Photochemistry volume 40

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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 If you buy this title on standing order, you will be given FREE access to the chapters online Please contact 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 Preface DOI: 10.1039/9781849734882-FP005 Volume 40 completes the new course of the periodic reports on photochemistry, where the topics are reviewed every other year Thus, the physicochemical 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 the work going on in the various areas of photochemistry is more important 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, and one chapter is devoted to the core physical and computational aspects We welcome here Professor Liu as a new contributor Adding to the review chapters a series of highlights devoted to important aspects of applied photochemistry has become an established feature of the series In the present volume, five highlights are presented These involve one of the industrially most significant, one may say ‘mature’ applications, UV filters, and two typical aspects of ‘academic’ (at present, but preparsing 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 Photochemistry Association and the Asian Oceanis Photochemistry Association Photochemistry as a science owns much to the effort for cultural communication 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 contributed 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  c The Royal Society of Chemistry 2012 CONTENTS Cover In 1912 Giacomo Luigi Ciamician, ‘‘The Father of Photochemistry’’ opened his address to the International Congress of Applied Chemistry with the paragraph detailed on the cover Photochemistry of the Future has been an inspiration to the field of Photochemistry ever since Preface Angelo Albini v Periodical reports: Organic and computational aspects Introduction and review of the years 2010–2011 Angelo Albini Introduction Review of the years 2010–2011 References 36 Computational Photochemistry and Photophysics: the state of the art 42 Ya-Jun 42 43 44 48 49 Liu, Daniel Roca-Sanjua´n and Roland Lindh Introduction The most basic concepts in photochemistry A brief history of computational photochemistry A critical point of view on methodology Development of computational photochemistry 2010–2011 Conclusion and outlook Acknowledgments References 66 67 67 Photochemistry, 2012, 40, vii–x | vii  c The Royal Society of Chemistry 2012 Alkenes, alkynes, dienes, polyenes 73 Takashi Tsuno Photochemistry Photochemistry Photochemistry Photochemistry Photooxidation References 73 94 96 96 98 99 of of of of alkenes dienes polyenes alkynes Photochemistry of aromatic compounds 106 Kazuhiko Mizuno Introduction Isomerization reactions Addition and cycloaddition reactions Substitution reactions Intramolecular cyclization reactions Inter- and intra-molecular dimerization reactions Lateral-nuclear rearrangements References 106 106 108 117 119 129 133 136 Organic aspects Oxygen-containing functions 146 M Consuelo Jime´nez and Miguel A Miranda Norrish type I reactions Hydrogen abstraction Paterno`-Buăchi photocycloadditions Photoreactions of enones and quinones Photoelimination Photo-Fries and photo-Claisen rearrangements Photocleavage of cyclic ethers References 146 147 154 156 160 165 167 168 Functions containing a heteroatom different from oxygen 174 Angelo Albini and Elisa Fasani Nitrogen containing functions Functions containing different heteroatoms References 174 186 189 viii | Photochemistry, 2012, 40, vii–x Highlights in photochemistry The history of the European Photochemistry Association Ugo Mazzucato Preliminary contacts for a new Association The Foundation and first steps of the European Photochemistry Association (1970–76) The EPA in its mature period (1977–2000) EPA in the last decade: a slackening period and a prompt revival Appendix - The history of the EPA Newsletter Acknowledgements 197 History of the Asian and Oceanian Photochemistry Association (APA) Haruo Inoue Foundation of the Asian and Oceanian Photochemistry Association (APA) Birth of the APA Pre-history of the APA Activities of the APA and the regional societies in Asia and Oceania Appendix 230 Photoprotection of human skin 245 Bernd Herzog Ambient UV radiation and properties of human skin UV filters for sunscreens Sunscreen formulations and their assessment Understanding sunscreens Conclusion Acknowledgments References 245 250 259 265 269 270 270 Photo-induced water oxidation: New photocatalytic processes and materials Serena Berardi, Giuseppina La Ganga, Fausto Puntoriero, Andrea Sartorel, Sebastiano Campagna and Marcella Bonchio Introduction Photo-induced water oxidation Photosensitizers for water oxidation 197 199 206 220 226 229 230 235 236 237 243 274 274 275 277 Photochemistry, 2012, 40, vii–x | ix C4H9 N C8H17 N C8H17 C4H O Br– O OH NMe3+ O OH N+ –O S 18 O N+ 19 SO3– N N O OH C8H17O O 20 Fig 10 Et N Et O OH –O S N+ O C12H23 21 Fig 11 weakly sensitive styrylpyridinium derivatives) makes these dyes suitable for multi-color imaging microscopy.78 Analogously, the zwitterionic flanonols N-[[4 -N,N-diethylamino-3hydroxy-6-flavonyl]methyl]-N-methyl-N-(3-sulfopropyl)-1-dodecanaminium inner salt (21, Fig 11), equipped with both a positively charged substituent and a hydrophobic tail, has been employed in the investigation of phospholipid unilamellar vesicles.79 21 has been also employed as fluorescent probe for sensing the changes occurring in lipid composition of the outer leaflet of the cell plasma membrane during the early steps of apoptosis The optical response has been quantified on an absolute scale, and monitored by laser scanner confocal microscopy.80 Furthermore, the use of 21 as a probe in investigation of cancer tissues development and in the evaluation of the efficiency of anticancer drugs has been also suggested.80 Furthermore, several non charged flavones have been employed as fluorescent probe in biological systems Thanks to the presence of two hydroxyethyl groups, 3HF derivative (22, Fig 12) is anchored at the membrane interface by means of H-bond interactions Apart from the observed satisfying sensitivity to both 308 | Photochemistry, 2012, 40, 295–322 OH N OH O 22 OH O N O O OH O O 23 HO Fig 12 O Cl OH 24 O Et N Et NH2 * HCl Fig 13 chemico-physical characteristics of solvents and membrane dipole potential changes, 22 can be also used to monitor interaction of ATP with lipidic membranes.81 Analogously, Turkmen et al reported the synthesis of -N,N-diethylamino-3-hydroxyflavone conjugated to a triterpenoic oleanolic acid, and its potentialities as environment sensitive biomembrane probe (23).82 Differently 2,6,8-trisubstituted 3-hydroxychromones such as 24 (Fig 13) able to be readily uptaken by cells have been investigated by Dyrager et al for Live-Cell Imaging by multi-photon laser scanning microscopy (MPLSM).83 Interaction of the probe with amyloid fibrils of the protein a-synuclein (AS) (that is a hallmark of the Parkinson’s disease and of related neurodegenerative disorders) leads to a spectroscopic differentiation of the supramolecular structures of the protein.84 The thermally induced structural Photochemistry, 2012, 40, 295–322 | 309 NEt2 NEt2 Br O Protein-SH O OH 25 -H+ S Protein O OH O Scheme changes in Eye lens a-crystallin, a member of the small heatshock proteins (sHSPs) superfamily that act as molecular chaperones on aggregation-prone damaged proteins preventing their aggregation under stress conditions, have been investigated through the use of 6-bromomethyl-4 -N,N-diethylamino-3-hydroxyflavone 25 The flavone derivative has been used to label both the Cys-131 residue of the aA subunit and the Lys residues of the protein (Scheme 7) Despite the poor chemoselectivity of 25 towards these nucleophilic residues, a ratiometric resolution of the emission arising from different labelled sites is feasible since the site of labelled Cys-131 is characterized by a significant proticity whereas the site of labelled NH2 is more screened from bulk water.85 Through this approach, the temperaturedependent structural changes occurring within the C-terminal domain of the a subunit of Eye lens a-crystallin have been monitored.86 The 2,4-dinitrobenzensulfonyl ester of has been recently proposed by Wang et al as a turn-on fluorescent sensor for -SH group in biomolecules.87 Technological applications of flavonols 5.1 Flavonols as wavelength shifters The large Stokes Shift (Dl=180 nm for the model compound 3HF) occurring in flavonols and their derivatives makes these molecules ideal dyes in the development of wavelength shifting devices for different applications Optical wavelength-shifters are usually employed to improve the spectral sensitivity of standard photodetectors (such as photodiodes) in the UV range.88 Hybrid organic–inorganic silica Xerogels that contain dispersed 3HF-molecules have been synthesized via sol-gel approach by Quarturan et al.88 Transparent monolithic samples of these materials have been used to overlay the detection area of a silicon photodiode in the aim of extending its response down to 400 nm A noteworthy enhancement (up to five times with respect the response of the untreated detector) has been observed An analogous approach has been investigated for GaAs based detectors, whose response drops to zero at 350 nm.89 The chance to tune the interaction between and its surrounding siloxane matrix and thus the optical properties of the fluorophore embedded by choosing the appropriate synthetic procedures has been recently reported.90 Due to the different interactions of flavonol with the transition metals used in synthesis, 3HF-doped samples obtained through room temperature vulcanization (RTV) by Pt catalyzed hydrosilylation (PtCAT, Fig 14), Sn catalyzed polycondensation (SnCAT) and moisture induced polycondensation (ACET) are characterized by 310 | Photochemistry, 2012, 40, 295–322 Fig 14 3HF embedded in siloxane matrices obtained by Pt catalyzed hydrosilylation (PtCAT), Sn catalyzed polycondensation (SnCAT) and moisture induced polycondensation (ACET) Reprinted with permission from M Buffa, S Carturan, A Quaranta, G Maggioni and G Della Mea, Opt Mater 2012, 34, 1219, Copyright 2012 Elsevier different wavelength emission maxima located at ca 430, 470 and 540 nm respectively An alternative technique to synthesize these xerogel matrices has been proposed by Mezzetti and coworkers91 and involves the introduction of 3HF molecule by a post doping procedure Contrary to what reported for other synthesized samples,88,90,92 the luminescence profile of this doped xerogel matrices showed only the emission related to 1T state of 3HF, highlighting a non protic microenvironment for the included flavonol By this approach, the synthesized matrices underwent stabilization before doping by heating at 850 1C, avoiding decomposition of organic dopant Some further advantages are related to the lower amount of residual solvent and unreacted silanol groups with respect to traditional xerogel matrices, that provide an improved transparency to UV visible light Furthermore post doping procedure ensure the specific introduction of dopant molecule avoiding interference from the organic solvents or ligands, insuring that photoluminescence properties are specific to the inserted probe molecule In addition, the use of xerogels doped with high fluorescent and photostable Al(III) complexes of 3HF15c in the aim of inhibiting the photodegradation of dopant molecules matrices has been successfully demonstrated Just as UV photodetectors, also active photovoltaic materials have a poor response to short-wavelength light and a significant fraction of the incident photons results unemployed Due to the poor blue sensitivity of solar cell, wavelengths in the range 350–500 nm must be shifted up to the range 500– 1000 nm to be efficiently collected in a solar cells.93 Buffa et al reported that the use of transparent polysilossane-based matrices dispersed with 3HF (0.37 g/L) as wavelength-shifting moieties (WLS) provided an improvement of the solar cell yield up to 5%, a value that drops to 2.5% after three weeks, probably due to the photodegradation of 3HF.93 The wavelength shifting properties of 3HF have been also exploited in the preparation of plastic scintillator plates or films to be employed as input window of photomultiplier tubes, to achieve a better match with the optimum response wavelength.94 Many efforts have been focused on the development of new scintillation films with highly efficient registration of different particles, high-time and energy resolutions, resistance to radiation damage, high signal-to-noise ratio and low cost.95 Astvatsaturov et al.95 reported the synthesis of Photochemistry, 2012, 40, 295–322 | 311 O OH 26 O Fig 15 (b) (a) n O OH (c) n m O O 27 OH n m O OH O O 28 29 Fig 16 polystirene based scintillator films including 3-hydroxyflavone or -vinyl-3hydroxyflavone (26, Fig 15) The presence of flavonol based dopant involved an increase in the light yield from 4% (in the film without dopant) up to 45% (in the presence of 1% 26) Fluorescent polymers having a 3-hydroxyflavone (3HF)-based pendant group (27–29, see Fig 16) has been synthesized by Dharia et al.96 In particular, the use of polivinyl-3-hydroxyflavone homopolymer 27 has been proposed as an effective wavelength shifter due to the larger stoke shift effect observed (Dl=190 nm) Analogously, new boron-containing polystyrene scintillators containing 3HF molecules have been fully characterized and employed to detect aparticles and neutrones, though their response resulted less satisfactory than scintillators of standard composition.97 5.2 Flavonols as probes to measure physical and chemical parameters The influence of temperature on both excited state and ground state proton transfer taking place in 3-hydroxyflavone98,99 has been early studied More recently, the dependence on temperature of the luminescence characteristics of the three forms of 3HF (normal, 384 nm; tautomeric, 525 nm and anionic, 475 nm) has been investigated by Tomin An increase of the luminescence intensity ratio of the normal and tautomeric forms (lex=280 nm), from up 0.5 up to 1.0 in the temperature range of 20–70 1C has been observed, allowing the Author to suggest the use of 3HF as a fluorescent thermometer in methanol solution.100 The temperature-induced coil-to-globule phase transition occurring to Poly N-isopropylacrylamide (PNIPAM) in aqueous suggested the use of this thermoresponsive material in molecular thermometers for biological systems The synthesis of PNIPAM based nanogels 312 | Photochemistry, 2012, 40, 295–322 O NH q n m O NH O NH 30 HN n: m : q = 100 : : O O OH O O Fig 17 OH PhCHO, OH– OH β-zeolite O Ph H2O2, OH– O Ph β-zeolite O OH O Scheme covalently linked with flavonol moieties (30, Fig 17) has been reported by Chen and co-workers.101 The introduced fluorophore is used to visualize the morphological transition induced by temperature variation Gratifyingly, the emission of synthesized nanogel shifts from blue to green in a temperature range of 33 to 41 1C, with a ratiometric magnitude of W8 fold, making the color change visible by naked eye Furthermore, the temperature- and pression- dependent dual emission arising from the second excited singlet state (S2) of 3-hydroxyflavone (5)102 in scCO2 has been used to measure the physical parameters of the medium.103 The ship-in-a-bottle synthesis of has been successfully carried out starting from o-hydroxyacetophenone in b-zeolites (Scheme 8) to afford photochemically stable fluorescent nanoparticles.104 Spectrofluorimetric investigation revealed that the marked protic environment of the zeolite micropores involved a strong stabilization of 1N state enhancing the emission from this state The use of 3HF doped zeolite nanoparticles covalently coated with pH sensitive fluorescein derivative has been proposed by Doussineau et al as a fluorimetric nanosensor for pH measurements in biological systems such as living cells or tissues.105 Analogously, the water-soluble flavonol 31 (Fig 18) has been employed as fluorescent pH-indicator in the range from to 12.106 5.3 Other technological applications of flavonols Chou et al reported the generation of amplified spontaneous emission (ASE) via ESIPT occurring in 3HF in neat solvents (1,4-dioxane and methylcyclohexane)107 as well as in the presence of conjugated laser dye Photochemistry, 2012, 40, 295–322 | 313 NMe2 OH O NMe2 OH 31 O Fig 18 such as tetraphenylbutadiene and diphenylbutadiene,108 suggesting the use of as an efficient laser dye The use of 3HF and on other flavonols (fisetin (6) and 3,4 ,7-trihydroxyflavone) as laser dyes has been further investigated by Kasha and co-workers.109,110 Morover, 3HF has been recently proposed by Chen and co-workers as free radical scavenging agent to improve both the photostability and the power conversion efficiency (PCE) of polymer solar cells.111 The deposition of polymeric film containing 3-hydroxyflavone (5) in high concentration through masks on the surface of photonic structures has been reported by Aparicio et al.112 and suggested as efficient method for the preparation of reusable photonic chips In addition, as reported by the authors, the same polymeric material could have multiple applications including UV sensors, wavelength shifting devices, UV filters and green emitters.112 The synthesis of selective optosensing device for the determination of flavonoids has been carried out via molecular imprinting approach Methacrylic acid/ethylenglycoldimethacrylate radical copolymerization in the presence of 3-hydroxyflavone (5) as guest molecule afforded a threedimensional network polymer that exhibits selectivity for rebinding the template that was used for its preparation The selectivity of the so prepared molecular imprinting polymer (MIP) has been checked in the presence of different flavonols (5, quercetin (1) and morin (8)113 An analogous MIP for the selective recognition of has been prepared by using the same flavonol as guest molecule and macroporous chitosan beads as functional matrix during copolymerization.114 This approach has been exploited in analytical chemistry for the Solid Phase Extraction (SPE) and determination of from complexes matrices such as red wine.115 Synthetic applications of flavonols Whereas ESIPT of 3HF (1) and its derivatives has been the subject of deep investigations in physical chemistry, the synthetic potentialities of the resulting intermediates have received only little attention.116–121 To the best of our knowledge, all of the efforts are devoted to exploit the 1,3-dipole reactivity of the resulting 3HFs tautomeric form in [3 ỵ 2] cycloaddition in multistep syntheses This approach has been exploited by both the Porco Jr and Rizzacasa groups for the biomimetic117 synthesis of natural occurring Rocaglates and Rocaglamides derivatives, that are known to display potent anticancer and antileukemic activity The natural product (Ỉ)-Me rocaglate 35 has thus been synthesized as a mixture of diasteroisomers by [3 ỵ 2] 314 | Photochemistry, 2012, 40, 295–322 O MeO HO CO2Me Ph CO2Me OMe O MeO O 34, 33% Ph hν, MeOH OH MeO OMe O O + OH 0°C OMe CO2Me OMe 33 MeO Ph 35, 17% OMe MeONa, MeOH, Δ Me4NBh(OAc)3, CH3COOH, MeCN HO MeO HO HO MeO HO CO2Me CO2Me + MeO O O MeO 36-exo, 27% 36-endo, 51% OMe OMe Scheme photoinduced cycloaddition of 3-hydroxyflavone derivative 32 with methyl cynnamate in methanol The cyclizated products 34 and 35 (50% overall yield) thus underwent a-ketol rearrangement and carbonyl reduction (Scheme 9).118 As previously described (see section 2) the solvent dependence of ESIPT in flavonols has been found to play a key role in the reactivity of the photogenerated intermediates Porco and co-workers reported that protic solvents such as 2,2,2-trifluoroethanol (TFE) are able to promote ESIPT pathway, leading to an increase of the population of the excited phototautomers (1T).119 Thus, the irradiation of 3-hydroxyflavone derivatives in chloroform/ TFE (TFE) 70:30 mixture and in the presence of methylcynnamate resulted in an improved cycloaddition yield (up to 55%) and diasteroselectivity (up to 5:1 d.r.) Furthermore, the use of protic TFE increased the phototautomerization yield, allowing the use of less reactive dipolarophiles including cinnamyl thioesters, amides or nitriles.119 The enanthioselective synthesis of potent cytotoxic (-)-Silvestrol (37) via TADDOL derivativesmediated [3 ỵ 2] cycloaddition has been reported (Scheme 10).120 Analogously, the total synthesis of 37, (-) Episilvestrol and their synthetic derivative (-)-4 -desmethoxyepisilvestrol starting from commercially available flavonols121 has been proposed by Rizzacasa and coworkers Photochemistry, 2012, 40, 295–322 | 315 OMe O OH MOMO CO2Me Ph R O O Ar Ar Ar HO O + R OMe HO 66% O Ar MeO HO CO2Me hν Ph CH2Cl2/Toluene –70 °C MOMO O MOM = –CH2OCH3 Ar = pyren-1-yl R = cyclooctyl OMe OH MeO HO CO2Me Ph O O HO H OH 37 OO OMe Scheme 10 Acknowledgments We thank Dr Sara Montanaro and Dr Davide Ravelli (University of Pavia) for carefully reading the manuscript Support to S P by the Ministero dell’Universita` e della Ricerca (MIUR), Rome (FIRB-Futuro in Ricerca 2008 project RBFR08J78Q) is gratefully acknowledged References W Oleszek, M J Amiot and S Y Aubert, J Agric Food Chem., 1994, 42, 1261; 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