The synthesis, physicochemical properties and anodic polymerization of a novel ladder pentaphenylene

Dyes and Pigments

Volumn 83, Issue 3, 2009, Pages 339-347

  Cocherel, Nicolas ^a,b   Poriel, Cyril ^a,b   Jeannin, Olivier ^a,b   Yassin, Ali ^a,b   Rault Berthelot, Joëlle ^a,b  

^a UNIVERSITÉ DE RENNES 1   (France)

^b INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

Author keywords

Blue light emission; Electropolymerization; Ladder phenylene materials; Optical properties; Spiroconjugation; Structure properties relationship

Indexed keywords

ANODIC POLYMERIZATION; BLUE LIGHT EMISSION; BLUE-EMITTING; ELECTROACTIVE MATERIAL; FLUORENE; PHYSICOCHEMICAL PROPERTY; SPIROCONJUGATION; STRUCTURE-PROPERTIES RELATIONSHIP;

ANODIC OXIDATION; AROMATIC COMPOUNDS; CRYSTAL STRUCTURE; ELECTROCHEMICAL PROPERTIES; ELECTROPOLYMERIZATION; LADDERS; LIGHT EMISSION; MATERIALS PROPERTIES;

OPTICAL PROPERTIES;

CRYSTAL; OPTICAL PROPERTY; OXIDATION; POLYMERIZATION; SYNTHESIS;

EID: 67650951111     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2009.06.001     Document Type: Article

References (54)

1. Thematic issue: organic electronics and optoelectronics. Chem Rev 107 (2007) 4
2. Grimsdale A.C., and Müllen K. Oligomers and polymers based on bridged phenylenes as electronic materials. Macromol Rapid Commun 28 (2007) 1676-1702
3. Jacob J., Sax S., Piok T., List E.J.W., Grimsdale A.C., and Müllen K. Ladder-type pentaphenylenes and their polymers: efficient blue-light emitters and electron-accepting materials via a common intermediate. J Am Chem Soc 126 (2004) 6987-6995
4. Jacob J., Sax S., Gaal M., List E.J.W., Grimsdale A.C., and Müllen K. A fully aryl-substituted poly(ladder-type pentaphenylene): a remarkably stable blue-light-emitting polymer. Macromolecules 38 (2005) 9933-9938
5. Schindler F., Jacob J., Grimsdale A.C., Scherf U., Müllen K., Lupton J.M., et al. Counting chromophores in conjugated polymers. Angew Chem Int Ed Engl 44 (2005) 1520-1525
6. Zhou G., Baumgarten M., and Müllen K. Arylamine-substituted oligo(ladder-type pentaphenylene)s: electronic communication between bridged redox centers. J Am Chem Soc 129 (2007) 12211-12221
7. Mishra A.K., Graf M., Grasse F., Jacob J., List E.J.W., and Müllen K. Blue-emitting carbon- and nitrogen-bridged poly(ladder-type tetraphenylene)s. Chem Mater 18 (2006) 2879-2885
8. Zhou G., Pschirer N., Schöneboom J.C., Eickemeyer F., Baumgarten M., and Müllen K. Ladder-type pentaphenylene dyes for dye-sensitized solar cells. Chem Mater 20 (2008) 1808-1815
9. Zhu Y., Gibbons K.M., Kulkarni A.P., and Jenekhe S.A. Polyfluorenes containing dibenzo[a, c]phenazine segments: synthesis and efficient blue electroluminescence from intramolecular charge transfer states. Macromolecules 40 (2007) 804-813
10. Tonzola C.J., Kulkarni A.P., Gifford A.P., Kaminsky W., and Jenekhe S.A. Blue-light-emitting oligoquinolines: synthesis, properties, and high-efficiency blue-light-emitting diodes. Adv Funct Mater 17 (2007) 863-874
11. Kim S.-K., Park Y.-I., Kang I.-N., and Park J.-W. New deep-blue emitting materials based on fully substituted ethylene derivatives. J Mater Chem 17 (2007) 4670-4678
12. Moorthy J.N., Venkatakrishnan P., Huang D.-F., and Chow T.J. Blue light-emitting and hole-transporting amorphous molecular materials based on diarylaminobiphenyl-functionalized bimesitylenes. Chem Commun (2008) 2146-2148
13. Kim S.-K., Yang B., Ma Y., Lee J.-H., and Park J.-W. Exceedingly efficient deep-blue electroluminescence from new anthracenes obtained using rational molecular design. J Mater Chem 18 (2008) 3376-3384
14. Tao S., Zhou Y., Lee C.-S., Lee S.-T., Huang D., and Zhang X. Highly efficient nondoped blue organic light-emitting diodes based on anthracene-triphenylamine derivatives. J Phys Chem C 112 (2008) 14603-14606
15. Tong Q.-X., Lai S.-L., Chan M.-Y., Zhou Y.-C., Kwong H.-L., Lee C.-S., et al. Highly efficient blue organic light-emitting device based on a nondoped electroluminescent material. Chem Mater 20 (2008) 6310-6312
16. Qin T., Zhou G., Scheiber H., Bauer R.E., Baumgarten M., Anson C.E., et al. Polytriphenylene dendrimers: a unique design for blue-light-emitting materials. Angew Chem Int Ed Engl 47 (2008) 8292-8296
17. Park Y.-I., Son J.-H., Kang J.-S., Kim S.-K., Lee J.-H., and Park J.-W. Synthesis and electroluminescence properties of novel deep blue emitting 6,12-dihydro-diindeno[1,2-b;1′,2′-e]pyrazine derivatives. Chem Commun (2008) 2143-2145
18. Lai M.-Y., Chen C.-H., Huang W.-S., Lin J.T., Ke T.-H., Chen L.-Y., et al. Benzimidazole/amine-based compounds capable of ambipolar transport for application in single-layer blue-emitting OLEDs and as hosts for phosphorescent emitters. Angew Chem Int Ed Engl 47 (2008) 581-585
19. Wei Y., and Chen C.-T. Doubly ortho-linked cis-4,4'-bis(diarylamino)stilbene/fluorene hybrids as efficient nondoped, sky-blue fluorescent materials for optoelectronic applications. J Am Chem Soc 129 (2007) 7478-7479
20. Poriel C., Liang J.-J., Rault-Berthelot J., Barrière F., Cocherel N., Slawin A.M.Z., et al. Dispirofluorene-indenofluorene derivatives as new building blocks for blue organic electroluminescent devices and electroactive polymers. Chem Eur J 13 (2007) 10055-10069
21. Poriel C., Rault-Berthelot J., Barrière F., and Slawin A.M.Z. New dispiro compounds: synthesis and properties. Org Lett 10 (2008) 373-376
22. Saragi T.P.I., Spehr T., Siebert A., Fuhrmann-Lieker T., and Salbeck J. Spiro compounds for organic optoelectronics. Chem Rev 107 (2007) 1011-1065
23. Merlet S., Birau M., and Wang Z.Y. Synthesis and characterization of highly fluorescent indenofluorenes. Org Lett 4 (2002) 2157-2159
24. Cocherel N., Poriel C., Rault-Berthelot J., Barrière F., Audebrand N., Slawin A.M.Z., et al. New 3π-2spiro ladder-type phenylene materials: synthesis, physicochemical properties and applications in OLEDs. Chem Eur J 14 (2008) 11328-11342
25. Xia C., and Advincula R.C. Ladder-type oligo(p-phenylene)s tethered to a poly(alkylene) main chain: the orthogonal approach to functional light-emitting polymers. Macromolecules 34 (2001) 6922-6928
26. Wong K.-T., Chi L.-C., Huang S.-C., Liao Y.-L., Liu Y.-H., and Wang Y. Coplanarity in the backbones of ladder-type oligo(p-phenylene) homologues and derivatives. Org Lett 8 (2006) 5029-5032
27. King S.M., Hintschich S.I., Dai D., Rothe C., and Monkman A.P. Spiroconjugation-enhanced intramolecular charge-transfer state formation in a polyspirobifluorene homopolymer. J Phys Chem C 111 (2007) 18759-18764
28. Johansson N., Dos Santos D.A., Guo S., Cornil J., Fahlman M., Salbeck J., et al. Electronic structure and optical properties of electroluminescent spiro-type molecules. J Chem Phys 107 (1997) 2542-2549
29. Rault-Berthelot J. Polyfluorenes, a family of versatile conjugated polymers. Anodic synthesis, physicochemical properties, electrochemical behaviour and application fields. Recent Res Dev Macromol Res 3 (1998) 425-437
30. Rault-Berthelot J., Poriel C., Justaud F., and Barrière F. Anodic oxidation of indenofluorene. Electrodeposition of electroactive poly(indenofluorene). New J Chem 32 (2008) 1259-1266
31. Lamba J.J.S., and Tour J.M. Imine-bridged planar poly(p-phenylene) derivatives for maximization of extended. π-conjugation. The common intermediate approach. J Am Chem Soc 116 (1994) 11723-11736
32. Sonntag M., Kreger K., Hanft D., Strohriegl P., Setayesh S., and de Leeuw D. Novel star-shaped triphenylamine-based molecular glasses and their use in OFETs. Chem Mater 17 (2005) 3031-3039
33. Belletête M., Beaupré S., Bouchard J., Blondin P., Leclerc M., and Durocher G. Theoretical and experimental investigations of the spectroscopic and photophysical properties of fluorene-phenylene and fluorene-thiophene derivatives: precursors of light-emitting polymers. J Phys Chem B 104 (2000) 9118-9125
34. Li T., Yamamoto T., Lan H.-L., and Kido J. Synthesis and electroluminescence properties of fluorene containing arylamine oligomer. Polym Adv Technol 15 (2004) 266-269
35. Kulkarni A.P., Tonzola C.J., Babel A., and Jenekhe S.A. Electron transport materials for organic light-emitting diodes. Chem Mater 16 (2004) 4556-4573
36. Altomare A., Cascarano G., Giacovazzo C., Guagliardi A., Burla M.C., Polidori G., et al. SIR92-a program for automatic solution of crystal structures by direct methods. J Appl Cryst 27 (1994) 435-436
37. Sheldrick G.M. SHELX97-programs for crystal structure analysis (Release 97-2) (1998)
38. Farrugia L. WinGX suite for small-molecule single-crystal crystallography. J Appl Cryst 32 (1999) 837-838
39. Janiak C. A critical account on π-π stacking in metal complexes with aromatic nitrogen-containing ligands. J Chem Soc, Dalton Trans (2000) 3885-3896
40. Nehls B.S., Galbrecht F., Bilge A., Brauer D.J., Lehmann C.W., Scherf U., et al. Synthesis and spectroscopy of an oligophenyl based cruciform with remarkable π-π assisted folding. Org Biomol Chem 3 (2003) 3213-3219
41. + complexes (bipy = 2,2′-bipyridine; terpy = 2,2′:6′,2{combining double acute accent}-terpyridine; L = imidazole, pyrazole and derivatives, cytochrome c). Dalton Trans (2005) 256-267 [and references therein]
42. Lukes V., Solc R., Milota F., Sperling J., and Kauffmann H.F. Theoretical investigation of the structure and the electron-vibrational dynamics of 9,9′-spirobifluorene. Chem Phys 349 (2008) 226-233
43. Boo B.H., Choi Y.S., Kim T.-S., Kang S.K., Kang Y.H., and Lee S.Y. Theoretical and jet spectroscopic investigations of energetics and structures for the low-lying singlet states of fluorene and 9,9′-spirobifluorene. J Mol Structure 377 (1996) 129-136
44. Salbeck J., Yu N., Bauer J., Weissörtel F., and Besten H. Low molecular organic glasses for blue electroluminescence. Synth Met 91 (1997) 209-215
45. Etori H., Jin X.L., Yasuda T., Mataka S., and Tsutsui T. Spirobifluorene derivatives for ultraviolet organic light-emitting diodes. Synth Met 156 (2006) 1090-1096
46. Keivanidis P.E., Jacob J., Oldridge L., Sonar P., Carbonnier B., Balutschev, et al. Photophysical characterization of light-emitting poly(indenofluorene)s. Chem Phys Chem 6 (2005) 1650-1660
47. Romaner L., Heimel G., Wiesenhofer H., Scandiucci de Freitas P., Scherf U., Brédas J.L., et al. Ketonic defects in ladder-type poly(p-phenylene)s. Chem Mater 16 (2004) 4667-4674
48. Gaal M., List E.J.W., and Scherf U. Excimers or emissive on-chain defects?. Macromolecules 36 (2003) 4236-4237
49. Montilla F., and Mallavia R. On the origin of green emission bands in fluorene-based conjugated polymers. Adv Mater 17 (2007) 71-78
50. Hapiot P., Lagrost C., Le Floch F., Raoult E., and Rault-Berthelot J. Comparative study of the oxidation of fluorene, 9,9-disubstituted-fluorenes and of their related 2,7′-dimer and trimer. Chem Mater 17 (2005) 2003-2012
51. 4. Electrochemical behaviour of the derived oxidation product. Synth Met 97 (1998) 211-215
52. Poriel C., Ferrand Y., Le Maux P., Rault-Berthelot J., and Simonneaux G. Poly(9,9′-spirobifluorene-manganese porphyrin):a new catalytic material for oxidation of alkenes by iodobenzene diacetate and iodosylbenzene. Chem Commun (2003) 1104-1105
53. Poriel C., Ferrand Y., Le Maux P., Rault-Berthelot J., and Simonneaux G. Organic cross-linked electropolymers as supported oxidation catalysts: poly(tetrakis(9,9′-spirobifluorenyl)porphyrin)manganese films. Inorg Chem 43 (2004) 5086-5095
54. Rault-Berthelot J., Questaigne V., Simonet J., and Peslerbe G. A new device for the in situ UV-visible spectroelectrochemical study of polymeric films set on solid surfaces: application to the study of the electrochemical behaviour of polyfluorenes. New J Chem 13 (1989) 45-52