Synthesis of meso-Substituted Tetrabenzotriazaporphyrins: Easy Access to Hybrid Macrocycles

Reaction for the synthesis of meso-Substituted Tetrabenzotriazaporphyrins, initiated by aminoisoindolenes, an easy access to to hybrid macrocycles.
Reaction for the synthesis of meso-Substituted Tetrabenzotriazaporphyrins, initiated by aminoisoindolenes, an easy access to to hybrid macrocycles.

Porphyrins and phthalocyanines are cyclic molecules with very characteristic physicochemical properties. Their molecular structure includes several conjugated aromatic rings, which is why they absorb visible light. Therefore, these compounds are colored. In them, four pyrrole (porphyrins) or indole (phthalocyanines) units are joined in a circle forming a planar macrocycle with the four nitrogen atoms pointing towards the centre. In this way metal atoms can be inserted into the center of the macrocycle.

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Each pyrrole ring is linked to the rest by a “bridge atom”. Porphyrins have a carbon atom, which may (or may not) incorporate a substituent. In the case of phthalocyanines, the bridging atoms are nitrogen.

In this article we describe an original methodology to synthesize a new type of hybrid molecule between porphyrins and phthalocyanines. They are called “tetrabenzotriazaporphyrins” and are basically phthalocyanines in which a bridging nitrogen atom has been replaced by a carbon atom (as in porphyrins). The new methodology makes it possible to obtain these molecules with a relatively high yield, which has allowed us to study them in detail and use them as part of larger constructions for the first time.

Reaction for the synthesis of meso-Substituted Tetrabenzotriazaporphyrins, initiated by aminoisoindolenes, an easy access to to hybrid macrocycles.
Tetrabenzotriazaporphyrin X-ray structure
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In the research article entitled “Synthesis of meso-Substituted Tetrabenzotriazaporphyrins: Easy Access to Hybrid Macrocycles”, we have been able to characterize this type of molecule by X-ray diffraction for the first time. We have also shown that they can be modified using several widely known chemical reactions. We can, for example, change (or even remove) the central metal atom. Also change the functional group on the bridging carbon atom. As well as incorporating other molecules in said position.

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