N-Confused Phlorin-Prodigiosin Chimera : meso-Aryl Oxidation and π-Extension Triggered by Peripheral Coordination

• An N-confused phlorin isomer bearing a dipyrrin moiety at the α-position of the confused pyrrole ring (1) was synthesized. PdII and BIII coordination at the peripheral prodigiosin-like moiety of 1 afforded the corresponding complexes 2 and 3. Reflux of 2 in triethylamine (TEA) converted the meso-phenyl into the PdII-coordinating phenoxy group to afford 4. Under the same reaction conditions, TEA was linked to the α-position of the dipyrrin unit in 3 as an N,N-diethylaminovinyl group to afford 5. Furthermore, peripheral coordination of BIII in 3 and 5 improved the planarity of the phlorin macrocycle and thus facilitated the coordination of AgIII at the inner cavity to afford 3-Ag and 5-Ag, respectively. These results provide an effective approach for developing unique porphyrinoids through peripheral coordination.

Ämnesord

NATURVETENSKAP  -- Kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences (hsv//eng)

Nyckelord

conjugation

coordination chemistry

oxidation

palladium

porphyrinoids

Chemical engineering

Chemical reactions

Chemistry

Co-ordination chemistries

Effective approaches

Inner cavities

Phenoxy groups

Reaction conditions

Triethylamines

Coordination reactions

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