Photochemistry Volume 38

401 Pages·2010·12.7 MB·English

by  Angelo Albini

Specialist Periodical Reports
Editor Angelo Albini
Photochemistry
Volume 38
Photochemistry
Volume 38

A Specialist Periodical Report
Photochemistry
Volume 38
A Review of the Literature Published between
July 2007 and December 2009
Editor
Angelo Albini, University of Pavia, Pavia, Italy
Authors
Francesco Barigelletti, Istituto ISOF-CNR, Italy
Adalbert Braig, Performance Chemicals Research, Switzerland
M. Consuelo Jime´nez, Universidad Polite´cnica de Valencia, Spain
Telma Costa, University of Coimbra, Portugal
Kurt Dietliker, Performance Chemicals Research, Switzerland
Daniele Dondi, University of Pavia, Italy
Rui Fausto, University of Coimbra, Portugal
Andrea Go´mez-Zavaglia, University of Coimbra, Portugal
Sylvie Lacombe, Universite´de Pau et Pays de l’Adour, France
Andrea Maldotti, Universita´degli Studi di Ferrara, Italy
Daniele Merli, University of Pavia, Italy
Miguel A. Miranda, Universidad Polite´cnica de Valencia, Spain
Kazuhiko Mizuno, Osaka Prefecture University, Japan
Gloria Olaso-Gonza´lez, Universitat de Vale`ncia, Spain
Thierry Pigot, Universite´de Pau et Pays de l’Adour, France
Joa˜o Pina, University of Coimbra, Portugal
Luca Pretali, University of Pavia, Italy
Andrea Ricci, Performance Chemicals Research, Switzerland
Daniel Roca-Sanjua´n, Universitat de Vale`ncia, Spain
J. Se´rgio Seixas de Melo, University of Coimbra, Portugal
Luis Serrano-Andre´s, Universitat de Vale`ncia, Spain
Takashi Tsuno, Nihon University, Japan
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ISBN 978-1-84755-054-5
ISSN 0556-3860
DOI: 10.1039/9781849730860
A catalogue record for this book is available from the British Library
& The Royal Society of Chemistry 2011
All rights reserved
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For further information see our web site at www.rsc.org
Preface
Angelo Albinia
DOI: 10.1039/9781849730860-FP005
This is Volume 38 in the series Specialist Periodical Reports on Photo-
chemistry and completes the updating process by reviewing the 21 years
2
periodfromJuly2007toDecember2009.From2010onitishopedthatthe
yearlyperiodicitywillberestatedandeveryeffortwillbegivenforreducing
thegapbetweenthepublicationdateoftheoriginalresearchandthereview
in this series. On the other hand, a rapid publication is no more the only
issue. New papers are nowadays available on the PC screen of everybody,
whether at work or at home, sometimes several months in advance to the
actual publication date and retrieving a desired information is easy and
rapid via any of the available search engines.
Thus, the newest aspects of each field will continue to find a mention in
thisseries,butthiswillbebasedonaindepthdiscussionofalimitedchoice
ofpapers,ratherthanonacomprehensivepresentationoftheactivityinthe
field. The review part will be accompanied by a second part containing
highlightsonspecificaspects.Thisisexpectedtobecomeasimportantasthe
former one in this series – and has already expanded in this volume.
The plan of the reports remains the same, articulated in three sections,
devoted respectively to the physical and theoretical, to the organic and to
theinorganicaspects.Inthefirstsectionareviewontheoreticalaspectshas
been inserted (by Prof. Serrano-Andre`s) and in the last one the very ex-
tensivematerialoninorganicphotochemistryhasbeensubdividedbetween
prof. Maldotti and Prof. Barigelletti.
The highlights section has doubled, growing fom 2 to 4 contributions.
These mainly concern applied and industrial aspects, viz. new materials as
photosensitizers, prebiotic photochemistry and a field characterized by a
rapid grow, such has photolithography. A further highlight concerns
coatings in the automobile industry and may be followed by further con-
tributions evidencing where one may look for photochemistry in the in-
dustry. This is probably not where photochemistry practitioners think it
should, but this is the state of affairs and there goes most of the money
investedinphotochemistry.Wearehappythatwellknownexpertsfromthe
industry found the time for contributing.
Asalways,commentsarehighlywelcome, weneedtoknowwhetherthis
workhastobecontinued–andhow.Theimpressionofthepresentreporter
is that having available a broad-scope information in a single book may
help in discovering connections with areas outside the everyday field of
activity, which is surely a plus. But it is the readers’ opinion that matters.
aOrganicChemistryDepartment,PaviaUniversity,vialeTaramelli,10,27100,Pavia,Italy
Photochemistry, 2011,38, v–v | v
(cid:2)c TheRoyalSocietyofChemistry2011

CONTENTS
Cover
Anenergyleveldiagram
overlaidonthesun.
Backgroundimagereporduced
bypermissionofNASA.
Preface v
Angelo Albini
Reports
Review of the period July 2007–December 2009 1
Angelo Albini
1 A bit of history 1
2 Photochemical literature: the present state 1
3 Review 3
References 8
Physical and theoretical aspects
Recent trends in computational photochemistry 10
Luis Serrano-Andre´s, Daniel Roca-Sanjua´n and
Gloria Olaso-Gonza´lez
1 Introduction 10
2 Theoretical methods and concepts for excited states 12
Photochemistry, 2011,38 , vii–xi | vii
(cid:2)c TheRoyalSocietyofChemistry2011
3 Recent studies on photophysics and photochemistry 16
4 Photochemistry: nonadiabatic processes and reactivity 19
5 Conclusions 28
References 29
Light induced reactions in cryogenic matrices 37
Rui Fausto and Andrea Go´mez-Zavaglia
1 Introduction 37
2 UV/visible-induced reactions in cryomatrices 38
3 IR-induced reactions in cryomatrices 60
References 63
Dynamics and photophysics of oligomers and polymers 67
Joa˜o Pina, Telma Costa and J. Se´rgio Seixas de Melo
1 Organic conjugated polymers and oligomers 67
2 Dynamics of polymers hydrophobically modified with 90
fluorescent probes
3 Conclusions 105
References 105
Organic aspects
Alkenes, alkynes, dienes, polyenes 110
Takashi Tsuno
1 Photochemistry of alkenes 110
2 Photochemistry of polyenes 131
3 Photochemistry of alkynes 132
4 Photochemistry of enynes 133
5 Photooxidation 134
References 135
Oxygen-containing functions 143
M. Consuelo Jime´nez and Miguel A. Miranda
1 Introduction 143
2 Norrish Type I reactions 143
3 Hydrogen abstraction 145
viii | Photochemistry, 2011, 38, vii–xi
4 Paterno`-Bu¨chi photocycloadditions 150
5 Photoreactions of enones and quinones 152
6 Photodecarbonylation 158
7 Photodecarboxylation 158
8 Photo-fries and photo-claisen rearrangements 160
9 Photocleavage of cyclic ethers 161
References 162
Photochemistry of aromatic compounds 168
Kazuhiko Mizuno
1 Introduction 168
2 Isomerization reactions 168
3 Addition and cycloaddition reactions 173
4 Substitution reactions 180
5 Intramolecular cyclization reactions 183
6 Inter- and intra-molecular dimerization reactions 189
7 Lateral-nuclear rearrangements 202
References 203
Functions containing a heteroatom different from oxygen 210
Angelo Albini and Elisa Fasani
1 Nitrogen containing functions 210
2 Functions containing different heteroatoms 226
References 230
Inorganic aspects and solar energy conversion
Photophysics of transition metal complexes 234
Francesco Barigelletti
1 Introduction 234
2 Ruthenium 234
3 Osmium 240
4 Rhenium 241
5 Iridium 243
6 Rhodium 247
7 Platinum 248
8 Palladium 250
9 Copper 251
10 Gold 252
Photochemistry, 2011, 38, vii–xi | ix