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