossRef
8.
Lu K, Liu Y (2010) Polythiophenes: important conjugated semiconducting polymers for organic field-effect transistors. Curr Org Chem 14(18):2017–2033CrossRef
9.
Wang CL, Dong HL, Hu WP, Liu YQ, Zhu DB (2012) Semiconducting pi-conjugated systems in field-effect transistors: a material odyssey of organic electronics. Chem Rev 112(4):2208–2267CrossRef
10.
Mei C-Y, Liang L, Zhao F-G, Wang J-T, Yu L-F, Li Y-X, Li W-S (2013) A family of donor-acceptor photovoltaic polymers with fused 4,7-dithienyl-2,1,3-benzothiadiazole units: effect of structural fusion and side chains. Macromolecules 46(19):7920–7931CrossRef
11.
Biniek L, Schroeder BC, Nielsen CB, McCulloch I (2012) Recent advances in high mobility donor-acceptor semiconducting polymers. J Mater Chem 22(30):14803–14813CrossRef
12.
Beaujuge PM, Reynolds JR (2010) Color control in π-conjugated organic polymers for use in electrochromic devices. Chem Rev 110(1):268–320CrossRef
13.
Balan A, Baran D, Toppare L (2011) Benzotriazole containing conjugated polymers for multipurpose organic electronic applications. Polym Chem 2(5):1029–1043CrossRef
14.
15.
Thakur VK, Ding G, Ma J, Lee PS, Lu X (2012) Hybrid materials and polymer electrolytes for electrochromic device applications. Adv Mater 24(30):4071–4096CrossRef
16.
Rosseinsky DR, Mortimer RJ (2001) Electrochromic systems and the prospects for devices. Adv Mater 13(11):783–793CrossRef
17.
Arias AC, MacKenzie JD, McCulloch I, Rivnay J, Salleo A (2010) Materials and applications for large area electronics: solution-based approaches. Chem Rev 110(1):3–24CrossRef
18.
Argun AA, Aubert P-H, Thompson BC, Schwendeman I, Gaupp CL, Hwang J, Pinto NJ, Tanner DB, MacDiarmid AG, Reynolds JR (2004) Multicolored electrochromism in polymers: structures and devices. Chem Mater 16(23):4401–4412CrossRef
19.
Krebs FC (2008) Electrochromic displays: the new black. Nat Mater 7(10):766–767CrossRef
20.
Yang Y, Li G (2015) Progress in high-efficient solution process organic photovoltaic devices. Springer, BerlinCrossRef
21.
Christoph B, Ullrich S, Vladimir D (2014) Organic photovoltaics: materials, device physics, and manufacturing technologies, 2nd Edn. Wiley-VCH, Hoboken
22.
Liu X, Li Q, Li Y, Gong X, Su SJ, Cao Y (2014) Indacenodithiophene core-based small molecules with tunable side chains for solution-processed bulk heterojunction solar cells. J Mater Chem A 2(11):4004–4013CrossRef
23.
Dang D, Chen W, Himmelberger S, Tao Q, Lundin A, Yang R, Zhu W, Salleo A, Müller C, Wang E (2014) Enhanced photovoltaic performance of indacenodithiophene-quinoxaline copolymers by side-chain modulation. Adv Energy Mater 4(15):1400680CrossRef
24.
Chen K-S, Zhang Y, Yip H-L, Sun Y, Davies JA, Ting C, Chen C-P, Jen AKY (2011) Highly efficient indacenodithiophene-based polymeric solar cells in conventional and inverted device configurations. Org Electron 12(5):794–801CrossRef
25.
Sun Y, Chien S-C, Yip H-L, Chen K-S, Zhang Y, Davies JA, Chen F-C, Lin B, Jen AKY (2012) Improved thin film morphology and bulk-heterojunction solar cell performance through systematic tuning of the surface energy of conjugated polymers. J Mater Chem 22(12):5587–5595CrossRef
26.
Yong W, Zhang M, Xin X, Li Z, Wu Y, Guo X, Yang Z, Hou J (2013) Solution-processed indacenodithiophene-based small molecule for bulk heterojunction solar cells. J Mater Chem A 1(45):14214–14220CrossRef
27.
Zhang Y, Zou J, Yip H-L, Chen K-S, Zeigler DF, Sun Y, Jen AKY (2011) Indacenodithiophene and quinoxaline-based conjugated polymers for highly efficient polymer solar cells. Chem Mater 23(9):2289–2291CrossRef
28.
Bronstein H, Frost JM, Hadipour A, Kim Y, Nielsen CB, Ashraf RS, Rand BP, Watkins S, McCulloch I (2013) Effect of fluorination on the properties of a donor-acceptor copolymer for use in photovoltaic cells and transistors. Chem Mater 25(3):277–285CrossRef
29.
Bronstein H, Leem DS, Hamilton R, Woebkenberg P, King S, Zhang W, Ashraf RS, Heeney M, Anthopoulos TD, de Mello J, McCulloch I (2011) Indacenodithiophene-co-benzothiadiazole copolymers for high performance solar cells or transistors via alkyl chain optimization. Macromolecules 44(17):6649–6652CrossRef
30.
Sun Y, Chien S-C, Yip H-L, Zhang Y, Chen K-S, Zeigler DF, Chen F-C, Lin B, Jen AKY (2011) Chemically doped and cross-linked hole-transporting materials as an efficient anode buffer layer for polymer solar cells. Chem Mater 23(22):5006–5015CrossRef
31.
Chen C-P, Chan S-H, Chao T-C, Ting C, Ko B-T (2008) Low-bandgap poly(thiophene-phenylene-thiophene) derivatives with broaden absorption spectra for use in high-performance bulk-heterojunction polymer solar cells. J Am Chem Soc 130(38):12828–12833CrossRef
32.
Wang M, Hu X, Liu L, Duan C, Liu P, Ying L, Huang F, Cao Y (2013) Design and synthesis of copolymers of indacenodithiophene and naphtho 1,2-c:5,6-c bis(1,2,5-thiadiazole) for polymer solar cells. Macromolecules 46(10):3950–3958CrossRef
33.
Zhang Y, Zou J, Yip H-L, Chen K-S, Davies JA, Sun Y, Jen AKY (2011) Synthesis, characterization, charge transport, and photovoltaic properties of dithienobenzoquinoxaline- and dithienobenzopyridopyrazine-based conjugated polymers. Macromolecules 44(12):4752–4758CrossRef
34.
Chan S-H, Chen C-P, Chao T-C, Ting C, Lin C-S, Ko B-T (2008) Synthesis, characterization, and photovoltaic properties of novel semiconducting polymers with thiophene-phenylene-thiophene (TPT) as coplanar units. Macromolecules 41(15):5519–5526CrossRef
35.
Zhang W, Smith J, Watkins SE, Gysel R, McGehee M, Salleo A, Kirkpatrick J, Ashraf S, Anthopoulos T, Heeney M, McCulloch I (2010) Indacenodithiophene semiconducting polymers for high-performance, air-stable transistors. J Am Chem Soc 132(33):11437–11439CrossRef
36.
Neo WT, Ye Q, Lin TT, Chua SJ, Xu J (2015) 4,9-Dihydro-s-indaceno[1,2-b:5,6-b’]dithiophene-embedded electrochromic conjugated polymers with high coloration efficiency and fast coloration time. Sol Energy Mater Sol Cells 136:92–99CrossRef
37.
Gunbas G, Toppare L (2012) Electrochromic conjugated polyheterocycles and derivatives-highlights from the last decade towards realization of long lived aspirations. Chem Commun 48(8):1083–1101CrossRef
38.
Gaupp CL, Zong K, Schottland P, Thompson BC, Thomas CA, Reynolds JR (2000) Poly(3,4-ethylenedioxypyrrole): organic electrochemistry of a highly stable electrochromic polymer. Macromolecules 33(4):1132–1133CrossRef
39.
Gaupp CL, Welsh DM, Reynolds JR (2002) Poly(ProDOT-Et2): a high-contrast, high-coloration efficiency electrochromic polymer. Macromol Rapid Commun 23(15):885–889CrossRef
40.
Giglioti M, Trivinho-Strixino F, Matsushima JT, Bulhões LOS, Pereira EC (2004) Electrochemical and electrochromic response of poly(thiophene-3-acetic acid) films. Sol Energy Mater Sol Cells 82(3):413–420CrossRef
41.
Shin H, Kim Y, Bhuvana T, Lee J, Yang X, Park C, Kim E (2012) Color combination of conductive polymers for black electrochromism. ACS Appl Mater Interf 4(1):185–191CrossRef
42.
Ah CS, Song J, Cho SM, Kim T-Y, Kim HN, Oh JY, Chu HY, Ryu H (2015) Double-layered black electrochromic device with a single electrode and long-term bistability. Bull Korean Chem Soc 36(2):548–552
43.
Neo WT, Cho CM, Song J, Chin JM, Wang X, He C, Chan HSO, Xu J (2013) Solution-processable multicolored dithienothiophene-based conjugated polymers for electrochromic applications. Eur Poly J 49(9):2446–2456CrossRef
44.
Aubert P-H, Knipper M, Groenendaal L, Lutsen L, Manca J, Vanderzande D (2004) Copolymers of 3,4-Ethylenedioxythiophene and of pyridine alternated with fluorene or phenylene units: synthesis, optical properties, and devices. Macromolecules 37(11):4087–4098CrossRef
45.
Sun Y, Chien S-C, Yip H-L, Zhang Y, Chen K-S, Zeigler DF, Chen F-C, Lin B, Jen AKY (2011) High-mobility low-bandgap conjugated copolymers based on indacenodithiophene and thiadiazolo[3,4-c]pyridine units for thin film transistor and photovoltaic applications. J Mater Chem 21(35):13247–13255CrossRef
46.
Beaujuge PM, Ellinger S, Reynolds JR (2008) Spray processable green to highly transmissive electrochromics via chemically polymerizable donor-acceptor heterocyclic pentamers. Adv Mater 20(14):2772–2776CrossRef
47.
Ye Q, Chang J, Huang KW, Shi X, Wu J, Chi C (2013) Cyanated diazatetracene diimides with ultrahigh electron affinity for n-channel field effect transistors. Organ Lett 15(6):1194–1197CrossRef
48.
Ye Q, Neo WT, Lin T, Song J, Yan H, Zhou H, Shah KW, Chua SJ, Xu J (2015) Pyrrolophthalazine dione (PPD)-based donor-acceptor polymers as high performance electrochromic materials. Polym Chem 6:1487–1494CrossRef
Metadata
Title
Red-to-black electrochromism of 4,9-dihydro-s-indaceno[1,2-b:5,6-b’]dithiophene-embedded conjugated polymers
Authors
Ching Mui Cho
Qun Ye
Wei Teng Neo
Tingting Lin
Jing Song
Xuehong Lu
Jianwei Xu
Publication date
01-09-2015
Publisher
Springer US
Published in
Journal of Materials Science / Issue 17/2015
Print ISSN: 0022-2461
Electronic ISSN: 1573-4803
DOI
https://doi.org/10.1007/s10853-015-9135-5

Other articles of this Issue 17/2015

Journal of Materials Science 17/2015 Go to the issue

Original Paper

An examination of strain ageing in a Mg–Y–Zn alloy containing Gd

Original Paper

Internal strains between grains during creep deformation of an austenitic stainless steel

Original Paper

Vanadium oxide films deposited on sapphire substrate with in situ AlN stress layer: structural, electric, and optical properties

Original Paper

Preparation and characterization of ammonium-functionalized polysulfone/Al2O3 composite membranes

Review

Electric double-layer transistors: a review of recent progress

Original Paper

Experimental investigation and thermodynamic assessment of the Al–Ca–Ti system

Premium Partners

    Image Credits