Introducing the substituted azobispyrrole framework: synthesis and properties

Adil Alkaş; Roberto M. Diaz-Rodriguez; Steve O. Sequeira; James W. Hilborn; Mmasinachi Atansi; Em C. Sullivan; Emily B. Brown; Rosinah Liandrah Gapare; Bulent Mutus; Katherine N. Robertson; Alison Thompson

doi:10.1039/D5CC02884A

Introducing the substituted azobispyrrole framework: synthesis and properties†

Adil Alkaş,

^a Roberto M. Diaz-Rodriguez,

^a Steve O. Sequeira,^a James W. Hilborn,^a Mmasinachi Atansi,^a Em C. Sullivan,

^a Emily B. Brown,^a Rosinah Liandrah Gapare,

^a Bulent Mutus,

^ac Katherine N. Robertson

^b and Alison Thompson

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, Dalhousie University, PO Box 15000, Halifax, Nova Scotia, Canada
E-mail: Alison.Thompson@dal.ca

^b Department of Chemistry, Saint Mary's University, Halifax, NS, Canada

^c Department of Chemistry & Biochemistry, University of Windsor, 401 Sunset Ave., Windsor N9B 3P4, Ontario, Canada

Abstract

An unprecedented azobispyrrole framework is introduced, wherein two aryl-substituted pyrroles are joined by an azo (–N [double bond, length as m-dash] N–) linkage. Functionalisation was demonstrated via pyrrolic N-methylation and by –BF₂ complexation using the coordinating abilities of the pyrrolic and azo nitrogen atoms. Control of co-planarity enables tunability with maximal absorption and emission spanning almost 300 nm.

Chemical Communications

Introducing the substituted azobispyrrole framework: synthesis and properties†

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Introducing the substituted azobispyrrole framework: synthesis and properties

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