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

Chem Commun (Camb). 2024 Nov 1;60(88):12852-12855. doi: 10.1039/d4cc04209c.

Authors

Xujun Qiu¹, Qianyu Cai¹, Eric Pohl², André Jung³, Haopu Su¹, Olaf Fuhr^{4

5}, Ute Schepers^{1

2}, Stefan Bräse^{1

3}

Affiliations

¹ Institute of Organic Chemistry (IOC), Karlsruhe Institute of Technology (KIT), Kaiserstraße 12, 76131 Karlsruhe, Germany. [email protected].
² Institute of Functional Interfaces (IFG), Karlsruhe Institute of Technology (KIT), Kaiserstraße 12, 76131 Karlsruhe, Germany.
³ Institute of Biological and Chemical Systems - Functional Molecular Systems (IBCS-FMS), Karlsruhe Institute of Technology (KIT), Kaiserstraße 12, 76131 Karlsruhe, Germany.
⁴ Institute of Nanotechnology (INT), Karlsruhe Institute of Technology (KIT), Kaiserstraße 12, 76131 Karlsruhe, Germany.
⁵ Karlsruhe Nano Micro Facility (KNMFi), Karlsruhe Institute of Technology (KIT), Kaiserstraße 12, 76131 Karlsruhe, Germany.

PMID: 39412510
DOI: 10.1039/d4cc04209c

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.