Synthesis of Tetraarylethene Luminogens by C−H Vinylation of Aromatic Compounds with Triazenes

Suleymanov, Abdusalom A.; Doll, Martin; Ruggi, Albert; Scopelliti, Rosario; Fadaei‐Tirani, Farzaneh; Severin, Kay

doi:10.1002/ange.201908755

Angewandte Chemie

2019

DOI: 10.1002/ange.201908755

|View full text |Cite

Synthesis of Tetraarylethene Luminogens by C−H Vinylation of Aromatic Compounds with Triazenes

Abdusalom A. Suleymanov

Martin Doll

Albert Ruggi

et al.

Abstract: Tetraarylethenes are obtained by acid‐induced coupling of vinyl triazenes with aromatic compounds. This new C−H activation route for the synthesis of aggregation‐induced emission luminogens is simple, fast, and versatile. It allows the direct grafting of triarylethenyl groups onto a variety of aromatic compounds, including heterocycles, supramolecular hosts, biologically relevant molecules, and commercial polymers.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2020

2022

Publication Types

Select...

Article5

Relationship

Self Cite2

Independent3

Authors

Journals

Cited by 13 publications

References 79 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Innovative Verfahren zur Synthese von Luminogenen mit aggregationsinduzierter Emission

Yan

Wang

et al. 2021

Angewandte Chemie

View full text Add to dashboard Cite

Wegen ihrer Vorteile haben Luminogene mit aggregationsinduzierter Emission (AIEgene) in einer Reihe von Anwendungsbereichen weltweit wachsendes Interesse auf sich gezogen. Während allgemeine Verfahren zur Synthese von AIEgenen im Wesentlichen auf schwierigen Abläufen und eingeschränkten Reaktionstypen beruhen, haben sich in diesem Zusammenhang verschiedene innovative Syntheseverfahren als ergänzende oder sogar alternative Strategien herausgebildet. In diesem Aufsatz zeigen wir systematisch die neuesten Fortschritte bei der metallkatalysierten Funktionalisierung und den nicht metallgeförderten Wegen zum Aufbau von AIEgenen der letzten fünf Jahre auf und erläutern kurz neue Perspektiven auf diesem Gebiet. Die Entwicklung innovativer Verfahren ist vielversprechend für die zukünftige Herstellung von AIEgenen, wobei eine einfache Synthese, eine große Strukturvielfalt und multifunktionale Anwendungen ermöglicht werden sollen.

show abstract

Innovative Verfahren zur Synthese von Luminogenen mit aggregationsinduzierter Emission

Yan

Wang

et al. 2021

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Divergent and Stereoselective Synthesis of Tetraarylethylenes from Vinylboronates

et al. 2020

View full text Add to dashboard Cite

The synthesis of an ew tetraborylethylene (TBE) is reported, and its application in the preparation of [4+ +0]tetraarylethenes (TAEs) is elucidated. TAEs have widespread applications in material science and supramolecular chemistry due to their aggregation-induced emission (AIE) properties. The divergent and stereoselective synthesis of [3+ +1]-, [2+ +2]-, and [2+ +1+ +1]-TAEs via multiple couplings of vinylboronates with aryl bromides is demonstrated. These couplings feature ab road substrate scope and excellent functional group compatibility due to mild reaction conditions.F acile access to various tetraarylethenes is provided. This strategy represents an important complement to the conventional methods employed for the synthesis of TAEs,a nd would be av aluable tool for synthesizing TAE-based molecules useful in functional materials,biological imaging and chemical sensing. Figure 1. The applications and classification of tetraarylethylene.

show abstract

Vinyl and Alkynyl Triazenes: Synthesis, Reactivity, and Applications

Suleymanov

Severin

2020

Angewandte Chemie

Self Cite

View full text Add to dashboard Cite

Aromatic compounds containing triazenyl groups (N3RR′) have a profound impact on synthetic organic and medicinal chemistry. In contrast, the chemistry of vinyl and alkynyl triazenes was a largely uncharted territory until recently. The situation has changed over the last five years, and it has become apparent that vinyl and alkynyl triazenes are highly interesting compounds with a unique reactivity. The electron‐donating properties of the triazenyl group provide alkynyl triazenes with an ynamide‐like reactivity, which can be exploited in reactions of the triple bond. Vinyl triazenes, on the other hand, can be used for electrophilic vinylation reactions. The foundation for this new triazene chemistry are synthetic pathways which allow preparing vinyl and alkynyl triazenes in few steps from readily available starting materials. In this Minireview, we summarize recent developments in this area.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

hi@scite.ai

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Synthesis of Tetraarylethene Luminogens by C−H Vinylation of Aromatic Compounds with Triazenes

Cited by 13 publications

References 79 publications

Innovative Verfahren zur Synthese von Luminogenen mit aggregationsinduzierter Emission

Innovative Verfahren zur Synthese von Luminogenen mit aggregationsinduzierter Emission

Divergent and Stereoselective Synthesis of Tetraarylethylenes from Vinylboronates

Vinyl and Alkynyl Triazenes: Synthesis, Reactivity, and Applications

Contact Info

Product

Resources

About