A helically twisted ribbon-shaped nanographene constructed around a fenestrindane core

Sun X-Q, Wong W-S, Li Y, Kuck D, Chow H-F (2021)
Organic Chemistry Frontiers.

Zeitschriftenaufsatz | E-Veröff. vor dem Druck | Englisch
 
Download
Es wurden keine Dateien hochgeladen. Nur Publikationsnachweis!
Autor*in
Sun, Xiao-Qing; Wong, Wai-Shing; Li, Yuke; Kuck, DietmarUniBi; Chow, Hak-Fun
Abstract / Bemerkung
A helically twisted ribbon-shaped nanographene 3 containing four pentagons, eighteen hexagons and four heptagons was synthesized by a cascade of classical Scholl and non-classical Scholl-type cycloheptatriene formation reactions. In the pivotal step of the synthesis, ten carbon-carbon bonds and four cycloheptatriene rings were formed in one single operation in 11% yield. In this way, the fenestrindane core 1 was annelated with two m-quaterphenyl units 4 at opposite rims, generating a unique helically twisted structure 3 with D-2-symmetry. X-ray crystallography confirmed this [5.5.5.5]fenestrane-based molecular topology and revealed the aggregation of a pair of antipodal enantiomers, (M)-3 and (P)-3, in the solid state. The torsion angles, planarity of hexagons in the two tribenzo[fg,ij,rst]pentaphene substructures and the local aromaticity of the hexagons were studied based on the crystal data. The optical and electronic properties of compound 3 were investigated by UV/Vis and fluorescence spectroscopy and cyclic voltammetry. Based on the reactions of several partially cyclized intermediates and DFT calculations, a mechanistic sequence of the reaction pathways towards the formation of the nanographene 3 is proposed. In particular, factors that affect the relative ease and the role of hydride abstraction from one of the sp(3)-hybridized benzhydrylic bridgeheads, giving rise to cycloheptatrien-7-ol side products, are unfolded in this study. It is demonstrated that this side track occurs exclusively at the most highly conjugated pi-electron system formed and efficiently competes with the classical and non-classical Scholl cyclodehydrogenation reactions in the last stage of the reaction sequence.
Erscheinungsjahr
2021
Zeitschriftentitel
Organic Chemistry Frontiers
eISSN
2052-4129
Page URI
https://pub.uni-bielefeld.de/record/2957353

Zitieren

Sun X-Q, Wong W-S, Li Y, Kuck D, Chow H-F. A helically twisted ribbon-shaped nanographene constructed around a fenestrindane core. Organic Chemistry Frontiers. 2021.
Sun, X. - Q., Wong, W. - S., Li, Y., Kuck, D., & Chow, H. - F. (2021). A helically twisted ribbon-shaped nanographene constructed around a fenestrindane core. Organic Chemistry Frontiers. https://doi.org/10.1039/d1qo00929j
Sun, X. - Q., Wong, W. - S., Li, Y., Kuck, D., and Chow, H. - F. (2021). A helically twisted ribbon-shaped nanographene constructed around a fenestrindane core. Organic Chemistry Frontiers.
Sun, X.-Q., et al., 2021. A helically twisted ribbon-shaped nanographene constructed around a fenestrindane core. Organic Chemistry Frontiers.
X.-Q. Sun, et al., “A helically twisted ribbon-shaped nanographene constructed around a fenestrindane core”, Organic Chemistry Frontiers, 2021.
Sun, X.-Q., Wong, W.-S., Li, Y., Kuck, D., Chow, H.-F.: A helically twisted ribbon-shaped nanographene constructed around a fenestrindane core. Organic Chemistry Frontiers. (2021).
Sun, Xiao-Qing, Wong, Wai-Shing, Li, Yuke, Kuck, Dietmar, and Chow, Hak-Fun. “A helically twisted ribbon-shaped nanographene constructed around a fenestrindane core”. Organic Chemistry Frontiers (2021).

Export

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®

Suchen in

Google Scholar