Synthesis of functionalized aryleneethynylene oligomers and polymers for organic electronics by Pd-catalyzed coupling reactions

Current Organic Synthesis

Volumn 9, Issue 6, 2012, Pages 764-778

  Operamolla, Alessandra ^a   Ragni, Roberta ^a   Omar, Omar H ^b   Iacobellis, Giuliano ^a   Cardone, Antonio ^b   Babudri, Francesco ^a   Farinolaa, Gianluca M ^a  

^a UNIVERSITY OF BARI   (Italy)

^b CNR   (Italy)

Author keywords

Anthraquinone; Aryleneethynylenes; Biopolymers; Chiral polymers; Conjugated oligomers; Conjugated polymers; Cross coupling; Molecular electronics; Molecular wires; Norbornadiene; Organic electronics; Photoisomerization; Self assembly; Sonogashira reaction; Thiol; Triple C C bonds

Indexed keywords

EID: 84876897327     PISSN: 15701794     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017912803901655     Document Type: Article

References (68)

1. Skotheim, T.A.; Reynolds, J.R. Handbook of Conducting Polymers 3rd ed., CRC Press: Boca Raton FL, 2007.
2. Müllen, K.; Wegner, G. Electronic Materials: The Oligomer Approach, Wiley-VCH: New York, 1998.
3. Meier in: Carbon Rich Compounds, M.M. Haley, R.R. Tykwinski Eds., Wiley-VCH: Weinheim, 2006, pp. 476-528.
4. Farinola, G.M.; Ragni, R. Electroluminescent materials for white organic light emitting diodes. Chem. Soc. Rev., 2011, 40, 3467-3482.
5. Operamolla, A.; Farinola, G.M. Molecular and supramolecular architectures of organic semiconductors for field-effect transistor devices and sensors: a synthetic chemical perspective. Eur. J. Org. Chem., 2011, 3, 423-450.
6. Brabec, C. J.; Gowrisanker, S.; Halls, J.J.M.; Laird, D.; Jia, S.; Williams, S. P. Polymer-fullerene bulk-heterojunction solar cells. Adv. Mater., 2010, 22, 3839-3856.
7. Babudri, F.; Farinola, G.M.; Naso, F. Synthesis of conjugated oligomers and polymers: the organometallic way. J. Mater. Chem., 2004, 14, 11-34.
8. Farinola, G.M.; Babudri, F; Cardone, A.; Omar, H.O.; Naso, F. Synthesis of substituted conjugated polymers: tuning properties by functionalization. Pure Appl. Chem., 2008, 80, 1735-1746.
9. Bunz, U.H. F. Poly(aryleneethynylene)s. Macromol. Rapid Commun., 2009, 30, 772-805.
10. Voskerician, G.; Weder C. Electronic properties of PAEs. Adv. Polym. Sci., 2005, 177, 209-248.
11. Weder, C.; Sarwa, C.; Montali, A.; Bastiaansen, C.; Smith, P. Incorporation of photoluminescent polarizers into liquid crystal displays. Science, 1998, 279, 835-837.
12. Silvestri, F.; Marrocchi, A.; Seri, M.; Kim, C.; Marks, T.J.; Facchetti, A.; Taticchi, A. Solution-processable low-molecular weight extended arylacetylenes: versatile p-type semiconductors for field-effect transistors and bulk heterojunction solar cells. J. Am. Chem. Soc., 2010, 132, 6108-6123.
13. Swager, T.M. The molecular wire approach to sensory signal amplification. Acc. Chem. Res., 1998, 31, 201-207.
14. J.M. Molecular Electronics. Synthesis and Testing of Components: Commercial Insights, Chemistry, Devices, Architecture, and Programming. World Scientific Publishing: River Edge, NJ, 2003.
15. Swager T.M.; Zheng, J. Poly(arylene ethynylene)s in chemosensing and biosensing. Adv. Polym. Sci., 2005, 177, 343-354.
16. Disney, M.D.; Zheng, J.; Swager, T. M.; Seeberger, P. H. Detenction of Bacteria with Carbohydrate-Functionalized Fluorescent Polymers. J. Am. Chem. Soc., 2004, 126, 13343-13446.
17. Kloppenburg, L.; Jones, D.; Bunz, U.H.F. High molecular weight poly(pphenyleneethynylene) s by alkyne metathesis utilizing "instant" catalysts: a synthetic study. Macromolecules, 1999, 32, 4194-4203;
18. Wilson, J.N.; Steffen, W.; McKenzie, T.G.; Lieser, G.; Oda, M.; Neher, D.; Bunz, U.H.F. Chiroptical properties of poly(p-phenyleneethynylene) copolymers in thin films: large g-values. J. Am. Chem. Soc., 2002, 124, 6830-6831.
19. Mardsen, J.A.; Haley M.M. in Metal-Catalyzed Cross-Coupling Reactions, 2nd ed., de Meijere, A.; Diederich, F. Eds., Wiley-VCH: Weinheim, 2004, 2, pp. 317-394.
20. Cassar, L. Synthesis of aryl-and vinyl-substituted acetylene derivatives by the use of nickel and palladium complexes. J. Organomet. Chem., 1975, 93, 253-257.
21. Dieck, H.A.; Heck, F.R. Palladium catalyzed synthesis of aryl, heterocyclic and vinylic acetylene derivatives. J. Organomet. Chem., 1975, 93 (2), 259-263.
22. Sonogashira, K.; Tohda, Y.; Hagihara, N. A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines. Tetrahedron Lett., 1975, 16, 4467-4470.
23. Stephens, R.D.; Castro, C.E. The substitution of aryl iodides with cuprous acetylides. A synthesis of tolanes and heterocyclics. J. Org. Chem., 1963, 28, 3313-3315.
24. Chinchilla, R.; Nájera, C. The Sonogashira reaction: a booming methodology in synthetic organic chemistry. Chem. Rev., 2007, 107, 874-922.
25. Kotora, M.; Takahashi, T. in Handbook of Organopalladium Chemistry for Organic Synthesis, Negishi, E., de Meijere, A. Eds.; Wiley-Interscience: New York, 2002; p. 973.
26. Mori, A.; Kondo, T.; Kato T.; Nishihara, Y. Palladium-catalyzed crosscoupling polycondensation of bisalkynes with dihaloarenes activated by tetrabutylammonium hydroxide or silver(I) oxide. Chem. Lett., 2001, 30, 286-287.
27. Babudri, F.; Farinola, G.M.; Naso, F. Organometallic strategies for the synthesis of conjugated oligomers. Synlett, 2009, 17, 2740-2748.
28. Hassan Omar, O; Babudri, F. Farinola, G. M.; Naso, F.; Operamolla, A. Synthesis of S-acetyl oligo-p-aryleneethynylene tetrathiols. Eur. J. Org. Chem., 2011, 529-537.
29. Babudri, F.; De Palma, D.; Farinola, G. M.; Ragni, R.; Naso, F. Synthesis of functionalized anthraquinones via coupling reactions of 2,6-diiodo-1,5-dioctyloxy-9,10-anthraquinone. Synthesis, 2008, 8, 1227-1232.
30. Joachim, C.; Gimzewski, J. K.; Aviram, A. Electronics using hybridmolecular and mono-molecular devices. Nature, 2000, 408, 541-548.
31. Ratner, M. A. Introducing Molecular Electronics. Mater. Today, 2002, 5, 20.
32. Luo, L.; Choi, S. H.; Frisbie, C.D. Probing hopping conduction in conjugated molecular wires connected to metal electrodes. Chem. Mater., 2011, 23 (3), 631-645.
33. James, P.V.; Sudeep, P.K.; Suresh, C.H.; Thomas, K.G. Photophysical and theoretical investigations of oligo(p-phenyleneethynylene)s: effect of alkoxy substitution and alkyne[1]aryl bond rotations. J. Phys. Chem. A, 2006, 110, 4329-4337.
34. Operamolla, A.; Omar O.H.; Babudri, F.; Farinola, G.M.; Naso, F. Synthesis of S-acetyl oligoarylenedithiols via Suzuki-Miyaura cross-coupling. J. Org. Chem., 2007, 72, 10272-10275.
35. Hsung, R.P.; Babcock, J.R.; Chidsey, C.E.D.; Sita, L.R. Thiophenol protecting groups for the palladium-catalyzed heck reaction: efficient syntheses of conjugated arylthiols. Tetrahedron Lett., 1995, 36, 4525-4528.
36. Tour, J.M.; Jones, L.R., II; Pearson, D L.; Lamba, J.J.S.; Burgin, T.P.; Whitesides, G.M.; Allara, D.L.; Parikh, A.N.; Atre, S.V. Self-assembled monolayers and multilayers of conjugated thiols, alpha, omega-dithiols, and thioacetyl-containing adsorbates. Understanding attachments between potential molecular wires and gold surfaces. J. Am. Chem. Soc., 1995, 117, 9529-9534.
37. Thorand, S.; Krause, N. J.; Improved procedures for the palladium-catalyzed coupling of terminal alkynes with aryl bromides (Sonogashira coupling). J. Org. Chem., 1998, 63, 8551-8553.
38. Babudri, F.; Farinola, G.M.; Naso, F.; Ragni, R. Fluorinated organic materials for electronic and optoelectronic applications: the role of the fluorine atom. Chem. Commun., 2007, 1003-1022.
39. Babudri, F.; Cardone, A.; Chiavarone L.; Ciccarella, G.; Farinola, G.M, Naso, F.; Scamarcio, G. Synthesis and characterization of poly(2,3,5,6-tetrafluoro-1,4-phenylenevinylene). Chem. Commun., 2001, 1940-1941.
40. Babudri, F.; Cardone, A.; Farinola, G.M.; Naso, F.; Cassano, T.; Chiavarone, L.; Tommasi, R. Synthesis and optical properties of a copolymer of tetrafluoro-and dialkoxy-substituted poly(p-phenylenevinylene) with a high percentage of fluorinated units. Macromol. Chem. Phys., 2003, 204, 1621-1627.
41. Losurdo, M.; Giangregorio, M.M.; Capezzuto, P.; Cardone, A.; Martinelli, C.; Farinola, G. M.; Babudri, F.; Naso, F.; Büchel, M.; Bruno, G. Blue-gap poly(p-phenylene vinylene)s with fluorinated double bonds: interplay between supramolecular organization and optical properties in thin films. Adv. Mater., 2009, 21, 1115-1120.
42. Ragni, R.; Plummer, E.A.; Brunner, K.; Hofstraat, J.W.; Babudri, F.; Farinola, G.M.; Naso, F.; De Cola, L. Blue emitting iridium complexes: synthesis, photophysics and phosphorescent devices. J. Mater. Chem., 2006, 16, 1161-1170.
43. Ragni, R.; Orselli, E.; Kottas, G.S.; Hassan Omar, O.; Babudri, F.; Pedone, A.; Naso, F.; Farinola, G.M.; De Cola, L. Iridium(III) complexes with sulfonyl and fluorine substituents: synthesis, stereochemistry and effect of functionalisation on their photophysical properties. Chem. Eur. J., 2009, 15 (1), 136-148.
44. Hundertmark, T.; Littke, A.F.; Buchwald, S.L.; Fu, G.C. Pd(PhCN)2Cl2/P(t-Bu)3: a versatile catalyst for Sonogashira reactions of aryl bromides at room temperature. Org. Lett., 2000, 2, 1729-1731.
45. Gelman, D.; Buchwald, S.L. Efficient palladium-catalyzed coupling of aryl chlorides and tosylates with terminal alkynes: use of a copper cocatalyst inhibits the reaction. Angew. Chem. Int. Ed., 2003, 42, 5993-5996.
46. Chinwangso, P.; Jamison, A.C.; Lee, R.T. Multidentate adsorbates for selfassembled monolayer films. Acc. Chem. Res., 2011, 44, 511-519.
47. Bruno, G.; Babudri, F.; Operamolla, A.; Bianco, G.V.; Losurdo, M.; Giangregorio, M. M.; Omar O.H.; Mavelli, F.; Farinola, G.M.; Capezzuto, P.; Naso, F. Tailoring density and optical and thermal behavior of gold surfaces and nanoparticles exploiting aromatic dithiols. Langmuir, 2010, 26 (11), 8430-8440.
48. Giangregorio, M.M.; Losurdo, M.; Bianco, G.V.; Operamolla, A.; Dilonardo, E.; Sacchetti, A.; Capezzuto, P.; Babudri, F.; Bruno, G. Insight into gold nanoparticle-hydrogen interaction: a way to tailor nanoparticle surface charge and self-assembled monolayer chemisorptions. J. Phys. Chem. C, 2011, 115, 19520-19528.
49. Van Dijk, E.H.; Myles, D.J.T.; Van der Meen, M.H.; Hummelen, J.C. Synthesis and properties of an anthraquinone-based redox switch for molecular electronics. Org. Lett., 2006, 8, 2333-2336.
50. Sabaa, M.W.; Oraby, E.H.; Abdel Naby, A.S.; Mohamed, R.R. Anthraquinone derivatives as organic stabilizers for rigid poly(vinylchloride) against photo-degradation. Eur. Polym. J., 2005, 41, 2530-2543.
51. Luzzati, S.; Sharber, M.; Catellani, M.; Giancalone, F.; Segura, J. L.; Martin, N.; Neugebauer, H.; Sariciftci, N. S. Long-lived photoinduced charges in donor [1]acceptor anthraquinone-substituted thiophene copolymers. J. Phys. Chem. B, 2006, 110, 5351-5358.
52. Park, J.H.; Chung, D.S.; Park, J.W.; Ahn, T.; Kong, H.; Jung, Y.K.; Lee, J.; Yi, M.H.; Park, C.E.; Kwon, S.K.; Shim, H.K. Soluble and easily crystallized anthracene derivatives: precursors of solution-processable semiconducting molecules. Org. Lett., 2007, 9, 2573-2576.
53. Galevskaya, T.P.; Moroz, A.A.; Myasnikova, R.N. Shvartsberg, R.S. Iodination of hydroxyanthraquinones. Zh. Org. Chim., 1988, 24, 405-410.
54. Wilson, J.N.; Wang, Y.Q.; Lavigne, J.J.; Bunz, U.H.F. A biosensing model system: selective interaction of biotinylated PPEs with streptavidincoated polystyrene microspheres. Chem. Commun., 2003, 1626-1627.
55. Kushon, S.A.; Bradford, K.; Marin, V.; Suhrada, C.; Armitage, B.A.; McBranch, D.; Whitten, D. Detection of Single Nucleotide Mismatches via Fluorescent Polymer Superquenching. Langmuir, 2003, 19, 6456-6464.
56. Babudri, F.; Colangiuli, D.; Di Lorenzo, P.A.; Farinola, G.M.; Omar O.H.; Naso, F. Synthesis of poly(aryleneethynylene)s bearing glucose units as substituent. Chem. Commun., 2003, 130-131.
57. Erdogan, B.; Wilson, J.N.; Bunz, U.H.F. Synthesis and mesoscopic order of a sugar-coated poly(p-phenyleneethynylene). Macromolecules, 2002, 35, 7863-7864.
58. Nair, V.; Joseph, J.P. Glycosylation of silyl ethers: a novel synthesis of oligosaccharides and aryl glycosides. Heterocycles, 1987, 25, 337-341.
59. Smits, E.; Engberts, J.B.F.N.; Kellogg, R.M.; van Doren, H.A. Reliable method for the synthesis of aryl β-D-glucopyranosides, using boron
60. Babudri, F.; Colangiuli, D.; Di Bari, L.; Farinola, G.M.; Omar, O.H.; Naso, F.; Pescitelli, G. Synthesis and chiroptical characterization of an amino acid functionalized dialkoxypoly(p-phenyleneethynylene). Macromolecules, 2006, 39, 5206-5212.
61. Tanese, M.C.; Omar, O.H.; Torsi, L.; Marinelli, F.; Colangiuli, D.; Farinola, G.M.; Babudri, F.; Naso, F.; Sabbatini, L.; Zambonin, P.G. A poly(phenyleneethynylene) polymer bearing amino acid substituents as active layer in enantioselective solid-state sensors. Proc. of SPIE, 2006, 6192, 61921E-1-61921E-6.
62. Zeggaf, C.; Poncet, J.; Jouin, P.; Dufour, M.N.; Castro, B. Isopropenyl chlorocarbonate (IPCC)1 in amino acid and peptide chemistry: esterification of N-protected amino acids; application to the synthesis of the depsipeptide valinomycin. Tetrahedron, 1989, 45, 5039-5050.
63. Farinola, G. M.; Omar, O.H.; Operamolla, A.; Babudri, F. In: Synthesis of organic semiconductors functionalized with biological molecules. ISIE 2010, 2010 Proceedings of the IEEE International Symposium on Industrial Electronics 2010, 505-510.
64. Tanese, M.C.; Torsi, L.; Cioffi, N.; Zotti, L.A.; Colangiuli, D.; Farinola, G.M.; Babudri, F.; Naso, F.; Giangregorio, M. M.; Sabbatini, L.; Zambonin, P.G. Poly(phenyleneethynylene) polymers bearing glucose substituents as promising active layers in enantioselective chemiresistors. Sensor Actuat. B, 2004, 100, 17-21.
65. Torsi, L.; Farinola, G.M.; Marinelli, F.; Tanese, M. C.; Omar, O.H.; Valli, L.; Babudri, F.; Palmisano, F.; Zambonin, P.G.; Naso, F. A sensitivityenhanced field-effect chiral sensor. Nat. Mater., 2008, 7, 412-417;
66. Hassan Omar, O.; Babudri, F.; Farinola, G.M.; Naso, F.; Operamolla, A.; Pedone, A. Synthesis of D-glucose and L-phenylalanine substituted phenyleneethiophene Oligomers. Tetrahedron, 2011, 67, 486-494.
67. Russew, M.M.; Hecht, S. Photoswitches: from molecules to materials. Adv. Mater., 2010, 22, 3348-3360.
68. Babudri, F.; Bilancia, G.; Cardone, A.; Coppo, P.; De Cola, L.; Farinola, G. M.; Hofstraat, J.W.; Naso, F. Photochemical tuning of light emission in a conjugated polymer containing norbornadiene units in the main chain. Photochem. Photobiol. Sci., 2007, 6, 361-364.