Breaking the bottleneck: stilbene as a model compound for optimizing 6π e− photocyclization efficiency

Joshua Seylar; Dmytro Stasiouk; Davide L. Simone; Vikas Varshney; James E. Heckler; Ruel McKenzie

doi:10.1039/D0RA10619D

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

Breaking the bottleneck: stilbene as a model compound for optimizing 6π e⁻ photocyclization efficiency†

Joshua Seylar,

^a Dmytro Stasiouk,^b Davide L. Simone,^c Vikas Varshney,

^c James E. Heckler

^cd and Ruel McKenzie

*^a

Author affiliations

* Corresponding authors

^a School of Polymer Science and Polymer Engineering, The University of Akron, Akron, OH, USA
E-mail: rmckenzie@uakron.edu

^b Department of Chemistry, The University of Akron, Akron, OH, USA

^c Materials and Manufacturing Directorate, Air Force Research Laboratory, WPAFB, OH, USA

^d ARCTOS Technology Solutions, Dayton, OH, USA

Abstract

TEMPO was more suitable at photocyclizing stilbene than iodine. As stilbene concentration increased, TEMPO produced a higher yield of phenanthrene at shorter times and significantly reduced the potential for undesired [2+2] cycloadditions. Iodine retarded phenanthrene formation because it promoted isomerization to (E)-stilbene which encouraged [2+2] cycloaddition.

This article is part of the themed collection: 2021 RSC Advances HOT Article Collection

Download options Please wait...

Supplementary files

Supplementary information PDF (1304K)

Article information

DOI: https://doi.org/10.1039/D0RA10619D
Article type: Paper
Submitted: 17 dek 2020
Accepted: 25 yan 2021
First published: 05 fev 2021
This article is Open Access

Download Citation

RSC Adv., 2021,11, 6504-6508

Permissions

Request permissions

Breaking the bottleneck: stilbene as a model compound for optimizing 6π e⁻ photocyclization efficiency

J. Seylar, D. Stasiouk, D. L. Simone, V. Varshney, J. E. Heckler and R. McKenzie, RSC Adv., 2021, 11, 6504 DOI: 10.1039/D0RA10619D

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Social activity

Fetching data from CrossRef.
This may take some time to load.

RSC Advances