Polar tagging in the synthesis of monodisperse oligo(p-pheny leneethynylene)s and an update on the synthesis of oligoPPEs

Sahoo D, Thiele S, Schulte M, Ramezanian N, Godt A (2010)
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 6.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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Abstract / Bemerkung
One important access to monodisperse (functionalized) oligoPPEs is based on the orthogonality of the alkyne protecting groups tri-isopropylsilyl and hydroxymethyl (HOM) and on the polar tagging with the hydroxymethyl moiety for an easy chromatographic separation of the products. This paper provides an update of this synthetic route. For the deprotection of HOM protected alkynes, gamma-MnO2 proved to be better than (highly) activated MnO2. The use of HOM as an alkyne protecting group is accompanied by carbometalation as a side reaction in the alkynyl-aryl coupling. The extent of carbometalation can be distinctly reduced through substitution of HOM for 1-hydroxyethyl. The strategy of polar tagging is extended by embedding ether linkages within the solubilising side chains. With building blocks such as 1,4-diiodo-2,5-bis(6-methoxyhexyl) less steps are needed to assemble oligoPPEs with functional end groups and the isolation of pure compounds becomes simple. For the preparation of 1,4-dialkyl-2,5-diiodobenzene a better procedure is presented together with the finding that 1,4-dialkyl-2,3-diiodobenzene, a constitutional isomer of 1,4-dialkyl-2,5-diiodobenzene, is one of the byproducts.
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BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
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6
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Sahoo D, Thiele S, Schulte M, Ramezanian N, Godt A. Polar tagging in the synthesis of monodisperse oligo(p-pheny leneethynylene)s and an update on the synthesis of oligoPPEs. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. 2010;6.
Sahoo, D., Thiele, S., Schulte, M., Ramezanian, N., & Godt, A. (2010). Polar tagging in the synthesis of monodisperse oligo(p-pheny leneethynylene)s and an update on the synthesis of oligoPPEs. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 6. doi:10.3762/bjoc.6.57
Sahoo, D., Thiele, S., Schulte, M., Ramezanian, N., and Godt, A. (2010). Polar tagging in the synthesis of monodisperse oligo(p-pheny leneethynylene)s and an update on the synthesis of oligoPPEs. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 6.
Sahoo, D., et al., 2010. Polar tagging in the synthesis of monodisperse oligo(p-pheny leneethynylene)s and an update on the synthesis of oligoPPEs. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 6.
D. Sahoo, et al., “Polar tagging in the synthesis of monodisperse oligo(p-pheny leneethynylene)s and an update on the synthesis of oligoPPEs”, BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, vol. 6, 2010.
Sahoo, D., Thiele, S., Schulte, M., Ramezanian, N., Godt, A.: Polar tagging in the synthesis of monodisperse oligo(p-pheny leneethynylene)s and an update on the synthesis of oligoPPEs. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. 6, (2010).
Sahoo, Dhananjaya, Thiele, Susanne, Schulte, Miriam, Ramezanian, Navid, and Godt, Adelheid. “Polar tagging in the synthesis of monodisperse oligo(p-pheny leneethynylene)s and an update on the synthesis of oligoPPEs”. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 6 (2010).

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23 References

Daten bereitgestellt von Europe PubMed Central.

Three-spin correlations in double electron-electron resonance.
Jeschke G, Sajid M, Schulte M, Godt A., Phys Chem Chem Phys 11(31), 2009
PMID: 19639133
Length-dependent convergence and saturation behavior of electrochemical, linear optical, quadratic nonlinear optical, and cubic nonlinear optical properties of dipolar alkynylruthenium complexes with oligo(phenyleneethynylene) bridges.
Babgi B, Rigamonti L, Cifuentes MP, Corkery TC, Randles MD, Schwich T, Petrie S, Stranger R, Teshome A, Asselberghs I, Clays K, Samoc M, Humphrey MG., J. Am. Chem. Soc. 131(29), 2009
PMID: 19621969
Electrical conductance of conjugated oligomers at the single molecule level.
Huber R, Gonzalez MT, Wu S, Langer M, Grunder S, Horhoiu V, Mayor M, Bryce MR, Wang C, Jitchati R, Schonenberger C, Calame M., J. Am. Chem. Soc. 130(3), 2007
PMID: 18163626
Tetrahedral onsager crosses for solubility improvement and crystallization bypass.
Aujard I, Baltaze JP, Baudin JB, Cogne E, Ferrage F, Jullien L, Perez E , Prevost V, Qian LM, Ruel O., J. Am. Chem. Soc. 123(34), 2001
PMID: 11516267
Synthesis of marine polyacetylenes callyberynes A-C by transition-metal-catalyzed cross-coupling reactions to sp centers.
Lopez S, Fernandez-Trillo F, Midon P, Castedo L, Saa C., J. Org. Chem. 71(7), 2006
PMID: 16555835
Spin pair geometry revealed by high-field DEER in the presence of conformational distributions.
Polyhach Y, Godt A, Bauer C, Jeschke G., J. Magn. Reson. 185(1), 2006
PMID: 17188008
Highly emissive pi-conjugated alkynylpyrene oligomers: their synthesis and photophysical properties.
Shimizu H, Fujimoto K, Furusyo M, Maeda H, Nanai Y, Mizuno K, Inouye M., J. Org. Chem. 72(4), 2007
PMID: 17243714
Single-molecule devices as scaffolding for multicomponent nanostructure assembly.
Guo X, Whalley A, Klare JE, Huang L, O'brien S, Steigerwald M, Nuckolls C., Nano Lett. 7(5), 2007
PMID: 17394373
Oligo(p-phenyleneethynylene)s with hydrogen-bonded coplanar conformation.
Hu W, Zhu N, Tang W, Zhao D., Org. Lett. 10(13), 2008
PMID: 18507389
Macrocyclic cyclophanes with two and three alpha,omega-dichalcogena-1,4-diethynylaryl units: syntheses and structural properties.
Werz DB, Fischer FR, Kornmayer SC, Rominger F, Gleiter R., J. Org. Chem. 73(20), 2008
PMID: 18795790
Synthesis of functional molecular rod oligomers.
Andersen CS, Gothelf KV., Org. Biomol. Chem. 7(1), 2008
PMID: 19081946
Synthesis of monodisperse oligo(1,4-phenyleneethynylene-alt-1,4-triptycyleneethynylene)s.
Maag D, Kottke T, Schulte M, Godt A., J. Org. Chem. 74(20), 2009
PMID: 19761236

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