Easy and mild fluoride-mediated direct mono- and dialkoxylation of perylenediimides

Zink‐Lorre, Nathalie; Font‐Sanchis, Enrique; Sastre‐Santos, Ángela; Fernández‐Lázaro, Fernando

doi:10.1016/j.dyepig.2015.12.011

Cited by 11 publications

(13 citation statements)

References 40 publications

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“…In the PMMA−PDI-1 composite, the substituents do not alter the optical properties of the compound. 28 Indeed, although the absorption spectra experience a 10 nm blue shift (see blue dashed line in Figure 2a), its shape is not significantly modified, indicating the absence of aggregation in the film. In addition, the broader PL spectrum (see red dashed line in Figure 3a) shows the activation of new vibrational modes in the solid-state composite (see Figure S6b of the Supporting Information).…”

Section: These Organic Compounds Represent An Outstanding Choicementioning

confidence: 94%

“…PDI-1 presents four diphenylphenoxy substituents in the 2, 5, 8, and 11 positions, so-called ortho positions, and PDI-2 does not present any substituent either in the ortho or bay positions. PDI-1 has been synthesized for the first time, by using the methodology previously described by our group, from 2,5,8,11-tetrabromoperylene-3,4:9,10-tetracarboxydiimide in the presence of 2,6-diphenylphenol, CsF, and 18-crown-6 (Scheme ; see SI for the synthetic methodology and characterization). PDI-2 was prepared following the procedure previously described in the literature …”

Section: Synthesis and Fabrication Of The Compositementioning

confidence: 99%

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Efficient Optical Amplification in a Sandwich-Type Active-Passive Polymer Waveguide Containing Perylenediimides

et al. 2017

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Polymer waveguides doped with luminescent materials serve as a suitable flexible platform for active elements (lasers and amplifiers) in on-chip optical circuits. However, at present, the best parameters (lowest thresholds) achieved with these devices are obtained with the use of the stripe excitation technique in the framework of which external illumination of an active material along the whole length of the waveguide is realized that is not convenient for the waveguide on-chip integration and requires high peak energies due to the large excitation area. In the present work, an elegant method is proposed to overcome this obstacle and provide efficient active material pumping along the whole waveguide length with use of on-chip integration compatible edge-type excitation light injection. This novel type of planar active-passive polymer waveguides includes a thin (50–100 nm) active layer of poly(methyl methacrylate) (PMMA), which is heavily doped with highly luminescent perylenediimide (PDI) molecules, sandwiched between two cladding (passive) PMMA layers. This structure efficiently exploits the excellent light-emitting properties of PDIs with a confinement of both the excitation beam and the photoluminescence in the active PMMA–PDI film. In this way, the absence of losses in the PMMA claddings guarantees the propagation of the pump beam along the whole length of the structure (≈1 mm) in order to provide the required excitation to obtain stimulated emission. Geometrical parameters are optimized to demonstrate the amplified spontaneous emission with a threshold as low as 0.9 μJ and a line width as narrow as 2 nm.

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Section: These Organic Compounds Represent An Outstanding Choicementioning

confidence: 94%

Section: Synthesis and Fabrication Of The Compositementioning

confidence: 99%

Efficient Optical Amplification in a Sandwich-Type Active-Passive Polymer Waveguide Containing Perylenediimides

et al. 2017

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“…Another means to access bay-alkoxylated PBIs from coreunsubstituted PBIs is by fluoride-mediated alkoxylation as proposed by Fernández-Lázaro and co-workers. 173 This reaction, as well as the analogous thiolation, 174 has, however, some limitations. Firstly, the scope of this novel reaction is still limited and the introduction of alkoxy or thio substituents occurs preferably for alkyl starting materials rather than aryl counterparts.…”

Section: Direct Hydroxylation Reactionsmentioning

confidence: 99%

“…Accordingly, the reaction with phenols did not take place for core-unsubstituted PBIs. 173 Likewise, introduction of two tert-butylthio substituents into bay areas was lowyielding, while the reaction of core-unsubstituted PBI with ethanedithiol, which was otherwise successful for halogenated precursors (see Scheme 30), proved ineffective. 174 It is also interesting to note that even for halogenated PBIs, fluorideassisted reactions with thiophenols are not well-suited as the yields are mediocre, whereas direct functionalization of the PBI core with thiophenols did not proceed at all.…”

Section: Direct Hydroxylation Reactionsmentioning

confidence: 99%

Progress in the synthesis of perylene bisimide dyes

2019

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“…In the present report, we have investigated the 1,7 and 1,6 isomers of dipiperidin-N-yl-substituted PDI, named PDI-1 and PDI-2, respectively. They can be straightforwardly synthesized through a metal-free approach [19][20][21][22][23][24][25][26][27]. The modification by the substituents twists the PDI core, which strongly affects its optoelectronic properties [3,28].…”

Section: Introductionmentioning

confidence: 99%

Substituents interplay in piperidinyl-perylenediimide as dopant-free hole-selective layer for perovskite solar cells fabrication

et al. 2021

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The charge selective layer is of significance for the fabrication of emerging photovoltaics, including perovskite-based solar cells. Molecular hole transport materials (HTMs) are being employed as charge transporters, owing to their synthetic molecular flexibility that allows the fine-tuning of their electro-optical properties. Typically, doping of HTMs is essential, but it is a trade-off between long-term durability and device performance. The energetic level of perylenediimides (PDIs) was altered by the position of the substituent. The substituent’s position influences the geometry of the PDI core, which can lose planarity, thus presenting a core twist angle between the two naphthalene subunits to find its application as hole-selective layers for fabrication. We have fabricated perovskite solar cells, with pristine PDI, and it gave a competitive performance. New design protocols for PDIs are required for aligned energetic levels, which will minimize recombination losses in solar cells, favoring a performance enhancement. Graphical abstract

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Easy and mild fluoride-mediated direct mono- and dialkoxylation of perylenediimides

Cited by 11 publications

References 40 publications

Efficient Optical Amplification in a Sandwich-Type Active-Passive Polymer Waveguide Containing Perylenediimides

Efficient Optical Amplification in a Sandwich-Type Active-Passive Polymer Waveguide Containing Perylenediimides

Progress in the synthesis of perylene bisimide dyes

Substituents interplay in piperidinyl-perylenediimide as dopant-free hole-selective layer for perovskite solar cells fabrication

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