Photophysical characterization of a 1,4,5,8-naphthalenediimide derivative

Barros, Teresa C.; Brochsztain, Sergio; Toscano, Vicente G.; Filho, Pedro Berci; Politi, Mário José

doi:10.1016/s1010-6030(97)00205-0

Cited by 134 publications

(97 citation statements)

References 24 publications

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“…The photophysics of N-substituted NDIs has already been investigated in detail. [22][23][24][25][26][27][28] These compounds are colorless, their first absorption band being located below 400 nm, and very weakly fluorescent because of fast intersystem crossing favored by the strong spin-orbit coupling introduced by the carbonyl groups. N-Substituted NDIs are often used as building blocks in dyads, triads, and donor-bridge-acceptor systems where they act as electron acceptor, [29][30][31][32][33] but their fast intersystem crossing prevents their use as light absorbers.…”

Section: Introductionmentioning

confidence: 99%

Ultrafast Photoinduced Charge Separation in Naphthalene Diimide Based Multichromophoric Systems in Liquid Solutions and in a Lipid Membrane

et al. 2008

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The photophysical properties of multichromophoric systems consisting of eight red or blue naphthalene diimides (NDIs) covalently attached to a p-octiphenyl scaffold, as well as a blue bichromophoric system with a biphenyl scaffold, have been investigated in detail using femtosecond time-resolved spectroscopy. The blue octachromophoric systems have been recently shown to self-assemble as supramolecular tetramers in lipid bilayer membranes and to enable generation of a transmembrane proton gradient upon photoexcitation (Bhosale, S.; Sisson, A. L.; Talukdar, P.; Fürstenberg, A.; Banerji, N.; Vauthey, E.; Bollot, G.; Mareda, J.; Röger, C.; Würthner, F.; Sakai, N.; Matile, S. Science 2006, 313, 84). A strong reduction of the fluorescence quantum yield was observed when going from the single NDI units to the multichromophoric systems in methanol, the effect being even stronger in a vesicular lipid membrane. Fluorescence up-conversion measurements reveal ultrafast self-quenching in the multichromophoric systems, whereas the formation of the NDI radical anion, evidenced by transient absorption measurements, points to the occurrence of photoinduced charge separation. The location of the positive charge could not be established unambiguously from the transient absorption measurements, but energetic considerations indicate that charge separation should occur between two NDI units in the blue systems, whereas both an NDI unit and the p-octiphenyl scaffold could act as electron donor in the red system. The lifetime of the charge-separated state was found to increase from 22 to 45 ps by going from the bi-to the octachromophoric blue systems in methanol, while a 400 ps decay component was observed in the lipid membrane. This lifetime lengthening is explained in terms of charge migration that is most efficient when the octachromophoric systems are assembled as supramolecular tetramers in the lipid membrane. Furthermore, the average charge-separated state lifetime of the red system in methanol is even larger and amounts to 750 ps. This effect cannot be simply explained in terms of Marcus inverted regime as the driving force for charge recombination in the red system is only slightly larger than in the blue one. A better spatial separation of the charges in the red system stemming from the localization of the hole on the p-octiphenyl scaffold could additionally contribute to the slowing down of charge recombination.

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Section: Introductionmentioning

confidence: 99%

Ultrafast Photoinduced Charge Separation in Naphthalene Diimide Based Multichromophoric Systems in Liquid Solutions and in a Lipid Membrane

et al. 2008

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“…The red-shifted, unstructured, excimerlike emission band observed for the film is in sharp contrast to the emission of DPN in water solution. The emission spectrum of the film was very similar to that of a suspension of microcrystalline N,Ndibutyl-1,4,5,8-naphthalenediimide in water (Barros et al 1997) (Fig. 2B).…”

Section: Scheme 1 Results and Discussionmentioning

confidence: 52%

“…The spectra of DPN in water and acetonitrile solutions are also shown for comparison. The spectrum in water is typical of monomeric 1,4,5,8-naphthalenediimides (Barros et al 1997, showing welldefined vibrational structure. In acetonitrile, on the other hand, loss in the vibrational structure is seen which is attributed to aggregated DPN .…”

Section: Scheme 1 Results and Discussionmentioning

confidence: 96%

“…Naphthalenediimides are a group of compounds that have become increasingly important in the past few years, due to their use in a series of applications, ranging from the biomedical area to the science of materials (Green & Fox 1995, Barros et al 1997, Kheifets et al 1977, Saito et al 1990. Chemical or electrochemical reduction of 1,4,5,8-naphthalenediimides gives rise to a stable anion radical, making them very attractive for the construction of conducting materials (Miller et al 1993) and for artificial photosynthesis (Greenfield et al 1996).…”

Section: Introductionmentioning

confidence: 99%

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Zirconium phosphonate/1,4,5,8-naphthalenediimides self-assembled films

Rodrigues

Petri

Politi

et al. 2000

An. Acad. Bras. Ciênc.

Self Cite

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The formation and characterization of self-assembled films of zirconium phosphonate / N,N'-di(2-phosphonoethyl)-1,4,5,8-naphthalenediimide (DPN) is presented. The films were produced on glass substrates by deposition of alternating layers of Zr +4 and DPN. Films containing up to 16 layers on each side of the substrate were obtained and monitored by absorption spectroscopy and ellipsometry. When irradiated, the initially colorless films turned to a persistent pinky color reminiscent of that of DPN anion radical. These films are a promising material to the development of photovoltaic devices.

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“…Charge transfer within an NDI dimer in solution leads to the formation of excimers that can be conveniently monitored by fluorescence spectroscopy. [27] Thus, the role of cyclic peptide backbone self-assembly in enhancing NDI-NDI interactions was probed through fluorescence measurements. Figure 3a shows the fluorescence spectra for single NDI containing peptides 1, 2, and 3 as well as the control compound 7 at 1.65 mM in CDCl 3 .…”

Section: Fluorescence Characterizationmentioning

confidence: 99%

Modulating Charge Transfer through CyclicD,L‐α‐Peptide Self‐Assembly

Horne

Ashkenasy

Ghadiri

2005

Chemistry A European J

118

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We describe a concise solid support-based synthetic method for the preparation of cyclic D,L α-peptides bearing 1,4,5,8-naphthalenetetracarboxylic diimide (NDI) side chains. Studies of the structural and photoluminescence properties of these molecules in solution show that the hydrogen bond directed self-assembly of the cyclic D,L α-peptide backbone promotes intermolecular NDI excimer formation. The efficiency of NDI charge transfer in the resulting supramolecular assemblies is shown to depend on the length of the linker between the NDI and the peptide backbone, the distal NDI substituent, and the number of NDIs incorporated in a given structure. The design rationale and synthetic strategies described here should provide a basic blueprint for a series of self-assembling cyclic D,L α-peptide nanotubes with interesting optical and electronic properties.

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Photophysical characterization of a 1,4,5,8-naphthalenediimide derivative

Cited by 134 publications

References 24 publications

Ultrafast Photoinduced Charge Separation in Naphthalene Diimide Based Multichromophoric Systems in Liquid Solutions and in a Lipid Membrane

Ultrafast Photoinduced Charge Separation in Naphthalene Diimide Based Multichromophoric Systems in Liquid Solutions and in a Lipid Membrane

Zirconium phosphonate/1,4,5,8-naphthalenediimides self-assembled films

Modulating Charge Transfer through CyclicD,L‐α‐Peptide Self‐Assembly

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