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Synthesis of meso-Pyrrole-Substituted 22-Oxacorroles by a '' 3+2 '' Approach

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Title Synthesis of meso-Pyrrole-Substituted 22-Oxacorroles by a '' 3+2 '' Approach
 
Creator KALITA, H
KALITA, D
LEE, WZ
BELLARE, J
RAVIKANTH, M
 
Subject ABC-type corroles
biocompatible
fluorescent probes
pyrrolyl-22-oxacorroles
UV
Vis spectroscopy
CORE-MODIFIED CORROLES
1ST EXAMPLES
DIPYRROMETHANES
SMARAGDYRINS
CONDENSATION
 
Description Unsymmetrical 22-oxacorrole containing two aryl groups and one pyrrole group at the meso position was synthesized by condensing one equivalent of 16-oxatripyrrane with one equivalent of meso aryl dipyromethane under mild acid-catalyzed conditions followed by oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). This [3+2] condensation approach was expected to yield meso-free 25-oxasmaragdyrin but unexpectedly afforded unsymmetrical meso-pyrrole-substituted 22-oxacorrole. We demonstrated the versatility of the reaction by synthesizing four new meso-pyrrole-substituted 22-oxacorroles. The reactivity of -position of meso-pyrrole was tested by carrying out various functionalization reactions such as bromination, formylation, and nitration and obtained the functionalized meso-pyrrole-substituted 22-oxacorroles in decent yields. The X-ray structure obtained for one of the functionalized meso-pyrrole substituted 22-oxacorrole revealed that the macrocycle was nearly planar and the meso-pyrrole was in the perpendicular orientation with respect to the macrocyclic plane. The meso-pyrrole-substituted 22-oxacorroles absorb strongly in 400-700nm region with one strong Soret band and four weak Q bands. The 22-oxacorroles are strongly fluorescent and showed emission maxima at approximate to 650nm with decent quantum yields and singlet-state lifetimes. The 22-oxacorroles are redox-active and exhibited three irreversible oxidations and one or two reversible reduction(s). A preliminary biological study indicated that meso-pyrrole corroles are biocompatible.
 
Publisher WILEY-V C H VERLAG GMBH
 
Date 2014-12-28T12:43:47Z
2014-12-28T12:43:47Z
2014
 
Type Article
 
Identifier CHEMISTRY-A EUROPEAN JOURNAL, 20(33)10404-10413
0947-6539
1521-3765
http://dx.doi.org/10.1002/chem.201402710
http://dspace.library.iitb.ac.in/jspui/handle/100/16581
 
Language English