Photochemistry and Photobiology

Cover image for Vol. 89 Issue 6

November/December 2013

Volume 89, Issue 6

Pages 1269–1506, E1–E8

  1. Editorial

    1. Top of page
    2. Editorial
    3. Special Issue Honouring the Memory of Elsa Abuin
    4. Special Issue Invited Review Articles
    5. Special Issue Research Articles
    6. Research Articles
    7. List of Reviewers
    1. Editorial (page 1269)

      Jean Cadet

      Article first published online: 4 NOV 2013 | DOI: 10.1111/php.12187

  2. Special Issue Honouring the Memory of Elsa Abuin

    1. Top of page
    2. Editorial
    3. Special Issue Honouring the Memory of Elsa Abuin
    4. Special Issue Invited Review Articles
    5. Special Issue Research Articles
    6. Research Articles
    7. List of Reviewers
    1. Special Issue Dedicated to the Memory of Elsa Beatriz Abuin Saccomano (1942–2012) (pages 1270–1272)

      Emilio Isaac Alarcon, Alexis Aspee, Carolina Aliaga and Silvia E. Braslavsky

      Article first published online: 4 NOV 2013 | DOI: 10.1111/php.12115

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      In memoriam of Elsa Abuin (1942–2012), teacher, mentor and friend. This Special Issue presents a collection of review articles and papers dedicated to the memory of Elsa Abuin and most of them presented during the Meeting of the Latin-American photochemists (Encuentro Latino-Americano de Fotoquímica y Fotobiología, ELAFOT) held in October 2012 in Córdoba, Argentina.

  3. Special Issue Invited Review Articles

    1. Top of page
    2. Editorial
    3. Special Issue Honouring the Memory of Elsa Abuin
    4. Special Issue Invited Review Articles
    5. Special Issue Research Articles
    6. Research Articles
    7. List of Reviewers
    1. You have free access to this content
      Effect of Concentration on the Photophysics of Dyes in Light-Scattering Materials (pages 1273–1282)

      Hernán B. Rodríguez and Enrique San Román

      Article first published online: 22 JUL 2013 | DOI: 10.1111/php.12107

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      Experimental methods based on measurements such as steady-state reflectance and fluorescence and laser-induced optoacoustic spectroscopy allow the quantitative evaluation of photophysical processes in light-scattering materials containing dyes at high loadings.

    2. You have free access to this content
      High-Performance Photoinitiating Systems for Free Radical Photopolymerization. Application to Holographic Recording (pages 1283–1290)

      Ahmad Ibrahim, Luciano Di Stefano, Olga Tarzi, Haja Tar, Christian Ley and Xavier Allonas

      Article first published online: 21 AUG 2013 | DOI: 10.1111/php.12132

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      To overcome the lack of reactivity of PIS for free radical photopolymerization under visible light, photocyclic initiating systems have been developed. In such systems not only the intrinsic problem of reactivity of the Type II system is circumvented, but also the dye is recovered after reaction. These systems are based on a dye as absorbing species, an electron or hydrogen donor as coinitiator and a redox additive which aims to react with the photoproduct formed from the dye. These systems can be used to improve the photosensitivity in holography recording.

    3. You have free access to this content
      Symbiosis Between Photoactive Nanoparticles and their Organic Ligands (pages 1291–1298)

      Julia Pérez-Prieto

      Article first published online: 19 JUL 2013 | DOI: 10.1111/php.12109

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      A spherical inorganic material combined with its organic capping can be considered as a nanohybrid with properties that differ from those of the individual components. The symbiotic effect arise from the possibility of placing a high local concentration of a functional group on the NP surface, the potential incorporation of simultaneous functionalities on the NP capping, the high encapsulating capacity of the nanohybrid, the capacity of the ligand to produce an efficient interdigitation of amphiphilic molecules, the potential of the ligand to be used for establish specific interactions, among others. Several examples of the application of this cooperative action are presented.

    4. You have free access to this content
      Efficiency of Electron Transfer Initiated Chemiluminescence (pages 1299–1317)

      Felipe A. Augusto, Glalci A. de Souza, Sergio P. de Souza Júnior, Muhammad Khalid and Wilhelm J. Baader

      Article first published online: 22 JUL 2013 | DOI: 10.1111/php.12102

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      Quantum yields are reported for several important chemiluminescence reactions, which involve electron transfer processes in the chemiexcitation step. Quantum yields are high for intramolecular transformations whereas they are very low for most intermolecular processes, with the notable exception of the peroxyoxalate reaction.

    5. You have free access to this content
      Current Status of Research on Fungal Bioluminescence: Biochemistry and Prospects for Ecotoxicological Application (pages 1318–1326)

      Cassius V. Stevani, Anderson G. Oliveira, Luiz F. Mendes, Fernanda F. Ventura, Hans E. Waldenmaier, Rodrigo P. Carvalho and Tatiana A. Pereira

      Article first published online: 20 AUG 2013 | DOI: 10.1111/php.12135

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      In this review we present the current state of fungal bioluminescence research and an overview of the application of bioluminescent fungi as an environmental toxicological tool. The enzyme catalyzed luminescent reaction of fungal luciferin is a two step process involving a soluble reductase and a membrane associated luciferase resulting in green light.

  4. Special Issue Research Articles

    1. Top of page
    2. Editorial
    3. Special Issue Honouring the Memory of Elsa Abuin
    4. Special Issue Invited Review Articles
    5. Special Issue Research Articles
    6. Research Articles
    7. List of Reviewers
    1. Solvent and Media Effects on the Photophysics of Naphthoxazole Derivatives (pages 1327–1334)

      Manuel Curitol, Xavier Ragas, Santi Nonell, Nancy Pizarro, María V. Encinas, Pedro Rojas, Renzo P. Zanocco, Else Lemp, Germán Günther and Antonio L. Zanocco

      Article first published online: 19 AUG 2013 | DOI: 10.1111/php.12133

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      The photophysical properties of 2-phenyl-naphtho[1,2-d][1,3]oxazole, 2(4-N,N-dimethylaminophenyl)naphtho[1,2-d][1,3]oxazole and 2(4-N,N-diphenylaminophenyl) naphtho[1,2-d][1,3]oxazole, were studied in a serie of solvents. The dyes show valuable spectroscopic and photochemical properties: large molar absorbility and fluorescence quantum yield, short fluorescence lifetime,solvent-dependent changes of the dipole moment on excitation and photostability comparableto commercially available laser dyes.These properties make the molecules valuable candidates as fluorescent probes to be used in fluorescence microscopy and to determine physicochemical properties in micro-organized systems.

    2. Unexpected Imidazoquinoxalinone Annulation Products in the Photoinitiated Reaction of Substituted-3-Methyl-Quinoxalin-2-Ones with N-Phenylglycine (pages 1335–1345)

      Julio R. De la Fuente, Álvaro Cañete, Carolina Jullian, Claudio Saitz and Christian Aliaga

      Article first published online: 4 NOV 2013 | DOI: 10.1111/php.12162

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      Photoinduced electron transfer between N-phenylglycine (NPG) and electronically excited triplets of 7-substituted-3-methyl-quinoxalin-2-ones generate the unexpected, 7-substituted-1,2,3,3a-tetrahydro-3a-methyl-2-phenylimidazo[1,5-a]quinoxalin-4(5H)-ones, annulation products. A reaction mechanism includes a photoinduced single electron transfer initiation step, propagation steps involving radical intermediates and NPG, with radical chain termination steps, leads to the respective products and NPG by-products.

    3. Modulation of the Photophysical Properties of Pyrene by the Microstructures of Five Poly(alkyl methacrylate)s Over a Broad Temperature Range (pages 1346–1353)

      Teresa D. Z. Atvars, Shibu Abraham, Anita J. Hill, Steven J. Pas, Carlos Chesta and Richard G. Weiss

      Article first published online: 8 JUL 2013 | DOI: 10.1111/php.12103

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      Subtle, temperature-induced changes in poly(alkyl methacrylate) film microstructures can be detected by careful analyses of fluorescence properties of pyrene guest molecules.

    4. A Versatile Near-Infrared Asymmetric Tricarbocyanine for Zinc Ion Sensing in Water (pages 1354–1361)

      Guillermo O. Menéndez, Cecilia Samaniego López, Elizabeth A. Jares-Erijman and Carla C. Spagnuolo

      Article first published online: 23 SEP 2013 | DOI: 10.1111/php.12160

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      A near infrared emissive asymmetric tricarbocyanine conveniently functionalized to improve water solubility and bioconjugation, has been evaluated as a highly sensitive sensor for zinc (II) in aqueous medium, which performs in an appropriate range for biological studies. The probe was successfully conjugated to a protein-ligand model with high affinity and specificity (biotin-streptavidin technology) rendering an excellent performance of sensing.

    5. Photochemistry of Tetraphenyldiboroxane and its Use as Photopolymerization Coinitiator (pages 1362–1367)

      Willy G. Santos, Carla C. Schmitt and Miguel G. Neumann

      Article first published online: 1 JUN 2013 | DOI: 10.1111/php.12084

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      Tetraphenyldiboroxane (TPhB) can be used as visible-light photopolymerization coinitiator with the dye Safranine (SfH+). The mechanism involves the formation of a radical cation of the boron compound. Photophysical properties of the excited states of TPhB were also determined.

    6. Photochemical and Thermal Stability of Some Dihydroxyacetophenones Used as UV-MALDI-MS Matrices (pages 1368–1374)

      Olga I. Tarzi, Luciano Di Stéfano, Juan E. Argüello, Gabriela Oksdath-Mansilla and Rosa Erra-Balsells

      Article first published online: 17 AUG 2013 | DOI: 10.1111/php.12130

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      2,4-, 2,5-, 2,6- and 3,5-dihydroxyacetophenone (DHA) used as matrices in matrix-assisted ultraviolet laser desorption/ionization mass spectrometry (UV-MALDI-MS) were studied by steady-state and transient-absorption spectroscopy, together with DFT calculations at the B3LYP level of theory. All compounds have low fluorescence quantum yields, possibly due to an efficient excited-state intramolecular proton transfer (ESIPT). Laser flash photolysis (LFP) results showed for 2,4-DHA a phototautomer detected at λ = 400 nm. Their photochemical stability in solution at different wavelengths and conditions was analyzed by different techniques. Only 3,5-DHA showed decomposition when irradiated, probably because phototautomerization is not possible.

    7. Photoinduced Electron Transfer in Perylene-TiO2 Nanoassemblies (pages 1375–1382)

      Manuel J. Llansola-Portoles, Jesse J. Bergkamp, John Tomlin, Thomas A. Moore, Gerdenis Kodis, Ana L. Moore, Gonzalo Cosa and Rodrigo E. Palacios

      Article first published online: 8 JUL 2013 | DOI: 10.1111/php.12108

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      A detailed study of the photosensitization of small (< 5 nm) TiO2 nanoparticles (NPs) suspended in THF by perylene dyes is presented herein. The figure shows a TiO2 nanoparticle (NP) with attached (green) and free (red) perylene derivatives. Arrows indicate elemental processes occurring in the system: photon (hν) absorption by the dye, photoinduced electron transfer (ET) from the dye to the TiO2 NP, back electron transfer (BET), and dye fluorescence (hν′). Steady state and transient absoption spectroscopy techniques were used to investigate these elemental processes. The right side graph shows absorption traces corresponding to the open-attached (green) and closed-free (red) forms of the dye.

    8. Spectroscopy, Microscopy and Fluorescence Imaging of Origanum vulgare L. Basis for Nondestructive Quality Assessment (pages 1383–1390)

      Johanna M. Novo, Analia Iriel, María Claudia Marchi and María Gabriela Lagorio

      Article first published online: 9 AUG 2013 | DOI: 10.1111/php.12131

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      Origanum vulgare L. plant was studied spectroscopically and microscopically. The main achievement of this work was obtaining optical indicators related to nutraceutics and water content. A comprehensive description of the places where these optical signals are originated is presented.

    9. Superresolution Imaging with Switchable Fluorophores Based on Oxazine Auxochromes (pages 1391–1398)

      Marco Petriella, Erhan Deniz, Subramani Swaminathan, Maria J. Roberti, Françisco M. Raymo and Mariano L. Bossi

      Article first published online: 28 JUN 2013 | DOI: 10.1111/php.12100

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      We present two alternative strategies to achieve controllable fluorescence modulation, based on a molecular assembly containing a [1,3]oxazine, for imaging with a spatial resolution below the diffraction limit in single-molecule localization fluorescence microscopies. The oxazine acts as a two-state, a dark and a bright one, molecular switch. The incorporation of the assemblies in micelles renders them compatible for cellular biology applications.

    10. Association of Valdecoxib, a Nonsteroidal Anti-Inflammatory Drug, with Human Serum Albumin (pages 1399–1405)

      Maria V. Encinas, Eduardo Lissi and Claudio Vergara

      Article first published online: 16 SEP 2013 | DOI: 10.1111/php.12158

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      Valdecoxib addition quenches the intrinsic fluorescence of HSA. The values obtained for the binding constant and the number of binding sites depend on the treatment of the fluorescence data. The most reliable procedure is the treatment of data using a combination of the Scatchard equation and data obtained at different protein concentrations.

    11. Structural and Photosensitizing Features of Phthalocyanine—Zeolite Hybrid Nanomaterials (pages 1406–1412)

      Malte Grüner, Vassilios Siozios, Birgit Hagenhoff, Daniel Breitenstein and Cristian A. Strassert

      Article first published online: 17 AUG 2013 | DOI: 10.1111/php.12141

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      The linkage of Si(IV) phthalocyanine to the surface of zeolite L nanoparticles enhances its singlet oxygen photosensitizing capability by suppressing the formation of inactive aggregates, even in aqueous environments.

    12. Evaluation of the Number of Binding Sites in Proteins from their Intrinsic Fluorescence: Limitations and Pitfalls (pages 1413–1416)

      Eduardo Lissi, Cristian Calderón and Ana Campos

      Article first published online: 26 AUG 2013 | DOI: 10.1111/php.12112

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      Fluorescence measurements have been profusely employed to determine binding of solutes to proteins (Ks and the number of binding sites n). These values are derived from double log plots where the slope is equated to the number of equivalent binding sites in the proteins. We propose that the measured slope is unrelated to n.

    13. Photoreduction of Azaoxoisoaporphines by Amines: Laser Flash and Steady-State Photolysis and Pulse Radiolysis Studies (pages 1417–1426)

      Julio R. de la Fuente, Christian Aliaga, Alvaro Cañete, Gabriel Kciuk, Tomasz Szreder and Krzysztof Bobrowski

      Article first published online: 10 JUN 2013 | DOI: 10.1111/php.12087

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      Photoreduction of 7H-benzo[e]perimidin-7-ones by amines proceeds through a stepwise electron-proton-electron transfer mechanism, which was studied by using laser flash photolysis, steady-state photolysis and pulse radiolysis. Later, to achieve the triplet state, the sequence of reaction generates a radical ion pair, which by proton transfer over the N1- and O-atoms of substrates yields two different hydrogenated radicals, likely in equilibrium. These neutral radicals by the second electron transfer lead to the metastable products. Transient absorptions for intermediaries were characterized by laser flash photolysis and pulse radiolysis.

    14. Naphthoxazole-Based Singlet Oxygen Fluorescent Probes (pages 1427–1432)

      Rubén Ruiz-González, Renzo Zanocco, Yasser Gidi, Antonio L. Zanocco, Santi Nonell and Else Lemp

      Article first published online: 8 JUL 2013 | DOI: 10.1111/php.12106

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      Conjugation of a fluorescent and a singlet oxygen trapping moieties leads to a dyad with a low fluorescence in its native state. In the presence of singlet oxygen, a new photooxidized chemical entity is born, leading to a fluorescence enhancement over two orders of magnitude at the optimal selected wavelength.

    15. Impact of Dye-Protein Interaction and Silver Nanoparticles on Rose Bengal Photophysical Behavior and Protein Photocrosslinking (pages 1433–1441)

      Madeline J. Simpson, Horacio Poblete, May Griffith, Emilio I. Alarcon and Juan C. Scaiano

      Article first published online: 17 AUG 2013 | DOI: 10.1111/php.12119

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      “Rose Bengal binds up to 10 molecules per Type-I collagen molecule in aqueous solutions. Upon binding of rose Bengal the photophysical and photochemical properties of the dye are strongly affected. The presence of silver nanoparticles in the near vicinity of the protein further modifies the photophysical properties of the dye”.

    16. Comparison of the Kinetics of Electron Transfer in the Diffusion Limit for the Singlet and Triplet Quenching of Eosin Y by Quinones (pages 1442–1447)

      Sonia G. Bertolotti, Hernán A. Montejano and Carlos M. Previtali

      Article first published online: 27 JUN 2013 | DOI: 10.1111/php.12089

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      Quenching rate constants for singlet (black) and triplet (red) excited states of eosin Y by benzoquinones in acetonitrile.

    17. Oxidation of Tyrosine Photoinduced by Pterin in Aqueous Solution (pages 1448–1455)

      Carolina Castaño, María L. Dántola, Esther Oliveros, Andrés H. Thomas and Carolina Lorente

      Article first published online: 27 JUN 2013 | DOI: 10.1111/php.12099

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      The oxidation of tyrosine (Tyr) sensitized by pterin under UV-A irradiation occurs by an electron transfer mechanism and is not mediated by singlet oxygen. The main reaction products are DOPA, dopachrome and tyrosine dimers. The latter are involved in the crosslinking of proteins.

    18. Type I Photosensitization of 2′-deoxyadenosine 5′-monophosphate (5′-dAMP) by Biopterin and its Photoproduct Formylpterin (pages 1456–1462)

      Mariana P. Serrano, Claudio D. Borsarelli and Andrés H. Thomas

      Article first published online: 3 AUG 2013 | DOI: 10.1111/php.12134

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      Biopterin (Bip) and its photoproduct 6-formylpterin (Fop) photosensitize the degradation of 2′-deoxyadenosine 5′-monophosphate (5′-dAMP) by electron transfer mechanism in aerated aqueous solutions.

    19. The NSAIDs Indomethacin and Diflunisal as Scavengers of Photogenerated Reactive Oxygen Species (pages 1463–1470)

      Rebeca Purpora, Walter Massad, Gabriela Ferrari, Eugenia Reynoso, Susana Criado, Sandra Miskoski, Adriana Pajares and Norman A. García

      Article first published online: 29 JUL 2013 | DOI: 10.1111/php.12114

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      The scavenging of reactive oxygen species (ROS) by Diflunisal (DFNS) and Indomethacin (IMTC), two profusely employed anti-inflammatory and analgesic NSAIDs, was systematically studied in pH 7 aqueous solution. The ROS O2(1Δg), O2•− and H2O2, generated by visible light irradiation of Riboflavin, are deactivated by the NSAIDs. DFNS quenches ROS in a dominant physical fashion. It constitutes an excellent protective-antioxidant provided that is practically not destroyed/oxidized after the ROS scavenging action. IMTC, being also an efficient interceptor of ROS, belong to the so-called group of sacrificial-ROS quenchers: It is easily degraded by the oxidative species in the scavenging action.

  5. Research Articles

    1. Top of page
    2. Editorial
    3. Special Issue Honouring the Memory of Elsa Abuin
    4. Special Issue Invited Review Articles
    5. Special Issue Research Articles
    6. Research Articles
    7. List of Reviewers
    1. Effect of the Phospholipid Chain Length and Head Group on Beta-Phase Formation of Poly(9,9-dioctylfluorene) Enclosed in Liposomes (pages 1471–1478)

      María J. Tapia, María Monteserín, Hugh D. Burrows, João S. Seixas de Melo and Joan Estelrich

      Article first published online: 7 SEP 2013 | DOI: 10.1111/php.12143

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      Poly(9,9-dioctylfluorene) is solubilized in phospholipid liposomes of DLPC, DMPC, DPPC, DMPE, DMPA, and DMPS giving rise to the formation of the ordered polymer β-phase which is characterized by a well-resolved characteristic vibronic structure in the emission spectra, higher luminescence efficiency and improved charge transport properties resulting from increased electron delocalization. This phase is better promoted by phospholipids with longer alkyl chain lengths or non-bulky and more hydrophobic head groups. The polymer agglomeration is considered the main mechanism for β-phase formation in these systems. A second driving force seems to be the interdigitation between the polymer and phospholipid alkyl chains.

    2. Photooxidation Mechanism of Levomepromazine in Different Solvents (pages 1479–1489)

      Luis E. Piñero-Santiago, Carmelo García, Virginie Lhiaubet-Vallet, Jerome Trzcionka, Rolando Oyola, Karen Torres, Jaysika Leguillú and Miguel A. Miranda

      Article first published online: 10 SEP 2013 | DOI: 10.1111/php.12147

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      Levomepromazine (LPZ, Levoprome® or Nozinan®) is indicated for the treatment of schizophrenia and other schizoaffective disorders. Nevertheless, it is photolabile under UV-A and UV-B light in aerobic conditions resulting in the formation of its sulfoxide (LPZO). LPZSO does not form by the reaction of singlet oxygen with ground state LPZ. This oxidation product is actually produced by the reaction of the cation radical of LPZ (LPZ·+) with molecular oxygen. This cation radical in turn, is produced by an electron transfer process between the 3LPZ* and ground state molecular oxygen.

    3. Time Courses and Time-Resolved Spectra of Firefly Bioluminescence Initiated by Two Methods of ATP Injection and Photolysis of Caged ATP (pages 1490–1496)

      Yuki Yanagisawa, Takeshi Kageyama, Naohisa Wada, Masatoshi Tanaka and Shin-ya Ohno

      Article first published online: 26 AUG 2013 | DOI: 10.1111/php.12146

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      Time evolution of firefly bioluminescence has been studied by time-adjusted manual injection of ATP into buffer solution containing other reactants. The rise and decay rates of the emission intensity decrease with lowering pH from 7.8 to 6.8, while the delay of rise due to diffusion of ATP changes slightly. This pH dependence is attributed to the rate of ATP binding at luciferase. The emission spectra composed of two bands do not change their line shape for duration time of 600 s. The emission intensity of band at 2.2 eV becomes weaker than that at 2.0 eV with lowering pH.

    4. Solar UV Exposure of Seafarers along Subtropical and Tropical Shipping Routes (pages 1497–1506)

      Uwe Feister, Gabriele Meyer and Ulrich Kirst

      Article first published online: 26 AUG 2013 | DOI: 10.1111/php.12144

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      Solar erythemal exposure at horizontal incidence and on different body parts of seafarers were measured on merchant vessels along 4 typical international routes and on RV METEOR at low latitudes. Maximum daily horizontal erythemal exposure in the tropics reached 96 SED (38 MED with phototype II). 40 to 80% of global erythemal exposure is received on the head. Ratios between direct-to-normal and global erythemal exposure derived from measurements and model calculations go up to 0.69. Maximum UV index values reached 22. A model has been proposed to estimate personal erythemal exposure of a seafarer from his/her personal record of sea service.

  6. List of Reviewers

    1. Top of page
    2. Editorial
    3. Special Issue Honouring the Memory of Elsa Abuin
    4. Special Issue Invited Review Articles
    5. Special Issue Research Articles
    6. Research Articles
    7. List of Reviewers

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