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Improved syntheses of meso-aryl tetrabenzotriazaporphyrins (TBTAPs)

DOI: 10.1016/j.tet.2014.06.086 DOI Help

Authors: Nuha Alharbi (University of East Anglia) , Alejandro Díaz-Moscoso (University of East Anglia) , Graham Tizzard (University of Southampton) , Simon Coles (University of Southampton) , Michael J. Cook (University of East Anglia) , Andrew N. Cammidge (University of East Anglia)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Tetrahedron , VOL 70 (40) , PAGES 7370 - 7379

State: Published (Approved)
Published: October 2014
Diamond Proposal Number(s): 8521

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.

Journal Keywords: Phthalocyanines; Porphyrins; Heterocycles; Synthesis; Hybrids; Pyrene

Subject Areas: Chemistry

Instruments: I19-Small Molecule Single Crystal Diffraction

Added On: 23/09/2015 15:44

Discipline Tags:

Chemistry Organic Chemistry

Technical Tags:

Diffraction Single Crystal X-ray Diffraction (SXRD)