Photochemistry Volume 40

333 Pages·2012·20.11 MB·English

by  Angelo Albini

Photochemistry
Volume 40

A Specialist Periodical Report
Photochemistry
Volume 40
A Review of the Literature Published between
May 2011 and April 2012
Editor
Angelo Albini, University of Pavia, Pavia, Italy
Authors
Serena Berardi, University of Padova, Italy
Marcella Bonchio, University of Padova, Italy
Sebastiano Campagna, Universita`di Messina, Italy
M. Consuelo Jime´nez, Universidad Polite´cnica de Valencia, Spain
Elisa Fasani, University of Pavia, Italy
Bernd Herzog, BASF Grenzach GmbH, Germany
Haruo Inoue, Tokyo Metropolitan University, Japan
Giuseppina La Ganga, Universita`di Messina, Italy
Roland Lindh, Uppsala University, Sweden
Ya-Jun Liu, Beijing Normal University, China
Ugo Mazzucato, Universita`di Perugia, Italy
Alberto Mezzetti, CNRS, France
Miguel A. Miranda, Universidad Polite´cnica de Valencia, Spain
Kazuhiko Mizuno, Nara, Japan
Stefano Protti, University of Pavia, Italy
Fausto Puntoriero, Universita`di Messina, Italy
Daniel Roca-Sanjua´n, Uppsala University, Sweden
Andrea Sartorel, University of Padova, Italy
Takashi Tsuno, Nihon University, Japan
Ifyoubuythistitleonstandingorder,youwillbegivenFREEaccess
to the chapters online. Please contact [email protected] with proof of
purchase to arrange access to be set up.
Thank you.
ISBN: 978-1-84973-437-0
ISSN: 0556-3860
DOI: 10.1039/9781849734882
A catalogue record for this book is available from the British Library
& The Royal Society of Chemistry 2012
All rights reserved
Apart from fair dealing for the purposes of research or private study for
non-commercial purposes, or for private study, criticism or review, as
permitted under the Copyright, Designs and Patents Act, 1988 and the
Copyright and Related Rights Regulations 2003, this publication may
not be reproduced, stored or transmitted, in any form or by any means,
without the prior permission in writing of The Royal Society of Chemistry,
or in the case of reproduction in accordance with the terms of the licences
issued by the Copyright Licensing Agency in the UK, or in accordance with
the terms of the licences issued by the appropriate Reproduction Rights
Organization outside the UK. Enquiries concerning reproduction outside
the terms stated here should be sent to The Royal Society of Chemistry
at the address printed on this page.
Published by The Royal Society of Chemistry,
Thomas Graham House, Science Park, Milton Road,
Cambridge CB4 0WF, UK
Registered Charity Number 207890
For further information see our web site at www.rsc.org
Preface
DOI: 10.1039/9781849734882-FP005
Volume 40 completes the new course of the periodic reports on photo-
chemistry,wherethetopicsarereviewedeveryotheryear.Thus,thephysico-
chemical and inorganic aspects as well as solar energy conversion have
been reviewed in Volume 39, while the present one includes the organic
aspects and computational photochemistry. A general introduction and
review referred to both years 2010 and 2011 is included in the present
volume. As discussed previously, this structure seems more appropriate to
the needs of present day research, where having an organized summary of
theworkgoingoninthevariousareasofphotochemistryismoreimportant
than receiving an ultrafast information about a new paper. Everybody has
now a rapid access to the literature through instruments different from a
yearly book, and in that capacity the present series would certainly be a
poor competitor.
The organic aspects are presented in four chapters, as in previous
volumes,andonechapterisdevotedtothecorephysicalandcomputational
aspects. We welcome here Professor Liu as a new contributor.
Addingtothereviewchaptersaseriesofhighlightsdevotedtoimportant
aspectsofappliedphotochemistryhasbecomeanestablishedfeatureofthe
series. In the present volume, five highlights are presented. These involve
one of the industrially most significant, one may say ‘mature’ applications,
UVfilters,andtwotypicalaspectsof‘academic’(atpresent,butpreparsing
future applications) topics, such as light-induced water oxidation and the
complex equilibria of flavanols. Then, two chapters concern the history of
two of the main Photochemical Societies worldwide, the European Photo-
chemistry Association and the Asian Oceanis Photochemistry Association.
Photochemistry as a science owns much to the effort for cultural commu-
nication and development national and international associations did,
particularly in the Sixties. Changes, mergings, developments have then
taken place and present day associations are quite differente and serve a
different function. It seemed timely to present these historic contribution,
further additions will follow.
I regret the untimely loss of Professor Luis Serrano-Andre´s, who con-
tributed to this series. Finally, I thank the staff of Specialist Periodical
Reports and my colleagues of the Photochemical Group at the University
of Pavia for their help.
Angelo Albini
Photochemistry, 2012,40, v–v | v
(cid:2)c TheRoyalSocietyofChemistry2012

CONTENTS
Cover
In1912GiacomoLuigiCiamician,‘‘The
FatherofPhotochemistry’’openedhis
addresstotheInternationalCongressof
AppliedChemistrywiththeparagraph
detailedonthecover.Photochemistryof
theFuturehasbeenaninspirationtothe
fieldofPhotochemistryeversince.
Preface v
Angelo Albini
Periodical reports: Organic and computational aspects
Introduction and review of the years 2010–2011 3
Angelo Albini
1 Introduction 3
2 Review of the years 2010–2011 5
References 36
Computational Photochemistry and Photophysics: the state of the art 42
Ya-Jun Liu, Daniel Roca-Sanjua´n and Roland Lindh
1 Introduction 42
2 The most basic concepts in photochemistry 43
3 A brief history of computational photochemistry 44
4 A critical point of view on methodology 48
5 Development of computational photochemistry 49
2010–2011
6 Conclusion and outlook 66
Acknowledgments 67
References 67
Photochemistry, 2012, 40, vii–x | vii
(cid:2)c TheRoyalSocietyofChemistry2012
Alkenes, alkynes, dienes, polyenes 73
Takashi Tsuno
1 Photochemistry of alkenes 73
2 Photochemistry of dienes 94
3 Photochemistry of polyenes 96
4 Photochemistry of alkynes 96
5 Photooxidation 98
References 99
Photochemistry of aromatic compounds 106
Kazuhiko Mizuno
1 Introduction 106
2 Isomerization reactions 106
3 Addition and cycloaddition reactions 108
4 Substitution reactions 117
5 Intramolecular cyclization reactions 119
6 Inter- and intra-molecular dimerization reactions 129
7 Lateral-nuclear rearrangements 133
References 136
Organic aspects. Oxygen-containing functions 146
M. Consuelo Jime´nez and Miguel A. Miranda
1 Norrish type I reactions 146
2 Hydrogen abstraction 147
3 Paterno`-Bu¨chi photocycloadditions 154
4 Photoreactions of enones and quinones 156
5 Photoelimination 160
6 Photo-Fries and photo-Claisen rearrangements 165
7 Photocleavage of cyclic ethers 167
References 168
Functions containing a heteroatom different from oxygen 174
Angelo Albini and Elisa Fasani
1 Nitrogen containing functions 174
2 Functions containing different heteroatoms 186
References 189
viii | Photochemistry, 2012, 40, vii–x
Highlights in photochemistry
The history of the European Photochemistry Association 197
Ugo Mazzucato
1 Preliminary contacts for a new Association 197
2 The Foundation and first steps of the European 199
Photochemistry Association (1970–76)
3 The EPA in its mature period (1977–2000) 206
4 EPA in the last decade: a slackening period and a prompt 220
revival
Appendix - The history of the EPA Newsletter 226
Acknowledgements 229
HistoryoftheAsianandOceanianPhotochemistryAssociation(APA) 230
Haruo Inoue
1 Foundation of the Asian and Oceanian Photochemistry 230
Association (APA)
2 Birth of the APA 235
3 Pre-history of the APA 236
4 Activities of the APA and the regional societies in Asia and 237
Oceania
Appendix 243
Photoprotection of human skin 245
Bernd Herzog
1 Ambient UV radiation and properties of human skin 245
2 UV filters for sunscreens 250
3 Sunscreen formulations and their assessment 259
4 Understanding sunscreens 265
5 Conclusion 269
Acknowledgments 270
References 270
Photo-induced water oxidation: New photocatalytic processes and 274
materials
Serena Berardi, Giuseppina La Ganga, Fausto Puntoriero,
Andrea Sartorel, Sebastiano Campagna and Marcella Bonchio
1 Introduction 274
2 Photo-induced water oxidation 275
3 Photosensitizers for water oxidation 277
Photochemistry, 2012,40, vii–x | ix