journal article·2024-04Open access

Modulating Aryl Azide Photolysis: Synthesis of a Room‐Temperature Phosphorescent Carboline in Cucurbit[7]uril Host

Xujun Qiu, Yichuan Wang, Sonja Leopold, Sergei Lebedkin, Ute Schepers, Manfred M. Kappes, Frank Biedermann, Stefan Bräse

Small· Volume 20· Issue 16

Abstract

Abstract Cucurbit[7]uril (CB7), a supramolecular host, is employed to control the pathway of photolysis of an aryl azide in an aqueous medium. Normally, photolysis of aryl azides in bulk water culminates predominantly in the formation of azepine derivatives via intramolecular rearrangement. Remarkably, however, when this process unfolds within the protective confinement of the CB7 cavity, it results in a carboline derivative, as a consequence of a C─H amination reaction. The resulting carboline caged by CB7 reveals long‐lived room temperature phosphorescence (RTP) in the solid state, with lifetimes extending up to 2.1 s. These findings underscore the potential of supramolecular hosts to modulate the photolysis of aryl azides and to facilitate novel phosphorescent materials.
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Research context

OpenAlex topics: Luminescence and Fluorescent Materials · Supramolecular Chemistry and Complexes · Catalytic Cross-Coupling Reactions

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

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

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

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

Institute of Physical Chemistry Karlsruhe Institute of Technology (KIT) Kaiserstrasse 76131 Karlsruhe Germany

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

Funding

China Scholarship Council · Deutsche Forschungsgemeinschaft · Helmholtz Association

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