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Macrocycle Contraction and Expansion of a Dihydrosapphyrin Isomer
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.ORCID iD: 0000-0001-6508-8355
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2013 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 135, no 51, 19119-19122 p.Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
2013. Vol. 135, no 51, 19119-19122 p.
Keyword [en]
N-Confused Porphyrin, Expanded Porphyrins, Ring Contraction, Corrole Isomers, Fused Porphyrin, Pentaphyrin, Chemistry, Sapphyrin, Core
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URN: urn:nbn:se:kth:diva-140674DOI: 10.1021/ja4112644ISI: 000329137300019ScopusID: 2-s2.0-84891297499OAI: diva2:692245

QC 20140130

Available from: 2014-01-30 Created: 2014-01-30 Last updated: 2014-01-30Bibliographically approved

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