Polyalkylthiophene-containing electron donor and acceptor heteroaromatic bicycles: Synthesis, photo-physical, and electroluminescent properties

Journal of Materials Science

Volumn 49, Issue 6, 2014, Pages 2456-2464

  Palai, Akshaya K ^a,c   Kumar, Amit ^b,c   Shashidhara, K ^a   Mishra, Sarada P ^a  

^a NAVAL MATERIALS RESEARCH LABORATORY   (India)

^b NATIONAL PHYSICAL LABORATORY   (India)

^c Konkuk University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROFORM SOLUTIONS; ELECTRO-LUMINESCENT; ELECTROLUMINESCENT PROPERTIES; HIGH MOLECULAR WEIGHT; POLYMER LIGHT EMITTING DIODE; RED PHOTOLUMINESCENCE; STILLE CROSS-COUPLING; SYNTHESIS AND CHARACTERIZATIONS;

BICYCLES; IONIZATION POTENTIAL; LIGHT EMITTING DIODES; LUMINESCENCE; MOLECULAR WEIGHT;

POLYMERS;

EID: 84893642565     PISSN: 00222461     EISSN: 15734803     Source Type: Journal    
DOI: 10.1007/s10853-013-7921-5     Document Type: Article

References (40)

1. Dang MT, Hirsch L, Wantz G, Wuest JD (2013) Controlling the morphology and performance of bulk heterojunctions in solar cells. Lessons learned from the benchmark poly(3-hexylthiophene):[6,6]-phenyl-C61-butyric acid methyl ester system. Chem Rev 113:3734-3765
2. Yang C, Song H-S, Liu D-B (2013) Pure blue light-emitting fluorene-based conjugated polymer with excellent thermal, photophysical, and electroluminescent properties. J Mater Sci 48:6719-6727. doi: 10.1007/s10853-013-7473-8
3. Dkhila SB, Bourguiga R, Davenas J, Cornu D (2012) Influence of the polymer matrix on the efficiency of hybrid solar cells based on silicon nanowires. Mater Sci Eng B 177:173-179
4. Grimsdale AC, Chan KL, Martin RE, Jokisz PG, Holmes AB (2009) Synthesis of light-emitting conjugated polymers for applications in electroluminescent devices. Chem Rev 109:897-1091
5. Cheng Y-J, Yang S-H, Hsu C-S (2009) Synthesis of conjugated polymers for organic solar cell applications. Chem Rev 109:5868-5923
6. Forrest SR, Thompson ME (2007) Introduction: organic electronics and optoelectronics. Chem Rev 107:923-925
7. Sondergaard RR, Hosel M, Krebs FC (2013) Roll-to-roll fabrication of large area functional organic materials. J Polym Sci B 51:16-34
8. Lanzi M, DiNicola FP, Livi M, Paganin L, Cappelli F, Pierini F (2013) Synthesis and characterization of conjugated polymers for the obtainment of conductive patterns through laser tracing. J Mater Sci 48:3877-3893. doi: 10.1007/s10853-013-7204-1
9. Lanzi M, Paganin L, Errani F (2012) Synthesis, characterization and photovoltaic properties of a new thiophene-based double-cable polymer with pendent fullerene group. Polymer 53:2134-2145
10. Chen CH, Hsieh CH, Dubosc M, Cheng YJ, Hsu CS (2010) Synthesis and characterization of bridged bithiophene-based conjugated polymers for photovoltaic applications: acceptor strength and ternary blends. Macromolecules 43:697-708
11. Palai AK, Mishra SP, Kumar A, Srivastava R, Kamalasanan MN, Patri M (2010) Synthesis and characterization of red-emitting poly(aryleneethynylene)s based on 2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1, 4(2h,5h)-dione (DPP). Macromol Chem Phys 211:1043-1053
12. Liu J, Zhang R, Sauve G, Kowalewski T, McCullough RD (2008) Highly disordered polymer field effect transistors: N-alkyl dithieno[3,2-b:2′, 3′-d]pyrrole based copolymers with surprisingly high charge carrier mobilities. J Am Chem Soc 130:13167-13176
13. Hwang YJ, Kim FS, Xin H, Jenekhe SA (2012) New thienothiadiazole-based conjugated copolymers for electronics and optoelectronics. Macromolecules 45:3732-3739
14. Mishra SP, Palai AK, Srivastava R, Kamalasanan MN, Patri M (2009) Dithieno[3,2-b:2′,3′-d]pyrrole-alkylthiophene-benzo[c][1,2,5] thiadiazole-based highly stable and low band gap polymers for polymer light-emitting diodes. J Polym Sci Part A 47:6514-6525
15. Intemann JJ, Hellerich ES, Tlach BC, Ewan MD, Barnes CA, Bhuwalka A, Cai M, Shinar J, Shinar R, Jeffries-EL M (2012) Altering the conjugation pathway for improved performance of benzobisoxazole-based polymer guest emitters in polymer light-emitting diodes. Macromolecules 45:6888-6897
16. Tamura K, Shiotsuki M, Kobayashi N, Masuda T, Sanda F (2009) Synthesis and properties of conjugated polymers containing 3,9- and 2,9-linked carbazole units in the main chain. J Polym Sci Part A 47:3506-3517
17. Blouin N, Leclerc M (2008) Poly(2,7-carbazole)s: structure-property relationships. Acc Chem Res 41:1110-1119
18. Ogawa K, Rasmussen SC (2006) N-Functionalized poly(dithieno[3,2-b:2',3'- d]pyrrole)s: highly fluorescent materials with reduced band gaps. Macromolecules 39:1771-1778
19. Shahid M, Ashraf RS, Klemm E, Sensfuss S (2006) Synthesis and properties of novel low-band-gap thienopyrazine-based poly(heteroarylenevinylene)s. Macromolecules 39:7844-7853
20. Poelking C, Cho E, Malafeev A, Ivanov V, Kremer K, Risko C, Brédas J-L, Andrienko D (2013) Characterization of charge-carrier transport in semicrystalline polymers: electronic couplings site energies and charge-carrier dynamics in poly(bithiophene-alt-thienothiophene) [PBTTT]. J Phys Chem C 117:1633-1640
21. Bijleveld JC, Verstrijden RAM, Wienk MM, Janssen RAJ (2011) Copolymer of diketopyrrolopyrole and thienothiophene for photovaltaic cells. J Mater Chem 21:9224
22. McCulloch I, Heeney M, Chabinyc ML, DeLongchamp D, Kline RJ, Colle M, Duffy W, Fischer D, Gundlach D, Hamadani B, Hamilton R, Richter L, Salleo A, Shkunov M, Sparrowe D, Tierney S, Zhang W (2009) Semiconducting thienothiophene copolymers: design, synthesis, morphology, and performance in thin-film organic transistors. Adv Mater 21:1091-1109
23. Murphy AR, Frechet JMJ (2007) Organic semiconducting oligomers for use in thin film transistors. Chem Rev 107:1066-1096
24. Biniek L, Chochos CL, Leclerc N, Hadziioannou G, Kallitsis JK, Bechara R, Leveque P, Heiser T (2009) Thienothiophene-alt-for photovoltaic applications: design, synthesis, material characterization and device performances. J Mater Chem 19:4946-4951
25. Biniek L, Chochos CL, Hadziioannou G, Leclerc N, Leveque P, Heiser T (2010) Electronic properties and photovoltaic performances of a series of oligothiophene copolymers incorporating both thieno[3,2-b]thiophene and 2,1,3-benzothiadiazole moieties. Macromol Rapid Commun 31:651-656
26. Lim E, Jung B-J, Lee J, Shim H-K, Lee J-I, Yang YS, DoL M (2005) Thin-film morphologies and solution-processable field-effect transistor behavior of a fluorene-thieno[3,2-b]thiophene-based conjugated copolymer. Macromolecules 38:4531-4535
27. Beaupre S, Leclerc M (2002) Fluorene-based copolymers for red-light-emitting diodes. Adv Funct Mater 12:192-196
28. Muller CD, Falcou A, Reckefuss N, Rojahn M, Wiederhirn V, Rudati P, Frohne H, Nuyken O, Becker H, Meerholz K (2003) Multi-colour organic light-emitting displays by solution processing. Nature 421:829-833
29. Johnson JR, Rotenberg DH, Ketcham R, Thiazolothiazoles II (1970) Parent heterocycle and its carboxylic and amino derivatives. J Am Chem Soc 92:4046-4050
30. Wen S, Pei J, Zhou Y, Li P, Xue L, Li Y, Xu B, Tian W (2009) Synthesis of 4,7-diphenyl-2,1,3-benzothiadiazole-based copolymers and their photovoltaic applications. Macromolecules 42:4977-4984
31. Wang J-L, Zhou Y, Li Y, Pei J (2009) Solution-processable gradient red-emitting π-conjugated dendrimers based on benzothiadiazole as core: synthesis, characterization, and device performances. J Org Chem 74:7449-7456
32. Liu J, Bu L, Dong J, Zhou Q, Geng Y, Ma D, Wang L, Jing X, Wang F (2007) Green light-emitting polyfluorenes with improved color purity incorporated with 4,7-diphenyl-2,1,3-benzothiadiazole moieties. J Mater Chem 17:2832-2838
33. Zhang X, Gorohmaru H, Kadowaki M, Kobayashi T, Ishi-iT Thiemann T, Mataka S (2004) Benzo-2,1,3-thiadiazole-based, highly dichroic fluorescent dyes for fluorescent host-guest liquid crystal displays. J Mater Chem 14:1901-1904
34. Kato S-I, Matsumoto T, Shigeiwa M, Gorohmaru H, Maeda S, Ishi-i T, Mataka S (2006) Novel 2,1,3-benzothiadiazole-based red-fluorescent dyes with enhanced two-photon absorption cross-sections. Chem Eur J 12:2303-2317
35. Karakus M, Apaydin DH, Yildin DE, Toppare L (2012) Benzotriazole and benzothiadiazole containing conjugated copolymers for organic solar cells. Polymer 53:1198-1202
36. Pei J, Wen S, Zhou Y, Dong Q, Liu Z, Zhang J, Tian WA (2011) low band gap donor-acceptor containing fluorene and benzothiadiazole units: synthesis and photovoltaic properties. New J Chem 35:385-393
37. Mishra SP, Palai AK, Srivastava R, Kamalasanan MN, Patri M (2010) Highly air-stable thieno[3,2-b]thiophene-thiophene-thiazolo[5,4-d]thiazole-based polymers for light-emitting diodes. Macromol Chem Phys 211:1890-1899
38. Marsitzky D, Vestberg R, Blainey P, Tang BT, Hawker CJ, Carter KR (2001) Self-encapsulation of poly-2,7-fluorenes in a dendrimer matrix. J Am Chem Soc 123:6965-6972
39. Kumar A, Srivastava R, Bawa SS, Singh D, Singh K, Chauhan G, Singh I, Kamalasanan MN (2010) Synthesis, characterization and luminescent properties of terbium complexes. J Lumin 130:1516-1520
40. Xue S, Yao L, Liu S, Gu C, Shen F, Li W, Zheng H, Wu H, Ma Y (2012) Simultaneous enhancement of the carrier mobility and luminous efficiency through thermal annealing a molecular glass material and device. J Mater Chem 22:21502-21506