Macrocycle Contraction and Expansion of a Dihydrosapphyrin Isomer

• Cyclization of a pentapyrrane with two terminal beta-linked pyrroles afforded a dihydrosapphyrin isomer (1) with the pyrroles linked in a unique beta,alpha-alpha,beta mode, which was rather reactive, and thus it readily underwent a ring-contracted rearrangement to a pyrrolyl norrole (2), and succeeding ring expansion to a terpyrrole-containing isosmaragdyrin analogue (4). 1, 2, and 4 contain the internal ring pathways with a minimum of 17, 15, and 16 atoms, respectively. 1, 2, and 4 are almost nonfluorescent, whereas the complex of 2 with Zn2+ shows a distinct NIR emission peak at 741 nm. The unprecedented pyrrole transformation chemistry by confusion approach is illustrated.

Ämnesord

NATURVETENSKAP  -- Kemi -- Annan kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences -- Other Chemistry Topics (hsv//eng)

Nyckelord

N-Confused Porphyrin

Expanded Porphyrins

Ring Contraction

Corrole Isomers

Fused Porphyrin

Pentaphyrin

Chemistry

Sapphyrin

Core

Publikations- och innehållstyp

ref (ämneskategori)

art (ämneskategori)