@article {32775,
	title = {Iron Porphyrins Embedded into a Supramolecular Porous Organic Cage for Electrochemical CO2 Reduction in Water},
	journal = {Angewandte Chemie International Edition},
	volume = {57},
	year = {2018},
	pages = {9684-9688},
	abstract = {<p>Abstract A porous organic cage composed of six iron tetraphenylporphyrins was used as a supramolecular catalyst for electrochemical CO2-to-CO conversion. This strategy enhances active site exposure and substrate diffusion relative to the monomeric catalyst, resulting in CO generation with near-quantitative Faradaic efficiency in pH 7.3 water, with activities reaching 55\&thinsp;250 turnovers. These results provide a starting point for the design of supramolecular catalysts that can exploit the properties of the surrounding matrix yet retain the tunability of the original molecular unit.</p>},
	keywords = {CO2 reduction, ELECTROCHEMISTRY, porous organic cages, porphyrins, supramolecular chemistry},
	doi = {10.1002/anie.201803873},
	url = {https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201803873},
	author = {Smith, Peter T. and Benke, Bahiru Punja and Cao, Zhi and Kim, Younghoon and Nichols, Eva M. and Kim, Kimoon and Chang, Christopher J.}
}
@article {2601,
	title = {Facile synthesis of dicyanovinyl-di(meso-aryl)dipyrromethenes via a dipyrromethene-DDQ adduct},
	journal = {Organic \& Biomolecular Chemistry},
	volume = {7},
	number = {10},
	year = {2009},
	note = {ISI Document Delivery No.: 442UHTimes Cited: 1Cited Reference Count: 16Shin, Ji-Young Patrick, Brian O. Dolphin, David},
	pages = {2032-2035},
	type = {Article},
	abstract = {The dicyano-substituted vinyl dipyrromethene 4 and compound 5 are near-planar and were prepared from a simple meso-aryl dipyrromethane via the DDQ adduct 3; the unique structures of 3, 4 and 5 were confirmed by X-ray diffraction analysis.},
	keywords = {CORROLES, OXIDATION, porphyrins, PYRROLE},
	isbn = {1477-0520},
	url = {<Go to ISI>://000265865600005},
	author = {Shin, J. Y. and Patrick, B. O. and Dolphin, D.}
}
@article {2599,
	title = {Linear fully conjugated meso-aryl pentapyrrins},
	journal = {Tetrahedron Letters},
	volume = {50},
	number = {49},
	year = {2009},
	note = {ISI Document Delivery No.: 517HDTimes Cited: 0Cited Reference Count: 34Shin, Ji-Young Hepperle, Steven S. Dolphin, David},
	month = {Dec},
	pages = {6909-6912},
	type = {Article},
	abstract = {A meso-2,6-dichlorophenyl pentapyrrin was prepared using a modified method for dipyrrane synthesis followed by simple DDQ oxidation. The fully conjugated structures formed via redox inter-conversions were studied using crystallographic as well as observed and calculated spectral data. (C) 2009 Elsevier Ltd. All rights reserved.},
	keywords = {ANISOTROPIC DIELECTRICS, AROMATICITY, BASIS-SET, DENSITY-FUNCTIONAL THEORY, EXPANDED, IMPLEMENTATION, macrocycles, MESOSUBSTITUTED DIPYRROMETHANES, MOLECULAR-ORBITAL METHODS, porphyrins, TRIPYRRANE},
	isbn = {0040-4039},
	url = {<Go to ISI>://000271603000047},
	author = {Shin, J. Y. and Hepperle, S. S. and Dolphin, D.}
}
@article {2617,
	title = {Observation of coexistence of 1D and 2D nanostructures in cobalt dipyrromethene trimer complexes adsorbed on a graphite surface},
	journal = {Applied Surface Science},
	volume = {256},
	number = {4},
	year = {2009},
	note = {ISI Document Delivery No.: 527BXTimes Cited: 0Cited Reference Count: 24Son, S. B. Lee, S. J. Hahn, J. R. Ma, L. Shin, J-Y. Dolphin, D.4th Vacuum and Surface Science Conference of Asia and AustraliaOCT 28-31, 2008Matsue City, JAPAN},
	month = {Nov},
	pages = {1176-1179},
	type = {Proceedings Paper},
	abstract = {We report the direct observation of 1D and 2D nanostructures of cobalt dipyrromethene trimer complexes adsorbed on a highly oriented pyrolytic graphite surface using scanning tunneling microscopy (STM). STM images showed two types of ordered structures coexisting on the surface: long 1D molecular chains isolated on the terraces, and 2D hexagonal patterns confined by a 1D chain and/or a graphite step edge. These 1D and 2D structures are attributed to {\textquoteright}edge-on{\textquoteright} and {\textquoteright}face-on{\textquoteright} complex alignments on the surface, respectively. In both configurations, substrate-mediated molecule-molecule interactions may play a significant role in stabilizing the nanostructures. (C) 2009 Elsevier B. V. All rights reserved.},
	keywords = {CHEMISTRY, dipyrromethene, Graphite, MANIPULATION, microscopy, MONOLAYER, PHTHALOCYANINES, PORPHYRIN, porphyrins, SCANNING TUNNELING MICROSCOPY, STM, Supramolecules, VACANCY},
	isbn = {0169-4332},
	url = {<Go to ISI>://000272342300062},
	author = {Son, S. B. and Lee, S. J. and Hahn, J. R. and Ma, L. and Shin, J. Y. and Dolphin, D.}
}
@article {2507,
	title = {Regioselective Reduction of 2,4-Diacylpyrroles and the Synthesis of a 2,4-Divinylpyrrole},
	journal = {European Journal of Organic Chemistry},
	number = {21},
	year = {2009},
	note = {ISI Document Delivery No.: 478ASTimes Cited: 0Cited Reference Count: 18Lin, Yan Dolphin, David},
	month = {Jul},
	pages = {3562-3566},
	type = {Article},
	abstract = {Reduction of 2,4-diacylpyrroles followed by dehydration to prepare the divinylpyrroles has been studied. The N-phenylsulfonyl group exhibited directing ability at the 4-position during the reduction of 2,4-diacylpyrrole and complete regioselectivity was achieved for formations of the 2- and 4-carbinols; several new derivatives, including 2,4-divinylpyrrole, have been prepared. ((C) Wiley-VCH Verlag GmbH \& Co. KGaA, 69451 Weinheim, Germany, 2009)},
	keywords = {DERIVATIVES, N Heterocycles, porphyrins, PYRROLES, QUARARIBEA METABOLITES, REDUCTION, regioselectivity, SUBSTITUENTS},
	isbn = {1434-193X},
	url = {<Go to ISI>://000268560700010},
	author = {Lin, Y. and Dolphin, D.}
}
@article {1067,
	title = {Preparation of [meso-tetraphenylchlorophinato]nickel(II) by stepwise deformylation of [meso-tetraphenyl-2,3-diformyl-secochlorinato]nickel(II): conformational consequences of breaking the structural integrity of nickel porphyrins},
	journal = {Inorganica Chimica Acta},
	volume = {358},
	number = {10},
	year = {2005},
	note = {ISI Document Delivery No.: 941PBTimes Cited: 10Cited Reference Count: 66},
	month = {Jun},
	pages = {2943-2953},
	type = {Article},
	abstract = {The stepwise, Wilkinson{\textquoteright}s catalyst-induced decarbonylation of [meso-tetraphenyl-2,3-diformylsecochlorinato]Ni(II) (4) to produce the monoformylated pigment [meso-tetraphenyl-2-formylsecochlorinato] (5) and [meso-tetrapheiiylchlorophinato]Ni(II) (6) is described. Thus, we have shown how to degrade one pyrrolic unit of the starting material, [meso-tetraphetiylporphyrinato]Ni(II) (2) in three steps to an aldimine linkage. The conformational changes of the porphyrinic macrocycle during the course of this degradation, as determined by comparison of the X-ray crystal structures of the compounds, are discussed. A comparative study delineates the UV-Vis spectroscopical consequences. In addition, the chemical reactivity of [meso-tetraphenylchlorophinato]Ni(II) (6) suggests the existence of an azepine-derived pyrrole-modified porphyrins (11, 12). (c) 2004 Elsevier B.V. All rights reserved.},
	keywords = {CHEMISTRY, CHIRALITY-MEMORY MOLECULE, CHLORIN, CHLOROPHIN, chlorophins, COMPLEXES, ELECTRONIC-SPECTRA, macrocycle, METHYLCOENZYME-M REDUCTASE, nickel(II) porphyrin conformations ruffling, porphyrins, secochlorins, SYSTEM, TUNICATE TRIDIDEMNUM-SOLIDUM, Wilkinson{\textquoteright}s catalyst},
	isbn = {0020-1693},
	url = {<Go to ISI>://000230225600013},
	author = {Bruckner, C. and Hyland, M. A. and Sternberg, E. D. and Macalpine, J. K. and Rettig, S. J. and Patrick, B. O. and Dolphin, D.}
}
@article {1230,
	title = {Separation of porphyrin-based photosensitizer isomers by laser-induced fluorescence capillary electrophoresis},
	journal = {Electrophoresis},
	volume = {26},
	number = {20},
	year = {2005},
	note = {ISI Document Delivery No.: 982VMTimes Cited: 3Cited Reference Count: 43},
	month = {Oct},
	pages = {3861-3868},
	type = {Article},
	abstract = {Methods for the separation of photosensitizer isomers, such as benzoporphyrin derivative monoacid, benzoporphyrin ethyl monoacid, 2-[1-hexyloxyethyl]-2-devinylpyropheophorbide-a, diethyleneglycol diester benzoporphyrin derivative, tin ethyl etiopurpurin, and phthalocyanine tetrasulfonate, have been systematically developed by CE. Detection was accomplished by UV absorption at 214 nm or by LIF with excitation at 442/488 nm and emission at 690 nm. The effects of three major experimental parameters of buffer types, organic solvents, and surfactant additives are described. The optimized separation conditions were determined so as to provide satisfactory separation efficiency and analysis time. The methods are shown to be suitable for the separation and determination of porphyrin and phthalocyanines regioisomers, diastereoisomers, and enantiomers.},
	keywords = {chiral additives, CHLORIN, DERIVATIVES, EFFICACY, ENANTIOMERS, FLUORESCENCE DETECTION, FRACTION, LIGHT, PANCREATIC-CANCER CELLS, PERFORMANCE LIQUID-CHROMATOGRAPHY, pharmacokinetics, PHOTODYNAMIC THERAPY, PHTHALOCYANINES, porphyrins, regioisomers},
	isbn = {0173-0835},
	url = {<Go to ISI>://000233189700008},
	author = {Peng, X. J. and Sternberg, E. and Dolphin, D.}
}
@article {1116,
	title = {Synthesis, structure, and computational studies of soluble conjugated multidentate macrocycles},
	journal = {J. Org. Chem.},
	volume = {70},
	number = {20},
	year = {2005},
	note = {ISI Document Delivery No.: 968MOTimes Cited: 47Cited Reference Count: 67},
	month = {Sep},
	pages = {7936-7946},
	type = {Article},
	abstract = {<p>Conjugated, shape-persistent macrocycles based on [3 + 3] Schiff-base condensation are of interest for supramolecular materials. In an effort to develop new discotic liquid crystals based on these compounds, a series of macrocycles with peripheral alkoxy groups of varying length have been prepared. The synthesis and mechanism of formation have been probed by isolation of oligomeric intermediates. A single-crystal X-ray diffraction study of one macrocycle revealed a nonplanar, strongly hydrogen-bonded structure. To our surprise, even with very long substituents, the macrocycles were not liquid crystalline. This has been rationalized by ab initio calculations that indicate the macrocycles are undergoing rotation of the dibydroxydiiminobenzene rings that may not allow a stable discotic liquid crystalline phase. These results provide new insight into the formation and properties of these large macrocycles and may provide guidance to developing stable liquid crystalline materials in the future.</p>},
	keywords = {CHEMISTRY, CRYSTAL-STRUCTURE, cyclodextrin, LIGANDS, LIQUID-CRYSTAL, METAL-COMPLEXES, porphyrins, RECEPTORS, SCHIFF-BASE MACROCYCLES, SHAPE-PERSISTENT MACROCYCLES, supramolecular},
	isbn = {0022-3263},
	url = {<Go to ISI>://000232166800015},
	author = {Gallant, A. J. and J. K.-H. Hui and Zahariev, F. E. and Y. A. Wang* and M. J. MacLachlan*}
}
@article {753,
	title = {Synthesis of the hemin of beta-tetrakis(trifluoromethyl)-meso-tetraphenylporphyrin and its evaluation as a P-450 mimic},
	journal = {Inorganica Chimica Acta},
	volume = {346},
	year = {2003},
	note = {ISI Document Delivery No.: 660EJTimes Cited: 4Cited Reference Count: 24},
	month = {Mar},
	pages = {261-264},
	type = {Article},
	abstract = {The hemin of beta-tetrakis(trifluoromethyl)-meso-tetraphenylporphyrin has been synthesized. Conventional methods for iron insertion failed; iron in low oxidation states (0 or II) brought about reduction of the macrocycle and Fe(III) failed to insert. Thus, insertion of iron into the macrocycle required the formation of the lithium complex, from lithium bis(trimethylsilyl)amide, followed by ferrous chloride. The novel hemin was tested as a catalyst for oxidations of cyclohexane and cyclohexene using iodosylbenzene as an oxidant and was found to be ineffective. (C) 2002 Elsevier Science B.V. All rights reserved.},
	keywords = {CATALYSIS, CATALYSTS, cytochrome P-450, ELECTROCHEMISTRY, METALLOPORPHYRINS, OXIDATION, PORPHYRIN, porphyrins, POSITIONS, POTENTIALS},
	isbn = {0020-1693},
	url = {<Go to ISI>://000181820600033},
	author = {Terazono, Y. and Dolphin, D.}
}
@article {376,
	title = {Carbonyl ylide 1,3-dipolar cycloadditions with porphyrins},
	journal = {Tetrahedron Letters},
	volume = {43},
	number = {40},
	year = {2002},
	note = {ISI Document Delivery No.: 594JVTimes Cited: 30Cited Reference Count: 10},
	month = {Sep},
	pages = {7281-7283},
	type = {Article},
	abstract = {Carbonyl ylides react with tetraarylporphyrins to afford the corresponding [3+2] tetrahydrofuran cycloaddition products in moderate yields. (C) 2002 Published by Elsevier Science Ltd.},
	keywords = {carbonyl ylide, chlorins, cycloadditions, porphyrins},
	isbn = {0040-4039},
	url = {<Go to ISI>://000178047100038},
	author = {Flemming, J. and Dolphin, D.}
}
@article {477,
	title = {Chiral separation of benzoporphyrin derivative mono- and diacids by laser induced fluorescence-capillary electrophoresis},
	journal = {Electrophoresis},
	volume = {23},
	number = {1},
	year = {2002},
	note = {ISI Document Delivery No.: 513ZATimes Cited: 9Cited Reference Count: 42},
	month = {Jan},
	pages = {93-101},
	type = {Article},
	abstract = {A method for the separation of benzoporphyrin derivative mono- and diacid (BPDMA, BPDDA) enantiomers; by laser induced fluorescence-capillary electrophoresis (LIF-CE) has been developed. By using 300 mm borate buffer, pH 9.2, 25 mm sodium cholate and 10\% acetronitrile as electrolyte, +10 kV electrokinetic sampling injection of 2 s and an applied +20 kV voltage across the ends of a 37 cm capillary (30 cm to the detector, 50 mum ID), all six BPD stereoisomers; were baseline-separated within 20 min. Formation constants, free electrophoretic and complexation mobilities with borate and cholate were determined based on dynamic complexation capillary electrophoresis theory. The BPD enantiomers can be quantitatively determined in the range of 10(-2)-10(-5) mg mL(-1). The correlation coefficients (r(2)) of the least-squares linear regression analysis of the BPD enantiomers are in the range of 0.9914-0.9997. Their limits of detection are 2.18-3.5 x 10(-3) mg mL(-1). The relative standard deviations for the separation were 2.90-4.64\% (n = 10). In comparison with high-performance liquid chromatography (HPLC), CE has better resolution and efficiency. This separation method was successfully applied to the BPD enantiomers obtained from a matrix of bovine serum and from liposomally formulated material as well as from studies with rat, dog and human microsomes.},
	keywords = {benzoporphyrin derivative mono- and diacids, BORATE COMPLEXATION, capillary electrophoresis, DYNAMIC COMPLEXATION MODEL, MIGRATION BEHAVIOR, PERFORMANCE LIQUID-CHROMATOGRAPHY, PHOTODYNAMIC THERAPY, PHOTOSENSITIZER, porphyrins, QUANTITATIVE DESCRIPTION, SYSTEM, TUMOR, ZONE ELECTROPHORESIS},
	isbn = {0173-0835},
	url = {<Go to ISI>://000173410100014},
	author = {Peng, X. J. and Sternberg, E. and Dolphin, D.}
}
@article {435,
	title = {Evaluation of tetraphenyl-2,3-dihydroxychlorins as potential photosensitizers},
	journal = {Journal of Porphyrins and Phthalocyanines},
	volume = {6},
	number = {2},
	year = {2002},
	note = {ISI Document Delivery No.: 595XYTimes Cited: 15Cited Reference Count: 33},
	pages = {146-155},
	type = {Article},
	abstract = {A series of beta,beta-dihydroxychlorins derived from meso-tetraphenylporphyrins (TPPs) have been synthesized. Their in vitro cytotoxicity has been measured and compared to BPDMA (verteporfin). Under the assay conditions BPDMA had an LD50 (lethal dose to kill 50\% of cells) value of 0.007 muM (5 ng/mL). The LD50 values for the TPP derivatives varied from 1.7 x 10(-2) to 9.9 muM depending upon the substituents and their position on the phenyl groups. One example of the dihydroxychlorin prepared from unsubstituted 5,15-diphenylporphyrin was examined and this exhibited an LD50 of 2.4 x 10(-3) muM! Copyright (C) 2002 Society of Porphyrins \& Phthalocyanines.},
	keywords = {AGGREGATION, BACTERIOCHLORINS, beta, beta-dihydroxychlorins, BIODISTRIBUTION, chlorins, cytotoxicity, DERIVATIVES, photodynamic, PHOTODYNAMIC THERAPY, PHOTOPHYSICAL PROPERTIES, PHOTOSENSITIZERS, porphyrins, PROTEIN-BINDING, SENSITIZERS, therapy, TUMOR PHOTOSENSITIZERS},
	isbn = {1088-4246},
	url = {<Go to ISI>://000178134600008},
	author = {Macalpine, J. K. and Boch, R. and Dolphin, D.}
}
@article {399,
	title = {Studies of a benzoporphyrin derivative with Pluronics},
	journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie},
	volume = {80},
	number = {10},
	year = {2002},
	note = {ISI Document Delivery No.: 623LCTimes Cited: 14Cited Reference Count: 22},
	month = {Oct},
	pages = {1321-1326},
	type = {Article},
	abstract = {The synthetic route for the benzoporphyrin derivatives produces two regioisomers in equimolar quantities (ring A and B isomers). A derivative of the A-ring product, BPD-MA (benzoporphyrin-derivative monoacid ring A, verteporfin), has recently been approved in North America and Europe for the treatment of age-related macular degeneration. The B-ring isomers, contrary to the A-ring isomers, exhibit high aggregation in many formulations, which results in inadequate drug delivery for clinical uses. To avoid aggregation, a non-ionic surfactant polymer such as a Pluronic - poly(ethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) - may be used as a formulation excipient. The triblock polymer investigated here is designated P123 (or poloxamer 403). When used to formulate a monoacid benzoporphyrin B-ring derivative (2), a critical micelle concentration of P123 in water occurred at approximately 0.015 to 0.03\%. The apparent pK(a) of compound 2 was dependent on its concentration in P123, and decreased as the molar ratio (P123:2) increased. High concentrations of P123 and neutral pH were found to be the best conditions to maintain the drug in its monomeric form. Kinetic studies suggest that the aggregate of 2 contains several molecules, and is formed by a catalyzed self-assembly process. Samples with 1 mg mL(-1) of drug, at pH = 7.4, and 4.8\% of Pluronic showed satisfactory capacity to load and keep monomers stable. This formulation has potential PDT applications.},
	keywords = {AGGREGATION, AQUEOUS-SOLUTIONS, block copolymers, BPD, COPOLYMERS, DYNAMICS, formulation, micelles, PHOTODYNAMIC THERAPY, photodynamic therapy (PDT), PHOTOSENSITIZERS, photosensitizing drug, Pluronic, poloxamers, porphyrins, SURFACTANTS, THERMODYNAMICS},
	isbn = {0008-4042},
	url = {<Go to ISI>://000179703700007},
	author = {Hioka, N. and Chowdhary, R. K. and Chansarkar, N. and Delmarre, D. and Sternberg, E. and Dolphin, D.}
}
@article {5046,
	title = {Aggregation studies of benzoporphyrin derivative},
	journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie},
	volume = {79},
	number = {5-6},
	year = {2001},
	note = {ISI Document Delivery No.: 456EVTimes Cited: 11Cited Reference Count: 33},
	month = {May},
	pages = {1068-1074},
	type = {Article},
	abstract = {The photophysical properties of a ring B benzoporphyrin derivative 1,3-diene dimethylester were investigated in solution (water-DMSO mixtures). At low proportions of water in DMSO, the diester obeys Beer{\textquoteright}s law at all pH values and ionic strengths investigated. For solvent systems containing more than 30\% water, the extent of deviation from Beer{\textquoteright}s law as a function of porphyrin concentration is attributed to formation of porphyrin dimers. Dimerization equilibrium constants (Kd) have been determined in different percentage of solvent mixtures, using absorption and fluorescence spectroscopies, and were found to exhibit a linear correlation between log (Kd) and the inverse of the dielectric constant (log (Kd) = 24.6 - 1060.4 x 1/epsilon (mix)). This equation permits the calculation of Kd in mixtures of water-DMSO.},
	keywords = {AGGREGATION, benzoporphyrin, BPD, DERIVATIVE, DIMERIZATION, FLUORESCENCE, PHOTODYNAMIC THERAPY, PHOTOSENSITIZERS, porphyrins, SPECTROSCOPY, therapy},
	isbn = {0008-4042},
	url = {<Go to ISI>://000170070900079},
	author = {Delmarre, D. and Hioka, N. and Boch, R. and Sternberg, E. and Dolphin, D.}
}
@article {4953,
	title = {Double-helical dinuclear bis(dipyrromethene) complexes formed by self-assembly},
	journal = {Journal of Organic Chemistry},
	volume = {65},
	number = {23},
	year = {2000},
	note = {ISI Document Delivery No.: 377BDTimes Cited: 55Cited Reference Count: 37},
	month = {Nov},
	pages = {7870-7877},
	type = {Article},
	abstract = {Bis(dipyrromethene) ligands linked by an alkyl spacer between beta and beta{\textquoteright} positions are shown to give helical dimers or monomers, dependent upon the length of the alkyl linker, upon complexation. Ligands consisting of methylene, ethylene, and propylene linkers -(CH2)(n)- (n = 1, 2, and 3) give helical dimers, while longer linking chains (n = 4, 5, or 6) give monomers or mixtures of dimers and monomers. X-ray crystal structures of the dimeric zinc complexes (n = 1, 2, and 3) reveal that the angles between dipyrromethene planes and the extent of helicity in the complexes differ as the length of the linker varies. The extent of helicity was assessed and found to be dependent upon the length and, specifically, the conformational preferences of the alkyl spacer unit. The presence of an ethylene linker gave complexes of greatest helicity. The use of a methylene spacer gave less helical structures upon complexation, while propylene spacers gave only slightly helical complexes. Our studies identify the crucial importance that the conformational preferences of the beta-beta{\textquoteright} alkyl spacer group plays in the coordination algorithm of self-assembly to form dipyrromethene based complexes.},
	keywords = {ARCHITECTURE, CU-I, LEAD(II) COMPLEXES, porphyrins, RAY CRYSTAL-STRUCTURE},
	isbn = {0022-3263},
	url = {<Go to ISI>://000165491300024},
	author = {Thompson, A. and Dolphin, D.}
}
@article {4929,
	title = {Regioselective halogenation and palladium-catalysed couplings on 5,15-diphenylporphyrin},
	journal = {Journal of Porphyrins and Phthalocyanines},
	volume = {4},
	number = {3},
	year = {2000},
	note = {ISI Document Delivery No.: 302BXTimes Cited: 53Cited Reference Count: 13},
	month = {Apr-May},
	pages = {228-232},
	type = {Article},
	abstract = {5,15-Diphenylporphyrin was regiospecifically halogenated in high yield to give 5-iodo-15-bromo-10.20-diphenylporphyrin, which was then subjected to Heck and Stille-type coupling reactions to form unsymmetrically substituted porphyrins. The regioselectivity of the iodination of diphenylporphyrins and subsequent formation of amphiphilic porphyrins via palladium-based methodology was also studied. The utility of this method for the synthesis of photodynamic sensitisers has been demonstrated on AR4-2J rat pancreatic carcinoma cells. Copyright (C) 2000 John Wiley \& Sons, Ltd.},
	keywords = {ALKYNYLATION, amphiphiles, CROSS-COUPLING, IODINATION, palladium, PHOTODYNAMIC THERAPY, porphyrins},
	isbn = {1088-4246},
	url = {<Go to ISI>://000086346000002},
	author = {Shanmugathasan, S. and Johnson, C. K. and Edwards, C. and Matthews, E. K. and Dolphin, D. and Boyle, R. W.}
}
@inbook {4485,
	title = {5-phenyldipyrromethane and 5,15-diphenylporphyrin},
	booktitle = {Organic Syntheses, Vol 76 - 1999},
	series = {Organic Syntheses},
	volume = {76},
	year = {1999},
	note = {ISI Document Delivery No.: BN52XTimes Cited: 27Cited Reference Count: 7Article605 3RD AVE, NEW YORK, NY 10016 USA},
	pages = {287-293},
	publisher = {John Wiley \& Sons Inc},
	organization = {John Wiley \& Sons Inc},
	address = {New York},
	keywords = {porphyrins},
	isbn = {0078-6209},
	url = {<Go to ISI>://000082119100029},
	author = {Boyle, R. W. and Bruckner, C. and Posakony, J. and James, Brian R. and Dolphin, D.}
}
@article {4610,
	title = {The metabolites of dietary chlorophylls},
	journal = {Phytochemistry},
	volume = {50},
	number = {2},
	year = {1999},
	note = {ISI Document Delivery No.: 160EBTimes Cited: 15Cited Reference Count: 70},
	month = {Jan},
	pages = {195-202},
	type = {Review},
	abstract = {Chlorophylls, the green pigments responsible for photosynthesis in plants, algae and bacteria, are also part of the daily diet of herbivorous feeders. Numerous metabolic derivatives of the major green pigment, chlorophyll-a, have been found in a wide variety of organisms during the last decade. Studies of these metabolites show that some are antioxidants or cellular signaling mediators in vivo. The metabolites of bacteriochlorophylls-c and d, recently found in the deep-sea dragon fish, Malacosteus niger, function as a visual photosensitizer, enabling the fish to seek their prey in {\textquoteright}the dark{\textquoteright}. Discovery of these metabolites as well as their interesting biological functions raises questions as to the roles of chlorophyll derivatives in the chemical ecology of herbivorous life forms. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.},
	keywords = {antioxidant, AUTOXIDATION, cell signaling, CHLORIN, CHLOROPHYLL, DERIVATIVES, DIET, ESTERS, MARINE ORGANISMS, METABOLISM, PHOTOSENSITIZER, PI-CATION RADICALS, porphyrins, PRODUCTS, RUDITAPES-PHILIPPINARUM, TUNICHLORIN},
	isbn = {0031-9422},
	url = {<Go to ISI>://000078216500001},
	author = {Ma, L. F. and Dolphin, D.}
}
@article {4631,
	title = {Stoichiometric O-2 oxidation of bis(thioether) (octaethylporphyrinato)ruthenium(II) complexes to the corresponding sulfoxide species in acidic media. Structural confirmation of S-bonded sulfoxides},
	journal = {Inorganic Chemistry},
	volume = {38},
	number = {24},
	year = {1999},
	note = {ISI Document Delivery No.: 262CATimes Cited: 7Cited Reference Count: 41},
	month = {Nov},
	pages = {5579-5587},
	type = {Article},
	abstract = {{Exposure to o(2) (or air) of a CH2Cl2, benzene, or toluene solution containing PhCO2H and Ru(OEP)(RR{\textquoteright}S)(2) (where OEP = the dianion of 2,3,7,8,12,13,17,1 8-octaethylporphyrin},
	keywords = {ACETONITRILE SOLUTION, CRYSTAL, ELECTRON-TRANSFER, LIGANDS, MOLECULAR-STRUCTURE, porphyrins, RUTHENIUM(II)},
	isbn = {0020-1669},
	url = {<Go to ISI>://000084047000016},
	author = {Pacheco, A. and James, Brian R. and Rettig, S. J.}
}
@article {3944,
	title = {Polyhaloporphyrins: Unusual ligands for metals and metal-catalyzed oxidations},
	journal = {Accounts of Chemical Research},
	volume = {30},
	number = {6},
	year = {1997},
	note = {ISI Document Delivery No.: XE058Times Cited: 283Cited Reference Count: 63},
	month = {Jun},
	pages = {251-259},
	type = {Review},
	keywords = {halogenated porphyrins, HYDROGEN-PEROXIDE, HYDROXYLATION, Iron(III), IRON-PORPHYRIN COMPLEXES, manganese porphyrins, METALLOPORPHYRINS, MODEL SYSTEMS, porphyrins, SATURATED-HYDROCARBONS, TERT-BUTYL HYDROPEROXIDE},
	isbn = {0001-4842},
	url = {<Go to ISI>://A1997XE05800004},
	author = {Dolphin, D. and Traylor, T. G. and Xie, L. Y.}
}
@article {3633,
	title = {Improved protocols for the synthesis and halogenation of sterically hindered metalloporphyrins},
	journal = {Synthesis-Stuttgart},
	number = {11},
	year = {1996},
	note = {ISI Document Delivery No.: VV383Times Cited: 31Cited Reference Count: 38},
	month = {Nov},
	pages = {1320-\&},
	type = {Article},
	abstract = {Improved procedures are described for the synthesis of meso-tetrakis(2,6-dichlorophenyl)porphyrin and for subsequent perhalogenation of the porphyrin ring.},
	keywords = {ACCESS, CATALYSTS, CATALYTIC OXYGENATION, EASY, EFFICIENT CATALYSTS, EPOXIDATION, halogenated porphyrins, HYDROXYLATION, metalloporphyrins halogenation, OXIDATION, OXIDATION REACTIONS, porphyrins, TETRAARYLPORPHYRINS, TETRAMESITYLPORPHYRIN, TETRAPHENYLPORPHYRINS},
	isbn = {0039-7881},
	url = {<Go to ISI>://A1996VV38300016},
	author = {Chorghade, M. S. and Dolphin, D. and Dupre, D. and Hill, D. R. and Lee, E. C. and Wijesekera, T. P.}
}
@article {3858,
	title = {Porphocyanines: Expanded aromatic tetrapyrrolic macrocycles},
	journal = {Journal of the American Chemical Society},
	volume = {118},
	number = {20},
	year = {1996},
	note = {ISI Document Delivery No.: UM416Times Cited: 18Cited Reference Count: 34},
	month = {May},
	pages = {4853-4859},
	type = {Article},
	abstract = {Porphocyanines are tetrapyrrolic macrocycles containing two dipyrromethene units linked together by two C=N-C bridges. The syntheses of 2,3,7,8,14,15,19,20-octaethylporphocyanine 5,17-diphenylporphocyanine, 2,3,7,8-tetraethyl-17-phenylporphocyanine and other meso-aryl and beta-alkyl, including a tetra-beta-propionate, derivatives and metal complexes are described. The physical and chemical properties of porphocyanines show them to be aromatic. The aromaticity is reflected in the large deshielding of the outer beta-protons and shielding of the inner pyrrolic protons in their NMR spectra. The optical spectra of these compounds exhibit Soret and Q bands similar to porphyrins but all significantly bathochromically shifted. The ability of porphocyanines to act as catalysts for the generation of singlet molecular oxygen was investigated using a cholesterol oxidation assay.},
	keywords = {COMPLEX, porphyrins},
	isbn = {0002-7863},
	url = {<Go to ISI>://A1996UM41600015},
	author = {Xie, L. Y. and Boyle, R. W. and Dolphin, D.}
}
@article {3262,
	title = {2,3-VIC-DIHYDROXY-MESO-TETRAPHENYLCHLORINS FROM THE OSMIUM-TETROXIDE OXIDATION OF MESO-TETRAPHENYLPORPHYRIN},
	journal = {Tetrahedron Letters},
	volume = {36},
	number = {19},
	year = {1995},
	note = {ISI Document Delivery No.: QY111Times Cited: 34Cited Reference Count: 25},
	month = {May},
	pages = {3295-3298},
	type = {Article},
	abstract = {meso-Tetraphenylporphyrins and meso-tetraphenylmetalloporphyrins were converted into stable 2,3-vic-dihydroxy-meso-tetraphenylchlorins and 2,3-vic-dihydroxy-meso-tetraphenylmetallochlorins by oxidation with stoichiometric amounts of OsO4 and subsequent reduction of the isolable osmate esters. The stable dihydroxychlorins were dehydrated under acid catalysis to yield 2-hydroxy-meso-tetraphenylporphyrins.},
	keywords = {BACTERIOCHLORINS, chlorins, EFFICIENT SYNTHESIS, PHOTODYNAMIC THERAPY, porphyrins, TUMOR PHOTOSENSITIZERS},
	isbn = {0040-4039},
	url = {<Go to ISI>://A1995QY11100002},
	author = {Bruckner, C. and Dolphin, D.}
}
@article {3017,
	title = {1993 SYNTEX-AWARD LECTURE - PHOTOMEDICINE AND PHOTODYNAMIC THERAPY},
	journal = {Canadian Journal of Chemistry-Revue Canadienne De Chimie},
	volume = {72},
	number = {4},
	year = {1994},
	note = {ISI Document Delivery No.: NN830Times Cited: 84Cited Reference Count: 47},
	month = {Apr},
	pages = {1005-1013},
	type = {Article},
	abstract = {Photodynamic therapy (PDT) involves the treatment of diseased tissue and cells using a photosensitizer and visible light. Such photomedical treatments have been known since the time of the ancient Egyptians but it was only just this year that this therapeutic modality was made available to modern medicine with the approval, in Canada, of Photofrin(R) for the treatment of bladder cancer. This paper reviews PDT with an emphasis on drug development, particulary for the second generation drugs, especially BPDMA (benzoporphyrin derivative-mono acid), which is now in human clinical trials.},
	keywords = {BENZOPORPHYRIN DERIVATIVES, CELLS, HEMATOPORPHYRIN, INACTIVATION, MICE, PHOTOSENSITIZATION, PLASMA-LIPOPROTEINS, porphyrins, PROTEIN DAMAGE, PROTOPORPHYRIN},
	isbn = {0008-4042},
	url = {<Go to ISI>://A1994NN83000001},
	author = {Dolphin, D.}
}
@article {2962,
	title = {ANOMALOUS DOUBLE CYCLIZATION REACTIONS OF BETA-FORMYLPORPHYRINS},
	journal = {Journal of Organic Chemistry},
	volume = {59},
	number = {26},
	year = {1994},
	note = {ISI Document Delivery No.: QA492Times Cited: 49Cited Reference Count: 23},
	month = {Dec},
	pages = {7976-7985},
	type = {Article},
	abstract = {Treatment of nickel(II) and copper(II) complexes of 2(beta)-formyl-meso-tetraphenylporphyrins with strong acid results in intramolecular cyclization involving the carbonyl carbon and the ortho-phenyl position leading to naphthoporphyrin derivatives. However, when electron-releasing groups are present at the m-phenyl positions, a second cyclization occurs involving the 3(beta) position and the ortho position of the adjacent phenyl ring to give an additional fused ring.},
	keywords = {DERIVATIVES, PHOTOSENSITIZERS, porphyrins},
	isbn = {0022-3263},
	url = {<Go to ISI>://A1994QA49200011},
	author = {Barloy, L. and Dolphin, D. and Dupre, D. and Wijesekera, T. P.}
}
@article {2766,
	title = {BIOMIMETIC DEGRADATION OF LIGNIN},
	journal = {Journal of Biotechnology},
	volume = {30},
	number = {1},
	year = {1993},
	note = {ISI Document Delivery No.: LP201Times Cited: 14Cited Reference Count: 37COLLOQUIUM ON LIGNIN BIODEGRADATION AND PRACTICAL UTILIZATIONJUN 27-30, 1990TRIESTE, ITALYINT CTR GENET ENGN \& BIOTECHNOL},
	month = {Jul},
	pages = {15-26},
	type = {Proceedings Paper},
	abstract = {The ligninolytic cultures of Phenarochaete chrysosporium produce two major groups of lignin degrading enzymes, the lignin peroxidase (Tien and Kirk, 1983) and the manganese-dependent peroxidase (Kuwahara et al., 1984). Both enzymes are hemeproteins and catalyze the oxidation of lignin model compounds by one-electron oxidations. The catalytic cycle of both enzymes involves the two-electron oxidation of iron(III) protoporphyrin IX, the prosthetic group of both enzymes, by hydrogen peroxide to give the highly reactive oxoiron(IV) protoporphyrin IX pi-cation radical, which returns to its resting state after two separate one-electron reductions by the substrates. The oxidation of simple metalloporphyrins can give similar highly oxidized species corresponding to the catalytic intermediates of the hemeprotein peroxidases. In the case of iron porphyrins (Groves et al., 1979; Chin et al., 1977) the oxidized intermediate is an oxoiron(IV) porphyrin cation radical and in the case of manganese porphyrins, the oxidized species is an oxomanganese(V) porphyrin (Groves et al., 1980). Shimada et al. (1977, 1984) have used commercially available metalloporphyrins as models of the lignin degrading enzymes. We have synthesized and used metalloporphyrins 1-4 (see Fig. 2) as biomimetic catalysts for lignin oxidation (Dolphin et al., 1987; Cui and Dolphin, 1989; Cui, 1990). The chloro substituents on the phenyl rings provide steric protection to increase the stability of the porphyrins (1-4) towards excess oxidants and the chlorines on the porphyrin periphery make 3 and 4 more powerful catalysts by increasing the redox potential at the metal centre.},
	keywords = {3, 4-DIMETHOXYBENZYL ALCOHOL, DEGRADING ENZYME, DIARYLPROPANE OXYGENASE, HEME-ENZYME, LIGNIN PEROXIDASE, METALLOPORPHYRIN, MN-DEPENDENT PEROXIDASE, MODEL-COMPOUND, ORGANIC MEDIA, PEROXIDASE, PHANEROCHAETE-CHRYSOSPORIUM, porphyrins, RING CLEAVAGE, WHITE ROT BASIDIOMYCETE},
	isbn = {0168-1656},
	url = {<Go to ISI>://A1993LP20100004},
	author = {Cui, F. T. and Wijesekera, T. and Dolphin, D. and Farrell, R. and Skerker, P.}
}
@article {7153,
	title = {A CONVENIENT SYNTHETIC ROUTE TO THE BACTERIOCHLORIN CHROMOPHORE},
	journal = {Tetrahedron Letters},
	volume = {32},
	number = {25},
	year = {1991},
	note = {ISI Document Delivery No.: FP135Times Cited: 21Cited Reference Count: 14},
	month = {Jun},
	pages = {2875-2878},
	type = {Article},
	abstract = {The reactions of an A,C-divinylporphyrin with activated dienophiles yield stable bis Diels-Alder adducts absorbing light at wavelengths above 735 nm. This provides a convenient general route to bacteriochlorin-like chromophores.},
	keywords = {DIELS-ALDER REACTIONS, porphyrins},
	isbn = {0040-4039},
	url = {<Go to ISI>://A1991FP13500009},
	author = {Yonhin, P. and Wijesekera, T. P. and Dolphin, D.}
}
@article {7102,
	title = {PHOTOSENSITIZING POTENCY OF STRUCTURAL ANALOGS OF BENZOPORPHYRIN DERIVATIVE (BPD) IN A MOUSE-TUMOR MODEL},
	journal = {British Journal of Cancer},
	volume = {63},
	number = {1},
	year = {1991},
	note = {ISI Document Delivery No.: ER853Times Cited: 85Cited Reference Count: 19},
	month = {Jan},
	pages = {87-93},
	type = {Article},
	abstract = {The in vivo characteristics of four analogues of benzoporphyrin derivative (BPD) have been investigated. Biodistribution data obtained in DBA/2J mice with BPD-MA (monoacid ring A analogue) which had been tritiated or internally labelled with C-14 showed that both labelled materials acted in an essentially identical manner during the period of study. Biodistribution and clearance studies showed that relative distribution in a variety of mouse tissues was similar for all BPD analogues. M1 tumour cells (rhabdomyosarcoma in DBA/2J mice) taken from tumours excised from animals treated 3 h earlier with BPD, and tested in vitro for photosensitivity provided evidence that significant levels of photosensitiser detected in tumour was both active and associated with tumour cells. The monoacid forms of BPD were found to be much more photodynamically active in this test that were the diacid analogues. The ability of the analogues to ablate tumours in mice by photodynamic therapy was also tested. Again, BPD-MA and BPD-MB proved to be measurably better than the diacid analogues. These findings are discussed in reference to structural and physical differences between the analogues.},
	keywords = {HEMATOPORPHYRIN, PHOTOFRIN-II, PHTHALOCYANINES, PLASMA-LIPOPROTEINS, porphyrins, TOXICITY},
	isbn = {0007-0920},
	url = {<Go to ISI>://A1991ER85300018},
	author = {Richter, A. M. and Waterfield, E. and Jain, A. K. and Allison, B. and Sternberg, E. D. and Dolphin, D. and Levy, J. G.}
}
