Green syntheses of stable and efficient organic dyes for organic hybrid light-emitting diodes

Huang, Yunping; Cohen, Theodore A.; Sommerville, Parker J. W.; Luscombe, Christine K.

doi:10.1039/d1tc01567b

Cited by 16 publications

(16 citation statements)

References 60 publications

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“…In the molecule design, alkylated theobromine increases PLQYs of the final products and their solubility in SBS, [7] while the central π- nm. [14] This highlights the excellent structural and spectral tunability of organic dyes. Scheme 1.…”

Section: Resultsmentioning

confidence: 94%

“…Scheme 1 shows the synthetic routes to converting alkylated theobromine into Theo-Blue, [7] Theo-Green [14] and Theo-Ruby. In the molecule design, alkylated theobromine increases PLQYs of the final products and their solubility in SBS, [7] while the central π- nm.…”

Section: Resultsmentioning

confidence: 99%

“…[16] More importantly, the final LED light-converting film only requires around 1 wt% of the theobromine dyes to be blended into an inexpensive industrial polymer, SBS (purchased from Sigma Aldrich at $ 82.4/kg), and thus the overall cost contribution from the theobromine dyes is minimal, as discussed in a previous report by our group. [14] .…”

Section: Resultsmentioning

confidence: 99%

“…Moreover, these dye-SBS composites only require low blending ratios of theobromine dyes, around 1 wt%. [14] In this paper, we further advance the efficacy of theobromine dyes in LED lightings with a new deep red-emitting dye, Theo-Ruby. We developed a white light converter by blending Theo-Ruby with two other theobromine dyes (Theo-Blue and Theo-Green) into SBS.…”

Section: Introductionmentioning

confidence: 99%

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Naturally Derived Organic Dyes for LED Lightings of High Color Rendering and Fidelity Index

Huang

Cohen

Luscombe

2021

Advanced Sustainable Systems

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Light-emitting diodes (LEDs) are a lighting technology with a huge and ascending market. Typically, LED backlights are often paired with inorganic phosphors made from rare-earth elements (REEs) to tune the emission lineshapes for different applications. However, REE production is a resource-intensive process with many negative environmental impacts. Herein we develop organic hybrid LEDs using organic dyes synthesized from an abundant and non-toxic natural product (theobromine) to replace REE phosphors. The resulting hybrid LED generates continuous emission from 400 -740 nm, resulting in high color rendering index (the current industry standard) of 90 and color fidelity index (the most advanced and comprehensive standard) of 92, challenging commercial LEDs based on REE phosphors. In addition, the light-converting composite is made from 99 wt% SBS, an inexpensive industrial polymer, and 1wt% theobromine dyes, reducing the cost of the light converter to ¢1.30 for a 1 W LED, compared to approximately ¢ 19.2 of commercial products. The light converting efficiency of the dye-SBS composite is 82%. Excited state kinetics experiments were also conducted to provide guidance to further increase the light-converting efficiency of the theobromine dyes while maintaining excellent color rendering and fidelity. File list (2) download file view on ChemRxiv Supporting Information.pdf (610.92 KiB) download file view on ChemRxiv Theobromine and CRI CFI.pdf (1.00 MiB)

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Section: Resultsmentioning

confidence: 94%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Naturally Derived Organic Dyes for LED Lightings of High Color Rendering and Fidelity Index

Huang

Cohen

Luscombe

2021

Advanced Sustainable Systems

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“…In addition, a deep lowest unoccupied molecular orbital level is demonstrated to reduce the photooxidation rate of organic dyes, and therefore we observed an increase in stability as the bandgap of the dyes decreases. [4] Table S1. The PLQYs of the theobromine dyes in different polymer matrices.…”

Section: Figure S4mentioning

confidence: 99%

Naturally Derived Organic Dyes for LED Lightings of High Color Rendering and Fidelity Index

Huang¹,

Cohen²,

Luscombe³

2021

Preprint

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<p>Light-emitting diodes (LEDs) are a lighting technology with a huge and ascending market. Typically, LED backlights are often paired with inorganic phosphors made from rare-earth elements (REEs) to tune the emission lineshapes for different applications. However, REE production is a resource-intensive process with many negative environmental impacts. Herein we develop organic hybrid LEDs using organic dyes synthesized from an abundant and non-toxic natural product (theobromine) to replace REE phosphors. The resulting hybrid LED generates continuous emission from 400 – 740 nm, resulting in high color rendering index (the current industry standard) of 90 and color fidelity index (the most advanced and comprehensive standard) of 92, challenging commercial LEDs based on REE phosphors. In addition, the light-converting composite is made from 99 wt% SBS, an inexpensive industrial polymer, and 1wt% theobromine dyes, reducing the cost of the light converter to ¢1.30 for a 1 W LED, compared to approximately ¢ 19.2 of commercial products. The light converting efficiency of the dye-SBS composite is 82%. Excited state kinetics experiments were also conducted to provide guidance to further increase the light-converting efficiency of the theobromine dyes while maintaining excellent color rendering and fidelity. </p>

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Leveraging Coupled Solvatofluorochromism and Fluorescence Quenching in Nitrophenyl‐Containing Thiazolothiazoles for Efficient Organic Vapor Sensing

et al. 2023

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Solvatofluorochromic molecules provide strikingly high fluorescent outputs to monitor a wide range of biological, environmental, or materials‐related sensing processes. Here, thiazolo[5,4‐d]thiazole (TTz) fluorophores equipped with simple alkylamino and nitrophenyl substituents for solid‐state, high‐performance chemo‐responsive sensing applications are reported. Nitroaromatic substituents are known to strongly quench dye fluorescence, however, the TTz core subtly modulates intramolecular charge transfer (ICT) enabling strong, locally excited‐state fluorescence in non‐polar conditions. In polar media, a planar ICT excited‐state shows near complete quenching, enabling a twisted excited‐state emission to be observed. These unique fluorescent properties (spectral shifts of 0.13 – 0.87 eV and large transition dipole moments Δµ = 20.4 – 21.3 D) are leveraged to develop highly sought‐after chemo‐responsive, organic vapor optical sensors. The sensors are developed by embedding the TTz fluorophores within a poly(styrene‐isoprene‐styrene) block copolymer to form fluorescent dye/polymer composites (ΦF = 70 – 97%). The composites respond reversibly to a comprehensive list of organic solvents and show low vapor concentration sensing (e.g., 0.04% solvent saturation vapor pressure of THF – 66 ppm). The composite films can distinguish between solvent vapors with near complete fluorescent quenching observed when exposed to their saturated solvent vapor pressures, making this an extremely promising material for optical chemo‐responsive sensing.

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Green syntheses of stable and efficient organic dyes for organic hybrid light-emitting diodes

Abstract: Organic hybrid light-emitting diodes (hybrid-LEDs) employ organic dyes as light converters on top of commercial blue inorganic LEDs, replacing incumbent inorganic phosphor light converters synthesized from rare-earth and/or toxic metallic...

Cited by 16 publications

References 60 publications

Naturally Derived Organic Dyes for LED Lightings of High Color Rendering and Fidelity Index

Naturally Derived Organic Dyes for LED Lightings of High Color Rendering and Fidelity Index

Naturally Derived Organic Dyes for LED Lightings of High Color Rendering and Fidelity Index

Leveraging Coupled Solvatofluorochromism and Fluorescence Quenching in Nitrophenyl‐Containing Thiazolothiazoles for Efficient Organic Vapor Sensing

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