Solid-State Enantiopure Organic Nanocubes Formed by Self Organization of a C-3-Symmetrical Tribenzotriquinacene

Struebe J, Neumann B, Stammler H-G, Kuck D (2009)
CHEMISTRY-A EUROPEAN JOURNAL 15(10): 2256-2260.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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DOI
Autor*in
Struebe, Joerg; Neumann, Beate; Stammler, Hans-GeorgUniBi; Kuck, DietmarUniBi
Einrichtung
Fakultät für Chemie > Industrielle Organische Chemie und Biotechnologie
Abstract / Bemerkung
Cubic aggregation: The racemic C(3)-symmetrical tribenzotriquinacene 1 was synthesized and found to crystallize in cubic aggregates consisting of eight homochiral molecules. The major driving force for this unique supramolecular aggregation may be attributed to the 24 equivalent sub-van der Waals interactions between the bromine atoms located at the convex surface of the triquinacene cores, rather than to polar interactions between the nitrobenzene units within and between the nanocubes.
Stichworte
noncovalent interactions; tribenzotriquinacenes; enantioselective; aggregation; convex-concave molecules; supramolecular chemistry; cubic structures
Erscheinungsjahr
2009
Zeitschriftentitel
CHEMISTRY-A EUROPEAN JOURNAL
Band
15
Ausgabe
10
Seite(n)
2256-2260
ISSN
0947-6539
eISSN
1521-3765
Page URI
https://pub.uni-bielefeld.de/record/1635294

Zitieren

Struebe J, Neumann B, Stammler H-G, Kuck D. Solid-State Enantiopure Organic Nanocubes Formed by Self Organization of a C-3-Symmetrical Tribenzotriquinacene. CHEMISTRY-A EUROPEAN JOURNAL. 2009;15(10):2256-2260.
Struebe, J., Neumann, B., Stammler, H. - G., & Kuck, D. (2009). Solid-State Enantiopure Organic Nanocubes Formed by Self Organization of a C-3-Symmetrical Tribenzotriquinacene. CHEMISTRY-A EUROPEAN JOURNAL, 15(10), 2256-2260. https://doi.org/10.1002/chem.200802371
Struebe, Joerg, Neumann, Beate, Stammler, Hans-Georg, and Kuck, Dietmar. 2009. “Solid-State Enantiopure Organic Nanocubes Formed by Self Organization of a C-3-Symmetrical Tribenzotriquinacene”. CHEMISTRY-A EUROPEAN JOURNAL 15 (10): 2256-2260.
Struebe, J., Neumann, B., Stammler, H. - G., and Kuck, D. (2009). Solid-State Enantiopure Organic Nanocubes Formed by Self Organization of a C-3-Symmetrical Tribenzotriquinacene. CHEMISTRY-A EUROPEAN JOURNAL 15, 2256-2260.
Struebe, J., et al., 2009. Solid-State Enantiopure Organic Nanocubes Formed by Self Organization of a C-3-Symmetrical Tribenzotriquinacene. CHEMISTRY-A EUROPEAN JOURNAL, 15(10), p 2256-2260.
J. Struebe, et al., “Solid-State Enantiopure Organic Nanocubes Formed by Self Organization of a C-3-Symmetrical Tribenzotriquinacene”, CHEMISTRY-A EUROPEAN JOURNAL, vol. 15, 2009, pp. 2256-2260.
Struebe, J., Neumann, B., Stammler, H.-G., Kuck, D.: Solid-State Enantiopure Organic Nanocubes Formed by Self Organization of a C-3-Symmetrical Tribenzotriquinacene. CHEMISTRY-A EUROPEAN JOURNAL. 15, 2256-2260 (2009).
Struebe, Joerg, Neumann, Beate, Stammler, Hans-Georg, and Kuck, Dietmar. “Solid-State Enantiopure Organic Nanocubes Formed by Self Organization of a C-3-Symmetrical Tribenzotriquinacene”. CHEMISTRY-A EUROPEAN JOURNAL 15.10 (2009): 2256-2260.

12 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Switching the Statistical C3 /C1 Ratio in the Threefold Aromatic Substitution of Tribenzotriquinacenes towards the C3 Isomer.
Wagner P, Rominger F, Mastalerz M., Angew Chem Int Ed Engl 57(35), 2018
PMID: 29938890
Stereoselective synthesis of enantiomerically pure bowl-shaped hydroxytribenzotriquinacenes.
Rommelmann P, Nachtigall B, Guntelmann T, Gröger H, Kuck D., Org Biomol Chem 16(31), 2018
PMID: 30033471
Centrohexaindane: six benzene rings mutually fixed in three dimensions - solid-state structure and six-fold nitration.
Kuck D, Linke J, Teichmann LC, Barth D, Tellenbröker J, Gestmann D, Neumann B, Stammler HG, Bögge H., Phys Chem Chem Phys 18(17), 2016
PMID: 26728545
M12L8 metallo-supramolecular cube with cyclotriguaiacylene-type ligand: spontaneous resolution of cube and its constituent host ligand.
Fowler JM, Thorp-Greenwood FL, Warriner SL, Willans CE, Hardie MJ., Chem Commun (Camb) 52(56), 2016
PMID: 27332990
From Fragmentation to Construction--from Void to Massive: Fascination with Organic Mass Spectrometry and the Synthesis of Novel Three-Dimensional Polycyclic Aromatic Hydrocarbons.
Kuck D., Chem Rec 15(6), 2015
PMID: 26202384
Enantiomerically Pure Tribenzotriquinacenes through Stereoselective Synthesis.
Greschner W, Neumann B, Stammler HG, Gröger H, Kuck D., Angew Chem Int Ed Engl 54(46), 2015
PMID: 26404021
Tribenzotriquinacene receptors for C60  fullerene rotors: towards C3 symmetrical chiral stators for unidirectionally operating nanoratchets.
Bredenkötter B, Grzywa M, Alaghemandi M, Schmid R, Herrebout W, Bultinck P, Volkmer D., Chemistry 20(29), 2014
PMID: 24965605
Tribenzotriquinacene: a versatile synthesis and C3-chiral platforms.
Markopoulos G, Henneicke L, Shen J, Okamoto Y, Jones PG, Hopf H., Angew Chem Int Ed Engl 51(51), 2012
PMID: 23144000
Tribenzotriquinacenes bearing three peripheral or bridgehead urea groups stretched into the 3-D space.
Tellenbröker J, Kuck D., Beilstein J Org Chem 7(), 2011
PMID: 21512595
Quantitative symmetry and chirality--a fast computational algorithm for large structures: proteins, macromolecules, nanotubes, and unit cells.
Dryzun C, Zait A, Avnir D., J Comput Chem 32(12), 2011
PMID: 21618558
Steroid/triterpenoid functional molecules based on "click chemistry".
Hu J, Lu JR, Ju Y., Chem Asian J 6(10), 2011
PMID: 21887746
Tribenzotriquinacenes based on regioselective bis-formylation: optical resolution and absolute configuration of inherently chiral derivatives and synthesis of the first cyclophane-type tribenzotriquinacene dimers.
Wang T, Hou QQ, Teng QF, Yao XJ, Niu WX, Cao XP, Kuck D., Chemistry 16(41), 2010
PMID: 20853291

80 References

Daten bereitgestellt von Europe PubMed Central.


Diederich, Angew. Chem. 104(), 1992

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. Engl. 31(), 1992

Stoddart, Angew. Chem. 108(), 1996

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. Engl. 35(), 1996

MacGillivray, Angew. Chem. 111(), 1999

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. 38(), 1999

Scarso, Top. Curr. Chem. 265(), 2006

Rowsell, Angew. Chem. 117(), 2005

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. 44(), 2005

Morris, Angew. Chem. 120(), 2008

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. Angew. Chem. Int. Ed. Engl. 47(), 2008

AUTHOR UNKNOWN, 0

Roche, Chem. Commun. (), 1998

Heinrich, Chem. Commun. (), 1998

Klausmeyer, Angew. Chem. 110(), 1998

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. 37(), 1998

Klausmeyer, J. Am. Chem. Soc. 121(), 1999

Abrahams, J. Am. Chem. Soc. 121(), 1999

Hong, J. Am. Chem. Soc. 122(), 2000

Berseth, J. Am. Chem. Soc. 122(), 2000
A nano-scale barrel and cube: transition metal-mediated self-assembly of CpCoCb-derived ligand scaffolds.
Johannessen SC, Brisbois RG, Fischer JP, Grieco PA, Counterman AE, Clemmer DE., J. Am. Chem. Soc. 123(16), 2001
PMID: 11457114
Giant metal-cyanide coordination clusters: tetracapped edge-bridged cubic Cr(12)Ni(12)(CN)(48) and double face-centered cubic Cr(14)Ni(13)(CN)(48) species.
Sokol JJ, Shores MP, Long JR., Inorg Chem 41(12), 2002
PMID: 12054982
Assembly of a supramolecular cube, [(Cp*WS3Cu3)8 Cl8(CN)12Li4] from a preformed incomplete cubane-like compound [PPh4][Cp*WS3(CuCN)3].
Lang JP, Xu QF, Chen ZN, Abrahams BF., J. Am. Chem. Soc. 125(42), 2003
PMID: 14558796

Liu, Chem. Commun. (), 2004
Self-assembly of discrete cyclic nanostructures mediated by transition metals.
Leininger S, Olenyuk B, Stang PJ., Chem. Rev. 100(3), 2000
PMID: 11749254
Chiral molecules with polyhedral T, O, or I symmetry: theoretical solution to a difficult problem in stereochemistry.
Narasimhan SK, Lu X, Luk YY., Chirality 20(8), 2008
PMID: 18266212

AUTHOR UNKNOWN, 0

Albrecht, Angew. Chem. 111(), 1999

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. 38(), 1999

Cronin, Angew. Chem. 118(), 2006

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. 38(), 1999

Gibson, Angew. Chem. 118(), 2006

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. 38(), 1999

AUTHOR UNKNOWN, 0
Three-dimensional hydrocarbon cores based on multiply fused cyclopentane and indane units: centropolyindanes.
Kuck D., Chem. Rev. 106(12), 2006
PMID: 17165679

Kuck, Pure Appl. Chem. 78(), 2006

Kuck, Top. Curr. Chem. 196(), 1998

Kuck, Tetrahedron 57(), 2001

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0

Kuck, 2009

AUTHOR UNKNOWN, 0
C3v-symmetrical tribenzotriquinacenes as hosts for C60 and C70 in solution and in the solid state.
Georghiou PE, Dawe LN, Tran HA, Strube J, Neumann B, Stammler HG, Kuck D., J. Org. Chem. 73(22), 2008
PMID: 18850747

AUTHOR UNKNOWN, 0

Bredenkötter, Chem. Eur. J. 13(), 2007
Three orthogonal chromophores operating independently within the same molecule.
Langhals H, Rauscher M, Strube J, Kuck D., J. Org. Chem. 73(3), 2008
PMID: 18184004

AUTHOR UNKNOWN, 0

Kamieth, Angew. Chem. 110(), 1998

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. 37(), 1998

Klärner, J. Mol. Model. 6(), 2000

AUTHOR UNKNOWN, 0

Tellenbröker, Angew. Chem. 111(), 1999

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. 38(), 1999

Harig, Eur. J. Org. Chem. (), 2004

Cao, Eur. J. Org. Chem. (), 2005

Zhou, Synlett (), 2005
C3v-symmetrical tribenzotriquinacenes extended by six C1-functional groups and the first triquinacene-based tris(dithiametacyclophanes).
Zhou L, Zhang TX, Li BR, Cao XP, Kuck D., J. Org. Chem. 72(17), 2007
PMID: 17658847

Zhang, Chin. J. Org. Chem. 27(), 2007
Edge-directed dynamic covalent synthesis of a chiral nanocube.
Xu D, Warmuth R., J. Am. Chem. Soc. 130(24), 2008
PMID: 18498163

Kuck, Angew. Chem. 96(), 1984

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. Engl. 23(), 1984

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0

Spek, Acta Crystallogr. Sect. A 46(), 1990

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0

Bent, Chem. Rev. 68(), 1968

Eaton, Adv. Mater. 12(), 2000

Rowland, J. Phys. Chem. 100(), 1996

Glusker, Top. Curr. Chem. 198(), 1998
An overview of halogen bonding.
Politzer P, Lane P, Concha MC, Ma Y, Murray JS., J Mol Model 13(2), 2006
PMID: 17013631

AUTHOR UNKNOWN, 0

Guo, Cryst. Growth Des. 1(), 2001

Ramasubbu, J. Am. Chem. Soc. 108(), 1086

Clark, New J. Chem. 23(), 1999

AUTHOR UNKNOWN, 0
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