Macrocycle Contraction and Expansion of a Dihydrosapphyrin Isomer
Cyclization of a pentapyrrane with two terminal β-linked pyrroles afforded a dihydrosapphyrin isomer (1) with the pyrroles linked in a unique β,α–α,β mode, which was rather reactive, and thus it readily underwent a ring-contracted rearrangement to a pyrrolyl norrole (2), and succeeding ring expansio...
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Veröffentlicht in: | Journal of the American Chemical Society 2013-12, Vol.135 (51), p.19119-19122 |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | Cyclization of a pentapyrrane with two terminal β-linked pyrroles afforded a dihydrosapphyrin isomer (1) with the pyrroles linked in a unique β,α–α,β 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. |
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ISSN: | 0002-7863 1520-5126 1520-5126 |
DOI: | 10.1021/ja4112644 |