Renewing accessible heptazine chemistry: 2,5,8-tris(3,5-diethyl-pyrazolyl)-heptazine, a new highly soluble heptazine derivative with exchangeable groups, and examples of newly derived heptazines and their physical chemistry

Abstract

We have prepared 2,5,8-tris(3,5-diethyl-pyrazolyl)-heptazine, the first highly soluble heptazine derivative possessing easily exchangeable leaving groups.

Characterization and Electronic Properties of Heptazine Layers: Towards Promising Interfacial Materials for Organic Optoelectronics

“…They are similar to those measured in solution [ 32 ], showing that no aggregation induced quenching occurs with these molecules (as is often the case with high nitrogen content azines). In addition, the QY steadily increases with the film thicknesses, as the probable result of fluorescence quenching for molecules close to the substrate surface; on the other hand, the decrease of luminescence by reabsorption for the thick layers is quite limited, because of the relatively large Stokes shift associated with heptazines.…”

“…Heptazines are electron deficient molecules whose interest is sharply rising, due to their exceptional characteristics like delayed fluorescence [ 27 ], photocatalysis [ 28 ], and others [ 29 , 30 , 31 ]. While their syntheses were delicate for a long time, an easy approach to this fascinating family was recently introduced by one of us [ 32 ]. In compound 1 ( Figure 1 ), the pyrazole moieties, besides the fact they are exchangeable, are also sufficiently electron-deficient to arouse interest to investigate its use as ETL.…”

“…Considering its suitable electronic properties, this molecule could, for example, promote electron injection in classical fullerene-based OPV devices. The synthesis of this heptazine has been recently described by some of us [ 32 ]. We show that, beyond energy level matching, this large conjugated molecule with a 3-fold symmetry forms very smooth uniform thin layers of controllable thickness, whether they are processed from physical deposition methods (thermal evaporation under vacuum) or from spin-coating, a rare feature with organic small molecules.…”

Photocatalytic efficacy of supported tetrazine on MgZnO nanoparticles for the heterogeneous photodegradation of methylene blue and ciprofloxacin

“…The tetrazine ring is strongly electron decient and can be reversibly reduced into its radical anion at a high reduction potential. 19,20 Therefore, the photocatalytic efficiency of MgZnO nanoparticles can be modied by the surface modication of MgZnO with 4-((6-chloro-1,2,4,5-tetrazine-3yl)oxy)butyl propylcarbamate (abbreviated as tetrazine). The obtained nanocatalyst was used in the photodegradation of MB and ciprooxacin and effects of some operational variables are investigated.…”

Synthesis of Thiocyameluric Acid C6N7S3H3, Its Reaction to Alkali Metal Thiocyamelurates and Organic Tris(dithio)cyamelurates

“…So far,c yameluric chloride has been almostu nrivaled for the synthesis of new molecular s-heptazine derivatives. Very recently,A udebert et al [24] described 2,5,8-tris(3,5-diethyl-pyrazolyl)-s-heptazine. It can be obtained via at wo-step synthesis startingf rom melem.…”