Synthesis and Properties of pi-Extended Derivatives of Tribenzotriquinacenes
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Tribenzotriquinacenes (TBTQ) are a class of centropolyindanes
with three indane wings mutually fused at a common carbon.[1] Starting with
trimethoxy-substitued TBTQ 1, the
synthesis of non-planar polycyclic aromatic compound (PAC) 2 bearing a TBTQ core and three heptagons was reported. The
intrinsically bowl-shaped TBTQ core, combined with the negative curvature
introduced by the heptagons,[2] give rise to the novel hat-shaped molecule and
was analyzed by X-ray crystallography. Through “bottom-up” strategy of graphite
cutting, the methoxy group on the periphery offers potential access to the
π-extended framework 3, which is
expected to possess special electronic and semiconducting properties compared
to planar PAC.[3]

[1] Kuck, D. Chem. Rev. 2006, 106, 4885–4925.
[2] Iijima, S.;
Ajayan, P.M.; Ichihashi, T. Phys. Rev.
1992, 69, 3100–3103.
[3] Zoppi, L.; Siegel, J. S.; Baldridge, K. K. WIREs Comput. Mol. Sci. 2013, 3, 1–12.

Acceptance Date13/07/2016
All Author(s) ListHo-Wang Ip, Hak-Fun Chow, Dietmar Kuck
Name of ConferenceThe 2nd International Symposium on the Synthesis and Application of Curved Organic Pi-Molecules & Materials
Start Date of Conference12/09/2016
End Date of Conference14/09/2016
Place of ConferenceUniversity of Oregon, Eugene
Country/Region of ConferenceUnited States of America
LanguagesEnglish-United Kingdom

Last updated on 2021-17-02 at 18:45