Rendering cross-conjugated azophenine derivatives emissive to probe the silent photophysical properties of emeraldine

Literature Information

Publication Date 2017-07-18
DOI 10.1039/C7CP04102K
Impact Factor 3.676
Authors

Hu Lei, Adam Langlois, Daniel Fortin, Paul-Ludovic Karsenti, Shawkat M. Aly, Pierre D. Harvey


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Abstract

An azophenine derivative was synthesized by coupling truxene and azophenine via the copper-free Sonagashira reaction using Pd2(dba)3 and As(PPh)3 as catalysts. The crystal structure of this heavy azophenine model (∼4000) was made and the identity of the structure was confirmed. By introducing truxene groups into this cross-conjugated structure, the deactivating rotations around the NH–C6H4 bonds were slowed down, which rendered this derivative near-IR emissive at 298 K. This species provided then the appropriate spectral and kinetic signatures for knowing where and what to look for in emeraldine, which was called non-emissive. Besides, two other compounds were also synthesized as models for this azophenine derivative for comparison and interpretation purposes.

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Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
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