
Angewandte Chemie - International Edition p. 2992 - 2996 (2014)
Update date:2022-07-31
Topics:
Pawlicki, Milosz
Hurej, Karolina
Szterenberg, Ludmila
Latos-Grazynski, Lechoslaw
Triangularly shaped, contracted porphyrinoids belong to a group of molecules where the geometry significantly modifies the observed electronic properties. The need for a controllable, effective, and widely applicable approach to triphyrins drives extensive research towards macrocyclic materials that act as potential controlling motifs by switching their aromaticity. Two isomeric thiophene-fused triphyrins(2.1.1) were synthesized by applying an innovative approach. Spectroscopic techniques (NMR, UV/Vis) show that both macrocycles are aromatic and quantitatively convert into anti-aromatic structures after reduction with a zinc amalgam. The reduced forms were stabilized through boron(III) coordination, thereby allowing the observation of anti-aromatic 16 π delocalization within a contracted porphyrin. Going for a spin: The precisely crafted thiophene-fused oxatriphyrins(2.1.1) show an aromatic character consistent with 14 π or 18 π delocalization pathways. The aromaticity is strongly dependent on a thiophene incorporation mode and can be switched to anti-aromatic (16 π electrons) or non-aromatic by reduction with a zinc amalgam. Both reduced structures are stable as boron(III) complexes.
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