The Porphyrin Handbook. Phthalocyanines: Properties and Materials PDF
Preview The Porphyrin Handbook. Phthalocyanines: Properties and Materials
Volumes in This Set Volume 11 / Bioinorganic and Bioorganic Chemistry Volume 12 / The Iron and Cobalt Pigments: Biosynthesis, Structure, and Degradation Volume 13/Chlorophylls and Bilins:Biosynthesis, Synthesis, and Degradation Volume 14/Medical Aspects of Porphyrins Volume 15/Phthalocyanines: Synthesis Volume 16/Phthalocyanines: Spectroscopic and Electrochemical Characterization Volume 17/ Phthalocyanines: Properties and Materials Volume 18/Multiporphyrins, Multiphthalocyanines, and Arrays Volume 19/Applications of Phthalocyanines Volume 20/Phthalocyanines: Structural Characterization The Porphyrin Handbook Volume 17 / Phthalocyanines: Properties and Materials Editors Karl M. Kadish Department of Chemistry University of Houston Houston, Texas Kevin M. Smith Department of Chemistry Louisiana State University Baton Rouge, Louisiana Roger Guilard Faculte des Sciences Gabriel Universite de Bourgogne Dijon, France @ ACADEMIC PRESS An imprintofElsevier Science Amsterdam· Boston· London· New York· Oxford· Paris San Diego· San Francisco· Singapore· Sydney · Tokyo AcademicPress An imprint ofElsevier Science 525BStreet, Suite 1900 San Diego, California92101-4495 USA © 2003 Elsevier Science (USA) All rights reserved. This workisprotectedundercopyrightbyElsevier Science,andthefollowingtermsandconditionsapplytoitsuse: Photocopying Single photocopies of single chaptersmaybe madefor personaluse as allowedby nationalcopyrightlaws. Permissionof the Publisherandpaymentof a feeisrequiredfor all otherphotocopying, includingmultipleor systematiccopying, copyingfor advertisingOfpromotionalpurposes, resale, and allforms of documentdelivery. 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TransferredtoDigital Printing2011 Preface Volumes 1-10 of The Porphyrin Handbook were 'first solidations were taking place in the publishing sector, published in late 1999 and met with resounding and the new set of volumes would be published by international acclaim. After only two months on the Elsevier. shelves,our publisher, Academic Press,wasawardedthe Our sequel,in ten more volumes (11-20), builds upon 1999ChemistryawardbytheProfessionaland Scholarly the first published set of works by extending its Publishing Division of the American Association of authoritative treatise of the tetrapyrroles. We have Publishers, Inc.; this honor recognized The Porphyrin moved on from synthesis, chemistry;spectroscopy and Handbook as the "best chemistry book of the year." At applications of porphyrins to address, in depth, many that time we,the three editors, began receivingcallsand of the sub-fields not covered in the first treatise requests from our colleagues and our Academic Press (Volumes 1-10). To be sure, there were still some publisherto "expandthe work and fillin the gaps" soas loose ends, but we believe that our plan was fairly to assemble the best ever up-to-date compendium of comprehensive. New topics this time include biology every possible aspect of the field of porphyrins, other and medical implications of porphyrin systems, the tetrapyrroles, and related macrocycles. biosynthesis of porphyrins, chlorophylls and vitamin Shortly after publication of the first ten volumes of B12. Other areas covered include clinical and biochem The Porphyrin Handbook, the First International ical aspects of genetically transmitted or drug induced Conference on Porphyrins and Phthalocyanines diseases associated with errors in heme metabolism, as (ICPP-l) took place in Dijon, France (June 2000), wellas the transformation of hemes into bile pigments, hosted by one of the three editors of the Handbook. At the organic synthesis of bilins, recent work on phyto thatmajorinternationalevent,the SocietyofPorphyrins chrome and the pathways of degradation ofchlorophyll and Phthalocyanines (SPP) was created, and in early in senescent plants. In addition, Volumes 11-20 address 2002 our fledgling SPP took over publication of the every aspect of the synthesis, chemistry, structure and Journal ofPorphyrins and Phthalocyanines (JPP) from spectroscopy of phthalocyanines. John Wiley & Sons, with one of the three Handbook Our 61 chapters (coincidentally the same number of editors serving as Editor-in-Chief. At ICPP-2 in Kyoto, chapters as in the 1-10 set of volumes) are once again Japan (July 2002),it became abundantly clear that The written by internationally recognized experts and we Porphyrin Handbook, Volumes 1-10, was serving well were particularly gratified by two organizational our community of research scientists. This applied aspects; firstly, we received almost no rejections of our equally to our society (SPP) and journal (JPP), which requests for chapters, and secondly, almost all of our are incrementally enhancing the international visibility contractedauthorsprovideduswith chaptersinatimely of our field.Our new seriesof Handbook volumes (11 manner which, we believe, are as good in quality, or 20) and the continuation of our popular international even better, than those in the first ten volumes. Indeed, conference series (ICPP-3, to be held in New Orleans, once again we believe that our contributors have USA, in 2004) each in their own way will contribute produced research articles that will be dominant in further to the scientificenrichmentofthe porphyrin and their specificareas for another fifteen years. phthalocyanine research areas. Wesincerelyhope thatour readers willappreciatethis However, even before publication of Volumes 1-10, newtreatise asmuch as they liked our firstventure. The we were becoming aware of the great interest and tetrapyrrolefieldcontinuesto expandinto newareas and excitement about the treatise from our real audience, togathernewrecruits and converts. Wethinkthathaving the scientists, clinicians, and engineers working in our the research fieldavailable at ones' fingertips (evenif it field- "you won't be covering biology or biosynthesis, comprises twenty volumes)isawonderfulthing, and this let's have Volume 11soon" - "what about phthalocya can only serveto facilitate future expansion whileat the nines? They're (tetraazatetrabenzo)porphyrins too!" same time recording our field's rich history. So,in very short order the three of us met, put together a plan for continuation, and obtained the publisher's Karl M. Kadish, Houston approval and blessings for ten more volumes; this Kevin M. Smith, Baton Rouge last action was no mean accomplishment since con- Roger Guilard, Dijon ix Contributors to Volumes 1-20 Takuzo Aida Karine Auclair Department of Chemistry and Biotechnology Departmentof Chemistry Graduate School of Engineering McGill University The University of Tokyo 801 Sherbrooke StreetWest Hongo, Bunkyo-ku, Tokyo 113-8656, Japan Montreal, Quebec, Canada H3A 2K6 [email protected] [email protected] Chapters 23, 42 Chapter 75 Muhammad Akhtar Nick Bampos School of Biological Sciences University Chemical Laboratory University of Southampton Cambridge University BassettCrescent East Cambridge, CB2 1EW, UK Southampton S016 7PX,UK Chapter 15 [email protected] Lucia Banci Chapter71 CERMand Department of Chemistry University of Florence Karl E.Anderson 50019 Sesto Fiorentino (Florence), Italy Departments of Preventive Medicine and [email protected] Community Health Internal Medicine, Chapter39 and Pharmacology and Toxicology The University of TexasMedical Branch atGalveston Jean-Michel Barbe Texas77555-1109, USA Laboratoire d'Ingenierie Moleculaire [email protected] pour la Separation et lesApplications desGaz Chapter 94 LIMSAG (UMR 5633) Universite de Bourgogne JohnArnold Faculte desSciences"Gabriel" Departmentof Chemistry 6, BdGabriel 21000 Dijon, France University of California, Berkeley [email protected] Berkeley, California 94720-1460, USA Chapters 19/ 116 [email protected] Chapter 17 Pierrette Battioni Universite ReneDescartes Laboratoire de Chimie et Biochimie Pharmacologiques etToxicologiques UMR 8061 75270 Paris,France [email protected] Chapter26 xi xii Contributors to Volumes 1-20 Carl E.Bauer Sylvia S.Bottomley Departmentof Biology Departmentof Medicine Indiana University University of Oklahoma College of Medicine and Bloomington, Indiana 47405, USA Departmentof Veterans Affairs Medical Center [email protected] Hematology-Oncology Section (111J) Chapter 80 921 N.E. 13th Street Oklahoma City Marc Benard Oklahoma 73104-5007, USA Laboratoire de Chimie Quantique UMR 7551 [email protected] Universite Louis Pasteur Chapter 85 67000 Strasbourg, France [email protected] Roman Boulatov Chapter 48 Department of Chemistry Stanford University EhudBen-Hur Stanford, California 94305-5080, USA Consultant in Photomedicine [email protected] 160 West EndAvenue # 24P, New York, NY 10023, USA Chapter 62 [email protected] Chapter 117 Marcel Bouvet Laboratoire de Chimie Inorganique et Materiaux Moleculaires JeanBernadou CNRS- UMR7071 Laboratoire de Chimie de Coordination du CNRS Universite Pierre et Marie Curie 31077 Toulouse, France 4, placelussieu, CaseCourrier 42 bernadou@lcc-toulouseJr 75252 Pariscedex 05, France Chapter 31 [email protected] Ivano Bertini Chapter 118 CERM and Department of Chemistry JohannW. Buchler University of Florence Institutfur Anorganische Chemie 50019 SestoFiorentino (Florence), Italy Darmstadt University of Technology [email protected] D-64287 Darmstadt, Germany Chapter 39 [email protected] David W. Bollivar [email protected] Department of Biology Chapter 20 Illinois Wesleyan University Henry J.Callot P.O. Box 2900, Bloomington, Illinois 61702-2900, USA Faculte de Chimie [email protected] Universite Louis Pasteur Chapter 78 F-67000 Strasbourg, France Arnaud Bondon [email protected] UMR 6509, Organometallique et Catalyse, Chapter 7 Chimie et Electrochirnie Moleculaires Isabelle Chambrier Universite de Rennes I Wolfson Materials & Catalysis Centre 35042 Rennes, France School of Chemical Sciences and Pharmacy [email protected] University of EastAnglia Chapter 38 Norwich NR4 7TJ,UK [email protected] Chapter 108 Contributors to Volumes 1-20 xiii Jean-ClaudeChambron Anne Corrigall Laboratoire de Chimie Organo-Minerale Lennox EalesPorphyria Laboratories Universite LouisPasteur Departmentof Medicine Institut LeBel University of Cape Town Medical School 67070 Strasbourg, France Observatory, South Africa 7925 [email protected] [email protected] Chapter40 Chapter 89 Wai-Shun Chan TimothyM. Cox Progenitor Cell Therapy, L.L.C. Departmentof Medicine Park80 West, Plaza II,Suite 200 University of Cambridge, Box 157 Saddle Brook, NewJersey07663, USA Addenbrooke's Hospital, Cambridge CB2 2QQ, UK [email protected] [email protected] Chapter 117 Chapter 90 JenniferCheek Claudia Crestini School of Medicine Dipartimento di Scienze eTecnologie Chimiche University of South Carolina Tor Vergata University Columbia, South Carolina 29208, USA Via Della Ricerca scientifica Chapter 53 00133, Rome, Italy LinCheng [email protected] Department of Chemistry and Biochemistry Chapter 66 University ofOklahoma Roman S.Czernuszewicz Norman, Oklahoma 73019, USA Department of Chemistry Chapter33 University of Houston Inn-Hong Chou Houston, Texas 77204-5003, USA School of Chemical Sciences [email protected] University of Illinois at Urbana-Champaign Chapter52 Urbana, Illinois 61801, USA Harry A. Dailey Chapter41 Biomedical and Health Sciences Institute Zoe Clyde-Watson Department of Microbiology, and University Chemical Laboratory Department of Biochemistry & Molecular Biology Cambridge University A220 Life Sciences Building Cambridge, CB2 1EW, UK University of Georgia Chapter 15 Athens, Georgia 30602-7229, USA James P.Collman [email protected] Departmentof Chemistry Chapter 72 Stanford University Tamara A. Dailey Stanford, California 94305-5080, USA Biomedical and Health Sciences Institute [email protected] Departmentof Microbiology, and Chapter 62 Departmentof Biochemistry & Molecular Biology Michael J.Cook A220 Life Sciences Building Wolfson Materials & Catalysis Centre University of Georgia School of Chemical Sciences and Pharmacy Athens, Georgia 30602-7229, USA University of EastAnglia [email protected] Norwich NR4 7TJ, UK Chapter 72 [email protected] Chapter 108 xiv Contributors to Volumes 1-20 ScottL. Darling Jean-CharlesDeybach University Chemical Laboratory Centre Francais desPorphyries, INSERMU409 Cambridge University 178 ruedesRenouillers Cambridge, CB2 1EW, UK 92701 Colombes Cedex, France; Chapter 15 andFacultede Medecine Xavier Bichat Universite ParisVII John Dawson 16 rue Henri Huchard Department of Chemistry and Biochemistry BP416, 75870 ParisCedex 18, France University of SouthCarolina [email protected] Columbia, SouthCarolina 29208, USA Chapter 86 [email protected] Chapter 53 Danilo Dini Institut fur Organische Chemie Gema de la Torre UniversitatTubingen Departamento de Qufmica Organica 72076 Tubingen, Germany Universidad Autonoma de Madrid [email protected] 28049 Cantoblanco, Madrid, Spain Chapters 107, 114 [email protected] Chapter 99 Maria Pia Donzello Dipartimento di Chimica FelixW. M. de Rooij Universita degli Studi di Roma"La Sapienza" Department of Internal Medicine, Erasmus MC P.IeAldo Moro 5, 1-00185Roma, Italy University Medical Center Rotterdam [email protected] P.B.2040, 3000 CA Rotterdam Chapter 112 The Netherlands [email protected] Annie Edixhoven Chapters93, 95 Departmentof Internal Medicine, Erasmus MC University Medical Center Rotterdam JefferyS.de Ropp P.B.2040, 3000 CA Rotterdam NMR Facility The Netherlands University of California, Davis [email protected] Davis, California 95616, USA Chapter 93 [email protected] Chapter 37 G. H. Elder Departmentof Medical Biochemistry Hubert de Verneuil University of Wales College of Medicine Laboratoire de Pathologie Heath Park,CardiffCF144XN, UK Moleculaire etTherapie Genique, INSERME0217 [email protected] Universite V SegalenBordeaux 2 Chapter 88 146 rue LeoSaignat 33076 Bordeaux cedex, France Michael Klaus Engel verneuil@u-bordeaux2Jr Dainippon Ink and Chemicals, Inc. Chapter 87 Central Research Laboratories 631 Sakado,Sakura-shi Chiba-ken 285-8668, Japan [email protected] Chapter 122 Contributors to Volumes 1-20 xv Christoph Erben Barbara Floris Lucent Technologies-Bell Laboratories Dipartimento di ScienzeeTecnologie Chimiche Murray Hill, New Jersey 07974, USA Universita di Roma"Tor Vergata" [email protected] Via della RicercaScientifica Chapter 12 1-00133,Roma,Italy [email protected] Claudio Ercolani Chapter 112 Dipartimento di Chimica Universita degli Studidi Roma"La Sapienza" Nicole Frankenberg P.IeAldo Moro 5, 1-00185Roma,Italy Sectionof Molecular and Cellular Biology [email protected] University of California, Davis Chapters 101, 112 One ShieldsAvenue Davis, California 95616, USA Peter Erk [email protected] PerformanceChemicals Research Chapter83 GVP/C- J550, BASF AG 67056 Ludwigshafen/Rh, Germany Yuichi Fujita [email protected] Graduate School of Bioagricultural Sciences Chapter 119 Nagoya University Nagoya 464-8601, Japan JeanFischer [email protected] Laboratoire deChimie Organornetallique etde Catalyse Chapter80 Institut Ie Bel Universite Louis Pasteurde Strasbourg Shunichi Fukuzumi 4, rue BlaisePascal, 67070 Strasbourg,France Department of Material and LifeSciences [email protected] Graduate School of Engineering Chapter 105 Osaka University Suita,Osaka 565-0871, Japan Steven R. Flom [email protected] Code 5613/ Naval Research Laboratory Chapter56 Washington, DC 20375-5338, USA [email protected] Philip A. Gale Chapter 121 Department of Chemistry University of Southampton Carlo Floriani Southampton, S0171BJ, UK Institut de Chimie Minerale etAnalytique, BCH [email protected] Universite de Lausanne Chapter45 LausanneCH-l015, Switzerland Chapters 24, 25 Andreas Gebauer Department of Chemistry Rita Floriani-Moro University of California at Berkeley Institut de Chimie Minerale etAnalytique, BCH Berkeley, California 94720, USA Universite de Lausanne [email protected] LausanneCH-l015, Switzerland Chapters 8, 9 Chapters 24, 25 xvi Contributors to Volumes 1-20 Cecile Ged Chantal Goulon-Ginet Laboratoire de Pathologie EuropeanSynchrotron Radiation Facility Moleculaire etTherapie Genique F-38043 Grenoble, France; and INSERME0217 Faculte de Pharmacie, Universite de Grenoble I Universite V SegalenBordeaux 2 F-38700 LaTronche, France 146 rue LeoSaignat [email protected] 33076 Bordeaux cedex, France Chapter49 [email protected] Harry B.Gray Chapter87 Beckman Institute, MC 139-74 Abhik Ghosh California Institute of Technology Institute of Chemistry, Faculty of Science Pasadena,California 91125, USA University of Tr0mS0 [email protected] Trernse, Norway; Chapter 63 andSanDiego Supercomputer Center Bernhard Grimm University of California at SanDiego Institute of Biology/Plant Physiology LaJolla, California 92093-0505, USA Humboldt University [email protected] Unter den Linden 6 Chapter47 D 10099 Berlin, Germany Avram Gold [email protected] Departmentof Environmental Science and Engineering Chapter69 The University of North Carolina atChapel Hill JohnT. Groves Chapel Hill, North Carolina 27599-7400, USA Department of Chemistry [email protected] Princeton University Chapter29 Princeton, NewJersey08544-1009, USA Albert Gossauer [email protected] Departmentof Chemistry Chapter27 University of Fribourg LenaGueletti Routedu Musee 9 Departmentof Chemistry CH-1700 Fribourg, Switzerland University of Houston [email protected] Houston, Texas77204-5003, USA Chapter84 Chapter59 Vincent Gotte RogerGuilard European Synchrotron Radiation Facility Laboratoire d'Ingenierie Moleculaire F-38043 Grenoble, France pour la Separation et lesApplications desGaz Chapter49 LIMSAG (UMR 5633) Jose Goulon Universite de Bourgogne EuropeanSynchrotron Radiation Facility Faculte desSciences"Gabriel" F-38043 Grenoble, France 6, BdGabriel 21000 Dijon, France [email protected] roger.guilard@u-bourgogneJr Chapter49 Chapters 19,21/ 116
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