Expanded Cyclotetrabenzoins

Andrew Eisterhold; Steffen Otterbach; Stefan Bräse; Patrick Weis; Xiqu Wang; Ksenia V. Kutonova; Ognjen Miljanic

doi:10.26434/chemrxiv.12739655.v1

Working Paper

Abstract

Cyclobenzoins are stable and shape-persistent macrocycles which offer promise as components of optoelectronic and porous materials. We report three new cyclotetrabenzoins, derived from biphenyl, naphthalene, and tolane skeletons. Their synthesis relied on the N-heterocyclic carbene-catalyzed benzoin condensation. Isolated as their acetic esters, these compounds are characterized by structures similar in shape, but larger in size than the parent cyclotetrabenzoin. Alkyne groups of the tolane-based cyclotetrabenzoin were post-synthetically functionalized with Co2(CO)6 moieties under mild reaction conditions.

Content

Supplementary material

Compound 3b

Compound 3d

2020 Eisterhold Cyclotetrabenzoins OrgLett SupportingInformation

Version History

Jul 31, 2020 Version 1

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The content is available under CC BY NC ND 4.0 License CreativeCommons.org

DOI

10.26434/chemrxiv.12739655.v1

Funding

We acknowledge the support from the US National Science Foundation (award DMR-1904998 to O. Š. M.), the Welch Foundation (award E-1768 to O. Š. M.), the donors of the American Chemical Society Petroleum Research Fund (award ND-58919 to O. Š. M.), and the University of Houston. K. V. K. thanks Deutsche Forschungsgemeinschaft (DFG) for funding under Germany’s Excellence Strategy – 2082/1 – 390761711. P. W. thanks the generous funding from the DFG Collaborative Centre SFB/TRR 88 “3MET” (Project C6). O. Š. M. thanks the Max Kade and Alexander von Humboldt Foundations for supporting his summer stay at the Ruprecht-Karls-Universität in Heidelberg (Germany), during which the collaboration that produced these results was initiated.

Author’s competing interest statement

None.

Keywords

macrocycles

benzoin condensation

cyclobenzoin

Publication

This content is an early or alternative research output and has not been peer-reviewed at the time of posting.