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CC BY 4.0 · Organic Materials 2020; 02(03): 248-252
DOI: 10.1055/s-0040-1716499
Focus Issue: Curved Organic π-Systems
Short Communication

An 80-Carbon Aromatic Saddle Enabled by a Naphthalene-Directed Scholl Reaction

Sai Ho Pun
a   Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China
,
Chi Kit Chan
a   Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China
,
Zhifeng Liu 
a   Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China
,
Qian Miao 
a   Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China
› Author Affiliations Funding Information This work was supported by the Research Grants Council of Hong Kong (GRF 14300919) and the Croucher Senior Research Fellowship.
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Abstract

Synthesis of an unprecedented aromatic saddle consisting of 80 sp2 carbons is enabled by including naphthylene groups in the substrate of the Scholl reaction. The negatively curved polycyclic framework of this aromatic saddle is revealed by the single crystal X-ray crystallography, and its stereodynamics are studied with density functional theory calculations.

Key words

polycyclic aromatics - eight-membered ring - scholl reaction - negative curvature

Supporting Information

Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1716499.


Supplementary Material



Publication History

Received: 16 July 2020

Accepted: 28 July 2020

Article published online:
21 September 2020

© 2020. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting unrestricted use, distribution, and reproduction so long as the original work is properly cited. (https://creativecommons.org/licenses/by/4.0/).

Georg Thieme Verlag KG
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