Abstract
New tetrabenzotriazaporphyrins are reported that are functionalised at the meso-position. The derivatives functionalised with meso-bromophenyl substituents are synthesised using an improved variation on the traditional reaction between phthalonitriles and Grignard reagents. For all other new derivatives, a modern protocol is employed that gives convenient access to these challenging materials by template co-macrocyclisation between phthalonitriles and aryl-aminoisoindoline derivatives like 15. The newly developed procedure allows design and synthesis of elaborate, functional composites and this is demonstrated by synthesis of meso-pyrenylTBTAP 24, a linked double chromophore in which the two complementary units lie perpendicular to each other and therefore have minimal ground state interaction.
Original language | English |
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Pages (from-to) | 7370-7379 |
Number of pages | 10 |
Journal | Tetrahedron |
Volume | 70 |
Issue number | 40 |
Early online date | 26 Jun 2014 |
DOIs | |
Publication status | Published - 7 Oct 2014 |
Keywords
- Phthalocyanines
- Porphyrins
- Heterocycles
- Synthesis
- Hybrids
- Pyrene