A simple method to modulate the selectivity of aryl azide photolysis using cucurbit[8]uril

Xujun Qiu; Qianyu Cai; Eric Pohl; André Jung; Haopu Su; Olaf Fuhr; Ute Schepers; Stefan Bräse

doi:10.1039/D4CC04209C

A simple method to modulate the selectivity of aryl azide photolysis using cucurbit[8]uril†

Xujun Qiu,*^a Qianyu Cai,

^a Eric Pohl,^b André Jung,

^c Haopu Su,^a Olaf Fuhr,

^de Ute Schepers^ab and Stefan Bräse

*^ac

Author affiliations

* Corresponding authors

^a Institute of Organic Chemistry (IOC), Karlsruhe Institute of Technology (KIT), Kaiserstraße 12, 76131 Karlsruhe, Germany
E-mail: xujun.qiu@kit.edu, braese@kit.edu

^b Institute of Functional Interfaces (IFG), Karlsruhe Institute of Technology (KIT), Kaiserstraße 12, 76131 Karlsruhe, Germany

^c Institute of Biological and Chemical Systems – Functional Molecular Systems (IBCS-FMS), Karlsruhe Institute of Technology (KIT), Kaiserstraße 12, 76131 Karlsruhe, Germany

^d Institute of Nanotechnology (INT), Karlsruhe Institute of Technology (KIT), Kaiserstraße 12, 76131 Karlsruhe, Germany

^e Karlsruhe Nano Micro Facility (KNMFi), Karlsruhe Institute of Technology (KIT), Kaiserstraße 12, 76131 Karlsruhe, Germany

Abstract

Photolysis of aryl azides typically involves multiple reaction pathways. This study designed and synthesized an aryl azide rotamer with two conformations. In aqueous media, its photolysis yields two main products. However, when stabilized in one conformation within the cucurbit[8]uril (CB8) host, the photoreaction selectively produces a single product.

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Article information

DOI: https://doi.org/10.1039/D4CC04209C
Article type: Communication
Submitted: 18 Aug 2024
Accepted: 02 Oct 2024
First published: 02 Oct 2024
This article is Open Access

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Chem. Commun., 2024,60, 12852-12855

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A simple method to modulate the selectivity of aryl azide photolysis using cucurbit[8]uril

X. Qiu, Q. Cai, E. Pohl, A. Jung, H. Su, O. Fuhr, U. Schepers and S. Bräse, Chem. Commun., 2024, 60, 12852 DOI: 10.1039/D4CC04209C

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Chemical Communications

A simple method to modulate the selectivity of aryl azide photolysis using cucurbit[8]uril†

Abstract

Supplementary files

Article information

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A simple method to modulate the selectivity of aryl azide photolysis using cucurbit[8]uril

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