Modulating and Accelerating Photolysis of Photoactivatable [2.2]Paracyclophane Aryl Azide in Supramolecular Host for Bioimaging

Author:

Qiu Xujun1ORCID,Pohl Eric2,Cai Qianyu1ORCID,Seibert Jasmin1ORCID,Li Yuting1,Leopold Sonja2,Fuhr Olaf34,Meier Michael A. R.15,Schepers Ute12,Bräse Stefan15ORCID

Affiliation:

1. Institute of Organic Chemistry (IOC) Karlsruhe Institute of Technology (KIT) Kaiserstrasse 12 76131 Karlsruhe Germany

2. Institute of Functional Interfaces (IFG) Karlsruhe Institute of Technology (KIT) Kaiserstrasse 12 76131 Karlsruhe Germany

3. Institute of Nanotechnology (INT) Karlsruhe Institute of Technology (KIT) Kaiserstrasse 12 76131 Karlsruhe Germany

4. Karlsruhe Nano Micro Facility (KNMFi) Karlsruhe Institute of Technology (KIT) Kaiserstrasse 12 76131 Karlsruhe Germany

5. Institute of Biological and Chemical Systems – Functional Molecular Systems (IBCS‐FMS) Karlsruhe Institute of Technology (KIT) Kaiserstrasse 12 76131 Karlsruhe Germany

Abstract

AbstractPhotolysis of aryl azides offers a versatile approach to achieve more sophisticated functionalization, for instance in the field of chemical biology. In this study, a photoactivatable aryl azide named Pcp‐Az is presented that forms three distinct emissive molecules after irradiation. Computational studies unveiled that the photolysis of Pcp‐Az in aqueous medium undergoes different reaction channels, leading to the three mentioned distinct products. When the photoreaction is performed using the supramolecular host cucurbit[8]uril(CB8) for Pcp‐Az, the reaction is found to be tuned and accelerated. Finally, the potential application of the photoproducts are showcased in bioimaging, and also the time‐dependent photoactivating imaging.

Funder

China Scholarship Council

Deutsche Forschungsgemeinschaft

Publisher

Wiley

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