Synthesis of hyperbranched conjugated polymers based on 3-hexylthiophene, triphenylamine and benzo [c] [1,2,5] thiadiazole moieties: convenient synthesis through suzuki polymerization and impact of structures on optical properties

Journal of Polymer Research

Volumn 21, Issue 9, 2014, Pages

  Nguyen, Ha Tran ^a   Nguyen, Le Thu T ^a   Nguyen, Trung Thanh ^a   Luu, Anh Tuan ^a   Van Le, Thang ^a  

^a VIETNAM NATIONAL UNIVERSITY   (Viet Nam)

Author keywords

3 hexylthiophene; Benzo c 1, 2, 5 thiadiazole; Hyperbranched conjugated polymers; Polycondensation; Triphenylamine

Indexed keywords

CONJUGATED POLYMERS; DIFFERENTIAL SCANNING CALORIMETRY; FLUORESCENCE SPECTROSCOPY; FOURIER TRANSFORM INFRARED SPECTROSCOPY; GEL PERMEATION CHROMATOGRAPHY; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC COMPOUNDS; POLYCONDENSATION; POLYMERIZATION; RED SHIFT; THERMOGRAVIMETRIC ANALYSIS; X RAY DIFFRACTION;

3-HEXYLTHIOPHENE; 5]THIADIAZOLE; FOURIER TRANSFORM INFRA RED (FTIR) SPECTROSCOPY; GEL PERMEATION CHROMATOGRAPHY (GPC); HYPERBRANCHED; PHOTOLUMINESCENCE QUANTUM YIELDS; PROTON NUCLEAR MAGNETIC RESONANCE; TRIPHENYL AMINES;

DENDRIMERS;

EID: 84905322823     PISSN: 10229760     EISSN: 15728935     Source Type: Journal    
DOI: 10.1007/s10965-014-0552-y     Document Type: Article

References (49)

1. McCullough RD, Tristram-Nagle S, Williams SP, Lowe RD, Jayaraman M (1993) Self-orienting head-to-tail poly (3-alkylthiophenes): new insights on structure–property relationships in conducting polymers. J Am Chem Soc 115:4910–4911
2. Chen T-A, Wu X, Rieke RD (1995) Regiocontrolled synthesis of poly (3-alkylthiophenes) mediated by Rieke Zinc: their characterization and solid-state properties. J Am Chem Soc 117:233–244
3. Bao Z, Dodabalapur A, Lovinger AJ (1996) Soluble and processable regioregular poly (3-hexylthiophene) for thin film field-effect transistor applications with high mobility. Appl Phys Lett 69:4108–4110
4. Sirringhaus H, Tessler N, Friend RH (1998) Integrated optoelectronic devices based on conjugated polymers. Science 280:1741–1744
5. Agrawal AK, Jenekhe SA (1993) Synthesis and processing of heterocyclic polymers as electronic, optoelectronic, and nonlinear optical materials. 2. New series of conjugated rigid-rod polyquinolines and polyanthrazolines. Macromolecules 26:895–905
6. Hancock JM, Gifford AP, Champion RD, Jenekhe SA (2008) Block Co-oligomers for Organic Electronics and Optoelectronics: Synthesis, Photophysics, Electroluminescence, and Field-Effect Charge Transport of Oligothiophene-b-oligoquinoline-b-oligothiophene Triblock Co-oligomers. Macromolecules 41:3588–3597
7. Arias AC, MacKenzie JD, McCulloch I, Rivnay J, Salleo A (2010) Materials and applications for large area electronics: solution-based approaches. Chem Rev 110:3–24
8. Pron A, Gawrys P, Zagorska M, Djurado D, Demadrille R (2010) Electroactive materials for organic electronics: preparation strategies, structural aspects and characterization techniques. Chem Soc Rev 39:2577–2632
9. Pan H, Wu Y, Li Y, Liu P, Ong BS, Zhu S, Xu G (2007) Benzodithiophene copolymer—A low-temperature, solution-processed high-performance semiconductor for thin-film transistors. Adv Funct Mater 17:3574–3579
10. Li Y, Wu Y, Liu P, Birau M, Pan H, Ong BS (2006) Poly (2,5-bis (2-thienyl) -3,6-dialkylthieno [3,2-b] thiophene)s—High-mobility semiconductors for thin-film transistors. Adv Mater 18:3029–3032
11. Chen L, Li X, Ying W, Zhang X, Guo F, Li J, Hua J (2013) 5,6-Bis (octyloxy) benzo [c] [1,2,5] thiadiazole-bridged dyes for dye-sensitized solar cells with high open-circuit voltage performance. Eur J Org Chem 2013:1770–1780
12. Ma F, Shi W, Mi H, Luo J, Lei Y, Tian Y (2013) Triphenylamine-based conjugated polymer/I − complex as turn-on optical probe for mercury (II) ion. Sensors Actuators B Chem 182:782–788
13. Lim ZB, Xue B, Bomma S, Li H, Sun S, Lam YM, Belcher WJ, Dastoor PC, Grimsdale AC (2011) New moderate bandgap polymers containing alkoxysubstituted-benzo [c] [1,2,5] thiadiazole and thiophene-based units. J Polym Sci A Polym Chem 49:4387–4397
14. Reisch A, Komber H, Voit B (2007) Kinetic Analysis of Two Hyperbranched A2 + B3 Polycondensation Reactions by NMR Spectroscopy. Macromolecules 40:6846–6858
15. Krämer M, Kopaczynska M, Krause S, Haag R (2007) Dendritic polyamine architectures with lipophilic shells as nanocompartments for polar guest molecules: A comparative study of their transport behavior. J Polym Sci A Polym Chem 45:2287–2303
16. Paul GK, Mwaura J, Argun AA, Taranekar P, Reynolds JR (2006) Cross-linked hyperbranched arylamine polymers as hole-transporting materials for polymer LEDs. Macromolecules 39:7789–7792
17. Dong H, Zheng R, Lam JWY, Häussler M, Qin A, Tang BZ (2005) A new route to hyperbranched macromolecules: syntheses of photosensitive poly (aroylarylene)s via 1,3,5-regioselective polycyclotrimerization of bis (aroylacetylene)s. Macromolecules 38:6382–6391
18. Sun M, Li J, Li B, Fu Y, Bo Z (2005) Toward high molecular weight triphenylamine-based hyperbranched polymers. Macromolecules 38:2651–2658
19. Sunder A, Mülhaupt R, Haag R, Frey H (2000) Hyperbranched polyether polyols: a modular approach to complex polymer architectures. Adv Mater 12:235–239
20. Liou G-S, Lin H-Y, Yen H-J (2009) Synthesis and characterization of electroactive hyperbranched aromatic polyamides based on A2B-type triphenylamine moieties. J Mater Chem 19:7666–7673
21. Bo Z, Schluter AD (2003) “AB2 + AC2” approach to hyperbranched polymers with a high degree of branching. Chemical Communications 2354–2355
22. J.H obson L, M. Kenwright A (1997) A simple ‘one pot’ route to the hyperbranched analogues of Tomalia's poly (amidoamine) dendrimers. Chemical Communications 1877–1879
23. Smet M, Schacht E, Dehaen W (2002) Synthesis, characterization, and modification of hyperbranched poly (arylene oxindoles) with a degree of branching of 100 %. Angew Chem Int Ed 41:4547–4550
24. Bharathi P, Moore JS (2000) controlled synthesis of hyperbranched polymers by slow monomer addition to a core. Macromolecules 33:3212–3218
25. Ishida Y, Sun ACF, Jikei M, M-a K (2000) Synthesis of hyperbranched aromatic polyamides starting from dendrons as ABx monomers: effect of monomer multiplicity on the degree of branching. Macromolecules 33:2832–2838
26. Li B, Li J, Fu Y, Bo Z (2004) Porphyrins with four monodisperse oligofluorene arms as efficient red light-emitting materials. J Am Chem Soc 126:3430–3431
27. Kanibolotsky AL, Berridge R, Skabara PJ, Perepichka IF, Bradley DDC, Koeberg M (2004) Synthesis and properties of monodisperse oligofluorene-functionalized truxenes: highly fluorescent star-shaped architectures. J Am Chem Soc 126:13695–13702
28. Tour JM (1996) Conjugated macromolecules of precise length and constitution organic synthesis for the construction of nanoarchitectures. Chem Rev 96:537–554
29. Belletête M, Bouchard J, Leclerc M, Durocher G (2005) Photophysics and solvent-induced aggregation of 2,7-carbazole-based conjugated polymers. Macromolecules 38:880–887
30. Li K, Wang Q (2004) Synthesis and solution aggregation of polystyrene − oligo (p-phenyleneethynylene) − polystyrene triblock copolymer. Macromolecules 37:1172–1174
31. Bouchard J, Belletête M, Durocher G, Leclerc M (2003) Solvatochromic properties of 2,7-carbazole-based conjugated polymers. Macromolecules 36:4624–4630
32. Ma H, Liu S, Luo J, Suresh S, Liu L, Kang SH, Haller M, Sassa T, Dalton LR, Jen AKY (2002) Highly efficient and thermally stable electro-optical dendrimers for photonics. Adv Funct Mater 12:565–574
33. Qu J, Shiotsuki M, Kobayashi N, Sanda F, Masuda T (2007) Synthesis and properties of carbazole-based hyperbranched conjugated polymers. Polymer 48:6481–6490
34. Li J, Sun M, Bo Z (2007) Synthesis of hyperbranched polymers with precise conjugation length. J Polym Sci A Polym Chem 45:1084–1092
35. Okamoto K, Housekeeper JB, Michael FE, Luscombe CK (2013) Thiophene based hyperbranched polymers with tunable branching using direct arylation methods. Polym Chem 4:3499–3506
36. He Q, Huang H, Yang J, Lin H, Bai F (2003) Synthesis and spectroscopic properties of a series of hyperbranched conjugated molecules with 1,3,5-triphenylbenzene as cores. J Mater Chem 13:1085–1089
37. Hollamby MJ, Nakanishi T (2013) The power of branched chains: optimising functional molecular materials. J Mater Chem C 1:6178–6183
38. Wang H-S, Su M-S, Wei K-H (2010) Synthesis and characterization of donor–acceptor poly (3-hexylthiophene) copolymers presenting 1,3,4-oxadiazole units and their application to photovoltaic cells. J Polym Sci A Polym Chem 48:3331–3339
39. Zen A, Saphiannikova M, Neher D, Grenzer J, Grigorian S, Pietsch U, Asawapirom U, Janietz S, Scherf U, Lieberwirth I, Wegner G (2006) Effect of molecular weight on the structure and crystallinity of poly (3-hexylthiophene). Macromolecules 39:2162–2171
40. Kim J (2002) Assemblies of conjugated polymers Intermolecular and intramolecular effects on the photophysical properties of conjugated polymers. Pure Appl Chem 74:2031–2044
41. Sonar P, Singh SP, Sudhakar S, Dodabalapur A, Sellinger A (2008) High-mobility organic thin film transistors based on benzothiadiazole-sandwiched dihexylquaterthiophenes. Chem Mater 20:3184–3190
42. Sonar P, Singh SP, Leclere P, Surin M, Lazzaroni R, Lin TT, Dodabalapur A, Sellinger A (2009) Synthesis, characterization and comparative study of thiophene-benzothiadiazole based donor-acceptor-donor (D-A-D) materials. J Mater Chem 19:3228–3237
43. Verploegen E, Miller CE, Schmidt K, Bao Z, Toney MF (2012) Manipulating the morphology of P3HT–PCBM bulk heterojunction blends with solvent vapor annealing. Chem Mater 24:3923–3931
44. Zha D, Chen L, Wu F, Wang H, Chen Y (2013) Donor–acceptor-integrated conjugated polymers based on carbazole [3,4-c:5,6-c] bis [1,2,5] thiadiazole with tight π–π stacking for photovoltaics. J Polym Sci, Part A: Polym Chem 51:565–574
45. Bredas JL, Heeger AJ (1990) Theoretical investigation of gas-phase torsion potentials along conjugated polymer backbones: polyacetylene, polydiacetylene, and polythiophene. Macromolecules 23:1150–1156
46. Gettinger CL, Heeger AJ (1994) The effect of intrinsic rigidity on the optical properties of PPV derivatives. Mol Cryst Liq Cyst 256:507–512
47. DiCésare N, Belletête M, Leclerc M, Durocher G (1999) Intermolecular Interactions in Conjugated Oligothiophenes. 2. Quantum Chemical Calculations Performed on Crystalline Structures of Terthiophene and Substituted Terthiophenes. J Phys Chem A 103:803–811
48. Ruini A, Caldas MJ, Bussi G, Molinari E (2002) Solid state effects on exciton states and optical properties of PPV. Phys Rev Lett 88:206403
49. Ferretti A, Ruini A, Molinari E, Caldas MJ (2003) Electronic properties of polymer crystals: the effect of interchain interactions. Phys Rev Lett 90:086401