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Dimerization of 9-phenylethynylfluorene to di-indeno-naphthacene and dispiro-[fluorene-dihydronaphthacene-fluorene]: an X-ray crystallographic and NMR study.

Organic letters

Harrington LE, Britten JF, McGlinchey MJ.
PMID: 14986975
Org Lett. 2004 Mar 04;6(5):787-90. doi: 10.1021/ol049967o.

The attempted Diels-Alder reaction between 9-phenylethynylfluorene and tetracyclone yields instead three products resulting from the dimerization of the isomeric allene. The major product is 8,16-diphenyl-diindeno[1,2,3-de:1',2',3'-mn]naphthacene, in which each terminal ring is derived from a fluorenyl unit; aerial oxidation then...

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Harrington LE, Britten JF, McGlinchey MJ. Dimerization of 9-phenylethynylfluorene to di-indeno-naphthacene and dispiro-[fluorene-dihydronaphthacene-fluorene]: an X-ray crystallographic and NMR study. Org Lett. 2004;6(5):787-90doi: 10.1021/ol049967o.
Harrington, L. E., Britten, J. F., & McGlinchey, M. J. (2004). Dimerization of 9-phenylethynylfluorene to di-indeno-naphthacene and dispiro-[fluorene-dihydronaphthacene-fluorene]: an X-ray crystallographic and NMR study. Organic letters, 6(5), 787-90. https://doi.org/10.1021/ol049967o
Harrington, Laura E, et al. "Dimerization of 9-phenylethynylfluorene to di-indeno-naphthacene and dispiro-[fluorene-dihydronaphthacene-fluorene]: an X-ray crystallographic and NMR study." Organic letters vol. 6,5 (2004): 787-90. doi: https://doi.org/10.1021/ol049967o
Harrington LE, Britten JF, McGlinchey MJ. Dimerization of 9-phenylethynylfluorene to di-indeno-naphthacene and dispiro-[fluorene-dihydronaphthacene-fluorene]: an X-ray crystallographic and NMR study. Org Lett. 2004 Mar 04;6(5):787-90. doi: 10.1021/ol049967o. PMID: 14986975.
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Facile synthesis and X-ray structure of alkoxy-functionalized dibenzo[fg,op]naphthacenes.

Organic letters

Cheng XH, Höger S, Fenske D.
PMID: 12868865
Org Lett. 2003 Jul 24;5(15):2587-9. doi: 10.1021/ol034626g.

[structure: see text] 1,3-Bis(2-bromophenyl)-2,5-diphenylbenzenes are readily available by the condensation of phenylacetates with the corresponding pyrylium salts and undergo a palladium-catalyzed dehydrohalogenation to give functionalized dibenzo[fg,op]naphthacenes.

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Cheng XH, Höger S, Fenske D. Facile synthesis and X-ray structure of alkoxy-functionalized dibenzo[fg,op]naphthacenes. Org Lett. 2003;5(15):2587-9doi: 10.1021/ol034626g.
Cheng, X. H., Höger, S., & Fenske, D. (2003). Facile synthesis and X-ray structure of alkoxy-functionalized dibenzo[fg,op]naphthacenes. Organic letters, 5(15), 2587-9. https://doi.org/10.1021/ol034626g
Cheng, Xiao Hong, et al. "Facile synthesis and X-ray structure of alkoxy-functionalized dibenzo[fg,op]naphthacenes." Organic letters vol. 5,15 (2003): 2587-9. doi: https://doi.org/10.1021/ol034626g
Cheng XH, Höger S, Fenske D. Facile synthesis and X-ray structure of alkoxy-functionalized dibenzo[fg,op]naphthacenes. Org Lett. 2003 Jul 24;5(15):2587-9. doi: 10.1021/ol034626g. PMID: 12868865.
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Smectic-A and Hexatic-B Liquid Crystal Phases of Sanidic Alkyl-Substituted Dibenzo[fg,op]naphthacenes.

The journal of physical chemistry. B

Repasky PJ, Agra-Kooijman DM, Kumar S, Hartley CS.
PMID: 26914988
J Phys Chem B. 2016 Mar 17;120(10):2829-37. doi: 10.1021/acs.jpcb.5b10990. Epub 2016 Mar 07.

Despite longstanding interest in liquid crystalline compounds with simple rod- or disc-like shapes (calamitics or discotics), very few examples of the analogous board-shaped, or "sanidic", liquid crystals exist. A new series of alkyl-substituted dibenzo[fg,op]naphthacenes have been prepared by planarization...

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Repasky PJ, Agra-Kooijman DM, Kumar S, et al. Smectic-A and Hexatic-B Liquid Crystal Phases of Sanidic Alkyl-Substituted Dibenzo[fg,op]naphthacenes. J Phys Chem B. 2016;120(10):2829-37doi: 10.1021/acs.jpcb.5b10990.
Repasky, P. J., Agra-Kooijman, D. M., Kumar, S., & Hartley, C. S. (2016). Smectic-A and Hexatic-B Liquid Crystal Phases of Sanidic Alkyl-Substituted Dibenzo[fg,op]naphthacenes. The journal of physical chemistry. B, 120(10), 2829-37. https://doi.org/10.1021/acs.jpcb.5b10990
Repasky, Paul J, et al. "Smectic-A and Hexatic-B Liquid Crystal Phases of Sanidic Alkyl-Substituted Dibenzo[fg,op]naphthacenes." The journal of physical chemistry. B vol. 120,10 (2016): 2829-37. doi: https://doi.org/10.1021/acs.jpcb.5b10990
Repasky PJ, Agra-Kooijman DM, Kumar S, Hartley CS. Smectic-A and Hexatic-B Liquid Crystal Phases of Sanidic Alkyl-Substituted Dibenzo[fg,op]naphthacenes. J Phys Chem B. 2016 Mar 17;120(10):2829-37. doi: 10.1021/acs.jpcb.5b10990. Epub 2016 Mar 07. PMID: 26914988.
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A convenient synthesis of tetrabenzo[de,hi,mn,qr]naphthacene from readily available 1,2-di(phenanthren-4-yl)ethyne.

The Journal of organic chemistry

Mukherjee A, Pati K, Liu RS.
PMID: 19601616
J Org Chem. 2009 Aug 21;74(16):6311-4. doi: 10.1021/jo901177e.

We report here a convenient synthesis of tetrabenzo[de,hi,mn,qr]naphthacenes from 1,2-di(phenanthren-4-yl)ethynes through initial Brønsted acid-catalyzed hydroarylation, followed by FeCl(3)-oxidative coupling reactions. This new method is applicable to tetrabenzo[de,hi,mn,qr]naphthacenes bearing various alkyl substituents.

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Mukherjee A, Pati K, Liu RS. A convenient synthesis of tetrabenzo[de,hi,mn,qr]naphthacene from readily available 1,2-di(phenanthren-4-yl)ethyne. J Org Chem. 2009;74(16):6311-4doi: 10.1021/jo901177e.
Mukherjee, A., Pati, K., & Liu, R. S. (2009). A convenient synthesis of tetrabenzo[de,hi,mn,qr]naphthacene from readily available 1,2-di(phenanthren-4-yl)ethyne. The Journal of organic chemistry, 74(16), 6311-4. https://doi.org/10.1021/jo901177e
Mukherjee, Anupam, et al. "A convenient synthesis of tetrabenzo[de,hi,mn,qr]naphthacene from readily available 1,2-di(phenanthren-4-yl)ethyne." The Journal of organic chemistry vol. 74,16 (2009): 6311-4. doi: https://doi.org/10.1021/jo901177e
Mukherjee A, Pati K, Liu RS. A convenient synthesis of tetrabenzo[de,hi,mn,qr]naphthacene from readily available 1,2-di(phenanthren-4-yl)ethyne. J Org Chem. 2009 Aug 21;74(16):6311-4. doi: 10.1021/jo901177e. PMID: 19601616.
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Synthesis, structure, and photophysical properties of dibenzo[de,mn]naphthacenes.

Angewandte Chemie (International ed. in English)

Wu TC, Chen CH, Hibi D, Shimizu A, Tobe Y, Wu YT.
PMID: 20715235
Angew Chem Int Ed Engl. 2010 Sep 17;49(39):7059-62. doi: 10.1002/anie.201001929.

No abstract available.

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Wu TC, Chen CH, Hibi D, et al. Synthesis, structure, and photophysical properties of dibenzo[de,mn]naphthacenes. Angew Chem Int Ed Engl. 2010;49(39):7059-62doi: 10.1002/anie.201001929.
Wu, T. C., Chen, C. H., Hibi, D., Shimizu, A., Tobe, Y., & Wu, Y. T. (2010). Synthesis, structure, and photophysical properties of dibenzo[de,mn]naphthacenes. Angewandte Chemie (International ed. in English), 49(39), 7059-62. https://doi.org/10.1002/anie.201001929
Wu, Tsun-Cheng, et al. "Synthesis, structure, and photophysical properties of dibenzo[de,mn]naphthacenes." Angewandte Chemie (International ed. in English) vol. 49,39 (2010): 7059-62. doi: https://doi.org/10.1002/anie.201001929
Wu TC, Chen CH, Hibi D, Shimizu A, Tobe Y, Wu YT. Synthesis, structure, and photophysical properties of dibenzo[de,mn]naphthacenes. Angew Chem Int Ed Engl. 2010 Sep 17;49(39):7059-62. doi: 10.1002/anie.201001929. PMID: 20715235.
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Showing 1 to 5 of 5 entries