Photophysical Properties of the Pyrromethene 597 Dye:  Solvent Effect

Bañuelos, Jorge; Arbeloa, F. López; Martínez, Virginia Martínez; Arbeloa, Teresa; Arbeloa, Í. López

doi:10.1021/jp0373898

Cited by 109 publications

(54 citation statements)

References 51 publications

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“…The bulky tert ‐butyl substituent at the pyrrole rings makes the ground and excited states of the molecule sterically distorted. However, the excited state is comparatively more relaxed, thus accounting for the observed result 6a,b. We hypothesised that an aza analogue of 1 that contains an Me 3 N + group in place of the Me 3 C moiety might also offer a good Stokes shift because of the steric crowding as well as improve its water solubility and also impart solvatochromism.…”

Section: Introductionmentioning

confidence: 99%

Rational Design of Boradiazaindacene (BODIPY)‐Based Functional Molecules

Gupta

Mula

Tyagi

et al. 2013

Chemistry A European J

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Three boradiazaindacene (BODIPY) dyes with different-coloured (greenish-yellow, orange and red) fluorescence and good Stokes shifts were synthesised starting from the greenish-yellow BODIPY dye PM546. The high Stokes shifts of the dyes are due to the release of the steric strain in their excited states relative to that in the highly twisted ground states. One of these compounds might be a useful water-soluble fluorophore, whereas the other two are promising H(+) sensors.

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Section: Introductionmentioning

confidence: 99%

Rational Design of Boradiazaindacene (BODIPY)‐Based Functional Molecules

Gupta

Mula

Tyagi

et al. 2013

Chemistry A European J

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“…The ultimately tailored dye sensitizer should be computer generated with all the physical and chemical properties predicted in advance and synthesized subsequently. It is possible to obtain the ab initio electronic structure 5 and therefore to predict the absorption and emission spectra of the dyes 6 , to systematically design and study the materials from dyes 7,8,9 , and to molecularly design dyes for DSSC, based upon the predictions on the effects of the functional groups and on the electronic levels 10 . It is also possible to predict the interactions of the dyes with the substrate, most notably TiO 2 11, 12 .…”

Section: Introductionmentioning

confidence: 99%

Effect of Molecular and Electronic Structure on the Light-Harvesting Properties of Dye Sensitizers

et al. 2007

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The systematic trends in structural and electronic properties of perylene diimide (PDI) derived dye molecules have been investigated by DFT calculations based on projector augmented wave (PAW) method including gradient corrected exchange-correlation effects. TDDFT calculations have been performed to study the visible absorbance activity of these complexes. The effect of different ligands and halogen atoms attached to PDI were studied to characterize the light harvesting properties. The atomic size and electronegativity of the halogen were observed to alter the relaxed molecular geometries which in turn influenced the electronic behavior of the dye molecules. Ground state molecular structure of isolated dye molecules studied in this work depends on both the halogen atom and the carboxylic acid groups. DFT calculations revealed that the carboxylic acid ligands did not play an important role in changing the HOMO-LUMO gap of the sensitizer. However, they serve as anchor between the PDI and substrate TiO 2 surface of the solar cell or photocatalyst. A commercially available dye-sensitizer, ruthenium bipyridine [Ru(bpy) 3 ] 2+ (RuBpy), was also studied for electronic and structural properties in order to make a comparison with PDI derivatives for light harvesting properties. Results of this work suggest that fluorinated, chlorinated, brominated, and iyodinated PDI compounds can be useful as sensitizers in solar cells and in artificial photosynthesis.

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“…Lindsey et al recently postulated that population of such a “dark state” involves coplanarization of the meso ‐substituent with a part of the dipyrromethene ring system 40. 41…”

Section: Resultsmentioning

confidence: 99%

Proton‐ and Redox‐Controlled Switching of Photo‐ and Electrochemiluminescence in Thiophenyl‐Substituted Boron–Dipyrromethene Dyes

Röhr

Trieflinger

Rurack

et al. 2006

Chemistry A European J

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A luminescent molecular switch in which the active thiol/disulfide switching element is attached to a meso-phenyl-substituted boron-dipyrromethene (BDP) chromophore as the signalling unit is presented. The combination of these two functional units offers great versatility for multimodal switching of luminescence: 1) deprotonation/protonation of the thiol/thiolate moiety allows the highly fluorescent meso-p-thiophenol-BDP and its nonfluorescent thiolate analogue to be chemically and reversibly interconverted, 2) electrochemical oxidation of the monomeric dyes yields the fluorescent disulfide-bridged bichromophoric dimer, also in a fully reversible process, and 3) besides conventional photoexcitation, the well separated redox potentials of the BDP also allow the excited BDP state to be generated electrochemically (i.e., processes 1) and 2) can be employed to control both photo- and electrochemiluminescence (ECL) of the BDP). The paper introduces and characterizes the various states of the switch and discusses the underlying mechanisms. Investigation of the ortho analogue of the dimer provided insight into potential chromophore-chromophore interactions in such bichromophoric architectures in both the ground and the excited state. Comparison of the optical and redox properties of the two disulfide dimers further revealed structural requirements both for redox switches and for ECL-active molecular ensembles. By employing thiol/disulfide switching chemistry and BDP luminescence features, it was possible to create a prototype molecular ensemble that shows both fully reversible proton- and redox-gated electrochemiluminescence.

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Photophysical Properties of the Pyrromethene 597 Dye: Solvent Effect

Cited by 109 publications

References 51 publications

Rational Design of Boradiazaindacene (BODIPY)‐Based Functional Molecules

Rational Design of Boradiazaindacene (BODIPY)‐Based Functional Molecules

Effect of Molecular and Electronic Structure on the Light-Harvesting Properties of Dye Sensitizers

Proton‐ and Redox‐Controlled Switching of Photo‐ and Electrochemiluminescence in Thiophenyl‐Substituted Boron–Dipyrromethene Dyes

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