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Synthesis and optoelectronic properties of hexahydroxylated 10-O-R-substituted anthracenes via a new modification of the Friedel-Crafts reaction using O-protected ortho-acetal diarylmethanols.

Chemistry (Weinheim an der Bergstrasse, Germany)

Bodzioch A, Marciniak B, Różycka-Sokołowska E, Jeszka JK, Uznański P, Kania S, Kuliński J, Bałczewski P.
PMID: 22438194
Chemistry. 2012 Apr 16;18(16):4866-76. doi: 10.1002/chem.201101909. Epub 2012 Mar 21.

A new modification of the Friedel-Crafts type intramolecular cyclization involving O-protected ortho-acetal diarylmethanols as a new type of reactant, was carried out for the first time in a medium containing a large amount of water at room temperature and...

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Bodzioch A, Marciniak B, Różycka-Sokołowska E, et al. Synthesis and optoelectronic properties of hexahydroxylated 10-O-R-substituted anthracenes via a new modification of the Friedel-Crafts reaction using O-protected ortho-acetal diarylmethanols. Chemistry. 2012;18(16):4866-76doi: 10.1002/chem.201101909.
Bodzioch, A., Marciniak, B., Różycka-Sokołowska, E., Jeszka, J. K., Uznański, P., Kania, S., Kuliński, J., & Bałczewski, P. (2012). Synthesis and optoelectronic properties of hexahydroxylated 10-O-R-substituted anthracenes via a new modification of the Friedel-Crafts reaction using O-protected ortho-acetal diarylmethanols. Chemistry (Weinheim an der Bergstrasse, Germany), 18(16), 4866-76. https://doi.org/10.1002/chem.201101909
Bodzioch, Agnieszka, et al. "Synthesis and optoelectronic properties of hexahydroxylated 10-O-R-substituted anthracenes via a new modification of the Friedel-Crafts reaction using O-protected ortho-acetal diarylmethanols." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 18,16 (2012): 4866-76. doi: https://doi.org/10.1002/chem.201101909
Bodzioch A, Marciniak B, Różycka-Sokołowska E, Jeszka JK, Uznański P, Kania S, Kuliński J, Bałczewski P. Synthesis and optoelectronic properties of hexahydroxylated 10-O-R-substituted anthracenes via a new modification of the Friedel-Crafts reaction using O-protected ortho-acetal diarylmethanols. Chemistry. 2012 Apr 16;18(16):4866-76. doi: 10.1002/chem.201101909. Epub 2012 Mar 21. PMID: 22438194.
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Minimally invasive characterization of covalent monolayer sheets using tip-enhanced Raman spectroscopy.

ACS nano

Opilik L, Payamyar P, Szczerbiński J, Schütz AP, Servalli M, Hungerland T, Schlüter AD, Zenobi R.
PMID: 25803562
ACS Nano. 2015 Apr 28;9(4):4252-9. doi: 10.1021/acsnano.5b00629. Epub 2015 Mar 31.

Synthetic covalent monolayer sheets and their subclass, two-dimensional polymers are of particular interest in materials science because of their special dimensionality which renders them very different from any bulk matter. However, structural analysis of such entities is rather challenging,...

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Opilik L, Payamyar P, Szczerbiński J, et al. Minimally invasive characterization of covalent monolayer sheets using tip-enhanced Raman spectroscopy. ACS Nano. 2015;9(4):4252-9doi: 10.1021/acsnano.5b00629.
Opilik, L., Payamyar, P., Szczerbiński, J., Schütz, A. P., Servalli, M., Hungerland, T., Schlüter, A. D., & Zenobi, R. (2015). Minimally invasive characterization of covalent monolayer sheets using tip-enhanced Raman spectroscopy. ACS nano, 9(4), 4252-9. https://doi.org/10.1021/acsnano.5b00629
Opilik, Lothar, et al. "Minimally invasive characterization of covalent monolayer sheets using tip-enhanced Raman spectroscopy." ACS nano vol. 9,4 (2015): 4252-9. doi: https://doi.org/10.1021/acsnano.5b00629
Opilik L, Payamyar P, Szczerbiński J, Schütz AP, Servalli M, Hungerland T, Schlüter AD, Zenobi R. Minimally invasive characterization of covalent monolayer sheets using tip-enhanced Raman spectroscopy. ACS Nano. 2015 Apr 28;9(4):4252-9. doi: 10.1021/acsnano.5b00629. Epub 2015 Mar 31. PMID: 25803562.
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Complementary Lock-and-Key Ligand Binding of a Triplet Transmitter to a Nanocrystal Photosensitizer.

Angewandte Chemie (International ed. in English)

Li X, Fast A, Huang Z, Fishman DA, Tang ML.
PMID: 28402601
Angew Chem Int Ed Engl. 2017 May 08;56(20):5598-5602. doi: 10.1002/anie.201701929. Epub 2017 Apr 12.

Owing to the difficulty in comprehensively characterizing nanocrystal (NC) surfaces, clear guidance for ligand design is lacking. In this work, a series of bidentate bis(pyridine) anthracene isomers (2,3-PyAn, 3,3-PyAn, 2,2-PyAn) that differ in their binding geometries were designed to...

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Li X, Fast A, Huang Z, et al. Complementary Lock-and-Key Ligand Binding of a Triplet Transmitter to a Nanocrystal Photosensitizer. Angew Chem Int Ed Engl. 2017;56(20):5598-5602doi: 10.1002/anie.201701929.
Li, X., Fast, A., Huang, Z., Fishman, D. A., & Tang, M. L. (2017). Complementary Lock-and-Key Ligand Binding of a Triplet Transmitter to a Nanocrystal Photosensitizer. Angewandte Chemie (International ed. in English), 56(20), 5598-5602. https://doi.org/10.1002/anie.201701929
Li, Xin, et al. "Complementary Lock-and-Key Ligand Binding of a Triplet Transmitter to a Nanocrystal Photosensitizer." Angewandte Chemie (International ed. in English) vol. 56,20 (2017): 5598-5602. doi: https://doi.org/10.1002/anie.201701929
Li X, Fast A, Huang Z, Fishman DA, Tang ML. Complementary Lock-and-Key Ligand Binding of a Triplet Transmitter to a Nanocrystal Photosensitizer. Angew Chem Int Ed Engl. 2017 May 08;56(20):5598-5602. doi: 10.1002/anie.201701929. Epub 2017 Apr 12. PMID: 28402601.
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Nanosized particles of organically modified silica as microreactors to enhance the regioselectivity in the photocycloaddition of 9-substituted anthracenes.

Organic letters

Wu DY, Chen B, Fu XG, Wu LZ, Zhang LP, Tung CH.
PMID: 12659577
Org Lett. 2003 Apr 03;5(7):1075-7. doi: 10.1021/ol0341041.

[reaction: see text] Nanosized particles of modified silica with 3-ammoniumpropyl residue have been prepared and successfully used as microreactors to control the regioselectivity of the photocycloaddition of five 9-substituted anthracences [AnCH(2)N(+)(CH(3))(3)Br(-) (1), AnCH(2)COO(-)Na(+) (2), AnCH(2)CH(2)COOH (3), AnCH(2)OH (4), AnCH(3)...

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Wu DY, Chen B, Fu XG, et al. Nanosized particles of organically modified silica as microreactors to enhance the regioselectivity in the photocycloaddition of 9-substituted anthracenes. Org Lett. 2003;5(7):1075-7doi: 10.1021/ol0341041.
Wu, D. Y., Chen, B., Fu, X. G., Wu, L. Z., Zhang, L. P., & Tung, C. H. (2003). Nanosized particles of organically modified silica as microreactors to enhance the regioselectivity in the photocycloaddition of 9-substituted anthracenes. Organic letters, 5(7), 1075-7. https://doi.org/10.1021/ol0341041
Wu, Da-Yong, et al. "Nanosized particles of organically modified silica as microreactors to enhance the regioselectivity in the photocycloaddition of 9-substituted anthracenes." Organic letters vol. 5,7 (2003): 1075-7. doi: https://doi.org/10.1021/ol0341041
Wu DY, Chen B, Fu XG, Wu LZ, Zhang LP, Tung CH. Nanosized particles of organically modified silica as microreactors to enhance the regioselectivity in the photocycloaddition of 9-substituted anthracenes. Org Lett. 2003 Apr 03;5(7):1075-7. doi: 10.1021/ol0341041. PMID: 12659577.
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Facile construction and divergent transformation of polycyclic isoxazoles: direct access to polyketide architectures.

Organic letters

Bode JW, Hachisu Y, Matsuura T, Suzuki K.
PMID: 12583726
Org Lett. 2003 Feb 20;5(4):391-4. doi: 10.1021/ol027283f.

[reaction: see text] Base-promoted cyclocondensation of C-chloro oximes with cyclic 1,3-diketones affords functionalized isoxazoles in good yield and under convenient reaction conditions. This process enables the synthesis of highly substituted products with notable functional group tolerance. The products obtained...

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Bode JW, Hachisu Y, Matsuura T, et al. Facile construction and divergent transformation of polycyclic isoxazoles: direct access to polyketide architectures. Org Lett. 2003;5(4):391-4doi: 10.1021/ol027283f.
Bode, J. W., Hachisu, Y., Matsuura, T., & Suzuki, K. (2003). Facile construction and divergent transformation of polycyclic isoxazoles: direct access to polyketide architectures. Organic letters, 5(4), 391-4. https://doi.org/10.1021/ol027283f
Bode, Jeffrey W, et al. "Facile construction and divergent transformation of polycyclic isoxazoles: direct access to polyketide architectures." Organic letters vol. 5,4 (2003): 391-4. doi: https://doi.org/10.1021/ol027283f
Bode JW, Hachisu Y, Matsuura T, Suzuki K. Facile construction and divergent transformation of polycyclic isoxazoles: direct access to polyketide architectures. Org Lett. 2003 Feb 20;5(4):391-4. doi: 10.1021/ol027283f. PMID: 12583726.
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Scanning tunneling microscopy of prochiral anthracene derivatives on graphite: chain length effects on monolayer morphology.

Journal of the American Chemical Society

Wei Y, Kannappan K, Flynn GW, Zimmt MB.
PMID: 15099117
J Am Chem Soc. 2004 Apr 28;126(16):5318-22. doi: 10.1021/ja038658a.

The morphology of monolayers formed upon adsorption of prochiral 1,5-substituted anthracene derivatives on highly oriented pyrolytic graphite is investigated using scanning tunneling microscopy at the liquid-solid interface. The adsorption orientation of these prochiral anthracene derivatives positions one of their...

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Wei Y, Kannappan K, Flynn GW, et al. Scanning tunneling microscopy of prochiral anthracene derivatives on graphite: chain length effects on monolayer morphology. J Am Chem Soc. 2004;126(16):5318-22doi: 10.1021/ja038658a.
Wei, Y., Kannappan, K., Flynn, G. W., & Zimmt, M. B. (2004). Scanning tunneling microscopy of prochiral anthracene derivatives on graphite: chain length effects on monolayer morphology. Journal of the American Chemical Society, 126(16), 5318-22. https://doi.org/10.1021/ja038658a
Wei, Yanhu, et al. "Scanning tunneling microscopy of prochiral anthracene derivatives on graphite: chain length effects on monolayer morphology." Journal of the American Chemical Society vol. 126,16 (2004): 5318-22. doi: https://doi.org/10.1021/ja038658a
Wei Y, Kannappan K, Flynn GW, Zimmt MB. Scanning tunneling microscopy of prochiral anthracene derivatives on graphite: chain length effects on monolayer morphology. J Am Chem Soc. 2004 Apr 28;126(16):5318-22. doi: 10.1021/ja038658a. PMID: 15099117.
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Molecular crystals with moving parts: synthesis, characterization, and crystal packing of molecular gyroscopes with methyl-substituted triptycyl frames.

The Journal of organic chemistry

Godinez CE, Zepeda G, Mortko CJ, Dang H, Garcia-Garibay MA.
PMID: 14987025
J Org Chem. 2004 Mar 05;69(5):1652-62. doi: 10.1021/jo035517i.

We report a highly convergent synthesis for the preparation of molecular gyroscopes consisting of para-phenylene rotors linked by triple bonds to methyl-substituted triptycenes acting as pivots and encapsulating frames. The desired 1,4-bis[2-(2,3,6,7,12,13-hexamethyl-10-alkyl-9-triptycyl)ethynyl]benzenes were prepared from 2,3-dimethyl-1,3-butadiene using Diels-Alder cycloadditions...

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Godinez CE, Zepeda G, Mortko CJ, et al. Molecular crystals with moving parts: synthesis, characterization, and crystal packing of molecular gyroscopes with methyl-substituted triptycyl frames. J Org Chem. 2004;69(5):1652-62doi: 10.1021/jo035517i.
Godinez, C. E., Zepeda, G., Mortko, C. J., Dang, H., & Garcia-Garibay, M. A. (2004). Molecular crystals with moving parts: synthesis, characterization, and crystal packing of molecular gyroscopes with methyl-substituted triptycyl frames. The Journal of organic chemistry, 69(5), 1652-62. https://doi.org/10.1021/jo035517i
Godinez, Carlos E, et al. "Molecular crystals with moving parts: synthesis, characterization, and crystal packing of molecular gyroscopes with methyl-substituted triptycyl frames." The Journal of organic chemistry vol. 69,5 (2004): 1652-62. doi: https://doi.org/10.1021/jo035517i
Godinez CE, Zepeda G, Mortko CJ, Dang H, Garcia-Garibay MA. Molecular crystals with moving parts: synthesis, characterization, and crystal packing of molecular gyroscopes with methyl-substituted triptycyl frames. J Org Chem. 2004 Mar 05;69(5):1652-62. doi: 10.1021/jo035517i. PMID: 14987025.
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Reversible intramolecular photocycloaddition of a bis(9-anthrylbutadienyl)paracyclophane--an inverse photochromic system. (Photoactive cyclophanes 5).

Beilstein journal of organic chemistry

Hopf H, Beck C, Desvergne JP, Bouas-Laurent H, Jones PG, Ernst L.
PMID: 19617913
Beilstein J Org Chem. 2009 May 07;5:20. doi: 10.3762/bjoc.5.20.

The title compound, 4,13-bis[(1E,3E)-4-(9-anthracenyl)buta-1,3-dienyl][2.2]paracyclophane (2), prepared in 35% overall yield from [2.2]paracyclophane, absorbs light at lambda(max) = 400 nm with a tail down to 480 nm. By irradiation into this band, 2 generates a single photoproduct, 4, whose absorption...

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Hopf H, Beck C, Desvergne JP, et al. Reversible intramolecular photocycloaddition of a bis(9-anthrylbutadienyl)paracyclophane--an inverse photochromic system. (Photoactive cyclophanes 5). Beilstein J Org Chem. 2009;5:20doi: 10.3762/bjoc.5.20.
Hopf, H., Beck, C., Desvergne, J. P., Bouas-Laurent, H., Jones, P. G., & Ernst, L. (2009). Reversible intramolecular photocycloaddition of a bis(9-anthrylbutadienyl)paracyclophane--an inverse photochromic system. (Photoactive cyclophanes 5). Beilstein journal of organic chemistry, 520. https://doi.org/10.3762/bjoc.5.20
Hopf, Henning, et al. "Reversible intramolecular photocycloaddition of a bis(9-anthrylbutadienyl)paracyclophane--an inverse photochromic system. (Photoactive cyclophanes 5)." Beilstein journal of organic chemistry vol. 5 (2009): 20. doi: https://doi.org/10.3762/bjoc.5.20
Hopf H, Beck C, Desvergne JP, Bouas-Laurent H, Jones PG, Ernst L. Reversible intramolecular photocycloaddition of a bis(9-anthrylbutadienyl)paracyclophane--an inverse photochromic system. (Photoactive cyclophanes 5). Beilstein J Org Chem. 2009 May 07;5:20. doi: 10.3762/bjoc.5.20. PMID: 19617913; PMCID: PMC2707062.
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Competing excited state intramolecular proton transfer pathways from phenol to anthracene moieties.

The Journal of organic chemistry

Basarić N, Wan P.
PMID: 16555820
J Org Chem. 2006 Mar 31;71(7):2677-86. doi: 10.1021/jo0524728.

Four new 9-(2'-hydroxyphenyl)anthracene derivatives 7-10 were synthesized and their potential excited state intramolecular proton transfer (ESIPT) reaction investigated. Whereas 7 reacted via the anticipated (formal) ESIPT reaction (proton transfer to the 10-position of the anthracene), derivatives 8-10 reacted via...

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Basarić N, Wan P. Competing excited state intramolecular proton transfer pathways from phenol to anthracene moieties. J Org Chem. 2006;71(7):2677-86doi: 10.1021/jo0524728.
Basarić, N., & Wan, P. (2006). Competing excited state intramolecular proton transfer pathways from phenol to anthracene moieties. The Journal of organic chemistry, 71(7), 2677-86. https://doi.org/10.1021/jo0524728
Basarić, Nikola, and Wan, Peter. "Competing excited state intramolecular proton transfer pathways from phenol to anthracene moieties." The Journal of organic chemistry vol. 71,7 (2006): 2677-86. doi: https://doi.org/10.1021/jo0524728
Basarić N, Wan P. Competing excited state intramolecular proton transfer pathways from phenol to anthracene moieties. J Org Chem. 2006 Mar 31;71(7):2677-86. doi: 10.1021/jo0524728. PMID: 16555820.
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Aromatic compounds in molecular phase of Baltic amber-synchronous luminescence analysis.

Talanta

Matuszewska A, Czaja M.
PMID: 18968585
Talanta. 2002 Apr 08;56(6):1049-59. doi: 10.1016/s0039-9140(01)00610-5.

Synchronous luminescence analysis was performed in order to identify aromatic compounds in solvent extracts of Baltic amber. The investigated extracts were obtained, for comparisons, as products of extraction by various techniques and solvents. Methylene chloride and ethanol were applied...

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Matuszewska A, Czaja M. Aromatic compounds in molecular phase of Baltic amber-synchronous luminescence analysis. Talanta. 2002;56(6):1049-59doi: 10.1016/s0039-9140(01)00610-5.
Matuszewska, A., & Czaja, M. (2002). Aromatic compounds in molecular phase of Baltic amber-synchronous luminescence analysis. Talanta, 56(6), 1049-59. https://doi.org/10.1016/s0039-9140(01)00610-5
Matuszewska, Aniela, and Czaja, Maria. "Aromatic compounds in molecular phase of Baltic amber-synchronous luminescence analysis." Talanta vol. 56,6 (2002): 1049-59. doi: https://doi.org/10.1016/s0039-9140(01)00610-5
Matuszewska A, Czaja M. Aromatic compounds in molecular phase of Baltic amber-synchronous luminescence analysis. Talanta. 2002 Apr 08;56(6):1049-59. doi: 10.1016/s0039-9140(01)00610-5. PMID: 18968585.
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Application of adsorptive stripping voltammetry to the simultaneous determination of bismuth and copper in the presence of nuclear fast red.

Analytica chimica acta

Gholivand MB, Romiani AA.
PMID: 17723426
Anal Chim Acta. 2006 Jun 30;571(1):99-104. doi: 10.1016/j.aca.2006.04.054. Epub 2006 May 05.

A sensitive and selective method for the simultaneous determination of copper and bismuth by adsorptive stripping was developed using nuclear fast red (2-anthracenesulfonic acid, 4-amino-9,10-dihydro-1,3-dihydroxy-9,10-dioxo-, monosodium salt) as selective complexing agent onto hanging mercury drop electrode. In a single...

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Gholivand MB, Romiani AA. Application of adsorptive stripping voltammetry to the simultaneous determination of bismuth and copper in the presence of nuclear fast red. Anal Chim Acta. 2006;571(1):99-104doi: 10.1016/j.aca.2006.04.054.
Gholivand, M. B., & Romiani, A. A. (2006). Application of adsorptive stripping voltammetry to the simultaneous determination of bismuth and copper in the presence of nuclear fast red. Analytica chimica acta, 571(1), 99-104. https://doi.org/10.1016/j.aca.2006.04.054
Gholivand, M B, and Romiani, A A. "Application of adsorptive stripping voltammetry to the simultaneous determination of bismuth and copper in the presence of nuclear fast red." Analytica chimica acta vol. 571,1 (2006): 99-104. doi: https://doi.org/10.1016/j.aca.2006.04.054
Gholivand MB, Romiani AA. Application of adsorptive stripping voltammetry to the simultaneous determination of bismuth and copper in the presence of nuclear fast red. Anal Chim Acta. 2006 Jun 30;571(1):99-104. doi: 10.1016/j.aca.2006.04.054. Epub 2006 May 05. PMID: 17723426.
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Highly brominated anthracenes as precursors for the convenient synthesis of 2,9,10-trisubstituted anthracene derivatives.

Beilstein journal of organic chemistry

Cakmak O, Aydogan L, Berkil K, Gulcin I, Buyukgungor O.
PMID: 19190741
Beilstein J Org Chem. 2008;4:50. doi: 10.3762/bjoc.4.50. Epub 2008 Dec 10.

When 9,10-dibromoanthracene was treated with bromine in CCl(4) without a catalyst, 1,2,3,4,9,10-hexabromo-1,2,3,4-tetrahydroanthracene (3) was obtained in 95% yield in the absence of other stereoisomers or rearomatization products. We investigated the base-induced elimination reaction of hexabromide 3 under various conditions....

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Cakmak O, Aydogan L, Berkil K, et al. Highly brominated anthracenes as precursors for the convenient synthesis of 2,9,10-trisubstituted anthracene derivatives. Beilstein J Org Chem. 2008;4:50doi: 10.3762/bjoc.4.50.
Cakmak, O., Aydogan, L., Berkil, K., Gulcin, I., & Buyukgungor, O. (2008). Highly brominated anthracenes as precursors for the convenient synthesis of 2,9,10-trisubstituted anthracene derivatives. Beilstein journal of organic chemistry, 450. https://doi.org/10.3762/bjoc.4.50
Cakmak, Osman, et al. "Highly brominated anthracenes as precursors for the convenient synthesis of 2,9,10-trisubstituted anthracene derivatives." Beilstein journal of organic chemistry vol. 4 (2008): 50. doi: https://doi.org/10.3762/bjoc.4.50
Cakmak O, Aydogan L, Berkil K, Gulcin I, Buyukgungor O. Highly brominated anthracenes as precursors for the convenient synthesis of 2,9,10-trisubstituted anthracene derivatives. Beilstein J Org Chem. 2008;4:50. doi: 10.3762/bjoc.4.50. Epub 2008 Dec 10. PMID: 19190741; PMCID: PMC2633663.
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Showing 1 to 12 of 187 entries