The Porphyrin Handbook. Multporphyrins, Multiphthalocyanines and Arrays

381 Pages·2003·45.34 MB·English

by  Karl Kadish

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 18/ Multiporphyrins,
Multiphthalocyanines, and Arrays
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
@
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Firstedition2003
ISBN: 0-12-393220-3(Set ofVolumes11-20)
0-12-393221-1(Volume 11)
0-12-393222-X (Volume 12)
0-12-393223-8(Volume 13)
0-12-393224-6(Volume 14)
0-12-393225-4(Volume 15)
0-12-393226-2 (Volume 16)
0-12-393227-0 (Volume 17)
0-12-393228-9(Volume 18)
0-12-393229-7(Volume 19)
0-12-393230-0 (Volume 20)
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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
1999Chemistry awardbythe Professionaland 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-1) 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 scientificenrichment ofthe 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, togathernewrecruitsand converts. Wethinkthathaving
the scientists, clinicians, and engineers working in our the research fieldavailable at ones' fingertips (even if 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
Karl M. Kadish, Houston
a plan for continuation, and obtained the publisher's
Kevin M. Smith, Baton Rouge
approval and blessings for ten more volumes; this
Roger Guilard, Dijon
last action was no mean accomplishment since con-
vii
Contributors to Volumes 1-20
Takuzo Aida Karine Auclair
Departmentof 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 Chapter75
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 Departmentof Chemistry
University of Florence
Karl E.Anderson
50019 SestoFiorentino (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 L1MSAG (UMR 5633)
Universite de Bourgogne
JohnArnold
Faculte desSciences"Gabriel"
Department of Chemistry
6, BdGabriel 21000 Dijon, France
University of California, Berkeley
jean-michel.barbe@u-bourgogneJr
Berkeley, California 94720-1460, USA
Chapters 19, 116
[email protected]
Pierrette Battioni
Chapter 17
Universite ReneDescartes
Laboratoire de Chimie et Biochimie
Pharmacologiques etToxicologiques UMR 8061
75270 Paris,France
[email protected]
Chapter26
ix
x Contributors to Volumes 1-20
Carl E.Bauer SylviaS.Bottomley
Departmentof Biology Departmentof Medicine
Indiana University University of Oklahoma College ofMedicine and
Bloomington, Indiana 47405, USA Departmentof VeteransAffairs 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 etMateriaux Moleculaires
Jean Bernadou
CNRS- UMR7071
Laboratoire de Chimie de Coordination du CNRS
Universite PierreetMarie Curie
31077 Toulouse, France
4, place Iussieu, CaseCourrier 42
[email protected]
75252 Pariscedex 05, France
Chapter 31
[email protected]
Ivano Bertini
Chapter 118
CERMand Department of Chemistry
JohannW. Buchler
University of Florence
Institut fur Anorganische Chemie
50019 SestoFiorentino (Florence), Italy
[email protected] Darmstadt University of Technology
Chapter 39 D-64287 Darmstadt, Germany
[email protected]
David W. Bollivar
[email protected]
Departmentof Biology
Chapter 20
Illinois Wesleyan University
Henry J. Callot
P.O. Box 2900, Bloomington, Illinois 61702-2900, USA
[email protected] Faculte de Chimie
Chapter 78 Universite Louis Pasteur
F-67000 Strasbourg,France
Arnaud Bondon
[email protected]
UMR 6509, Organornetallique et Catalyse,
Chapter 7
Chimie et Electrochirnie Moleculaires
Universite de RennesI Isabelle Chambrier
35042 Rennes,France Wolfson Materials &CatalysisCentre
[email protected] School of Chemical Sciencesand Pharmacy
Chapter 38 University of EastAnglia
Norwich NR4 7Tj, UK
[email protected]
Chapter 108
Contributors to Volumes 1-20 xi
Jean-ClaudeChambron Anne Corrigall
Laboratoire deChimie Organo-Minerale Lennox Eales Porphyria Laboratories
Universite Louis Pasteur Department of Medicine
Institut LeBel University of CapeTown Medical School
67070 Strasbourg,France Observatory, SouthAfrica 7925
[email protected] [email protected]
Chapter 40 Chapter 89
Wai-Shun Chan Timothy M. Cox
Progenitor Cell Therapy, L.L.C. Department of Medicine
Park80 West, PlazaII,Suite 200 Universityof Cambridge, Box 157
SaddleBrook, New Jersey 07663, USA Addenbrooke's Hospital, Cambridge CB2 200, UK
[email protected] [email protected]
Chapter 117 Chapter 90
JenniferCheek Claudia Crestini
School of Medicine Dipartimento di ScienzeeTecnologie Chimiche
University of SouthCarolina Tor Vergata University
Columbia, SouthCarolina 29208, USA Via Della Ricercascientifica
Chapter53 00133, Rome,Italy
LinCheng [email protected]
Departmentof Chemistry and Biochemistry Chapter 66
University of Oklahoma
RomanS.Czernuszewicz
Norman, Oklahoma 73019, USA
Department of Chemistry
Chapter33
University of Houston
Inn-Hong Chou Houston, Texas77204-5003, USA
School of Chemical Sciences [email protected]
University of Illinois at Urbana-Champaign Chapter52
Urbana, Illinois 61801, USA
Harry A. Dailey
Chapter 41
Biomedical and Health SciencesInstitute
Zoe Clyde-Watson Department of Microbiology, and
University Chemical Laboratory Departmentof Biochemistry &Molecular Biology
Cambridge University A220 LifeSciencesBuilding
Cambridge, CB2 1EW, UK University of Georgia
Chapter 15 Athens, Georgia 30602-7229, USA
James P.Collman [email protected]
Department of Chemistry Chapter72
Stanford University Tamara A. Dailey
Stanford,California 94305-5080, USA Biomedical and Health SciencesInstitute
[email protected] Departmentof Microbiology, and
Chapter 62 Departmentof Biochemistry &Molecular Biology
Michael J.Cook A220 LifeSciencesBuilding
Wolfson Materials & CatalysisCentre University of Georgia
School of Chemical Sciencesand Pharmacy Athens, Georgia 30602-7229, USA
University of EastAnglia [email protected]
Norwich NR4 7T], UK Chapter72
[email protected]
Chapter 108
xii Contributors to Volumes 1-20
ScottL. Darling Jean-Charles Deybach
University Chemical Laboratory Centre FrancaisdesPorphyries, INSERMU409
Cambridge University 178 ruedesRenouillers
Cambridge, CB2 1EW, UK 92701 Colombes Cedex, France;
Chapter 15 and Facultede 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 Organics
72076 TUbingen, Germany
Universidad Autonorna 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"
Departmentof 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
JefferyS.de Ropp University Medical Center Rotterdam
NMR Facility P.B.2040, 3000 CA Rotterdam
The Netherlands
University of California, Davis
[email protected]
Davis, California 95616, USA
[email protected] Chapter 93
Chapter 37 G. H. Elder
Hubert de Verneuil Department of Medical Biochemistry
Laboratoire de Pathologie University of Wales College of Medicine
Moleculaire etTherapie Genique, INSERME0217 Heath Park,CardiffCF144XN, UK
Universite V SegalenBordeaux 2 [email protected]
146 rue LeoSaignat Chapter 88
33076 Bordeaux cedex, France Michael Klaus Engel
[email protected] 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 xiii
Christoph Erben Barbara Floris
Lucent Technologies-Bell Laboratories Dipartimento di Scienze eTecnologie Chimiche
Murray Hill, NewJersey 07974, USA Universita di Roma"Tor Vergata"
[email protected] Via della Ricerca Scientifica
Chapter 12 1-00133, Roma,Italy
[email protected]
Claudio Ercolani
Chapter 112
Dipartimento di Chimica
Universita degli Studi di Roma "La Sapienza" Nicole Frankenberg
P.IeAldo Moro 5, 1-00185Roma, Italy Section of Molecular and Cellular Biology
[email protected] University of California, Davis
Chapters 101, 112 One ShieldsAvenue
Davis, California 95616, USA
Peter Erk
[email protected]
Performance Chemicals Research
Chapter 83
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 de Chimie Organornetallique et de Catalyse
Chapter 80
Institut Ie Bel
Universite Louis Pasteurde Strasbourg Shunichi Fukuzumi
4, rue BlaisePascal,67070 Strasbourg,France Departmentof Material and Life Sciences
[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
Chapter 56
Washington, DC 20375-5338, USA
[email protected] Philip A. Gale
Chapter 121 Departmentof Chemistry
University of Southampton
Carlo Floriani
Southampton, S017 1BJ, UK
Institut de Chimie Minerale etAnalytique, BCH
[email protected]
Universite de Lausanne
Chapter 45
LausanneCH-l015, Switzerland
Chapters24, 25 Andreas Gebauer
Departmentof 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
Chapters8, 9
Chapters24, 25
xiv Contributors to Volumes 1-20
Cecile Ged Chantal Goulon-Ginet
Laboratoirede Pathologie European Synchrotron 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 cgoulon@esrfJr
33076 Bordeaux cedex, France Chapter49
[email protected]
Harry B.Gray
Chapter 87
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]
Tromse, Norway; Chapter 63
andSanDiego SupercomputerCenter
Bernhard Grimm
University of California atSanDiego
Institute of Biology/Plant Physiology
LaJolla, California 92093-0505, USA
Humboldt University
[email protected]
Unterden Linden 6
Chapter 47
D 10099 Berlin, Germany
Avram Gold [email protected]
Department of Environmental Science and Engineering Chapter 69
The University of North Carolina atChapel Hill
JohnT. Groves
Chapel Hill, North Carolina 27599-7400, USA
Departmentof Chemistry
[email protected]
Princeton University
Chapter 29
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
EuropeanSynchrotron Radiation Facility
Laboratoire d'Ingenierle 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] [email protected]
Chapter 49 Chapters 19, 21 116
1