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Configurationally Stable Atropisomeric Acridinium Fluorophores

Fischer, Christian and Sparr, Christof. (2018) Configurationally Stable Atropisomeric Acridinium Fluorophores. Synlett, 29 (16). pp. 2176-2180.

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Official URL: https://edoc.unibas.ch/68655/

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Abstract

Arylated heterocyclic fluorophores are particularly useful scaffolds for numerous applications, such as bioimaging or synthetic photochemistry. While variation of the substitution pattern at the heterocycle and aryl groups allows dye modulation, the bond rotational barriers are also strongly affected. Unsymmetrically substituted ring systems of rotationally restricted arylated heterocycles therefore lead to configurationally stable atropisomeric fluorophores. Herein, we describe these characteristics by determining the properties and configurational stability of atropisomeric, tri-ortho-substituted naphthyl-acridinium fluorophores. A significant barrier to rotation of >120 kJ mol–1 was measured, which renders these dyes and related compounds distinct ­atropisomers with stereoisomer-specific properties over a broad temperature range.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Organische Chemie (Sparr)
UniBasel Contributors:Sparr, Christof and Fischer, Christian
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Georg Thieme Verlag
ISSN:0936-5214
e-ISSN:1437-2096
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:30 Jul 2019 13:34
Deposited On:30 Jul 2019 13:34

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