An organic white light-emitting dye: very small molecular architecture displays panchromatic emission

Nandhikonda, Premchendar; Heagy, Michael D.

doi:10.1039/c0cc02598d

Cited by 55 publications

(29 citation statements)

References 14 publications

(3 reference statements)

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“…A mix of π-π* and n-π* excited states is the origin of such panchromatic emission with a quantum yield of 46%. [111] Baumgartner and co-workers developed a single white-emissive molecule 57 (2,8-…”

Section: Charge Transfermentioning

confidence: 99%

Single‐Molecular White‐Light Emitters and Their Potential WOLED Applications

et al. 2020

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White organic light‐emitting diodes (WOLEDs) are superior to traditional incandescent light bulbs and compact fluorescent lamps in terms of their merits in ensuring pure white‐light emission, low‐energy consumption, large‐area thin‐film fabrication, etc. Unfortunately, WOLEDs based on multilayered or multicomponent (red, green, and blue (RGB)) emissive layers can suffer from some remarkable disadvantages, such as intricate device fabrication and voltage‐dependent emission color, etc. Single molecules, which can emit white light, can be used to replace multiple emitters, leading to a simplified fabrication process, stable and reproducible WOLEDs. Recently, the performance of WOLEDs by using single molecules is catching up with that of the state‐of‐the‐art devices fabricated by multicomponent emitters. Therefore, an increasing attention has been paid on single white‐light‐emitting materials for efficient WOLEDs. In this review, different mechanisms of white‐light emission from a single molecule and the performance of single‐molecule‐based WOLEDs are collected and expounded, hoping to light up the interesting subject on single‐molecule white‐light‐emitting materials, which have great potential as white‐light emitters for illumination and lighting applications in the world.

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Section: Charge Transfermentioning

confidence: 99%

Single‐Molecular White‐Light Emitters and Their Potential WOLED Applications

et al. 2020

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“…As a result, compound 6 in cyclohexane and CCl 4 solutions emits very efficiently. Although there are examples of nitro derivatives possessing fluorescence properties, they are rather rare in the literature, [16,17,19,20] and to the best of our knowledge no nitro derivatives with almost 100% fluorescence quantum yield have been reported. When increasing the solvent polarity, the single bonds at positions 2 and 5 adopt a partial double-bond character in favor of the ICT state (Figure 4), form B), resulting in a more planar structure quenching the fluorescence as is typical for the nitro group.…”

Section: Linear Spectroscopic Characteristicsmentioning

confidence: 99%

Pyrrolo[3,2‐b]pyrroles—From Unprecedented Solvatofluorochromism to Two‐Photon Absorption

Friese

Mikhaylov

Krzeszewski

et al. 2015

Chemistry A European J

114

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A combined experimental and theoretical study of the two-photon absorption properties of a series of quadrupolar molecules possessing a highly electron-rich heterocyclic core, pyrrolo[3,2-b]pyrrole is presented. In agreement with quantum-chemical calculations, we observe large two-photon absorption (2PA) cross-section values, σ2PA ~ 102–103 GM (1GM = 1050 cm4 s photon−1) at wavelengths 650–700 nm, corresponding to the 2-photon allowed but 1-photon forbidden transitions. The calculations also predict that increased planarity of this molecule via removal of two N-substituents leads to further increase in the σ2PA values. Surprisingly, the most quadrupolar pyrrolo[3,2-b]pyrrole derivative bearing two 4-nitrophenyl substituents at positions 2 and 5 demonstrates very strong solvatofluorochromic effect, with the fluorescence quantum yield as high as 0.96 in cyclohexane, while the fluorescence vanishes in DMSO.

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“…18 Nandhikonda and Heagy have shown that incorporating various substituents at the periphery of the naphthalimide core can produce fluorescent dyes with interesting applications. 19 For example, compound 4b exhibits a dual emission that is conducive to ratiometric detection of DNA and suitable for applications in white-light emitting fluorophores. 19a On the other hand, compound 4c was designed to bind to the α-helical region of cardiac troponin I allowing its ratiometric detection at clinically relevant concentrations.…”

Section: Dual-emission Fluorophoresmentioning

confidence: 99%

“…19 For example, compound 4b exhibits a dual emission that is conducive to ratiometric detection of DNA and suitable for applications in white-light emitting fluorophores. 19a On the other hand, compound 4c was designed to bind to the α-helical region of cardiac troponin I allowing its ratiometric detection at clinically relevant concentrations. 19c Similarly, peripheral functionalization of the related N -aryl-1,8-naphthalimide scaffold ( 5a ) produces fluorescent dyes for various applications.…”

Section: Dual-emission Fluorophoresmentioning

confidence: 99%

“…19a On the other hand, compound 4c was designed to bind to the α-helical region of cardiac troponin I allowing its ratiometric detection at clinically relevant concentrations. 19c Similarly, peripheral functionalization of the related N -aryl-1,8-naphthalimide scaffold ( 5a ) produces fluorescent dyes for various applications. 20 As compared to 5a , the pyridyl derivative 5b was shown to shift both absorption and emission bands toward the red, while attachment of a boronic acid unit at the phenyl ring produced compound 5c that is amenable to ratiometric detection of carbohydrates.…”

Section: Dual-emission Fluorophoresmentioning

confidence: 99%

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Ratiometric mechanosensitive fluorescent dyes: design and applications

2016

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Fluorescent molecules, with their almost instantaneous response to external influences and relatively low-cost measurement instrumentation, have been attractive analytical tools and biosensors for centuries. More recently, advanced chemical synthesis and targeted design have accelerated the development of fluorescent probes. This article focuses on dyes with segmental mobility (known as fluorescent molecular rotors) that act as mechanosensors, which are known for their relationship of emission quantum yield with microviscosity. Fluorescence lifetime is directly related to quantum yield, but steady-state emission intensity is not. To remove confounding factors with steady-state instrumentation, dual-band emission dyes can be used, and molecular rotors have been developed that either have intrinsic dual emission or that have a non-sensitive reference unit to provide a calibration emission band. We report on theory, chemical structure, applications and targeted design of several classes of dual-emission molecular rotors.

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An organic white light-emitting dye: very small molecular architecture displays panchromatic emission

Abstract: The synthesis and photophysical characterization of a new white-light fluorophore is described. The optimization of excitation wavelengths allows the naphthalimide (NI) dyes to display blue, green or white light emission depending on the excitation wavelength.

Cited by 55 publications

References 14 publications

Single‐Molecular White‐Light Emitters and Their Potential WOLED Applications

Single‐Molecular White‐Light Emitters and Their Potential WOLED Applications

Pyrrolo[3,2‐b]pyrroles—From Unprecedented Solvatofluorochromism to Two‐Photon Absorption

Ratiometric mechanosensitive fluorescent dyes: design and applications

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