Design and synthesis of new 4,4′-difluoro-4-bora-3a,4a-diaza-s- indacene based electrochromic polymers

Electrochimica Acta

Volumn 109, Issue , 2013, Pages 766-774

  Algia, Melek Pamuk ^a   Tirkesb, Seha ^b   Ertanb, Salih ^b   Ergunb, Emine Gul Cansu ^b   Cihanerb, Atilla ^b   Algia, Fatih ^a  

^a ÇANAKKALE ONSEKIZ MART UNIVERSITY   (Turkey)

^b ATILIM UNIVERSITY   (Turkey)

Author keywords

BODIPY; EDOT; Electrochemical polymerization; Electrochromics; Thiophene

Indexed keywords

ELECTROLYTES; ELECTROPOLYMERIZATION; ENERGY GAP; POLYMERIZATION; THIOPHENE;

BODIPY; DONOR-ACCEPTOR COMPOUNDS; EDOT; ELECTROCHROMIC POLYMERS; ELECTROCHROMICS; HALF-WAVE POTENTIAL; REVERSIBLE OXIDATION; STRUCTURE PROPERTY RELATIONSHIPS;

COLOR;

EID: 84884517609     PISSN: 00134686     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.electacta.2013.07.179     Document Type: Article

References (47)

1. O.R. Miranda, C.-C. You, R. Phillips, I.-B. Kim, P.S. Ghosh, U.H.F. Bunz, V.M.Rotello, Array-Based sensing of proteins using conjugated polymers, Journalof the American Chemical Society 129 2007 9856.
2. A.M. Buono, I. Immediata, P. Rizzo, G.J. Guerra, Detection and memory of non-Racemic molecules by a racemic host polymer film, Journal of the AmericanChemical Society 129 2007 10992.
3. S.H. Lee, S.K. Kim, J.H. Jung, J.S. Kim, Fluorescence ratiometry ofmonomer/excimer emissions in a space-Through PET system, Journal ofOrganic Chemistry 70 2005 9288.
4. N.C. Greenham, S. Moratti, D.D.C. Bradley, R.H. Friend, A.B. Holmes, Efficientlight-Emitting diodes based on polymers with high electron affinities, Nature365 1993 628.
5. A. Goel, G.M. Dixit, S. Chaurasia, A. Kumar, R. Raghunandan, P.R. Maulik, R.S.Anand, Vapor-Phase processable novel nonplanar donor-Acceptor quaterarylsfor blue OLEDs, Organic Letters 10 2008 2553.
6. L. Schmidt-Mende, A. Fechtenkotter, K. Mullen, E. Moons, R.H. Friend, J.D.Mackenzie, Self-Organized discotic liquid crystals for high-Efficiency organicphotovoltaics, Science 293 2001 1119.
7. A. Liscio, G. De Luca, F. Nolde, V. Palermo, K. Müllen, P. Samori, Photovoltaiccharge generation visualized at the nanoscale: A proof of principle, Journal ofthe American Chemical Society 130 2008 780.
8. B.C. Thompson, J.M.J. Fréchet, Polymer-Fullerene composite solar cells, Ange-wandte Chemie International Edition 47 2007 58.
9. I. Schwendeman, R. Hickman, G. Sonmez, P. Schottland, K. Zong, D. Welsh, J.R.Reynolds, Enhanced contrast dual polymer electrochromic devices, Chemistryof Materials 14 2002 3118
10. H. Meng, D. Tucker, S. Chaffins, Y. Chen, R. Helgeson, B. Dunn, F. Wudl, Anunusual electrochromic device based on a new low-Bandgap conjugated poly-Mer, Advanced Materials 15 2003 146.
11. A. Cihaner, F. Algi, A processable rainbow mimic fluorescent polymer and itsunprecedented coloration efficiency in electrochromic device, ElectrochimicaActa 53 2008 2574.
12. K. Bange, T. Gambke, Electrochromic materials for optical switching devices,Advanced Materials 2 1990 10.
13. G. Cooke, J. Garety, S. Mabruk, V. Rotello, G. Surpateanu, P. Woisel, The elec-Trochemically tuneable recognition properties of an electropolymerised flavinderivative, Chemical Communications 23 2004 2722.
14. D. Asil, A. Cihaner, F. Algi, A.M. Önal, A diverse-Stimuli responsive chemi-Luminescent probe with luminol scaffold and its electropolymerization,Electroanalysis 22 2010 2254.
15. D.N. Buckley, L.D. Burke, J.K. Mukahy, The oxygen electrode. Part 7-Influence ofsome electrical and electrolyte variables on the charge capacity of iridium inthe anodic region, Journal of the Chemical Society, Faraday Transactions 1 721976 1896.
16. L.D. Burke, T.A.M. Thomey, D.P. Whelan, Growth of an electrochromic film ontungsten in acid under potential cycling conditions, Journal of ElectroanalyticalChemistry 107 1979 201.
17. W.C. Dautremont-Smith, Transition metal oxide electrochromic materials anddisplays: A review, Displays 3 1982 3.
18. M. Samiero, T. Gonçalves, Fluorescent labeling of biomolecules with organicprobes, Chemical Reviews 109 2009 190.
19. M.D. Yilmaz, O.A. Bozdemir, E.U. Akkaya, Light harvesting and efficient energytransfer in a boron-Dipyrrin BODIPY functionalized perylenediimide deriva-Tive, Organic Letters 8 2006 2871.
20. T. Rousseau, A. Cravino, E. Ripaud, P. Leriche, S. Rihn, A. De Nicola, R. Ziessel,J. Roncali, A tailored hybrid BODIPY-Oligothiophene donor for molecular bulkheterojunction solar cells with improved performances, Chemical Communi-Cations 46 2010 5082.
21. R. Ziessel, A. Harriman, Artificial light-Harvesting antennae: electronic energytransfer by way of molecular funnels, Chemical Communications 47 2011611.
22. S. At?lgan, Z. Ekmekçi, A.L. Do?gan, D. Güç, E.U. Akkaya, Water soluble distyryl-Boradiazaindacenes as efficient photosensitizers for photodynamic therapy,Chemical Communications 2006 4398.
23. S. Ozlem, E.U. Akkaya, Thinking outside the silicon box: Molecular and logic asan additional layer of selectivity in singlet oxygen generation for photodynamictherapy, Journal of the American Chemical Society 131 2009 48.
24. A. Coskun, E.U. Akkaya, Signal ratio amplification via modulation of resonanceenergy transfer: Proof of principle in an emission ratiometric HgII sensor,Journal of the American Chemical Society 128 2006 14474.
25. R. Guliyev, A. Coskun, E.U. Akkaya, Design strategies for ratiometric chemosen-Sors: Modulation of excitation energy transfer at the energy donor site, Journalof the American Chemical Society 131 2009 9007.
26. A. Kaloudi, A. Chantzea, N. Karakostas, C.P. Raptopoulou, V. Psycharis, E. Sari-Dakis, J. Griebel, R. Hermann, Coordination-Driven self assembly of a brilliantlyfluorescent rhomboid cavitand composed of BODIPY-Dye subunits, Journal ofthe American Chemical Society 132 2010 16327.
27. T. Tachikawa, N. Wang, S. Yamashita, S.C. Cui, T. Majima, Design of a highlysensitive fluorescent probe for interfacial electron transfer on a TiO2surface,Angewandte Chemie International Edition 49 2010 8593.
28. M. Benstead, G.H. Mehl, R.W. Boyle, 4,4-Difluoro-4-Bora-3a,4a-Diaza-S- Indacenes BODIPYs as components of novel light active materials,Tetrahedron 67 2011 3573.
29. V.R. Donuru, G.K. Vegesna, S. Velayudham, G. Meng, H.J. Liu, Deep-Red emissiveconjugated poly2,6-BODIPY-Ethynylenes bearing alkyl side chains, Journal ofPolymer Science Part A: Polymer Chemistry 47 2009 5354.
30. B.S. Kim, B. Ma, V.R. Donuru, H. Liu, J.M. Frechet, BODIPY-Backboned polymersas electron donor in bulk heterojunction solar cells, Chemical Communications46 2010 4148.
31. M. Zhu, L. Jiang, M. Yuan, X. Liu, C. Ouyang, H. Zheng, X. Yin, Z. Zuo, H. Liu, Y.Li, Efficient tuning nonlinear optical properties: Synthesis and characterizationof a series of novel polyaryleneethynylenes co-Containing BODIPY, Journal ofPolymer Science Part A: Polymer Chemistry 46 2008 7401.
32. F.E. Alemdaroglu, S.C. Alexander, D. Ji, D.K. Prusty, M. Borsch, A. Herrmann,PolyBODIPYs: A new class of tunable polymeric dyes, Macromolecules 422009 6529.
33. Y. Cakmak, E.U. Akkaya, Phenylethynyl-BODIPY oligomers: bright dyes andfluorescent building blocks, Organic Letters 11 2009 85.
34. A. Nagai, Y. Chujo, Aromatic ring-Fused BODIPY-Based conjugated polymersexhibiting narrow near-Infrared emission bands, Macromolecules 43 2010193.
35. A. Nagai, J. Miyake, K. Kokado, Y. Nagata, Y. Chujo, Highly luminescentBODIPY-Based organoboron polymer exhibiting supramolecular self-Assemblestructure, Journal of the American Chemical Society 130 2008 15276.
36. G. Meng, S. Velayudham, A. Smith, R. Luck, H. Liu, Color tuning of polyfluoreneemission with BODIPY monomers, Macromolecules 42 2009 1995.
37. V.R. Donuru, G.K. Vegesna, S. Velayudham, S. Green, H. Liu, Synthesis and opticalproperties of red and deep-Red emissive polymeric and copolymeric BODIPYdyes, Chemistry of Materials 21 2009 2130.
38. R. Paris, I. Quijada, I. Garrido, O. Garcia, M. Liras, BODIPY-Conjugatedthermo-Sensitive fluorescent polymers based on 2-2-Methoxyethoxyethylmethacrylate, Macromolecules 44 2011 80.
39. C. Thivierge, A. Loudet, K. Burgess, Brilliant BODIPY-Fluorene copolymers withdispersed absorption and emission maxima, Macromolecules 44 2011 4012.
40. B.C. Popere, A.M.D. Pelle, S. Thayumanavan, BODIPY-Based donor-Acceptor-Conjugated alternating copolymers, Macromolecules 44 2011 4767.
41. J.C. Forgie, P.J. Skabara, I. Stibor, F. Vilela, Z. Vobecka, New redox stable lowband gap conjugated polymer based on an EDOT-BODIPY-EDOT repeat unit,Chemistry of Materials 21 2009 1784.
42. A. Cihaner, F. Algi, A new conducting polymer bearing 4,4-Difluoro-4-Bora-3a,4a-Diaza-S-Indacene BODIPY subunit: Synthesis and characterization,Electrochimica Acta 54 2008 786.
43. A. Cihaner, F. Algi, Synthesis and properties of 4,4-Difluoro-4-Bora-3a, 4a-Diaza-S-Indacene BODIPY-Based conducting copolymers, Reactive and FunctionalPolymers 69 2009 62.
44. F. Algi, A. Cihaner, An ambipolar low band gap material based on BODIPY andEDOT, Organic Electronics 10 2009 453.
45. F. Algi, A. Cihaner, A novel terthienyl based polymer electrochrome with periph-Eral BODIPY, Polymer 53 2012 3469.
46. L. Jiao, C. Yu, J. Li, Z. Wang, M. Wu, E. Hao,-Formyl-BODIPYs from theVilsmeier-Haack reaction, Journal of Organic Chemistry 74 2009 7525.
47. S.S. Zhu, T.M. Swager, Conducting polymetallorotaxanes: Metal ion mediatedenhancements in conductivity and charge localization, Journal of the AmericanChemical Society 119 1997 12568..