A new class of N-confused porphyrin 1 embedded
with
a carbazole subunit was prepared via [3 + 1] acid-catalyzed condensation
of appropriate precursors. 1 underwent smooth metal complexation
with Pd(II) and Cu(II) salts to provide the corresponding diamagnetic 1-Pd and paramagnetic 1-Cu, respectively. The
single-crystal X-ray structure of 1-Pd is evident with
a square-planar Pd-center through C–H activation of inverted
pyrrole. Superconducting quantum interference device analysis combined
with electron paramagnetic resonance (EPR) results provided insights
into the paramagnetic nature of 1-Cu. Further, a ratiometric
enhancement of near-IR fluorescence at 746 nm was found to be reversible
upon adding CN– and F– ions. The
solid-state structure of 1-Pd confirms that the anionic
species is due to NH deprotonation.