Pyrene−Indole Exciplexes as Positive Photocatalysts

Cuquerella, M. Consuelo; Amrani, Soumaya El; Miranda, Miguel A.; Pérez‐Prieto, Julia

doi:10.1021/jo900356c

Cited by 10 publications

(4 citation statements)

References 27 publications

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“…Two years later, the same group showed that the pyrene-indole bichromophoric complex 496 could also catalyze the above-mentioned [2 + 2] photocycloaddition ( Scheme 167 , MBOH = 2-methyl-2-butanol). 857 Within complex 496 , pyrene served as the acceptor moiety, and indole acted as the donor moiety. Mechanistic studies indicated that this reaction proceeded through a photoinduced charge separation in complex 496 .…”

Section: Pet Catalysis–photoredox Catalysismentioning

confidence: 99%

“…Subsequently, the exciplex reacts with cyclohexadiene or styrene to give an excited triplex that undergoes [2 + 2] photocycloaddition to the final products rac - 497 and rac - 498 . Two years later, the same group showed that the pyrene-indole bichromophoric complex 496 could also catalyze the above-mentioned [2 + 2] photocycloaddition (Scheme , MBOH = 2-methyl-2-butanol) . Within complex 496 , pyrene served as the acceptor moiety, and indole acted as the donor moiety.…”

Section: Pet Catalysis–photoredox Catalysismentioning

confidence: 99%

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Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

et al. 2016

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The [2 + 2] photocycloaddition is undisputedly the most important and most frequently used photochemical reaction. In this review, it is attempted to cover all recent aspects of [2 + 2] photocycloaddition chemistry with an emphasis on synthetically relevant, regio-, and stereoselective reactions. The review aims to comprehensively discuss relevant work, which was done in the field in the last 20 years (i.e., from 1995 to 2015). Organization of the data follows a subdivision according to mechanism and substrate classes. Cu(I) and PET (photoinduced electron transfer) catalysis are treated separately in sections 2 and 4, whereas the vast majority of photocycloaddition reactions which occur by direct excitation or sensitization are divided within section 3 into individual subsections according to the photochemically excited olefin.

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Section: Pet Catalysis–photoredox Catalysismentioning

confidence: 99%

Section: Pet Catalysis–photoredox Catalysismentioning

confidence: 99%

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

et al. 2016

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“…These observations led us to hypothesize the in situ formation of an exciplex or a triphenylene-like derivative that could play the role of a photocatalyst. This hypothesis was further supported by the in situ observation of a weak broad fluorescence band in the reaction mixture centered at 472 nm while irradiating at 460 nm (see Figure ).…”

Section: Process Development: Results and Discussionmentioning

confidence: 99%

Development and Scale-Up of a Novel Photochemical C–N Oxidative Coupling

Robinson

Dieckmann

Krieger

et al. 2021

Org. Process Res. Dev.

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A visible light promoted C−N-coupling of a functionalized pyridazinone with veratrole was developed to forge the central C−N bond of an agrochemical intermediate. Dosing aqueous NaOCl and 4% O 2 in N 2 under blue light irradiation (460 nm)was key to promote the desired transformation while generating benign wastes. Mechanistic studies suggest the formation of a Nchloro species that undergoes selective coupling via a radical pathway induced by the combination of light and oxygen. Further development led to an optimized semi-batch process, which was successfully scaled up to an initial 20 L and then 1.2 m 3 .

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“…2 Recently, pyrene has been used in various fields involving photo-catalysts, 3 semiconductors, 4 charge-transfer, 5 crystals, 6 carbon nanotubes, 7 DNA probes, 8 and dendrimers. 9 In particular, blue fluorescent emitters based on pyrene units have attracted considerable attention for organic light-emitting diodes (OLEDs), owing to the advantages of pyrene.…”

Section: Introductionmentioning

confidence: 99%

Highly Efficient Multi-Functional Material for Organic Light-Emitting Diodes; Hole Transporting Material, Blue and White Light Emitter

Kim¹,

Kwon²,

Hong³

et al. 2011

Bulletin of the Korean Chemical Society

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We have demonstrated that TPyPA can be used as an efficient multi-functional material for OLEDs; hole transporting material (HTL), blue and white-light emitter. The device based on TPyPA as the HTL exhibited an external quantum efficiency of 1.7% and a luminance efficiency of 4.2 cd/A; these values are 40% higher than the external quantum efficiency and luminance efficiency of the NPD-based reference device. The device based on TPyPA as a blue-light emitter exhibited an external quantum efficiency of 4.2% and a luminance efficiency of 5.3 cdA -1 with CIE coordinates at (0.16, 0.14), the device based on TPyPA as a white-light emitter exhibited an external quantum efficiency of 3.2% and a luminance efficiency of 7.7 cdA -1 with CIE coordinates at (0.33, 0.39). Also, TPyPA-based organic solar cell (OSC) exhibited a maximum power conversion efficiency of 0.35%. TPyPA-based organic thin-film transistors (OTFTs) exhibited highly efficient field-effect mobility (µ FET ) of 1.7 × 10, a threshold voltage (V th ) of -15.9 V, and an on/off current ratio of 8.6 × 10 3 .

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Pyrene−Indole Exciplexes as Positive Photocatalysts

Abstract: Photoinduced charge separation in pyrene-based bichromophoric systems provides an effective strategy in organic synthesis, as shown for the [2 + 2] cycloaddition between 1,3-cyclohexadiene and styrenes as a model reaction.

Cited by 10 publications

References 27 publications

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Development and Scale-Up of a Novel Photochemical C–N Oxidative Coupling

Highly Efficient Multi-Functional Material for Organic Light-Emitting Diodes; Hole Transporting Material, Blue and White Light Emitter

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Pyrene−Indole Exciplexes as Positive Photocatalysts

Abstract: Photoinduced charge separation in pyrene-based bichromophoric systems provides an effective strategy in organic synthesis, as shown for the [2 + 2] cycloaddition between 1,3-cyclohexadiene and styrenes as a model reaction.

Cited by 10 publications

References 27 publications

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Development and Scale-Up of a Novel Photochemical C–N Oxidative Coupling

Highly Efficient Multi-Functional Material for Organic Light-Emitting Diodes; Hole Transporting Material, Blue and White Light Emitter

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Product

Resources

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Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions