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Tripyrrin-armed isosmaragdyrins: synthesis, heterodinuclear coordination, and protonation-triggered helical inversion
East China Univ Sci & Technol, Joint Int Res Lab Precis Chem & Mol Engn, Feringa Nobel Prize Scientist Joint Res Ctr,Sch C, Shanghai Key Lab Funct Mat Chem,Key Lab Adv Mat, 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 C, Shanghai Key Lab Funct Mat Chem,Key Lab Adv Mat, Shanghai 200237, Peoples R China..
Kyushu Univ, Dept Chem & Biochem, Grad Sch Engn, Ctr Mol Syst, Fukuoka 8190395, Japan..
East China Univ Sci & Technol, Joint Int Res Lab Precis Chem & Mol Engn, Feringa Nobel Prize Scientist Joint Res Ctr,Sch C, Shanghai Key Lab Funct Mat Chem,Key Lab Adv Mat, Shanghai 200237, Peoples R China..
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2020 (English)In: Chemical Science, ISSN 2041-6520, E-ISSN 2041-6539, Vol. 11, no 10, p. 2790-2795Article in journal (Refereed) Published
Abstract [en]

Oxidative ring closure of linear oligopyrroles is one of the synthetic approaches to novel porphyrinoids with dinuclear coordination sites and helical chirality. The spatial arrangement of the pyrrolic groups of octapyrrole (P8) affected the position of the intramolecular oxidative coupling of the pyrrolic units; tripyrrin-armed isosmaragdyrin analogue (1) containing a beta,beta-linked bipyrrole moiety was synthesized regioselectively in a high yield by using FeCl3. Ni-II-coordination at the armed tripyrrin site of 1 allowed the formation of diastereomeric helical twisted complexes (2A and 2B) and succeeding Cu-II-coordination at the macrocyclic core afforded heterodinuclear Ni-II/Cu-II-complexes (3A and 3B). Each of them comprised a pair of separable enantiomers, exhibiting P- and M-helices, respectively. Notably, diastereomeric interconversion from 2A to 2B was quantitatively achieved as a consequence of helical transformation under acidic conditions.

Place, publisher, year, edition, pages
ROYAL SOC CHEMISTRY , 2020. Vol. 11, no 10, p. 2790-2795
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Theoretical Chemistry
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URN: urn:nbn:se:kth:diva-271757DOI: 10.1039/c9sc06197eISI: 000519742300019Scopus ID: 2-s2.0-85081982643OAI: oai:DiVA.org:kth-271757DiVA, id: diva2:1422343
Note

QC 20200407

Available from: 2020-04-07 Created: 2020-04-07 Last updated: 2020-04-07Bibliographically approved

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Baryshnikov, Gleb V.Li, Xin

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