meso-Arylporpholactones and their Reduction Products

The rational syntheses of meso-tetraaryl-3-oxo-2-oxaporphyrins 5, known as porpholactones, via MnO4 –-mediated oxidations of the corresponding meso-tetraaryl-2,3-dihydroxychlorins (7) is detailed. Since chlorin 7 is prepared from the parent porphyrin 1, this amounts to a 2-step replacement of a pyrr...

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Published inJournal of organic chemistry Vol. 77; no. 15; pp. 6480 - 6494
Main Authors Brückner, Christian, Ogikubo, Junichi, McCarthy, Jason R, Akhigbe, Joshua, Hyland, Michael A, Daddario, Pedro, Worlinsky, Jill L, Zeller, Matthias, Engle, James T, Ziegler, Christopher J, Ranaghan, Matthew J, Sandberg, Megan N, Birge, Robert R
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.08.2012
Amer Chemical Soc
Subjects
Chemical reactivity
Chemistry
Chemistry, Organic
chlorins
Crystallography, X-Ray
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Lactones - chemical synthesis
Lactones - chemistry
Lewis bases
Models, Molecular
moieties
Molecular Structure
optical properties
Organic chemistry
oxazoles
oxidation
Oxidation-Reduction
oxygen
Physical Sciences
Preparations and properties
Reactivity and mechanisms
Science & Technology
PRESSURE-SENSITIVE PAINT
PORPHYRIN CHEMISTRY
PHOTODYNAMIC THERAPY
CORE CONSTRUCTS
ORBITAL THEORY
CHLOROPHYLL ANALOG CHEMISTRY
PHOTOPHYSICAL PROPERTIES
SPARSELY SUBSTITUTED CHLORINS
SYNTHETIC ANALOGS
EXCITED-STATES
MO method
Molecular structure
Nitrogen heterocycle
Molecular interaction
Pyrrole derivatives
Chemical reduction
Steric effect
Optical properties
Chlorins
Oxidation
Chemical reactivity
Chemical synthesis
Oxazole derivatives
Chromophore
Oxygen nitrogen heterocycle
Permanganates
Electronic properties
Theoretical study
Stepwise mechanism
Ketone
X ray diffraction
Planar molecule
Valence
MNDO method
Porphyrin
Oscillator strength
Nucleophilic substitution
Porphyrin derivatives
Conformation
Nucleophile
Crystalline structure
Online AccessGet full text
ISSN0022-3263
1520-6904
1520-6904
DOI10.1021/jo300963m

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Abstract The rational syntheses of meso-tetraaryl-3-oxo-2-oxaporphyrins 5, known as porpholactones, via MnO4 –-mediated oxidations of the corresponding meso-tetraaryl-2,3-dihydroxychlorins (7) is detailed. Since chlorin 7 is prepared from the parent porphyrin 1, this amounts to a 2-step replacement of a pyrrole moiety in 1 by an oxazolone moiety. The stepwise reduction of the porpholactone 5 results in the formation of chlorin analogues, meso-tetraaryl-3-hydroxy-2-oxachlorin (11) and meso-tetraaryl-2-oxachlorins (12). The reactivity of 11 with respect to nucleophilic substitution by O-, N-, and S-nucleophiles is described. The profound photophysical consequences of the formal replacement of a pyrrole with an oxazolone (porphyrin-like chromophore) or (substituted) oxazole moiety (chlorin-like chromophore with, for the parent oxazolochlorin 12, red-shifted Q x band with enhanced oscillator strengths) are detailed and rationalized on the basis of SAC–CI and MNDO-PSDCI molecular orbital theory calculations. The single crystal X-ray structures of the porpholactones point at a minor steric interaction between the carbonyl oxygen and the flanking phenyl group. The essentially planar structures of all chromophores in all oxidation states prove that the observed optical properties originate from the intrinsic electronic properties of the chromophores and are not subject to conformational modulation.
AbstractList The rational syntheses of meso-tetraaryl-3-oxo-2-oxaporphyrins 5, known as porpholactones, via MnO(4)(-)-mediated oxidations of the corresponding meso-tetraaryl-2,3-dihydroxychlorins (7) is detailed. Since chlorin 7 is prepared from the parent porphyrin 1, this amounts to a 2-step replacement of a pyrrole moiety in 1 by an oxazolone moiety. The stepwise reduction of the porpholactone 5 results in the formation of chlorin analogues, meso-tetraaryl-3-hydroxy-2-oxachlorin (11) and meso-tetraaryl-2-oxachlorins (12). The reactivity of 11 with respect to nucleophilic substitution by O-, N-, and S-nucleophiles is described. The profound photophysical consequences of the formal replacement of a pyrrole with an oxazolone (porphyrin-like chromophore) or (substituted) oxazole moiety (chlorin-like chromophore with, for the parent oxazolochlorin 12, red-shifted Q(x) band with enhanced oscillator strengths) are detailed and rationalized on the basis of SAC-CI and MNDO-PSDCI molecular orbital theory calculations. The single crystal X-ray structures of the porpholactones point at a minor steric interaction between the carbonyl oxygen and the flanking phenyl group. The essentially planar structures of all chromophores in all oxidation states prove that the observed optical properties originate from the intrinsic electronic properties of the chromophores and are not subject to conformational modulation.
The rational syntheses of meso-tetraaryl-3-oxo-2-oxaporphyrins 5, known as porpholactones, via MnO(4)(-)-mediated oxidations of the corresponding meso-tetraaryl-2,3-dihydroxychlorins (7) is detailed. Since chlorin 7 is prepared from the parent porphyrin 1, this amounts to a 2-step replacement of a pyrrole moiety in 1 by an oxazolone moiety. The stepwise reduction of the porpholactone 5 results in the formation of chlorin analogues, meso-tetraaryl-3-hydroxy-2-oxachlorin (11) and meso-tetraaryl-2-oxachlorins (12). The reactivity of 11 with respect to nucleophilic substitution by O-, N-, and S-nucleophiles is described. The profound photophysical consequences of the formal replacement of a pyrrole with an oxazolone (porphyrin-like chromophore) or (substituted) oxazole moiety (chlorin-like chromophore with, for the parent oxazolochlorin 12, red-shifted Q(x) band with enhanced oscillator strengths) are detailed and rationalized on the basis of SAC-CI and MNDO-PSDCI molecular orbital theory calculations. The single crystal X-ray structures of the porpholactones point at a minor steric interaction between the carbonyl oxygen and the flanking phenyl group. The essentially planar structures of all chromophores in all oxidation states prove that the observed optical properties originate from the intrinsic electronic properties of the chromophores and are not subject to conformational modulation.The rational syntheses of meso-tetraaryl-3-oxo-2-oxaporphyrins 5, known as porpholactones, via MnO(4)(-)-mediated oxidations of the corresponding meso-tetraaryl-2,3-dihydroxychlorins (7) is detailed. Since chlorin 7 is prepared from the parent porphyrin 1, this amounts to a 2-step replacement of a pyrrole moiety in 1 by an oxazolone moiety. The stepwise reduction of the porpholactone 5 results in the formation of chlorin analogues, meso-tetraaryl-3-hydroxy-2-oxachlorin (11) and meso-tetraaryl-2-oxachlorins (12). The reactivity of 11 with respect to nucleophilic substitution by O-, N-, and S-nucleophiles is described. The profound photophysical consequences of the formal replacement of a pyrrole with an oxazolone (porphyrin-like chromophore) or (substituted) oxazole moiety (chlorin-like chromophore with, for the parent oxazolochlorin 12, red-shifted Q(x) band with enhanced oscillator strengths) are detailed and rationalized on the basis of SAC-CI and MNDO-PSDCI molecular orbital theory calculations. The single crystal X-ray structures of the porpholactones point at a minor steric interaction between the carbonyl oxygen and the flanking phenyl group. The essentially planar structures of all chromophores in all oxidation states prove that the observed optical properties originate from the intrinsic electronic properties of the chromophores and are not subject to conformational modulation.
The rational syntheses of meso-tetraary1-3-oxo-2-oxaporphyrins 5, known as porpholactones, via MnO4--mediated oxidations of the corresponding meso-tetraary1-2,3-dihydroxychlorins (7) is detailed. Since chlorin 7 is prepared from the parent porphyrin 1, this amounts to a 2-step replacement of a pyrrole moiety in 1 by an oxazolone moiety. The stepwise reduction of the porpholactone 5 results in the formation of chlorin analogues, meso-tetraary1-3-hydroxy-2-oxachlorin (11) and meso-tetraaryl-2-oxachlorins (12). The reactivity of 11 with respect to nucleophilic substitution by O-, N-, and S-nucleophiles is described. The profound photophysical consequences of the formal replacement of a pyrrole with an oxazolone (porphyrin-like chromophore) or (substituted) oxazole moiety (chlorin-like chromophore with, for the parent oxazolochlorin 12, red-shifted Q(x)band with enhanced oscillator strengths) are detailed and rationalized on the basis of SACCI and MNDO-PSDCI molecular orbital theory calculations. The single crystal X-ray structures of the porpholactones point at a minor steric interaction between the carbonyl oxygen and the flanking phenyl group. The essentially planar structures of all chromophores in all oxidation states prove that the observed optical properties originate from the intrinsic electronic properties of the chromophores and are not subject to conformational modulation.
The rational syntheses of meso-tetraaryl-3-oxo-2-oxaporphyrins 5, known as porpholactones, via MnO4−-mediated oxidations of the corresponding meso-tetraaryl-2,3-dihydroxychlorins (7) is detailed. Since chlorin 7 is prepared from the parent porphyrin 1, this amounts to a 2-step replacement of a pyrrolemoiety in 1 by a oxazolone moiety. The step-wise reduction of the porpholactone 5 results in the formation of chlorin analogues, meso-tetraaryl-3-hydroxy-2-oxachlorin (11) and meso-tetraaryl-2-oxachlorins (12). The reactivity of 11 with respect to nucleophilic substitution by O-, N-, and S-nucleophiles is described. The profound photophysical consequences of the formal replacement of a pyrrole with an oxazolone (porphyrin-like chromophore) or (substituted) oxazole moiety (chlorin-like chromophore with, for the parent oxazolochlorin 12, red-shifted Qx band with enhanced oscillator strengths) are detailed and rationalized on the basis of SAC-CI and MNDO-PSDCI molecular orbital theory calculations. The single crystal X-ray structures of the porpholactones point at a minor steric interaction between the carbonyl oxygen and the flanking phenyl group. The essentially planar structures of all chromophores in all oxidation states prove that the observed optical properties originate from the intrinsic electronic properties of the chromophores and are not subject to conformational modulation.
The rational syntheses of meso-tetraaryl-3-oxo-2-oxaporphyrins 5, known as porpholactones, via MnO4 –-mediated oxidations of the corresponding meso-tetraaryl-2,3-dihydroxychlorins (7) is detailed. Since chlorin 7 is prepared from the parent porphyrin 1, this amounts to a 2-step replacement of a pyrrole moiety in 1 by an oxazolone moiety. The stepwise reduction of the porpholactone 5 results in the formation of chlorin analogues, meso-tetraaryl-3-hydroxy-2-oxachlorin (11) and meso-tetraaryl-2-oxachlorins (12). The reactivity of 11 with respect to nucleophilic substitution by O-, N-, and S-nucleophiles is described. The profound photophysical consequences of the formal replacement of a pyrrole with an oxazolone (porphyrin-like chromophore) or (substituted) oxazole moiety (chlorin-like chromophore with, for the parent oxazolochlorin 12, red-shifted Q x band with enhanced oscillator strengths) are detailed and rationalized on the basis of SAC–CI and MNDO-PSDCI molecular orbital theory calculations. The single crystal X-ray structures of the porpholactones point at a minor steric interaction between the carbonyl oxygen and the flanking phenyl group. The essentially planar structures of all chromophores in all oxidation states prove that the observed optical properties originate from the intrinsic electronic properties of the chromophores and are not subject to conformational modulation.
The rational syntheses of meso-tetraaryl-3-oxo-2-oxaporphyrins 5, known as porpholactones, via MnO₄–-mediated oxidations of the corresponding meso-tetraaryl-2,3-dihydroxychlorins (7) is detailed. Since chlorin 7 is prepared from the parent porphyrin 1, this amounts to a 2-step replacement of a pyrrole moiety in 1 by an oxazolone moiety. The stepwise reduction of the porpholactone 5 results in the formation of chlorin analogues, meso-tetraaryl-3-hydroxy-2-oxachlorin (11) and meso-tetraaryl-2-oxachlorins (12). The reactivity of 11 with respect to nucleophilic substitution by O-, N-, and S-nucleophiles is described. The profound photophysical consequences of the formal replacement of a pyrrole with an oxazolone (porphyrin-like chromophore) or (substituted) oxazole moiety (chlorin-like chromophore with, for the parent oxazolochlorin 12, red-shifted Qₓ band with enhanced oscillator strengths) are detailed and rationalized on the basis of SAC–CI and MNDO-PSDCI molecular orbital theory calculations. The single crystal X-ray structures of the porpholactones point at a minor steric interaction between the carbonyl oxygen and the flanking phenyl group. The essentially planar structures of all chromophores in all oxidation states prove that the observed optical properties originate from the intrinsic electronic properties of the chromophores and are not subject to conformational modulation.
Author McCarthy, Jason R
Hyland, Michael A
Engle, James T
Birge, Robert R
Ranaghan, Matthew J
Akhigbe, Joshua
Ziegler, Christopher J
Brückner, Christian
Ogikubo, Junichi
Sandberg, Megan N
Zeller, Matthias
Daddario, Pedro
Worlinsky, Jill L
AuthorAffiliation Youngstown State University
University of Akron
University of Connecticut
AuthorAffiliation_xml – name: University of Connecticut
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– name: Youngstown State University
– name: University of Connecticut, Department of Molecular and Cell Biology
– name: University of Connecticut, Department of Chemistry United States
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  givenname: Christian
  surname: Brückner
  fullname: Brückner, Christian
  email: c.bruckner@uconn.edu
– sequence: 2
  givenname: Junichi
  surname: Ogikubo
  fullname: Ogikubo, Junichi
– sequence: 3
  givenname: Jason R
  surname: McCarthy
  fullname: McCarthy, Jason R
– sequence: 4
  givenname: Joshua
  surname: Akhigbe
  fullname: Akhigbe, Joshua
– sequence: 5
  givenname: Michael A
  surname: Hyland
  fullname: Hyland, Michael A
– sequence: 6
  givenname: Pedro
  surname: Daddario
  fullname: Daddario, Pedro
– sequence: 7
  givenname: Jill L
  surname: Worlinsky
  fullname: Worlinsky, Jill L
– sequence: 8
  givenname: Matthias
  surname: Zeller
  fullname: Zeller, Matthias
– sequence: 9
  givenname: James T
  surname: Engle
  fullname: Engle, James T
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  givenname: Christopher J
  surname: Ziegler
  fullname: Ziegler, Christopher J
– sequence: 11
  givenname: Matthew J
  surname: Ranaghan
  fullname: Ranaghan, Matthew J
– sequence: 12
  givenname: Megan N
  surname: Sandberg
  fullname: Sandberg, Megan N
– sequence: 13
  givenname: Robert R
  surname: Birge
  fullname: Birge, Robert R
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Issue 15
Keywords PRESSURE-SENSITIVE PAINT
PORPHYRIN CHEMISTRY
PHOTODYNAMIC THERAPY
CORE CONSTRUCTS
ORBITAL THEORY
CHLOROPHYLL ANALOG CHEMISTRY
PHOTOPHYSICAL PROPERTIES
SPARSELY SUBSTITUTED CHLORINS
SYNTHETIC ANALOGS
EXCITED-STATES
MO method
Molecular structure
Nitrogen heterocycle
Molecular interaction
Pyrrole derivatives
Chemical reduction
Steric effect
Optical properties
Chlorins
Oxidation
Chemical reactivity
Chemical synthesis
Oxazole derivatives
Chromophore
Oxygen nitrogen heterocycle
Permanganates
Electronic properties
Theoretical study
Stepwise mechanism
Ketone
X ray diffraction
Planar molecule
Valence
MNDO method
Porphyrin
Oscillator strength
Nucleophilic substitution
Porphyrin derivatives
Conformation
Nucleophile
Crystalline structure
Language English
License CC BY 4.0
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National Science Foundation
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Current address: Center for Systems Biology, Massachusetts General Hospital, Boston, MA 02114, United States.
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PublicationTitle Journal of organic chemistry
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Snippet The rational syntheses of meso-tetraaryl-3-oxo-2-oxaporphyrins 5, known as porpholactones, via MnO4 –-mediated oxidations of the corresponding...
The rational syntheses of meso-tetraary1-3-oxo-2-oxaporphyrins 5, known as porpholactones, via MnO4--mediated oxidations of the corresponding...
The rational syntheses of meso-tetraaryl-3-oxo-2-oxaporphyrins 5, known as porpholactones, via MnO(4)(-)-mediated oxidations of the corresponding...
The rational syntheses of meso-tetraaryl-3-oxo-2-oxaporphyrins 5, known as porpholactones, via MnO₄–-mediated oxidations of the corresponding...
The rational syntheses of meso-tetraaryl-3-oxo-2-oxaporphyrins 5, known as porpholactones, via MnO4−-mediated oxidations of the corresponding...
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SubjectTerms Chemical reactivity
Chemistry
Chemistry, Organic
chlorins
Crystallography, X-Ray
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Lactones - chemical synthesis
Lactones - chemistry
Lewis bases
Models, Molecular
moieties
Molecular Structure
optical properties
Organic chemistry
oxazoles
oxidation
Oxidation-Reduction
oxygen
Physical Sciences
Preparations and properties
Reactivity and mechanisms
Science & Technology
Title meso-Arylporpholactones and their Reduction Products
URI http://dx.doi.org/10.1021/jo300963m
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https://www.ncbi.nlm.nih.gov/pubmed/22734444
https://www.proquest.com/docview/1031157152
https://www.proquest.com/docview/2010202361
https://pubmed.ncbi.nlm.nih.gov/PMC3411881
Volume 77
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