Air-Stable N,N′-Dihydroporphycene: A Quinoxaline-Fused Tetrapyrrolic Macrocycle That Detects Fluoride Anion via Deprotonation

An air-stable N,N'-dihydroporphycene, the two-electron reduced form of porphycene, possessing two quinoxaline moieties fused at meso positions, was prepared and characterized. Nuclear magnetic resonance (NMR) and ultraviolet-visible light (UV-vis) spectroscopic studies and single-crystal X-ray diffraction analyses support its formulation as a nonaromatic species. Upon treatment with tetrabutylammonium fluoride (TBAF) in chloroform, a color change is produced that is consistent with deprotonation. Selective detection of this anion is readily achieved.