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Synthetic Chlorins, Possible Surrogates for Chlorophylls, Prepared by Derivatization of Porphyrins

Journal Article · · Chemical Reviews
 [1];  [2]
  1. North Carolina State Univ., Raleigh, NC (United States); DOE/OSTI
  2. North Carolina State Univ., Raleigh, NC (United States)
+ Show Author Affiliations

Chlorophylls make Earth green, are the central constituents in the engine of photosynthesis, and not surprisingly have garnered extensive attention. A chlorin, the core chromophore of a chlorophyll, is a dihydroporphyrin macrocycle that contains one pyrroline ring and three pyrrole rings. The dominant method for the synthesis of chlorins has entailed the derivatization of porphyrins. The present review covers the ostensibly simple conversion of porphyrins, regardless of synthetic or biological origin, to chlorins. The period covered encompasses the entire history since the beginnings of chlorin synthetic chemistry in the early 20th century through 2015. Representative transformations include hydrogenation, cycloaddition, annulation, and diverse “breaking and mending” approaches. Altogether, the synthesis of >1000 chlorins or chlorin-like compounds (containing >50 distinct pyrroline motifs) is described. Such diversity animates the question “what structural features are essential for a chlorin to resemble chlorophyll?” To begin to address the structure–spectrum relationship, > 250 absorption spectra are provided for representative structures. The synthesis and spectral properties of the vast collection of compounds described herein are expected to illuminate the scope to which synthetic chlorins can serve as surrogates for chlorophylls and be exploited in diverse ways.

Research Organization:
North Carolina State Univ., Raleigh, NC (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division
Grant/Contract Number:
FG02-96ER14632
OSTI ID:
1534468
Journal Information:
Chemical Reviews, Journal Name: Chemical Reviews Journal Issue: 2 Vol. 117; ISSN 0009-2665
Publisher:
American Chemical SocietyCopyright Statement
Country of Publication:
United States
Language:
English

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Facile syntheses of tetraalkylchlorin and tetraalkylporphyrin complexes and comparison of the structures of the tetramethylchlorin and tetramethylporphyrin complexes of nickel(II) journal October 1980
Mechanistic study of the synthesis and spectral properties of meso-tetraarylporphyrins journal May 1972
Chemistry of porphyrins. IV. Behavior of di- and tetrahydroporphyrins under alkaline conditions. Direct observation of the chlorin-phlorin equilibrium journal August 1973
Cavitand−Porphyrins journal May 2001
Diimide reduction of porphyrins journal December 1969
Mechanistic Investigations of Porphyrin Syntheses. I. Preliminary Studies on ms -Tetraphenylporphin journal August 1964
The Spectra of α,β,γ,δ-Tetraphenylchlorin and its Metallo-derivatives journal August 1952
Pyridinate Complexes of Some Metallo-derivatives of Tetraphenylporphine and Tetraphenylchlorin 1 journal August 1952
An Attempted Preparation of a Simple Tetrahydroporphine 1 journal December 1952
Synthetic Chlorins and Dihydrochlorins 1,2 journal July 1950
A Further Study of the Porphine-like Products of the Reaction of Benzaldehyde and Pyrrole journal November 1946
α,β,γ,δ-Tetraphenylchlorin journal November 1943
Porphyrin Studies. III. 1 The Structure of the Porphine 2 Ring System journal October 1939
A New Porphyrin Synthesis. The Synthesis of Porphin 1 journal April 1936
Formation of Porphyrins from Pyrrole and Aldehydes journal October 1935
Studies in the Chlorophyll Series. iii. Products of the Phase test journal July 1930
THE REDUCTION OF OLEFINS BY MEANS OF AZODICARBOXYLIC ACID in situ journal September 1961
REDUCTION OF ISOLATED OLEFINIC BONDS BY MEANS OF p-TOLUENESULFONYLHYDRAZINE journal September 1961
Selectivity and Mechanism of Diimide Reductions journal October 1961
A new Aspect of the Chemistry of Chlorins journal November 1961
The Total Synthesis of Chlorophyll journal July 1960
Tetraphenylporphine and Some para-Substituted Derivatives 1,2 journal April 1956
Spectroscopic Determination of Proton Position in the Proton-Coupled Electron Transfer Pathways of Donor−Acceptor Supramolecule Assemblies journal August 2006
meso -Aryl-Substituted Subporphyrins:  Synthesis, Structures, and Large Substituent Effects on Their Electronic Properties journal April 2007
Synthesis and Characterization of meso -Aryl-Substituted Subchlorins journal January 2008
Helimeric Porphyrinoids: Stereostructure and Chiral Resolution of meso -Tetraarylmorpholinochlorins journal June 2011
Expansion by Contraction: Diversifying the Photochemical Reactivity Scope of Diazo-oxochlorins toward Development of in Situ Alkylating Agents journal October 2008
Chlorin-Oligonucleotide Conjugates:  Synthesis, Properties, and Red Light-Induced Photochemical Sequence-Specific DNA Cleavage in Duplexes and Triplexes † , ‡ journal January 1996
The Synthesis, Properties, and Reactivities of Free-Base- and Zn(II)- N -Methyl Hydroporphyrin Compounds. The Unexpected Selectivity of the Direct Methylation of Free-Base Hydroporphyrin Compounds journal December 1997
Absorption spectra of copper and zinc complexes of pheophytins and pheophorbides journal January 1968
New sensitizers for photodynamic therapy. Controlled synthesis of purpurins and their effect on normal tissue journal April 1989
Porphyrin dimers as photosensitizers in photodynamic therapy journal July 1990
Comparison between 5,10,15,20-Tetraaryl- and 5,15-Diarylporphyrins as Photosensitizers:  Synthesis, Photodynamic Activity, and Quantitative Structure−Activity Relationship Modeling journal June 2006
Improvement of meta -tetra(Hydroxyphenyl)chlorin-Like Photosensitizer Selectivity with Folate-Based Targeted Delivery. Synthesis and in Vivo Delivery Studies journal July 2008
In Vitro Heavy-Atom Effect of Palladium(II) and Platinum(II) Complexes of Pyrrolidine-Fused Chlorin in Photodynamic Therapy journal April 2009
Vilsmeier reactions of porphyrins and chlorins with 3-(dimethylamino)acrolein to give meso-(2-formylvinyl)porphyrins: new syntheses of benzochlorins, benzoisobacteriochlorins, and benzobacteriochlorins and reductive coupling of porphyrins and chlorins using low-valent titanium complexes journal July 1991
A new method for regiospecific deuteration and reduction of 5,10,15,20-tetraphenylporphyrins: nucleophilic reaction of borohydride ion with 2-nitro-5,10,15,20-tetraphenylporphyrins journal July 1993
Anomalous Double Cyclization Reactions of .beta.-Formylporphyrins journal December 1994
Magnetic circular dichroism studies. 66. Synthesis of demethyl monosubstituted porphyrins. The effect of substituent conformation on the magnetic circular dichroism spectra of ethoxycarbonyl porphyrins journal September 1984
C-Hydroxy- and C-methylchlorins. A convenient route to heme d and bonellin model compounds journal November 1985
Tautomerism in 2-hydroxy-5,10,15,20-tetraphenylporphyrin: an equilibrium between enol, keto, and aromatic hydroxyl tautomers journal March 1988
Investigation of the synthesis of ortho-substituted tetraphenylporphyrins journal February 1989
Synthesis and atropisomer separation of porphyrins containing functionalization at the 5,15-meso positions: application to the synthesis of binuclear ligand systems journal November 1981
The Diels-Alder reactions of protoporphyrin IX dimethyl ester with electron-deficient alkynes journal April 1986
Observations on the synthesis and spectroscopic characteristics of purpurins journal April 1986
A novel method of functionalizing the ethyl chain of octaethylporphyrin journal March 1987
Effect of M eso- Substituents on the Osmium Tetraoxide Reaction and Pinacol−Pinacolone Rearrangement of the Corresponding v ic -Dihydroxyporphyrins journal June 2001
Reduction of Tin Porphyrins to Tin Chlorins 1 journal September 1962
THE PORPHYRIN-LIKE PRODUCTS OF THE REACTION OF PYRROLE WITH BENZALDEHYDE 1 journal May 1943
Reactions of protoporphyrin with tetracyanoethylene journal December 1980
The Rational Synthesis of Chlorins via Rearrangement of Porphodimethenes:  Influence of β-Substituents on the Regioselectivity and Stereoselectivity of Pyrroline Ring Formation journal May 2002
Synthesis and Reactions of Aminoporphyrazines with Annulated Five- and Seven-Membered Rings journal March 2003
Functionalization of OEP-Based Benzochlorins To Develop Carbohydrate-Conjugated Photosensitizers. Attempt To Target β-Galactoside-Recognized Proteins journal December 2003
1,3-Dipolar Cycloaddition Reactions of Porphyrins with Azomethine Ylides † journal March 2005
Synthesis of Swallowtail-Substituted Multiporphyrin Rods journal August 2004
Porphyrin Architectures Tailored for Studies of Molecular Information Storage journal October 2004
Swallowtail Porphyrins:  Synthesis, Characterization and Incorporation into Porphyrin Dyads journal May 2004
O -Confused OxaporphyrinAn Intermediate in Formation of 3-Substituted 2-Oxa-21-Carbaporphyrins journal November 2005
Acylation of Nickel m eso -Tetraarylporphyrins:  Porphyrin to Corrole Ring Contraction and Formation of s eco -Porphyrins journal April 2006
Synthesis of Locked meso-β-Substituted Chlorins via 1,3-Dipolar Cycloaddition journal August 2006
Porphyrins in 1,3-Dipolar Cycloaddition Reactions. Synthesis of New Porphyrin−Chlorin and Porphyrin−Tetraazachlorin Dyads journal October 2006
A Facile Synthetic Method for Conversion of Chlorophyll- a to Bacteriochlorophyll- c journal May 2007
Meso- 13 C-Labeled Porphyrins for Studies of Ground-State Hole Transfer in Multiporphyrin Arrays journal June 2007
Regioselective Transformation of Octaethylporphyrin into a Phytoporphyrin Analogue journal September 2007
Chlorin Photosensitizers Sterically Designed To Prevent Self-Aggregation journal November 2011
1,3-Dipolar Cycloaddition of 2,6-Dichlorobenzonitrile Oxide to 2-Methyl-N-confused Porphyrin. Regio- and Stereoselective Synthesis and Structural Characterization of 2-Aza-21-carbabacteriochlorin and Resolution of 2-Aza-21-carbachlorin Enantiomers journal February 2012
meso -Tetrakis(pentafluorophenyl)porphyrin-Derived Chromene-Annulated Chlorins journal March 2012
meso -Arylporpholactones and their Reduction Products journal July 2012
meso -Aryl-3-alkyl-2-oxachlorins journal July 2012
Synthesis and Reactivity of Carbachlorins and Carbaporphyrins journal July 2014
Mono- and Bisquinoline-Annulated Porphyrins from Porphyrin β,β′-Dione Oximes journal December 2014
Design, Synthesis, and Photophysical Characterization of Water-Soluble Chlorins journal April 2008
A New Synthetic Approach to N -Arylquinolino[2,3,4- at ]porphyrins from β-Arylaminoporphyrins journal August 2008
MTO/H 2 O 2 /Pyrazole-Mediated N-Oxidation of meso -Tetraarylporphyrins and -chlorins, and S-Oxidation of a meso -Tetraaryldithiaporphyrin and -chlorin journal May 2009
Oxazolochlorins. 2. Intramolecular Cannizzaro Reaction of meso -Tetraphenylsecochlorin Bisaldehyde journal June 2009
Synthesis and Photochemical Properties of 12-Substituted versus 13-Substituted Chlorins journal August 2009
OsO 4 -Mediated Dihydroxylation of meso -Tetraphenylporphyrin N -Oxide and Transformation of the Resulting Diolchlorin N -Oxide Regioisomers journal January 2010
De Novo Synthesis of Long-Wavelength Absorbing Chlorin-13,15-dicarboximides journal March 2010
Pinacol−Pinacolone Rearrangements in vic- Dihydroxychlorins and Bacteriochlorins:  Effect of Substituents at the Peripheral Positions journal March 1997
Formation of a meso -Tetraphenylsecochlorin and a Homoporphyrin with a Twist journal April 1998
Seco-Porphyrazines:  Synthetic, Structural, and Spectroscopic Investigations journal December 1997
Dihydroporphyrin Synthesis:  New Methodology † journal October 1998
Ultrafast Energy Transfer from a Carotenoid to a Chlorin in a Simple Artificial Photosynthetic Antenna journal September 2002
Photophysical Properties and Electronic Structure of Chlorin-Imides: Bridging the Gap between Chlorins and Bacteriochlorins journal December 2014
Extending the Short and Long Wavelength Limits of Bacteriochlorin Near-Infrared Absorption via Dioxo- and Bisimide-Functionalization journal March 2015
Quinoxaline-Fused Porphyrins for Dye-Sensitized Solar Cells journal February 2008
Complexation and Interchromophoric Interactions in Self-Organized Porphyrin and Chlorin Triads journal January 1996
Free Base m eso -Tetraaryl-morpholinochlorins and Porpholactone from m eso -Tetraaryl-2,3-dihydroxy-chlorin journal December 2002
Simple Approach to “Locked” Chlorins journal April 2005
Locked π-Expanded Chlorins in Two Steps from Simple Tetraarylporphyrins journal November 2005
Synthesis of Pyrrolidine-Fused [34]- and [36]Octaphyrins via 1,3-Dipolar Cycloaddition journal February 2006
Development of Strategies for the Regiocontrolled Synthesis of meso -5,10,20-Triaryl-2,3-chlorins journal October 2007
Quinoline-Annulated Porphyrins journal March 2011
Tunable meso -Tetraphenyl-alkyloxazolo-chlorins and -bacteriochlorins † † Oxazolochlorins 4 . Oxazolochlorins 3 : Khalil, G. E.; Daddario, P.; Lau, K. S. F.; Imtiaz, S.; King, M.; Gouterman, M.; Sidelev, A.; Ghandehari, M.; Brückner, C. Analyst 2010 , 135 , 2125−2131. journal May 2011
Multigram Synthesis of a Water-Soluble Porphyrazine and Derived seco -Porphyrazine Labeling Agents journal November 2007
Unprecedented Degradation of Nickel(II) 2,3,12,13-Tetrabromo-5,10,15,20-tetraarylporphyrins by the Anion of E -Benzaldoxime: A Novel Approach to Nickel(II) Chlorophins and Bacteriophins journal May 2009
Effect of Substituents in Directing the Formation of Benzochlorins and Isobacteriochlorins in Porphyrin and Chlorin Systems journal November 1999
Porphyrins and Their Derivatives: XXII. A New Product of Intramolecular Cyclization of 5,10,15,20-Tetraphenyl-2-formylporphyrin Copper Complex journal February 2001
Chemistry of Oximes of meso-Porphyrin Metal Complexes. Synthesis of Chlorine with Fused 1,2-Oxazocine Ring journal March 2003
Methods of Attaching Unprotected Oligonucleotides to DNA-binding, Fluorescent, or Reactive Ligands for Synthesis of Antisense or Gene-directed Agents and Probes journal November 2000
Modification of the Peripheral Substituents in Chlorophylls a and b and Their Derivatives (Review) journal April 2004
Effect of the Electron-Vibrational Interaction on the Second Electron Transition of Tetraazaporphin and Tetraazachlorin Molecules journal January 2004
Indaphyrin, a meso-tetraphenylsecochlorin-derived chromophore incorporating o-phenyl-to-β-linkages journal January 2003
Synthesis of indaphyrins: meso-tetraarylsecochlorin-based porphyrinoids containing direct o-phenyl-to-β-linkages journal January 2004
Elucidation of the extraordinary 4-membered pyrrole ring-contracted azeteoporphyrinoid as an intermediate in chlorin oxidation journal January 2006
Photochemical preparation of pyrrole ring-contracted chlorins by the Wolff rearrangement journal January 2006
Soluble precipitable porphyrins for use in targeted molecular brachytherapy journal January 2008
A compact water-soluble porphyrin bearing an iodoacetamido bioconjugatable site journal January 2008
Structural characteristics that make chlorophylls green: interplay of hydrocarbon skeleton and substituents journal January 2011
Diels–Alder additions to protoporphyrin IX dimethyl ester journal January 1968
The Baylis–Hillman reaction: a novel concept for creativity in chemistry journal January 2012
Synthesis and characterization of mono- and dinuclear phenanthroline-extended tetramesitylporphyrin complexes as well as UV-Vis and EPR studies on their one-electron reduced species journal January 2013
Novel heterocyclic systems from selective oxidation at the β-pyrrolic position of porphyrins journal January 1984
Ready syntheses of benzoporphyrins via Diels–Alder reactions with protoporphyrin IX journal January 1984
Control of reactivity at the porphyrin periphery by metal ion co-ordination: a general method for specific nitration at the β-pyrrolic position of 5,10,15,20-tetra-arylporphyrins journal January 1984
Synthesis relevant to vitamin B 12 biosynthesis: synthesis of (±)Faktor-I octamethyl ester journal January 1985
Diels–Alder reactions of protoporphyrin dimethyl esters with nitrosobenzenes; a novel degradation to formyl porphyrins journal January 1985
A new method for the synthesis of porphyrin-α-diones that is applicable to the synthesis of trans-annular extended porphyrin systems journal January 1991
The 2,3-secochlorin-2,3-dione system journal January 1993
Synthesis of 5,10,15,20-meso-unsubstituted and 5,10,15,20-meso-substituted-21,23-ditellura/diselena core-modified porphyrinogens: oxidation and detection of mercury( ii ) journal January 2014
Chemical modification of temoporfin – a second generation photosensitizer activated using upconverting nanoparticles for singlet oxygen generation journal January 2014
PEGylated meso-arylporpholactone metal complexes as optical cyanide sensors in water journal January 2014
How green is green chemistry? Chlorophylls as a bioresource from biorefineries and their commercial potential in medicine and photovoltaics journal January 2015
adj-Dicarbachlorin, the first free base carbaporphyrinoid system with an internal methylene unit journal January 2015
Isoxazolidine-fused meso-tetraarylchlorins as key tools for the synthesis of mono- and bis-annulated chlorins journal January 2015
Benziporphyrins, a unique platform for exploring the aromatic characteristics of porphyrinoid systems journal January 2015
meso-Substitution products of ætioporphyrin I journal January 1966
Additions to porphins involving the formation of new carbon–carbon bonds journal January 1973
Second generation tumour photosensitisers: the synthesis and biological activity of octaalkyl chlorins and bacteriochlorins with graded amphiphilic character journal January 1992
N-methyltetraphenylporphyrin with an inverted N-methylpyrrole ring: the first isomer of N-methyltetraphenylporphyrin journal January 1995
Cleavage of (octaethyl-2,3-dihydroxychlorinato)nickel(II) to give the novel 2,3-dioxo-2,3-secochlorin system journal January 1997
meso-Arylporphyrins as dienophiles in Diels–Alder reactions: a novel approach to the synthesis of chlorins, bacteriochlorins and naphthoporphyrins journal January 1997
Novel synthesis and new chemistry of naphthochlorins journal January 1998
A study on the oxidation of 2-hydroxyporphyrins to porphyrin-α-diones journal January 1998
Cruciform porphyrin pentamers journal January 1998
Decapitation of dihydroporphyrazinediol derivatives: synthesis and X-ray structure of a novel seco-porphyrazine journal January 1999
Porphodimethylidenes from porphyrin-fused 3-sulfolenes—versatile porphyrin dienes for cycloadditions journal January 1999
meso-Tetraarylporphyrins as dipolarophiles in 1,3-dipolar cycloaddition reactions journal January 1999
Synthesis and excited‐state photodynamics of phenylethyne‐linked porphyrin–phthalocyanine dyads journal January 2000
Tetrapyrroles: the pigments of life journal January 2000
A new synthetic approach to porphyrin-α-diones and a -2,3,12,13-tetraone: building blocks for laterally conjugated porphyrin arrays journal January 2001
Synthesis of hydrolytically stable porphyrin C- and S-glycoconjugates in high yields journal January 2001
A one-step synthesis of a free base secochlorin from a 2,3-dimethoxy porphyrin journal January 2001
A novel synthetic route to fused propenochlorin and benzochlorin photodynamic therapy probes journal April 2002
Nitrogen extrusion from pyrazoline-substituted porphyrins and chlorins using long wavelength visible light journal October 2002
Studies on seco-porphyrazines: a case study on serendipity journal January 2003
Porphyrin ring contraction: a one-pot reaction leading to divalent corrolesElectronic supplementary information (ESI) available: experimental procedures for syntheses of corrole 4 and ketone 3 (R = OEt), and for preparing 4 from 11 (R = H). See http://www.rsc.org/suppdata/cc/b4/b400812j/ journal January 2004
Hydrogenated tetraazaporphyrins—old but new core-modified phthalocyanine analogues journal January 2008
Synthesis and biological investigations of tetrakis(p-carboranylthio-tetrafluorophenyl)chlorin (TPFC) journal January 2008
Synthesis of a pyridine-fused porphyrinoid: oxopyridochlorin journal January 2009
Photosensitizing properties of chlorins in solution and in membrane-mimicking systems journal January 2009
High-yielding syntheses of hydrophilic conjugatable chlorins and bacteriochlorins journal January 2009
Syntheses, structures, modification, and optical properties of meso-tetraaryl-2,3-dimethoxychlorin, and two isomeric meso-tetraaryl-2,3,12,13-tetrahydroxybacteriochlorins journal January 2010
meso-Tetraarylporpholactones as high pH sensors journal January 2010
Stirring the porphyrin alphabet soup—functionalization reactions for porphyrins journal January 2011
Unexpected hydroxylamine-induced ring-closure reactions of meso-tetraphenylsecochlorin bisaldehyde journal January 2011
A novel conversion of porphyrins into chlorins journal January 1966
Rational syntheses of chlorocruoroporphyrin (Spirographis porphyrin) and pemptoporphyrin journal January 1967
Porpholactams and chlorolactams: replacement of a β,β′-double bond in meso-tetraphenyl-porphyrin and -chlorin by a lactam moiety journal January 2011
De novo synthesis and properties of analogues of the self-assembling chlorosomal bacteriochlorophylls journal January 2011
Disulfonated tetraphenyl chlorin (TPCS2a), a novel photosensitizer developed for clinical utilization of photochemical internalization journal January 2011
N-methylation of octaethylporphyrin and octaethylchlorin journal January 1970
Facile one-pot synthesis of unprecedented β,β′-linked porphyrin–chlorin heterodimers journal January 2012
Synthesis of stable free base secochlorins and their corresponding metal complexes from meso-tetraarylporphyrin derivatives journal January 2012
Hydrogenation effects in metalloporphycenes: synthesis and redox behavior of Ni(ii)–tetra(n-propyl)dihydroporphycene journal January 2012
Dual facet of gold(iii) in the reactions of gold(iii) and porphyrins journal January 2012
An insight into solvent-free diimide porphyrin reduction: a versatile approach for meso-aryl hydroporphyrin synthesis journal January 2012
Comparative photodynamic inactivation of antibiotic resistant bacteria by first and second generation cationic photosensitizers journal January 2012
Synthetic 2- and 4-monoacetyldeuteroporphyrin IX journal January 1972
Cyclisations involving meso-substituents of crowded porphyrins journal January 1978
Efficient synthesis of 2-oxy-5,10,15,20-tetraphenylporphyrins from a nitroporphyrin by a novel multi-step cine-substitution sequence journal January 1984
Serendipitous desymmetrisation during porphyrazine synthesis: an X-ray crystallographic study of 2,3,7,8,12,13,17,18-octakis(dimethylamino)-2-secoporphyrazine-2,3-dione journal January 1994
5,15-Diphenyl-7-oxobenzochlorins. Novel long-wavelength absorbing photosensitizers for photodynamic therapy journal January 1994
Carbolithiation of meso-aryl-substituted 5,15-diazaporphyrin selectively provides 3-alkylated diazachlorins journal January 2013
Serendipitous synthetic entrée to tetradehydro analogues of cobalamins journal January 2013
Formation, structure, and reactivity of meso-tetraaryl-chlorolactones, -porpholactams, and -chlorolactams, porphyrin and chlorin analogues incorporating oxazolone or imidazolone moieties journal January 2013
Porphothionolactones: synthesis, structure, physical, and chemical properties of a chemodosimeter for hypochlorite journal January 2013
Synthesis and photophysical properties of chlorins bearing 0–4 distinct meso-substituents journal January 2013
Photophysical properties and electronic structure of retinylidene–chlorin–chalcones and analogues journal January 2014
Design and synthesis of β-multi-substituted push–pull porphyrins journal January 2013
A convenient synthesis of functionalized tetraphenylchlorins journal January 1996
A photophysical study of some purpurins journal January 1990
Reaction of singlet oxygen with vinyl-substituted porphyrins. A kinetic study by laser flash photolysis journal January 1992
Pyrroles and related compounds. Part XI. Synthesis of two acetamidoethyl porphyrins and their conversion into vinyl porphyrins and chlorins journal January 1967
The meso-reactivity of porphyrins and related compounds. Part IV. Introduction of oxygen functions journal January 1969
Cation-radicals: tris-(p-bromophenyl)amminium perchlorate and hexachloroantimonate journal January 1969
944. Conjugated macrocylces. Part XXII. Tetrazaporphin and its metallic derivatives journal January 1952
Discoveries among conjugated macrocyclic compounds journal January 1953
Chlorophyll and related substances. Part I. The synthesis of chlorin journal January 1955
328. Chlorophyll and related substances. Part III. The synthesis of octamethylchlorin journal January 1956
142. Chlorophyll and related compounds. Part VI. The synthesis of octaethylchlorin journal January 1957
161. Synthesis of mesotetramethychlorin journal January 1957
N-methylation and electrophilic substitution reactions of octa-alkyl-porphins, octaethylchlorin, and metalloporphins journal January 1972
The meso-reactivity of porphyrins and related compounds. Part VII. Benzoyloxylation of phenylpyrroles and of octaethylporphyrin journal January 1976
Some reactions of meso-formyloctaethylporhyrin journal January 1978
Wittig condensation products from nickel meso-formyl-octaethyl-porphyrin and -aetioporphyrin I and some cyclisation reactions journal January 1978
Syntheses of chlorins from unsymmetrically substituted iron porphyrins journal January 1988
Long wavelength photosensitizers related to chlorins and bacteriochlorins for use in photodynamic therapy journal January 1992
Benzoporphyrin derivatives: synthesis, structure and preliminary biological activity journal January 1994
Reaction of metallo-2-nitro-5,10,15,20-tetraphenylporphyrins with oxyanions. Temperature-dependent competition between nucleophilic addition and single-electron transfer processes journal January 1996
Preparation and spectroscopic properties of pure tetrabenzoporphyrins journal January 1981
Hydroporphyrins of the meso-tetra(hydroxyphenyl)porphyrin series as tumour photosensitizers journal July 1989
Efficient One-Pot Regioselective Synthesis of 2,3-Dibromo-5,10,15,20-tetra­arylporphyrins from 5,10,15,20-Tetraarylchlorins journal September 2009
Diels-Alder Reaction of Ni(II) β-Vinyl- meso -tetraphenylporphyrin; A General Method for Synthesis of Functionalized Porphyrins journal February 2000
Porphyrins in 1,3-Dipolar Cycloaddition Reactions: Synthesis of a Novel Pyrazoline-fused Chlorin and a Pyrazole-fused Porphyrin journal January 2002
Porphyrins in 1,3-Dipolar Cycloadditions with Sugar Azomethine Ylides. Synthesis of Pyrrolidinoporphyrin Glycoconjugates journal January 2005
Porphyrins as Dipolarophiles in 1,3-Dipolar Cycloaddition Reactions with Nitrile Oxide journal March 2005
Synthesis of Novel Isoxazole-Fused Chlorins and Bacteriochlorins via 1,3-Dipolar Cycloaddition Reactions of Nitrile Oxides with Porphyrins journal January 2005
A Facile Synthesis of 2-Diazo-3-oxochlorins by Lewis Acid Activation: Selective Modification of π-Electron Conjugated Macrocycles journal September 2006
Efficient Silver-Mediated Acetalation of β,β′-Functionalized Chlorins journal June 2008
Chemistry of meso-Dimethylaminopropenyl- porphyrins and -bisporphyrins: the Synthesis of Australochlorin, a Benzochlorin Isomer. journal January 1997
Porphyrins. VII. The synthesis of porphyrins by the Rothemund reaction journal January 1964
The chemistry of pyrrolic compounds. VI. Chlorins and related compounds journal January 1967
Chemistry of pyrrolic compounds. XXVII. Some aspects of the mass spectra and chemistry of meso-substituted porphyrins journal January 1974
The chemistry of pyrrolic compounds. LIV. The chemistry of rhodins, verdins and related compounds journal January 1984
Purpurins Bearing Functionality at the 6,16-meso-Positions: Synthesis From 5,15-Disubstituted meso-[β-(Methoxycarbonyl)vinyl]porphyrins journal January 1990
Synthesis of Chlorin-Fused Monospirooxindolopyrrolidines Through a Facile [3 + 2]-Cycloaddition of Azomethine Ylides journal July 2010
Synthesis and characterization of soluble seco -porphyrazines with bulky substituents journal July 2009
Spectra of Porphyrins and Chlorophyll journal July 1944
On the Chromophores of Porphyrin Systems journal October 1973
Photooxidation and Singlet Oxygen Sensitization by Protoporphyrin ix and its Photooxidation Products journal October 1982
Verdins: new Photosensitizers for Photodynamic Therapy journal September 1987
OBSERVATIONS ON THE SYNTHESIS AND in vivo PHOTODYNAMIC ACTIVITY OF SOME BENZOCHLORINS journal January 1992
AGGREGATION OF 2,3-DIHYDROXY-ETIOCHLORIN I. AN AMPHIPHILIC MODEL COMPOUND FOR PHOTODYNAMIC THERAPY AND GREEN HEME d journal November 1993
Determination of Stereochemistry of Bacteriochlorophyll gF and 81-Hydroxy-chlorophyll aF from Heliobacterium modesticaldum¶ journal May 2005
Stability of Tin Etiopurpurin¶ journal January 2005
PhotochemCAD 2: A Refined Program with Accompanying Spectral Databases for Photochemical Calculations¶ journal January 2005
Effects of Substituents on Synthetic Analogs of Chlorophylls. Part 1: Synthesis, Vibrational Properties and Excited-state Decay Characteristics journal September 2007
Effects of Substituents on Synthetic Analogs of Chlorophylls. Part 2: Redox Properties, Optical Spectra and Electronic Structure journal September 2007
Temoporfin (Foscan®, 5,10,15,20-Tetra(m-hydroxyphenyl)chlorin)-A Second-generation Photosensitizer†,‡: Photochemistry and Photobiology journal September 2011
Effects of Substituents on Synthetic Analogs of Chlorophylls. Part 3: The Distinctive Impact of Auxochromes at the 7- versus 3-Positions journal February 2012
Photophysics of Glycosylated Derivatives of a Chlorin, Isobacteriochlorin and Bacteriochlorin for Photodynamic Theragnostics: Discovery of a Two-photon-absorbing Photosensitizer journal November 2013
Effects of Substituents on Synthetic Analogs of Chlorophylls. Part 4: How Formyl Group Location Dictates the Spectral Properties of Chlorophylls b , d and f journal January 2015
Chlorin-type photosensitizers derived from vinyl porphyrins conference January 1995
Cyanopurpurins: synthesis from meso-(2-cyanovinyl)porphyrins conference April 1996
A Red-Shifted Chlorophyll: Fig. 1 journal August 2010
Primary Production of the Biosphere: Integrating Terrestrial and Oceanic Components journal July 1998
The fluorescence and electronic structure of phenyl-substituted tetraazachlorin molecules journal November 2014
Effect of pyridine on the reaction of “spanned” zinc porphyrin with organic peroxides journal July 2007
Synthesis and spectral characteristics of (tetrabenzoporphyrinato)chloromanganese(III) journal February 2010
Modern aspects of the Chemistry of protoporphyrin IX journal January 2007
Porphyrins and their derivatives: XXV. Reaction of 2-formyl-5,10,15,20-tetraphenylporphyrin with diazomethane journal July 2008
Porphyrins and their derivatives: XXVI. Synthesis and properties of 2-(3-butenyl)-5,10,15,20-tetraphenylporphyrin journal September 2010
The preparation of porphyrin S-411 (dehydrocoproporphyrin) and harderoporphyrin from protoporphyrin IX journal March 1981
Evaluation of tetraphenyl-2,3-dihydroxychlorins as potential photosensitizers journal February 2002
Porphyrins with fused exocyclic rings journal January 2004
The chemistry of porphyrazines: an overview journal September 2004
A short route to chlorin-α-diones journal June 2005
Imine-substituted dipyrromethanes in the synthesis of porphyrins bearing one or two meso substituents journal August 2005
Molecular structure and spectroscopic properties of octaethylbenzochloracene, the porphycene analog of a benzochlorin journal December 2005
Partially oxidized porphyrazines journal July 2006
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Photodynamic therapy with glycoconjugated chlorin photosensitizer journal May 2013
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Recent progress in chlorophyll and porphyrin chemistry journal January 1968
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Nomenclature of tetrapyrroles (Recommendations 1986) journal January 1987
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The global distribution of net primary production: resolving the paradox journal August 2009
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Microwave-Assisted Synthesis and Reactivity of Porphyrins journal April 2014
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Figures / Tables (200)

Scheme 1(p. 2)figure Scheme 1
Scheme 2(p. 3)figure Scheme 2
Scheme 3(p. 4)figure Scheme 3
Scheme 4(p. 5)figure Scheme 4
Scheme 5(p. 6)figure Scheme 5
Scheme 6(p. 6)figure Scheme 6
Scheme 7(p. 6)figure Scheme 7
Scheme 10(p. 7)figure Scheme 10
Scheme 8(p. 7)figure Scheme 8
Scheme 9(p. 7)figure Scheme 9
Scheme 11(p. 8)figure Scheme 11
Figure 1(p. 9)figure Figure 1
Figure 2(p. 10)figure Figure 2
Table 1(p. 11)table Table 1
Scheme 12(p. 12)figure Scheme 12
Table 2(p. 13)table Table 2
Scheme 13(p. 14)figure Scheme 13
Scheme 14(p. 15)figure Scheme 14
Scheme 15(p. 15)figure Scheme 15
Scheme 16(p. 16)figure Scheme 16
Scheme 17(p. 17)figure Scheme 17
Table 3(p. 18)table Table 3
Table 3 (Continued)(p. 19)table Table 3 (Continued)
Table 4(p. 20)table Table 4
Table 5(p. 21)table Table 5
Table 6(p. 22)table Table 6
Scheme 18(p. 23)figure Scheme 18
Table 7(p. 23)table Table 7
Scheme 19(p. 24)figure Scheme 19
Scheme 20(p. 24)figure Scheme 20
Scheme 21(p. 24)figure Scheme 21
Scheme 22(p. 25)figure Scheme 22
Scheme 23(p. 25)figure Scheme 23
Scheme 24(p. 26)figure Scheme 24
Table 8(p. 26)table Table 8
Scheme 25(p. 27)figure Scheme 25
Scheme 26(p. 28)figure Scheme 26
Scheme 27(p. 28)figure Scheme 27
Scheme 28(p. 29)figure Scheme 28
Scheme 29(p. 30)figure Scheme 29
Scheme 30(p. 31)figure Scheme 30
Figure 3(p. 32)figure Figure 3
Scheme 31(p. 32)figure Scheme 31
Scheme 32(p. 32)figure Scheme 32
Scheme 33(p. 33)figure Scheme 33
Scheme 34(p. 33)figure Scheme 34
Table 9(p. 34)table Table 9
Table 10(p. 35)table Table 10
Table 11(p. 35)table Table 11
Table 12(p. 36)table Table 12
Table 13(p. 37)table Table 13
Scheme 35(p. 38)figure Scheme 35
Table 13 (Continued)(p. 38)table Table 13 (Continued)
Scheme 36(p. 39)figure Scheme 36
Scheme 37(p. 40)figure Scheme 37
Scheme 38(p. 40)figure Scheme 38
Scheme 39(p. 40)figure Scheme 39
Scheme 40(p. 41)figure Scheme 40
Scheme 41(p. 41)figure Scheme 41
Scheme 42(p. 41)figure Scheme 42
Scheme 43(p. 42)figure Scheme 43
Scheme 44(p. 42)figure Scheme 44
Scheme 45(p. 42)figure Scheme 45
Scheme 46(p. 43)figure Scheme 46
Scheme 47(p. 44)figure Scheme 47
Scheme 48(p. 45)figure Scheme 48
Scheme 49(p. 45)figure Scheme 49
Scheme 50(p. 46)figure Scheme 50
Scheme 51(p. 46)figure Scheme 51
Scheme 52(p. 47)figure Scheme 52
Scheme 53(p. 47)figure Scheme 53
Scheme 54(p. 48)figure Scheme 54
Scheme 55(p. 49)figure Scheme 55
Scheme 56(p. 50)figure Scheme 56
Scheme 57(p. 50)figure Scheme 57
Figure 4(p. 51)figure Figure 4
Scheme 58(p. 51)figure Scheme 58
Scheme 59(p. 51)figure Scheme 59
Figure 5(p. 52)figure Figure 5
Scheme 60(p. 52)figure Scheme 60
Scheme 61(p. 52)figure Scheme 61
Figure 6(p. 53)figure Figure 6
Scheme 62(p. 53)figure Scheme 62
Figure 7(p. 54)figure Figure 7
Scheme 63(p. 54)figure Scheme 63
Figure 8(p. 55)figure Figure 8
Scheme 64(p. 55)figure Scheme 64
Scheme 65(p. 56)figure Scheme 65
Figure 10(p. 57)figure Figure 10
Figure 9(p. 57)figure Figure 9
Scheme 66(p. 57)figure Scheme 66
Figure 11(p. 58)figure Figure 11
Table 14(p. 58)table Table 14
Sccheme 68(p. 59)figure Sccheme 68
Scheme 67(p. 59)figure Scheme 67
Figure 12(p. 60)figure Figure 12
Scheme 69(p. 60)figure Scheme 69
Figure 13(p. 61)figure Figure 13
Scheme 70(p. 61)figure Scheme 70
Scheme 71(p. 61)figure Scheme 71
Scheme 72(p. 62)figure Scheme 72
Scheme 73(p. 62)figure Scheme 73
Figure 14(p. 63)figure Figure 14
Figure 15(p. 63)figure Figure 15
Scheme 74(p. 63)figure Scheme 74
Scheme 75(p. 64)figure Scheme 75
Scheme 76(p. 64)figure Scheme 76
Scheme 77(p. 65)figure Scheme 77
Table 15(p. 65)table Table 15
Scheme 78(p. 66)figure Scheme 78
Scheme 79(p. 66)figure Scheme 79
Scheme 80(p. 67)figure Scheme 80
Figure 16(p. 68)figure Figure 16
Scheme 81(p. 68)figure Scheme 81
Scheme 82(p. 69)figure Scheme 82
Scheme 83(p. 69)figure Scheme 83
Figure 17(p. 70)figure Figure 17
Figure 18(p. 70)figure Figure 18
Scheme 84(p. 70)figure Scheme 84
Figure 19(p. 71)figure Figure 19
Scheme 85(p. 71)figure Scheme 85
Scheme 86(p. 71)figure Scheme 86
Figure 20(p. 72)figure Figure 20
Figure 21(p. 72)figure Figure 21
Scheme 87(p. 72)figure Scheme 87
Scheme 88(p. 72)figure Scheme 88
Figure 22(p. 73)figure Figure 22
Scheme 89(p. 73)figure Scheme 89
Scheme 90(p. 73)figure Scheme 90
Figure 23(p. 74)figure Figure 23
Scheme 91(p. 74)figure Scheme 91
Scheme 92(p. 74)figure Scheme 92
Figure 24(p. 75)figure Figure 24
Figure 25(p. 75)figure Figure 25
Scheme 93(p. 75)figure Scheme 93
Scheme 94(p. 75)figure Scheme 94
Scheme 95(p. 75)figure Scheme 95
Scheme 96(p. 76)figure Scheme 96
Scheme 97(p. 76)figure Scheme 97
Figure 26(p. 77)figure Figure 26
Scheme 98(p. 77)figure Scheme 98
Scheme 100(p. 78)figure Scheme 100
Scheme 99(p. 78)figure Scheme 99
Figure 27(p. 79)figure Figure 27
Scheme 101(p. 79)figure Scheme 101
Scheme 102(p. 79)figure Scheme 102
Figure 28(p. 80)figure Figure 28
Scheme 103(p. 80)figure Scheme 103
Scheme 104(p. 81)figure Scheme 104
Scheme 105(p. 81)figure Scheme 105
Scheme 106(p. 82)figure Scheme 106
Scheme 107(p. 82)figure Scheme 107
Scheme 108(p. 83)figure Scheme 108
Scheme 109(p. 84)figure Scheme 109
Scheme 110(p. 84)figure Scheme 110
Figure 29(p. 85)figure Figure 29
Figure 30(p. 85)figure Figure 30
Scheme 111(p. 85)figure Scheme 111
Scheme 112(p. 86)figure Scheme 112
Scheme 113(p. 86)figure Scheme 113
Scheme 114(p. 87)figure Scheme 114
Scheme 115(p. 87)figure Scheme 115
Figure 31(p. 88)figure Figure 31
Scheme 116(p. 88)figure Scheme 116
Scheme 117(p. 89)figure Scheme 117
Scheme 118(p. 89)figure Scheme 118
Figure 32(p. 90)figure Figure 32
Scheme 119(p. 90)figure Scheme 119
Scheme 120(p. 91)figure Scheme 120
Figure 33(p. 92)figure Figure 33
Figure 34(p. 92)figure Figure 34
Scheme 121(p. 92)figure Scheme 121
Scheme 122(p. 93)figure Scheme 122
Scheme 123(p. 93)figure Scheme 123
Figure 35(p. 94)figure Figure 35
Scheme 124(p. 94)figure Scheme 124
Figure 36(p. 95)figure Figure 36
Scheme 125(p. 95)figure Scheme 125
Table 16(p. 95)table Table 16
Table 17(p. 95)table Table 17
Figure 37(p. 96)figure Figure 37
Scheme 126(p. 96)figure Scheme 126
Table 18(p. 96)table Table 18
Figure 38(p. 97)figure Figure 38
Scheme 127(p. 97)figure Scheme 127
Scheme 128(p. 98)figure Scheme 128
Scheme 129(p. 98)figure Scheme 129
Scheme 130(p. 99)figure Scheme 130
Scheme 131(p. 100)figure Scheme 131
Scheme 132(p. 100)figure Scheme 132
Scheme 133(p. 100)figure Scheme 133
Figure 39(p. 101)figure Figure 39
Scheme 134(p. 101)figure Scheme 134
Scheme 135(p. 101)figure Scheme 135
Scheme 136(p. 102)figure Scheme 136
Table 19(p. 102)table Table 19
Figure 40(p. 103)figure Figure 40
Scheme 137(p. 103)figure Scheme 137
Scheme 138(p. 103)figure Scheme 138
Scheme 139(p. 104)figure Scheme 139

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Absorption spectroscopy
Chemistry
Cyclization
Mixtures
Molecular structure
Pyrroles