Molecular Tuning of Phenylene-Vinylene Derivatives for Two-Photon Photosensitized Singlet Oxygen Production

Publication: Research - peer-reviewJournal article – Annual report year: 2009

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Substituent-dependent features and properties of the sensitizer play an important role in the photosensitized production of singlet oxygen, O2(a1Δg). In this work, we systematically examine the effect of molecular changes in the sensitizer on the efficiency of singlet oxygen production using, as the sensitizer, oligophenylene-vinylene derivatives designed to optimally absorb light in a nonlinear two-photon process. We demonstrate that one cannot always rely on rule-of-thumb guidelines when attempting to construct efficient two-photon singlet oxygen sensitizers. Rather, as a consequence of behavior that can deviate from the norm, a full investigation of the photophysical properties of the system is generally required. For example, it is acknowledged that the introduction of a ketone moiety to the sensitizer chromophore often results in more efficient production of singlet oxygen. However, we show here that the introduction of a carbonyl into a given phenylene-vinylene can, rather, have adverse effects on the yield of singlet oxygen produced. Using these molecules, we show that care must also be exercised when using qualitative symmetry-derived arguments to predict the relationship between one-and two-photon absorption spectra.
Original languageEnglish
JournalJournal of Organic Chemistry
Publication date2009
Volume74
Issue23
Pages9094-9104
ISSN0022-3263
DOIs
StatePublished
CitationsWeb of Science® Times Cited: 30

Keywords

  • Polymer solar cells, Solar energy
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