From Fenestrindane towards Saddle-Shaped Nanographenes Bearing a Tetracoordinate Carbon Atom
Wong W-S, Ng C-F, Kuck D, Chow H-F (2017)
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 56(40): 12356-12360.
Zeitschriftenaufsatz
| Veröffentlicht | Englisch
Download
Es wurden keine Dateien hochgeladen. Nur Publikationsnachweis!
Autor*in
Wong, Wai-Shing;
Ng, Chun-Fai;
Kuck, DietmarUniBi;
Chow, Hak-Fun
Abstract / Bemerkung
Two saddle-shaped polycyclic aromatic compounds (8a and 8b) bearing an all-cis-[5.5.5.5]fenestrane core surrounded by an o,p,o,p,o,p,o,p-cyclooctaphenylene belt were synthesized and characterized by NMR spectroscopy and mass spectrometry. The key step of this synthesis involves the formation of four cycloheptatriene rings from the corresponding electron-rich 1,4,9,12-tetraarylfenestrindane derivatives 7a and 7b in Scholl-type cyclizations. The structural details of the D-2d-symmetric saddle compound 8a were determined by X-ray crystallography, and the properties of 8a and 8b were studied by UV/Vis and fluorescence spectroscopy and cyclic voltammetry.
Stichworte
fenestrane;
nanographene;
polycyclic aromatic compounds;
saddle-shaped;
structures;
Scholl cyclization
Erscheinungsjahr
2017
Zeitschriftentitel
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Band
56
Ausgabe
40
Seite(n)
12356-12360
ISSN
1433-7851
eISSN
1521-3773
Page URI
https://pub.uni-bielefeld.de/record/2914411
Zitieren
Wong W-S, Ng C-F, Kuck D, Chow H-F. From Fenestrindane towards Saddle-Shaped Nanographenes Bearing a Tetracoordinate Carbon Atom. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION. 2017;56(40):12356-12360.
Wong, W. - S., Ng, C. - F., Kuck, D., & Chow, H. - F. (2017). From Fenestrindane towards Saddle-Shaped Nanographenes Bearing a Tetracoordinate Carbon Atom. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 56(40), 12356-12360. doi:10.1002/anie.201707505
Wong, Wai-Shing, Ng, Chun-Fai, Kuck, Dietmar, and Chow, Hak-Fun. 2017. “From Fenestrindane towards Saddle-Shaped Nanographenes Bearing a Tetracoordinate Carbon Atom”. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 56 (40): 12356-12360.
Wong, W. - S., Ng, C. - F., Kuck, D., and Chow, H. - F. (2017). From Fenestrindane towards Saddle-Shaped Nanographenes Bearing a Tetracoordinate Carbon Atom. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 56, 12356-12360.
Wong, W.-S., et al., 2017. From Fenestrindane towards Saddle-Shaped Nanographenes Bearing a Tetracoordinate Carbon Atom. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 56(40), p 12356-12360.
W.-S. Wong, et al., “From Fenestrindane towards Saddle-Shaped Nanographenes Bearing a Tetracoordinate Carbon Atom”, ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, vol. 56, 2017, pp. 12356-12360.
Wong, W.-S., Ng, C.-F., Kuck, D., Chow, H.-F.: From Fenestrindane towards Saddle-Shaped Nanographenes Bearing a Tetracoordinate Carbon Atom. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION. 56, 12356-12360 (2017).
Wong, Wai-Shing, Ng, Chun-Fai, Kuck, Dietmar, and Chow, Hak-Fun. “From Fenestrindane towards Saddle-Shaped Nanographenes Bearing a Tetracoordinate Carbon Atom”. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 56.40 (2017): 12356-12360.
5 Zitationen in Europe PMC
Daten bereitgestellt von Europe PubMed Central.
Enantiopure distorted ribbon-shaped nanographene combining two-photon absorption-based upconversion and circularly polarized luminescence.
Cruz CM, Márquez IR, Mariz IFA, Blanco V, Sánchez-Sánchez C, Sobrado JM, Martín-Gago JA, Cuerva JM, Maçôas E, Campaña AG., Chem Sci 9(16), 2018
PMID: 29780523
Cruz CM, Márquez IR, Mariz IFA, Blanco V, Sánchez-Sánchez C, Sobrado JM, Martín-Gago JA, Cuerva JM, Maçôas E, Campaña AG., Chem Sci 9(16), 2018
PMID: 29780523
Rigid tetraarylene-bridged cavitands from reduced-symmetry resorcin[4]arene derivatives.
Smith JN, Lucas NT., Chem Commun (Camb) 54(37), 2018
PMID: 29683182
Smith JN, Lucas NT., Chem Commun (Camb) 54(37), 2018
PMID: 29683182
Synthesis of distorted nanographenes containing seven- and eight-membered carbocycles.
Márquez IR, Castro-Fernández S, Millán A, Campaña AG., Chem Commun (Camb) 54(50), 2018
PMID: 29799051
Márquez IR, Castro-Fernández S, Millán A, Campaña AG., Chem Commun (Camb) 54(50), 2018
PMID: 29799051
Dodecabromo- and Dodecaiodocentrohexaindane: Td -Symmetrical Key Building Blocks for Twelve-Fold Cross-Coupling Reactions and Six-Fold Orthogonal Extension.
Linke J, Neumann B, Stammler HG, Kuck D., Chemistry 24(37), 2018
PMID: 29738094
Linke J, Neumann B, Stammler HG, Kuck D., Chemistry 24(37), 2018
PMID: 29738094
Trefoil-Shaped Porous Nanographenes Bearing a Tribenzotriquinacene Core by Three-fold Scholl Macrocyclization.
He L, Ng CF, Li Y, Liu Z, Kuck D, Chow HF., Angew Chem Int Ed Engl 57(41), 2018
PMID: 30152145
He L, Ng CF, Li Y, Liu Z, Kuck D, Chow HF., Angew Chem Int Ed Engl 57(41), 2018
PMID: 30152145
91 References
Daten bereitgestellt von Europe PubMed Central.
AUTHOR UNKNOWN, 0
Greenberg, 1978
Dodziuk, 2009
AUTHOR UNKNOWN, 0
Venepalli, Chem. Rev. 87(), 1987
Agosta, 1992
AUTHOR UNKNOWN, 0
Luef, 1993
Carbon flatland: planar tetracoordinate carbon and fenestranes.
Keese R., Chem. Rev. 106(12), 2006
PMID: 17165674
Keese R., Chem. Rev. 106(12), 2006
PMID: 17165674
AUTHOR UNKNOWN, 0
Kuck, 1998
Three-dimensional hydrocarbon cores based on multiply fused cyclopentane and indane units: centropolyindanes.
Kuck D., Chem. Rev. 106(12), 2006
PMID: 17165679
Kuck D., Chem. Rev. 106(12), 2006
PMID: 17165679
Fenestranes in synthesis: unique and highly inspiring scaffolds.
Boudhar A, Charpenay M, Blond G, Suffert J., Angew. Chem. Int. Ed. Engl. 52(49), 2013
PMID: 24281879
Boudhar A, Charpenay M, Blond G, Suffert J., Angew. Chem. Int. Ed. Engl. 52(49), 2013
PMID: 24281879
AUTHOR UNKNOWN, Angew. Chem. 125(), 2013
Röttger, Angew. Chem. Int. Ed. Engl. 36(), 1997
AUTHOR UNKNOWN, Angew. Chem. 109(), 1997
Siebert, Chem. Soc. Rev. 28(), 1999
Corbett, J. Chem. Soc. Perkin Trans. 1 (), 1979
Monkhorst, Chem. Commun. (London) (), 1968
AUTHOR UNKNOWN, 0
Hoffmann, J. Am. Chem. Soc. 92(), 1970
Hoffmann, Pure Appl. Chem. 28(), 1971
Böhm, Tetrahedron Lett. 20(), 1979
AUTHOR UNKNOWN, 0
Würthwein, Tetrahedron Lett. 22(), 1981
Chandrasekhar, Tetrahedron 37(), 1981
AUTHOR UNKNOWN, 0
Luef, Helv. Chim. Acta 70(), 1987
Macchi, Tetrahedron 69(), 2013
Planar-Tetracoordinate Carbon in a Neutral Saturated Hydrocarbon: Theoretical Design and Characterization.
Rasmussen DR, Radom L., Angew. Chem. Int. Ed. Engl. 38(19), 1999
PMID: 10540378
Rasmussen DR, Radom L., Angew. Chem. Int. Ed. Engl. 38(19), 1999
PMID: 10540378
AUTHOR UNKNOWN, Angew. Chem. 111(), 1999
AUTHOR UNKNOWN, 0
Hopf, 2000
Krohn, 1991
AUTHOR UNKNOWN, 0
Wolff, J. Am. Chem. Soc. 110(), 1988
Grieco, J. Org. Chem. 54(), 1989
Keese, Angew. Chem. Int. Ed. Engl. 31(), 1992
AUTHOR UNKNOWN, Angew. Chem. 104(), 1992
Luyten, Angew. Chem. Int. Ed. Engl. 23(), 1984
AUTHOR UNKNOWN, Angew. Chem. 96(), 1984
Deshpande, J. Am. Chem. Soc. 107(), 1985
AUTHOR UNKNOWN, 0
Kuck, J. Am. Chem. Soc. 108(), 1986
Kuck, Chem. Ber. 127(), 1994
AUTHOR UNKNOWN, 0
Yamamoto, J. Am. Chem. Soc. 105(), 1983
Yamamoto, Angew. Chem. Int. Ed. Engl. 30(), 1991
AUTHOR UNKNOWN, Angew. Chem. 103(), 1991
Twisted polycyclic arenes by intramolecular Scholl reactions of C3-symmetric precursors.
Pradhan A, Dechambenoit P, Bock H, Durola F., J. Org. Chem. 78(6), 2013
PMID: 23374076
Pradhan A, Dechambenoit P, Bock H, Durola F., J. Org. Chem. 78(6), 2013
PMID: 23374076
Curved polycyclic aromatic molecules that are π-isoelectronic to hexabenzocoronene.
Luo J, Xu X, Mao R, Miao Q., J. Am. Chem. Soc. 134(33), 2012
PMID: 22827492
Luo J, Xu X, Mao R, Miao Q., J. Am. Chem. Soc. 134(33), 2012
PMID: 22827492
A grossly warped nanographene and the consequences of multiple odd-membered-ring defects.
Kawasumi K, Zhang Q, Segawa Y, Scott LT, Itami K., Nat Chem 5(9), 2013
PMID: 23965674
Kawasumi K, Zhang Q, Segawa Y, Scott LT, Itami K., Nat Chem 5(9), 2013
PMID: 23965674
Aromatic saddles containing two heptagons.
Cheung KY, Xu X, Miao Q., J. Am. Chem. Soc. 137(11), 2015
PMID: 25741577
Cheung KY, Xu X, Miao Q., J. Am. Chem. Soc. 137(11), 2015
PMID: 25741577
Synthesis, Properties, and Packing Structures of Corannulene-Based π-Systems Containing Heptagons.
Kato K, Segawa Y, Scott LT, Itami K., Chem Asian J 10(8), 2015
PMID: 26062779
Kato K, Segawa Y, Scott LT, Itami K., Chem Asian J 10(8), 2015
PMID: 26062779
AUTHOR UNKNOWN, 0
A pentacene with a 144 degrees twist.
Lu J, Ho DM, Vogelaar NJ, Kraml CM, Pascal RA Jr., J. Am. Chem. Soc. 126(36), 2004
PMID: 15355095
Lu J, Ho DM, Vogelaar NJ, Kraml CM, Pascal RA Jr., J. Am. Chem. Soc. 126(36), 2004
PMID: 15355095
Xiao, Chem. Sci. 4(), 2013
Arslan, Chem. Sci. 4(), 2013
Synthesis, Structures, and Properties of π-Extended Double Helicene: A Combination of Planar and Nonplanar π-Systems.
Fujikawa T, Segawa Y, Itami K., J. Am. Chem. Soc. 137(24), 2015
PMID: 26028308
Fujikawa T, Segawa Y, Itami K., J. Am. Chem. Soc. 137(24), 2015
PMID: 26028308
Unexpected Scholl Reaction of 6,7,13,14-Tetraarylbenzo[k]tetraphene: Selective Formation of Five-Membered Rings in Polycyclic Aromatic Hydrocarbons.
Liu J, Narita A, Osella S, Zhang W, Schollmeyer D, Beljonne D, Feng X, Mullen K., J. Am. Chem. Soc. 138(8), 2016
PMID: 26859522
Liu J, Narita A, Osella S, Zhang W, Schollmeyer D, Beljonne D, Feng X, Mullen K., J. Am. Chem. Soc. 138(8), 2016
PMID: 26859522
A Conformationally Stable Contorted Hexabenzoovalene.
Baumgartner K, Meza Chincha AL, Dreuw A, Rominger F, Mastalerz M., Angew. Chem. Int. Ed. Engl. 55(50), 2016
PMID: 27649907
Baumgartner K, Meza Chincha AL, Dreuw A, Rominger F, Mastalerz M., Angew. Chem. Int. Ed. Engl. 55(50), 2016
PMID: 27649907
AUTHOR UNKNOWN, Angew. Chem. 128(), 2016
Octulene: A Hyperbolic Molecular Belt that Binds Chloride Anions.
Majewski MA, Hong Y, Lis T, Gregolinski J, Chmielewski PJ, Cybinska J, Kim D, Stepien M., Angew. Chem. Int. Ed. Engl. 55(45), 2016
PMID: 27709735
Majewski MA, Hong Y, Lis T, Gregolinski J, Chmielewski PJ, Cybinska J, Kim D, Stepien M., Angew. Chem. Int. Ed. Engl. 55(45), 2016
PMID: 27709735
AUTHOR UNKNOWN, Angew. Chem. 128(), 2016
AUTHOR UNKNOWN, 0
Merging tribenzotriquinacene with hexa-peri-hexabenzocoronene: a cycloheptatriene unit generated by Scholl reaction.
Mughal EU, Kuck D., Chem. Commun. (Camb.) 48(71), 2012
PMID: 22810270
Mughal EU, Kuck D., Chem. Commun. (Camb.) 48(71), 2012
PMID: 22810270
Mughal, Eur. J. Org. Chem. (), 2014
Three-Fold Scholl-Type Cycloheptatriene Ring Formation around a Tribenzotriquinacene Core: Toward Warped Graphenes.
Ip HW, Ng CF, Chow HF, Kuck D., J. Am. Chem. Soc. 138(42), 2016
PMID: 27478989
Ip HW, Ng CF, Chow HF, Kuck D., J. Am. Chem. Soc. 138(42), 2016
PMID: 27478989
Ip, Org. Chem. Front. 4(), 2017
Tetrabenzo[8]circulene: aromatic saddles from negatively curved graphene.
Sakamoto Y, Suzuki T., J. Am. Chem. Soc. 135(38), 2013
PMID: 24015972
Sakamoto Y, Suzuki T., J. Am. Chem. Soc. 135(38), 2013
PMID: 24015972
AUTHOR UNKNOWN, 0
Bredenkötter, Eur. J. Org. Chem. (), 2014
An, Synlett 27(), 2016
Bredenkötter, Eur. J. Org. Chem. (), 2017
AUTHOR UNKNOWN, 0
Oxidative C-C bond formation (Scholl reaction) with DDQ as an efficient and easily recyclable oxidant.
Zhai L, Shukla R, Rathore R., Org. Lett. 11(15), 2009
PMID: 19594139
Zhai L, Shukla R, Rathore R., Org. Lett. 11(15), 2009
PMID: 19594139
Kuck, J. Org. Chem. 56(), 1991
AUTHOR UNKNOWN, 0
Dehydrogenation mechanisms. On the mechanism of dehydrogenation of acenaphthene by quinones .
Trost BM., J. Am. Chem. Soc. 89(8), 1967
PMID: 6040521
Trost BM., J. Am. Chem. Soc. 89(8), 1967
PMID: 6040521
Mechanisms of hydride abstractions by quinones.
Guo X, Zipse H, Mayr H., J. Am. Chem. Soc. 136(39), 2014
PMID: 25196576
Guo X, Zipse H, Mayr H., J. Am. Chem. Soc. 136(39), 2014
PMID: 25196576
AUTHOR UNKNOWN, 0
Weinberg, Chem. Rev. 68(), 1968
Roth, Synlett 27(), 2016
AUTHOR UNKNOWN, 0
AUTHOR UNKNOWN, 0
Facile Assembly of Chiral Metallosquares by Using Enantiopure Tribenzotriquinacene Corner Motifs.
Xu WR, Xia GJ, Chow HF, Cao XP, Kuck D., Chemistry 21(34), 2015
PMID: 26126897
Xu WR, Xia GJ, Chow HF, Cao XP, Kuck D., Chemistry 21(34), 2015
PMID: 26126897
AUTHOR UNKNOWN, 0
Covalent organic frameworks (COFs): from design to applications.
Ding SY, Wang W., Chem Soc Rev 42(2), 2013
PMID: 23060270
Ding SY, Wang W., Chem Soc Rev 42(2), 2013
PMID: 23060270
Chemistry of Covalent Organic Frameworks.
Waller PJ, Gandara F, Yaghi OM., Acc. Chem. Res. 48(12), 2015
PMID: 26580002
Waller PJ, Gandara F, Yaghi OM., Acc. Chem. Res. 48(12), 2015
PMID: 26580002
Electrochemical considerations for determining absolute frontier orbital energy levels of conjugated polymers for solar cell applications.
Cardona CM, Li W, Kaifer AE, Stockdale D, Bazan GC., Adv. Mater. Weinheim 23(20), 2011
PMID: 21462372
Cardona CM, Li W, Kaifer AE, Stockdale D, Bazan GC., Adv. Mater. Weinheim 23(20), 2011
PMID: 21462372
Export
Markieren/ Markierung löschen
Markierte Publikationen
Web of Science
Dieser Datensatz im Web of Science®Quellen
PMID: 28766911
PubMed | Europe PMC
Suchen in
Google Scholar