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Skeletal Rearrangement of Twisted Thia-Norhexaphyrin: Multiply Annulated Polypyrrolic Aromatic Macrocycles
East China Univ Sci & Technol, Key Lab Adv Mat, Feringa Nobel Prize Scientist Joint Res Ctr, Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China.;East China Univ Sci & Technol, Joint Int Res Lab Precis Chem & Mol Engn, Feringa Nobel Prize Scientist Joint Res Ctr, Sch Chem & Mol Engn, 130 Meilong Rd, Shanghai 200237, Peoples R China..
Kyushu Univ, Dept Chem & Biochem, Grad Sch Engn, Fukuoka 8190395, Japan.;Kyushu Univ, Ctr Mol Syst, Fukuoka 8190395, Japan..ORCID iD: 0000-0002-1117-2188
Kyushu Univ, Dept Chem & Biochem, Grad Sch Engn, Fukuoka 8190395, Japan.;Kyushu Univ, Ctr Mol Syst, Fukuoka 8190395, Japan..
Jiangsu Univ, Sch Chem & Chem Engn, Zhenjiang 212013, Jiangsu, Peoples R China..
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2019 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 58, no 18, p. 5925-5929Article in journal (Refereed) Published
Abstract [en]

A hybrid thia-norhexaphyrin comprising a directly linked N-confused pyrrole and thiophene unit (1) revealed unique macrocycle transformations to afford multiply inner-annulated aromatic macrocycles. Oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone triggered a cleavage of the C-S bond of the thiophene unit, accompanied with skeletal rearrangement to afford unique pi-conjugated products: a thiopyrrolo-pentaphyrin embedded with a pyrrolo[1,2]isothiazole (2), a sulfur-free pentaphyrin incorporating an indolizine moiety (3), and a thiopyranyltriphyrinoid containing a 2H-thiopyran unit (4). Furthermore, 2 underwent desulfurization reactions to afford a fused pentaphyrin containing a pyrrolizine moiety (5) under mild conditions. Using expanded porphyrin scaffolds, oxidative thiophene cleavage and desulfurization of the hitherto unknown N-confused core-modified macrocycles would be a practical approach for developing unique polypyrrolic aromatic macrocycles.

Place, publisher, year, edition, pages
WILEY-V C H VERLAG GMBH , 2019. Vol. 58, no 18, p. 5925-5929
Keywords [en]
aromaticity, macrocycles, porphyrinoids, skeletal rearrangement
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-251277DOI: 10.1002/anie.201900010ISI: 000465413400019PubMedID: 30843636Scopus ID: 2-s2.0-85063590252OAI: oai:DiVA.org:kth-251277DiVA, id: diva2:1316412
Note

QC 20190517

Available from: 2019-05-17 Created: 2019-05-17 Last updated: 2019-05-17Bibliographically approved

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Ishida, MasatoshiLi, XinBaryshnikov, GlibÅgren, HansFuruta, Hiroyuki
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